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For my daughter, Avary, and my dad
If the soul is left in darkness, sins will be committed. The
guilty one is not he who commits the sin, but the one who
causes the darkness.
—Victor Hugo, Les Misérables
Much of this book comes from my own memory. For events during which I
was not present, I relied on conversations and interviews, many of which are
recorded, with members of my family, family friends, neighbors, and
associates. I’ve reconstructed some dialogue according to what I personally
remember and what others have told me. Where dialogue appears, my
intention was to re-create the essence of conversations rather than provide
verbatim quotes. I have also relied on legal documents, bank statements, tax
returns, private journals, family documents, correspondence, emails, texts,
photographs, and other records.
For general background, I relied on the New York Times, in particular the
investigative article by David Barstow, Susanne Craig, and Russ Buettner
that was published on October 2, 2018; the Washington Post; Vanity Fair;
Politico; the TWA Museum website; and Norman Vincent Peale’s The Power
of Positive Thinking. For background on Steeplechase Park, I thank the
Coney Island History Project website, Brooklyn Paper, and a May 14, 2018,
article on 6sqft.com by Dana Schulz. For his insights into “the episodic man,”
thank you to Dan P. McAdams. For family history and information regarding
Trump family businesses and alleged crimes, I am grateful for the reporting
of the late Wayne Barrett, David Corn, Michael D’Antonio, David Cay
Johnston, Tim O’Brien, Charles P. Pierce, and Adam Serwer. Thanks also to
Gwenda Blair, and Michael Kranish and Marc Fisher—but my dad was fortytwo, not forty-three, when he died.
I’d always liked my name. As a kid at sailing camp in the 1970s, everybody
called me Trump. It was a source of pride, not because the name was
associated with power and real estate (back then my family was unknown
outside of Brooklyn and Queens) but because something about the sound of it
suited me, a tough six-year-old, afraid of nothing. In the 1980s, when I was in
college and my uncle Donald had started branding all of his buildings in
Manhattan, my feelings about my name became more complicated.
Thirty years later, on April 4, 2017, I was in the quiet car of an Amtrak
train headed to Washington, DC, for a family dinner at the White House. Ten
days earlier I had received an email inviting me to a birthday celebration for
my aunts Maryanne, turning eighty, and Elizabeth, turning seventy-five.
Their younger brother Donald had occupied the Oval Office since January.
After I emerged into Union Station, with its vaulted ceilings and blackand-white marble floors, I passed a vendor who had set up an easel with
buttons for sale: my name in a red circle with a red slash through it, “DEPORT
TRUMP,” “DUMP TRUMP,” and “TRUMP IS A WITCH.” I put on my sunglasses and
picked up my pace.
I took a cab to the Trump International Hotel, which was comping my
family for one night. After checking in, I walked through the atrium and
looked up at the glass ceiling and the blue sky beyond. The three-tiered
crystal chandeliers that hung from the central beam of interconnected girders
arching overhead cast a soft light. On one side, armchairs, settees, and
couches—royal blue, robin’s-egg blue, ivory—were arranged in small
groups; on the other, tables and chairs circled a large bar where I was later
scheduled to meet my brother. I had expected the hotel to be vulgar and
gilded. It wasn’t.
My room was also tasteful. But my name was plastered everywhere, on
everything: TRUMP shampoo, TRUMP conditioner, TRUMP slippers,
TRUMP shower cap, TRUMP shoe polish, TRUMP sewing kit, and TRUMP
bathrobe. I opened the refrigerator, grabbed a split of TRUMP white wine,
and poured it down my Trump throat so it could course through my Trump
bloodstream and hit the pleasure center of my Trump brain.
An hour later I met my brother, Frederick Crist Trump, III, whom I’ve
called Fritz since we were kids, and his wife, Lisa. Soon we were joined by
the rest of our party: my aunt Maryanne, the eldest of Fred and Mary
Trump’s five children and a respected federal appeals court judge; my uncle
Robert, the baby of the family, who for a short time had been one of Donald’s
employees in Atlantic City before leaving on bad terms in the early 1990s,
and his girlfriend; my aunt Elizabeth, the middle Trump child, and her
husband, Jim; my cousin David Desmond (Maryanne’s only child and the
oldest Trump grandchild) and his wife; and a few of my aunts’ closest
friends. The only Trump sibling who would be missing from the celebration
was my father, Frederick Crist Trump, Jr., the oldest son, whom everybody
had called Freddy. He had died more than thirty-five years before.
When we were finally all together, we checked in with the White House
security agents outside, then piled haphazardly into the two White House
vans like a JV lacrosse team. Some of the older guests had trouble
negotiating the steps. Nobody was comfortable squeezing onto the bench
seats. I wondered why the White House hadn’t thought to send at least one
limo for my aunts.
As we pulled into the South Lawn driveway ten minutes later, two guards
came out of the security hut to inspect the underside of the van before we
drove through the front gate. After a short drive we stopped at a small
security building adjacent to the East Wing and disembarked. We went inside
one by one as our names were called, handed over our phones and bags, and
walked through a metal detector.
Once inside the White House, we walked in twos and threes through the
long corridors, past windows looking out on gardens and lawns, past lifesized paintings of former first ladies. I stopped in front of Hillary Clinton’s
portrait and stood silently for a minute. I wondered again how this could have
There was no reason for me ever to have imagined that I’d visit the White
House, certainly not under these circumstances. The whole thing felt surreal.
I looked around. The White House was elegant, grand, and stately, and I was
about to see my uncle, the man who lived here, for the first time in eight
We emerged from the shadows of the hallway onto the portico
surrounding the Rose Garden and stopped outside the Oval Office. Through
the French doors, I could see that a meeting was still in progress. Vice
President Mike Pence stood off to the side, but Speaker of the House Paul
Ryan, Senator Chuck Schumer, and a dozen other congresspeople and
staffers were gathered around Donald, who sat behind the Resolute Desk.
The tableau reminded me of one of my grandfather’s tactics: he always
made his supplicants come to him, either at his Brooklyn office or his house
in Queens, and he remained seated while they stood. In late autumn 1985, a
year after I had taken a leave of absence from Tufts University, I took my
place in front of him and asked his permission to return to school. He looked
up at me and said, “That’s stupid. What do you want to do that for? Just go to
trade school and become a receptionist.”
“Because I want to get my degree.” I must have said it with a hint of
annoyance, because my grandfather narrowed his eyes and looked at me for a
second as if reevaluating me. The corner of his mouth lifted in a sneer, and he
laughed. “That’s nasty,” he said.
A few minutes later, the meeting broke up.
The Oval Office was both smaller and less intimate than I’d imagined. My
cousin Eric and his wife, Lara, whom I’d never met, were standing right by
the door, so I said, “Hi, Eric. It’s your cousin Mary.”
“Of course I know who you are,” he said.
“Well, it’s been a while,” I said. “I think the last time we saw each other,
you were still in high school.”
He shrugged and said, “That’s probably true.” He and Lara walked away
without his introducing us. I looked around. Melania, Ivanka, Jared, and
Donny had arrived and were standing next to Donald, who remained seated.
Mike Pence continued to lurk on the other side of the room with a half-dead
smile on his face, like the chaperone everybody wanted to avoid.
I stared at him, hoping to make eye contact, but he never looked my way.
“Excuse me, everyone,” the White House photographer, a petite young
woman in a dark pantsuit, announced in an upbeat voice. “Let’s get you all
together so I can take some pictures before we go upstairs.” She instructed us
to surround Donald, who still had not gotten up from the desk.
The photographer raised her camera. “One, two, three, smile,” she said.
After the pictures had been taken, Donald stood up and pointed to a
framed black-and-white photograph of my grandfather, which was propped
up on a table behind the desk. “Maryanne, isn’t that a great picture of Dad?”
It was the same photograph that had sat on the side table in the library of my
grandparents’ house. In it, my grandfather was still a young man, with
receding dark hair, a mustache, and a look of command that I had never seen
falter until his dementia set in. We’d all seen it thousands of times.
“Maybe you should have a picture of Mom, too,” Maryanne suggested.
“That’s a great idea,” Donald said as though it had never occurred to him.
“Somebody get me a picture of Mom.”
We spent a few more minutes in the Oval Office, taking turns sitting
behind the Resolute Desk. My brother took a picture of me, and when I
looked at it later, I noticed my grandfather hovering behind me like a ghost.
The White House historian joined us just outside the Oval Office, and we
proceeded to the Executive Residence on the second floor for a tour to be
followed by dinner. Once upstairs, we proceeded to the Lincoln Bedroom. I
took a quick look inside and was surprised to see a half-eaten apple on the
bedside table. As the historian told us stories about what had happened in the
room through the years, Donald pointed vaguely once in a while and
declared, “This place has never looked better since George Washington lived
here.” The historian was too polite to point out that the house hadn’t been
opened until after Washington had died. The group moved down the hall
toward the Treaty Room and the Executive Dining Room.
Donald stood in the doorway, greeting people as they entered. I was one of
the last to arrive. I hadn’t yet said hello, and when he saw me, he pointed at
me with a surprised look on his face, then said, “I specifically asked for you
to be here.” That was the kind of thing he often said to charm people, and he
had a knack for tailoring his comment to the occasion, which was all the
more impressive because I knew it wasn’t true. He opened his arms, and then,
for the first time in my life, he hugged me.
The first thing I noticed about the Executive Dining Room was its beauty:
the dark wood polished to perfection, the exquisite place settings, and the
hand-drawn calligraphy on the place cards and menus (iceberg lettuce salad,
mashed potatoes—Trump family staples—and Wagyu beef filet). The second
thing I noticed after sitting down was the seating arrangement. In my family,
you could always gauge your worth by where you were seated, but I didn’t
mind: all of the people I felt comfortable with—my brother and sister-in-law,
Maryanne’s stepdaughter and her husband—were seated near me.
Each of the waiters carried a bottle of red wine and a bottle of white. Real
wine, not TRUMP wine. That was unexpected. In my entire life, there had
never been any alcohol at a family function. Only Coke and apple juice had
been served at my grandparents’ house.
Halfway through the meal, Jared walked into the dining room. “Oh, look,”
Ivanka said, clapping her hands, “Jared’s back from his trip to the Middle
East,” as if we hadn’t just seen him in the Oval Office. He walked over to his
wife, gave her a quick kiss on the cheek, then bent over Donald, who was
seated next to Ivanka. They spoke quietly for a couple of minutes. And then
Jared left. He didn’t acknowledge anybody else, not even my aunts. As he
crossed the threshold, Donny leapt out of his chair and bounded after him like
an excited puppy.
As dessert was being served, Robert stood up, wineglass in hand. “It is
such an honor to be here with the president of the United States,” he said.
“Thank you, Mr. President, for allowing us to be here to celebrate our sisters’
I thought back to the last time the family had celebrated Father’s Day at
Peter Luger Steak House in Brooklyn. Then, as now, Donald and Rob had
been sitting next to each other with me directly across from them. Without
any explanation, Donald had turned to Rob and said, “Look.” He’d bared his
teeth and pointed at his mouth.
“What?” Rob had asked.
Donald had simply pulled his lips back farther and pointed more
Rob had started to look nervous. I had no idea what was going on but
watched with amusement while I sipped my Coke.
“Look!” Donald had said through his gritted teeth. “What do you think?”
“What do you mean?” Rob’s embarrassment was palpable. He had
glanced around him to make sure nobody was looking at him and whispered,
“Is there something in my teeth?” The bowls of creamed spinach scattered
around the table rendered that a distinct possibility.
Donald had relaxed his mouth and stopped pointing. The contemptuous
look on his face summed up the entire history of their relationship. “I got my
teeth whitened. What do you think?” he had asked dryly.
After Rob’s remarks, Donald shot him the same dismissive look I’d seen
at Peter Luger’s almost twenty years before. Then, Diet Coke glass in hand,
Donald made some perfunctory remarks about my aunts’ birthdays, after
which he gestured toward his daughter-in-law. “Lara, there,” he said. “I
barely even knew who the fuck she was, honestly, but then she gave a great
speech during the campaign in Georgia supporting me.” By then, Lara and
Eric had been together for almost eight years, so presumably Donald had at
least met her at their wedding. But it sounded as if he hadn’t known who she
was until she had said something nice about him at a campaign rally during
the election. As usual with Donald, the story mattered more than the truth,
which was easily sacrificed, especially if a lie made the story sound better.
When Maryanne’s turn came, she said, “I want to thank you for making
the trip to celebrate our birthdays. We’ve come a long way since that night
when Freddy dumped a bowl of mashed potatoes on Donald’s head because
he was being such a brat.” Everybody familiar with the legendary mashed
potato story laughed—everyone except Donald, who listened with his arms
tightly crossed and a scowl on his face, as he did whenever Maryanne
mentioned it. It upset him, as if he were that seven-year-old boy. He clearly
still felt the sting of that long-ago humiliation.
Unprompted, my cousin Donny, who’d returned from chasing down Jared,
stood up to speak. Instead of toasting our aunts, he gave a sort of campaign
speech. “Last November, the American people saw something special and
voted for a president who they knew understood them. They saw what a great
family this is, and they connected with our values.” I glanced at my brother
and rolled my eyes.
I flagged down one of the waiters. “Can I have some more wine?” I asked.
He returned quickly with two bottles and asked if I preferred red or white.
“Yes, please,” I said.
As soon as we finished dessert, everybody rose. Only two hours had
elapsed since we’d entered the Oval Office, but the meal was over, and it was
time to leave. From beginning to end we had spent about twice as much time
at the White House as we ever had at my grandparents’ house for
Thanksgiving or Christmas but still less time with Donald than Kid Rock,
Sarah Palin, and Ted Nugent would two weeks later.
Somebody suggested that we all take individual pictures with Donald
(though not with the guests of honor). When it was my turn, Donald smiled
for the camera and gave a thumbs-up, but I could see the exhaustion behind
the smile. It seemed that keeping up the cheerful facade was wearing on him.
“Don’t let them get you down,” I said to him as my brother took the
picture. It wasn’t long after his first national security advisor had been fired
in disgrace, and the cracks in his presidency were already beginning to show.
Donald jutted out his chin and clenched his teeth, looking for a moment
like the ghost of my grandmother. “They’re not going to get me,” he said.
When Donald announced his run for the presidency on June 16, 2015, I didn’t
take it seriously. I didn’t think Donald took it seriously. He simply wanted
the free publicity for his brand. He’d done that sort of thing before. When his
poll numbers started to rise and he may have received tacit assurances from
Russian president Vladimir Putin that Russia would do everything it could to
swing the election in his favor, the appeal of winning grew.
“He’s a clown,” my aunt Maryanne said during one of our regular lunches
at the time. “This will never happen.”
We talked about how his reputation as a faded reality star and failed
businessman would doom his run. “Does anybody even believe the bullshit
that he’s a self-made man? What has he even accomplished on his own?” I
“Well,” Maryanne said, as dry as the Sahara, “he has had five
When Donald started addressing the opioid crisis and using my father’s
history with alcoholism to burnish his anti-addiction bona fides to seem more
sympathetic, both of us were angry.
“He’s using your father’s memory for political purposes,” Maryanne said,
“and that’s a sin, especially since Freddy should have been the star of the
We thought the blatant racism on display during Donald’s announcement
speech would be a deal breaker, but we were disabused of that idea when
Jerry Falwell, Jr., and other white evangelicals started endorsing him.
Maryanne, a devout Catholic since her conversion five decades earlier, was
incensed. “What the fuck is wrong with them?” she said. “The only time
Donald went to church was when the cameras were there. It’s mind boggling.
He has no principles. None!”
Nothing Donald said during the campaign—from his disparagement of
Secretary of State Hillary Clinton, arguably the most qualified presidential
candidate in the history of the country, as a “nasty woman,” to his mocking
of Serge Kovaleski, a disabled New York Times reporter—deviated from my
expectation of him. In fact, I was reminded of every family meal I’d ever
attended during which Donald had talked about all of the women he
considered ugly fat slobs or the men, usually more accomplished or powerful,
he called losers while my grandfather and Maryanne, Elizabeth, and Robert
all laughed and joined in. That kind of casual dehumanization of people was
commonplace at the Trump dinner table. What did surprise me was that he
kept getting away with it.
Then he received the nomination. The things I had thought would
disqualify him seemed only to strengthen his appeal to his base. I still wasn’t
concerned—I was confident he could never be elected—but the idea that he
had a shot at it was unnerving.
Late in the summer of 2016, I considered speaking out about the ways I
knew Donald to be completely unqualified. By this time, he had emerged
relatively unscathed from the Republican National Convention and his call
for “Second Amendment people” to stop Hillary Clinton. Even his attack on
Khizr and Ghazala Khan, Gold Star parents whose son Humayun, a US Army
captain, had died in Iraq, seemed not to matter. When the majority of
Republicans polled still supported him after the Access Hollywood tape was
released, I knew I had made the right decision.
I began to feel as though I were watching my family history, and Donald’s
central role in it, playing out on a grand scale. Donald’s competition in the
race was being held to higher standards, just as my father had always been,
while he continued to get away with—and even be rewarded for—
increasingly crass, irresponsible, and despicable behavior. This can’t possibly
be happening again, I thought. But it was.
The media failed to notice that not one member of Donald’s family, apart
from his children, his son-in-law, and his current wife said a word in support
of him during the entire campaign. Maryanne told me she was lucky because,
as a federal judge, she needed to maintain her objectivity. She may have been
the only person in the country, given her position as his sister and her
professional reputation, who, if she had spoken out about Donald’s complete
unfitness for the office, might have made a difference. But she had her own
secrets to keep, and I wasn’t entirely surprised when she told me after the
election that she’d voted for her brother out of “family loyalty.”
Growing up in the Trump family, particularly as Freddy’s child, presented
certain challenges. In some ways I’ve been extremely fortunate. I attended
excellent private schools and had the security of first-rate medical insurance
for much of my life. There was also, though, a built-in sense of scarcity that
applied to all of us, except Donald. After my grandfather died in 1999, I
learned that my father’s line had been erased from the will as if Fred Trump’s
oldest son had never existed, and a lawsuit followed. In the end, I concluded
that if I spoke publicly about my uncle, I would be painted as a disgruntled,
disinherited niece looking to cash in or settle a score.
In order to understand what brought Donald—and all of us—to this point, we
need to start with my grandfather and his own need for recognition, a need
that propelled him to encourage Donald’s reckless hyperbole and unearned
confidence that hid Donald’s pathological weaknesses and insecurities.
As Donald grew up, he was forced to become his own cheerleader, first,
because he needed his father to believe he was a better and more confident
son than Freddy was; then because Fred required it of him; and finally
because he began to believe his own hype, even as he paradoxically
suspected on a very deep level that nobody else did. By the time of the
election, Donald met any challenges to his sense of superiority with anger,
his fear and vulnerabilities so effectively buried that he didn’t even have to
acknowledge they existed. And he never would.
In the 1970s, after my grandfather had already been preferring and
promoting Donald for years, the New York media picked up the baton and
began disseminating Donald’s unsubstantiated hype. In the 1980s, the banks
joined in when they began to fund his ventures. Their willingness (and then
their need) to foster his increasingly unfounded claims to success hung on the
hopes of recouping their losses.
After a decade during which Donald floundered, dragged down by
bankruptcies and reduced to fronting for a series of failed products from
steaks to vodka, the television producer Mark Burnett gave him yet another
chance. The Apprentice traded on Donald’s image as the brash, self-made
dealmaker, a myth that had been the creation of my grandfather five decades
earlier and that astonishingly, considering the vast trove of evidence
disproving it, had survived into the new millennium almost entirely
unaltered. By the time Donald announced his run for the Republican Party
nomination in 2015, a significant percentage of the American population had
been primed to believe that myth.
To this day, the lies, misrepresentations, and fabrications that are the sum
total of who my uncle is are perpetuated by the Republican Party and white
evangelical Christians. People who know better, such as Senate majority
leader Mitch McConnell; true believers, such as Representative Kevin
McCarthy, Secretary of State Mike Pompeo, and Attorney General William
Barr; and others too numerous to name, have become, unwittingly or not,
complicit in their perpetuation.
None of the Trump siblings emerged unscathed from my grandfather’s
sociopathy and my grandmother’s illnesses, both physical and psychological,
but my uncle Donald and my father, Freddy, suffered more than the rest. In
order to get a complete picture of Donald, his psychopathologies, and the
meaning of his dysfunctional behavior, we need a thorough family history.
In the last three years, I’ve watched as countless pundits, armchair
psychologists, and journalists have kept missing the mark, using phrases such
as “malignant narcissism” and “narcissistic personality disorder” in an
attempt to make sense of Donald’s often bizarre and self-defeating behavior. I
have no problem calling Donald a narcissist—he meets all nine criteria as
outlined in the Diagnostic and Statistical Manual of Mental Disorders
(DSM-5)—but the label gets us only so far.
I received my PhD in clinical psychology from the Derner Institute of
Advanced Psychological Studies, and while doing research for my
dissertation I spent a year working on the admissions ward of Manhattan
Psychiatric Center, a state facility, where we diagnosed, evaluated, and
treated some of the sickest, most vulnerable patients. In addition to teaching
graduate psychology, including courses in trauma, psychopathology, and
developmental psychology, for several years as an adjunct professor, I
provided therapy and psychological testing for patients at a community clinic
specializing in addictions.
Those experiences showed me time and again that diagnosis doesn’t exist
in a vacuum. Does Donald have other symptoms we aren’t aware of? Are
there other disorders that might have as much or more explanatory power?
Maybe. A case could be made that he also meets the criteria for antisocial
personality disorder, which in its most severe form is generally considered
sociopathy but can also refer to chronic criminality, arrogance, and disregard
for the rights of others. Is there comorbidity? Probably. Donald may also
meet some of the criteria for dependent personality disorder, the hallmarks of
which include an inability to make decisions or take responsibility,
discomfort with being alone, and going to excessive lengths to obtain support
from others. Are there other factors that should be considered? Absolutely.
He may have a long undiagnosed learning disability that for decades has
interfered with his ability to process information. Also, he is alleged to drink
upward of twelve Diet Cokes a day and sleep very little. Does he suffer from
a substance- (in this case caffeine-) induced sleep disorder? He has a horrible
diet and does not exercise, which may contribute to or exacerbate his other
The fact is, Donald’s pathologies are so complex and his behaviors so
often inexplicable that coming up with an accurate and comprehensive
diagnosis would require a full battery of psychological and
neuropsychological tests that he’ll never sit for. At this point, we can’t
evaluate his day-to-day functioning because he is, in the West Wing,
essentially institutionalized. Donald has been institutionalized for most of his
adult life, so there is no way to know how he would thrive, or even survive,
on his own in the real world.
At the end of my aunts’ birthday party in 2017, as we lined up for our
pictures, I could see that Donald was already under a kind of stress he’d
never experienced before. As the pressures upon him have continued to
mount over the course of the last three years, the disparity between the level
of competence required for running a country and his incompetence has
widened, revealing his delusions more starkly than ever before.
Many, but by no means all of us, have been shielded until now from the
worst effects of his pathologies by a stable economy and a lack of serious
crises. But the out-of-control COVID-19 pandemic, the possibility of an
economic depression, deepening social divides along political lines thanks to
Donald’s penchant for division, and devastating uncertainty about our
country’s future have created a perfect storm of catastrophes that no one is
less equipped than my uncle to manage. Doing so would require courage,
strength of character, deference to experts, and the confidence to take
responsibility and to course correct after admitting mistakes. His ability to
control unfavorable situations by lying, spinning, and obfuscating has
diminished to the point of impotence in the midst of the tragedies we are
currently facing. His egregious and arguably intentional mishandling of the
current catastrophe has led to a level of pushback and scrutiny that he’s never
experienced before, increasing his belligerence and need for petty revenge as
he withholds vital funding, personal protective equipment, and ventilators
that your tax dollars have paid for from states whose governors don’t kiss his
In the 1994 film based on Mary Wollstonecraft Shelley’s novel,
Frankenstein’s monster says, “I do know that for the sympathy of one living
being, I would make peace with all. I have love in me the likes of which you
can scarcely imagine and rage the likes of which you would not believe. If I
cannot satisfy the one, I will indulge the other.” After referencing that quote,
Charles P. Pierce wrote in Esquire, “[Donald] doesn’t plague himself with
doubt about what he’s creating around him. He is proud of his monster. He
glories in its anger and its destruction and, while he cannot imagine its love,
he believes with all his heart in its rage. He is Frankenstein without
That could more accurately have been said about Donald’s father, Fred,
with this crucial difference: Fred’s monster—the only child of his who
mattered to him—would ultimately be rendered unlovable by the very nature
of Fred’s preference for him. In the end, there would be no love for Donald at
all, just his agonizing thirsting for it. The rage, left to grow, would come to
overshadow everything else.
When Rhona Graff, Donald’s longtime gatekeeper, sent me and my daughter
an invitation to attend Donald’s election-night party in New York City, I
declined. I wouldn’t be able to contain my euphoria when Clinton’s victory
was announced, and I didn’t want to be rude. At 5:00 the next morning, only
a couple of hours after the opposite result had been announced, I was
wandering around my house, as traumatized as many other people but in a
more personal way: it felt as though 62,979,636 voters had chosen to turn this
country into a macro version of my malignantly dysfunctional family.
Within a month of the election, I found myself compulsively watching the
news and checking my Twitter feed, anxious and unable to concentrate on
anything else. Though nothing Donald did surprised me, the speed and
volume with which he started inflicting his worst impulses on the country—
from lying about the crowd size at the inauguration and whining about how
poorly he was treated to rolling back environmental protections, targeting the
Affordable Care Act in order to take affordable health care away from
millions of people, and enacting his racist Muslim ban—overwhelmed me.
The smallest thing—seeing Donald’s face or hearing my own name, both of
which happened dozens of times a day—took me back to the time when my
father had withered and died beneath the cruelty and contempt of my
grandfather. I had lost him when he was only forty-two and I was sixteen.
The horror of Donald’s cruelty was being magnified by the fact that his acts
were now official US policy, affecting millions of people.
The atmosphere of division my grandfather created in the Trump family is
the water in which Donald has always swum, and division continues to
benefit him at the expense of everybody else. It’s wearing the country down,
just as it did my father, changing us even as it leaves Donald unaltered. It’s
weakening our ability to be kind or believe in forgiveness, concepts that have
never had any meaning for him. His administration and his party have
become subsumed by his politics of grievance and entitlement. Worse,
Donald, who understands nothing about history, constitutional principles,
geopolitics, diplomacy (or anything else, really) and was never pressed to
demonstrate such knowledge, has evaluated all of this country’s alliances,
and all of our social programs, solely through the prism of money, just as his
father taught him to do. The costs and benefits of governing are considered in
purely financial terms, as if the US Treasury were his personal piggy bank.
To him, every dollar going out was his loss, while every dollar saved was his
gain. In the midst of obscene plenty, one person, using all of the levers of
power and taking every advantage at his disposal, would benefit himself and,
conditionally, his immediate family, his cronies, and his sycophants; for the
rest, there would never be enough to go around, which was exactly how my
grandfather ran our family.
It’s extraordinary that for all of the attention and coverage that Donald has
received in the last fifty years, he’s been subjected to very little scrutiny.
Though his character flaws and aberrant behavior have been remarked upon
and joked about, there’s been very little effort to understand not only why he
became who he is but how he’s consistently failed up despite his glaring lack
Donald has, in some sense, always been institutionalized, shielded from
his limitations or his need to succeed on his own in the world. Honest work
was never demanded of him, and no matter how badly he failed, he was
rewarded in ways that are almost unfathomable. He continues to be protected
from his own disasters in the White House, where a claque of loyalists
applauds his every pronouncement or covers up his possible criminal
negligence by normalizing it to the point that we’ve become almost numb to
the accumulating transgressions. But now the stakes are far higher than
they’ve ever been before; they are literally life and death. Unlike any
previous time in his life, Donald’s failings cannot be hidden or ignored
because they threaten us all.
Although my aunts and uncles will think otherwise, I’m not writing this
book to cash in or out of a desire for revenge. If either of those had been my
intention, I would have written a book about our family years ago, when there
was no way to anticipate that Donald would trade on his reputation as a
serially bankrupt businessman and irrelevant reality show host to ascend to
the White House; when it would have been safer because my uncle wasn’t in
a position to threaten and endanger whistleblowers and critics. The events of
the last three years, however, have forced my hand, and I can no longer
remain silent. By the time this book is published, hundreds of thousands of
American lives will have been sacrificed on the altar of Donald’s hubris and
willful ignorance. If he is afforded a second term, it would be the end of
No one knows how Donald came to be who he is better than his own
family. Unfortunately, almost all of them remain silent out of loyalty or fear.
I’m not hindered by either of those. In addition to the firsthand accounts I can
give as my father’s daughter and my uncle’s only niece, I have the
perspective of a trained clinical psychologist. Too Much and Never Enough is
the story of the most visible and powerful family in the world. And I am the
only Trump who is willing to tell it.
I hope this book will end the practice of referring to Donald’s “strategies”
or “agendas,” as if he operates according to any organizing principles. He
doesn’t. Donald’s ego has been and is a fragile and inadequate barrier
between him and the real world, which, thanks to his father’s money and
power, he never had to negotiate by himself. Donald has always needed to
perpetuate the fiction my grandfather started that he is strong, smart, and
otherwise extraordinary, because facing the truth—that he is none of those
things—is too terrifying for him to contemplate.
Donald, following the lead of my grandfather and with the complicity,
silence, and inaction of his siblings, destroyed my father. I can’t let him
destroy my country.
The Cruelty Is the Point
“Daddy, Mom’s bleeding!”
They’d lived in the “House,” as my grandparents’ home was known, for
less than a year, and it still felt unfamiliar, especially in the middle of the
night, so when twelve-year-old Maryanne found her mother lying
unconscious in one of the upstairs bathrooms—not the master bathroom but
the bathroom she and her sister shared down the hall—she was already
disoriented. There was blood all over the bathroom floor. Maryanne’s terror
was so great that it overcame her usual reluctance to disturb her father in his
bedroom, and she flew to the other end of the house to rouse him.
Fred got out of bed, walked quickly down the hall, and found his wife
unresponsive. With Maryanne at his heels, he rushed back to his bedroom,
where there was a telephone extension, and placed a call.
Already a powerful man with connections at Jamaica Hospital, Fred was
immediately put into touch with someone who could get an ambulance to the
House and make sure the best doctors were waiting for them when they
arrived at the emergency room. Fred explained the situation as best he could
to the person on the other end. Maryanne heard him say “menstruation,” an
unfamiliar word that sounded strange coming out of her father’s mouth.
Shortly after Mary arrived at the hospital, she underwent an emergency
hysterectomy after doctors found that serious postpartum complications had
gone undiagnosed after Robert’s birth nine months earlier. The procedure led
to an abdominal infection, and then further complications arose.
From what would become his usual spot by the telephone table in the
library, Fred spoke briefly with one of Mary’s doctors and, after hanging up
the phone, called Maryanne to join him.
“They told me your mother won’t make it through the night,” he said to
A little while later, as he was leaving for the hospital to be with his wife,
he told her, “Go to school tomorrow. I’ll call you if there’s any change.”
She understood the implication: I will call you if your mother dies.
Maryanne spent the night crying alone in her room while her younger
siblings remained asleep in their beds, unaware of the calamity. She went to
school the next day full of dread. Dr. James Dixon, the headmaster of KewForest, a private school she had begun attending when her father joined the
board of directors, came to get her from study hall. “There’s a phone call for
you in my office.”
Maryanne was convinced that her mother was dead. The walk to the
principal’s office was like a walk to the scaffold. All the twelve-year-old
could think was that she was going to be the acting mother of four children.
When she picked up the phone, her father simply said, “She’s going to
Mary would undergo two more surgeries over the next week, but she did
indeed make it. Fred’s pull at the hospital, which ensured that his wife got the
very best doctors and care, had probably saved her life. But it would be a
long road back to recovery.
For the next six months, Mary was into and out of the hospital. The longterm implications for her health were serious. She eventually developed
severe osteoporosis from the sudden loss of estrogen that went with having
her ovaries removed along with her uterus, a common but often unnecessary
medical procedure performed at the time. As a result, she was often in
excruciating pain from spontaneous fractures to her ever-thinning bones.
If we’re lucky, we have, as infants and toddlers, at least one emotionally
available parent who consistently fulfills our needs and responds to our
desires for attention. Being held and comforted, having our feelings
acknowledged and our upsets soothed are all critical for the healthy
development of young children. This kind of attention creates a sense of
safety and security that ultimately allows us to explore the world around us
without excessive fear or unmanageable anxiety because we know we can
count on the bedrock support of at least one caregiver.
Mirroring, the process through which an attuned parent reflects, processes,
and then gives back to the baby the baby’s own feelings, is another crucial
part of a young child’s development. Without mirroring, children are denied
crucial information both about how their minds work and about how to
understand the world. Just as a secure attachment to a primary caregiver can
lead to higher levels of emotional intelligence, mirroring is the root of
Mary and Fred were problematic parents from the very beginning. My
grandmother rarely spoke to me about her own parents or childhood, so I can
only speculate, but she was the youngest of ten children—twenty-one years
younger than her oldest sibling and four years younger than the second
youngest—and she grew up in an often inhospitable environment in the early
1910s. Whether her own needs weren’t sufficiently met when she was young
or for some other reason, she was the kind of mother who used her children
to comfort herself rather than comforting them. She attended to them when it
was convenient for her, not when they needed her to. Often unstable and
needy, prone to self-pity and flights of martyrdom, she frequently put herself
first. Especially when it came to her sons, she acted as if there were nothing
she could do for them.
During and after her surgeries, Mary’s absence—both literal and
emotional—created a void in the lives of her children. As hard as it must
have been for Maryanne, Freddy, and Elizabeth, they were old enough to
understand what was happening and could, to some extent, take care of
themselves. The impact was especially dire for Donald and Robert, who at
two and a half years and nine months old, respectively, were the most
vulnerable of her children, especially since there was no one else to fill the
void. The live-in housekeeper was undoubtedly overwhelmed by the sheer
volume of housework. Their paternal grandmother, who lived nearby,
prepared meals, but she was as terse and physically unaffectionate as her son.
When Maryanne wasn’t in school, much of the responsibility of taking care
of the younger kids fell to her. (As a boy, Freddy wouldn’t have been
expected to help.) She gave them baths and got them ready for bed, but at
twelve there was only so much she could do. The five kids were essentially
Whereas Mary was needy, Fred seemed to have no emotional needs at all.
In fact, he was a high-functioning sociopath. Although uncommon,
sociopathy is not rare, afflicting as much as 3 percent of the population.
Seventy-five percent of those diagnosed are men. Symptoms of sociopathy
include a lack of empathy, a facility for lying, an indifference to right and
wrong, abusive behavior, and a lack of interest in the rights of others. Having
a sociopath as a parent, especially if there is no one else around to mitigate
the effects, all but guarantees severe disruption in how children understand
themselves, regulate their emotions, and engage with the world. My
grandmother was ill equipped to deal with the problems caused in her
marriage by Fred’s callousness, indifference, and controlling behaviors.
Fred’s lack of real human feeling, his rigidity as a parent and a husband, and
his sexist belief in a woman’s innate inferiority likely left her feeling
Since Mary was emotionally and physically absent due to her injuries,
Fred became, by default, the only available parent, but it would be a mistake
to refer to him as a caregiver. He firmly believed that dealing with young
children was not his job and kept to his twelve-hour-a-day, six-day-a-week
job at Trump Management, as if his children could look after themselves. He
focused on what was important to him: his increasingly successful business,
which at the time was developing Shore Haven and Beach Haven, two
massive residential projects in Brooklyn that were to date the most significant
of his life.
Again, Donald and Robert in particular would have been in the most
precarious position vis-à-vis Fred’s lack of interest. All behavior exhibited by
infants and toddlers is a form of attachment behavior, which seeks a positive,
comforting response from the caregiver—a smile to elicit a smile, tears to
prompt a hug. Even under normal circumstances, Fred would have
considered any expressions of that kind an annoyance, but Donald and Robert
were likely even needier because they missed their mother and were actively
distressed by her absence. The greater their distress, however, the more Fred
rebuffed them. He did not like to have demands made of him, and the
annoyance provoked by his children’s neediness set up a dangerous tension in
the Trump household: by engaging in behaviors that were biologically
designed to trigger soothing, comforting responses from their parents, the
little boys instead provoked their father’s anger or indifference when they
were most vulnerable. For Donald and Robert, “needing” became equated
with humiliation, despair, and hopelessness. Because Fred didn’t want to be
disturbed when he was home, it worked in his favor if his children learned
one way or another not to need anything.
Fred’s parenting style actually exacerbated the negative effects of Mary’s
absence. As a result of it, his children were isolated not just from the rest of
the world but from one another. From then on it would become increasingly
difficult for the siblings to find solidarity with other human beings, which is
one of the reasons Freddy’s brothers and sisters ultimately failed him;
standing up for him, even helping him, would have risked their father’s
When Mary became ill and Donald’s main source of comfort and human
connection was suddenly taken away from him, not only was there no one to
help him make sense of it, Fred was the only person left that he could depend
on. Donald’s needs, which had been met inconsistently before his mother’s
illness, were barely met at all by his father. That Fred would, by default,
become the primary source of Donald’s solace when he was much more
likely to be a source of fear or rejection put Donald into an intolerable
position: being totally dependent on his father, who was also likely to be a
source of his terror.
Child abuse is, in some sense, the experience of “too much” or “not
enough.” Donald directly experienced the “not enough” in the loss of
connection to his mother at a crucial developmental stage, which was deeply
traumatic. Without warning, his needs weren’t being met, and his fears and
longings went unsoothed. Having been abandoned by his mother for at least a
year, and having his father fail not only to meet his needs but to make him
feel safe or loved, valued or mirrored, Donald suffered deprivations that
would scar him for life. The personality traits that resulted—displays of
narcissism, bullying, grandiosity—finally made my grandfather take notice
but not in a way that ameliorated any of the horror that had come before. As
he grew older, Donald was subjected to my grandfather’s “too-muchness” at
second hand—witnessing what happened to Freddy when he was on the
receiving end of too much attention, too much expectation, and, most
saliently, too much humiliation.
From the beginning, Fred’s self-interest skewed his priorities. His care of
his children, such as it was, reflected his own needs, not theirs. Love meant
nothing to him, and he could not empathize with their plight, one of the
defining characteristics of a sociopath; he expected obedience, that was all.
Children don’t make such distinctions, and his kids believed that their father
loved them or that they could somehow earn his love. But they also knew, if
only on an unconscious level, that their father’s “love,” as they experienced
it, was entirely conditional.
Maryanne, Elizabeth, and Robert, to greater or lesser degrees, experienced
the same treatment as Donald because Fred wasn’t interested in children at
all. His oldest son and namesake received Fred’s attention simply because he
was being raised to carry on Fred’s legacy.
In order to cope, Donald began to develop powerful but primitive
defenses, marked by an increasing hostility to others and a seeming
indifference to his mother’s absence and father’s neglect. The latter became a
kind of learned helplessness over time because although it insulated him from
the worst effects of his pain, it also made it extremely difficult (and in the
long run I would argue impossible) for him to have any of his emotional
needs met at all because he became too adept at acting as though he didn’t
have any. In place of those needs grew a kind of grievance and behaviors—
including bullying, disrespect, and aggressiveness—that served their purpose
in the moment but became more problematic over time. With appropriate care
and attention, they might have been overcome. Unfortunately for Donald and
everybody else on this planet, those behaviors became hardened into
personality traits because once Fred started paying attention to his loud and
difficult second son, he came to value them. Put another way, Fred Trump
came to validate, encourage, and champion the things about Donald that
rendered him essentially unlovable and that were in part the direct result of
Mary never completely recovered. Restless to begin with, she became an
insomniac. The older kids would find her wandering around the House at all
hours like a soundless wraith. Once Freddy found her standing at the top of a
ladder painting the hallway in the middle of the night. In the morning her
children sometimes found her unconscious in unexpected places; more than
once, she ended up having to go to the hospital. That behavior became part of
the life of the House. Mary got help for the physical injuries she sustained but
none for whatever underlying psychological problems made her put herself
into high-risk situations.
Beyond his wife’s occasional injuries, Fred was aware of none of this and
wouldn’t have acknowledged the effects his particular brand of parenting had
on his children then or later, even if he had recognized them. As far as he was
concerned, he had been, for a brief time, faced with the limits of his wealth
and power in fixing his wife’s near-death health crisis. But ultimately Mary’s
medical challenges were a small blip in the grand scheme of things. Once she
was on the mend and his Shore Haven and Beach Haven real estate
developments, both phenomenal successes, were nearing completion,
everything seemed once again to be going Fred’s way.
When eight-year-old Freddy Trump asked why his very pregnant mother was
getting so fat, talk at the dinner table ground to a halt. It was 1948, and the
Trump family, which now consisted of four children—ten-year-old
Maryanne, Freddy, five-year-old Elizabeth, and one-and-a-half-year-old
Donald—were weeks away from moving into the twenty-three-room house
that Fred was in the process of building. Mary looked down at her plate, and
Fred’s mother, also named Elizabeth, an almost daily visitor to the house,
Table etiquette at my grandparents’ house was strict, and there were
certain things Fred did not tolerate. “Keep your elbows off the table, this is
not a horse’s stable” was a frequent refrain, and Fred, knife in hand, would
tap its handle against the forearm of any transgressor. (Rob and Donald took
over that task when Fritz, David, and I were growing up, with a bit too much
enthusiasm.) There were also things the children were not supposed to talk
about, especially in front of their father or grandmother. When Freddy
wanted to know how the baby had gotten there, Fred and his mother stood up
as one, left the table without saying a word, and walked off. Fred wasn’t a
prude, but Elizabeth, a stern, formal woman who adhered to Victorian mores,
very likely was.
Despite her own rigid views regarding gender roles, however, she had,
many years earlier, made an exception for her son; a couple of years after
Fred’s father had died suddenly, Elizabeth had become her fifteen-year-old
son’s business partner.
That was made possible in part because her husband, Friedrich Trump,
something of an entrepreneur, had left money and property valued at
approximately $300,000 in today’s currency.
Friedrich, born in Kallstadt, a small village in western Germany, left for
the United States when he turned eighteen in 1885 in order to avoid
mandatory military service. He eventually made the bulk of his money
through ownership of restaurants and brothels in British Columbia. He lit out
for the Yukon territories in time for the Gold Rush, cashing out just before
the boom collapsed near the turn of the century.
In 1901, while visiting his family in Germany, Friedrich met and married
Elizabeth Christ, a petite blond woman nearly twelve years his junior. He
brought his new bride to New York, but one month after the birth of their
first child, a girl they named Elizabeth, the couple returned to Germany with
the intention of settling there permanently. Because of the circumstances
under which Friedrich had originally left the country, he was told by
authorities that he could not stay. Friedrich, his wife—now four months
pregnant with their second child—and their two-year-old daughter returned
for the last time to the United States in July 1905. Their two sons, Frederick
and John, were born in 1905 and 1907, respectively. They eventually settled
in Woodhaven, Queens, where all three children grew up speaking German.
When Friedrich died of the Spanish flu, twelve-year-old Fred became the
man of the house. Despite the size of her husband’s estate, Elizabeth found it
difficult to make ends meet. The flu epidemic, which killed upward of 50
million people worldwide, had a destabilizing effect on what otherwise might
have been a booming wartime economy. While still in high school, Fred took
a series of odd jobs in order to help his mother financially and began to study
the building trade. Becoming a builder had been his dream for as long as he
could remember. He took every opportunity to learn the business, all aspects
of which intrigued him, and during his sophomore year, with his mother’s
backing, he began building and selling garages in his neighborhood. He
realized he was good at it, and from then on he had no other interests—none.
Two years after Fred’s high school graduation, Elizabeth created E. Trump
and Son. She recognized her son’s aptitude, and the business, which enabled
her to handle financial transactions for her underage middle child—in the
early twentieth century, people didn’t attain legal majority until the age of
twenty-one—was her way of supporting him. Both the business and the
When Fred was twenty-five years old, he attended a dance where he met
Mary Anne MacLeod, recently arrived from Scotland. According to family
legend, when he returned home, he told his mother that he had met the girl he
was going to marry.
Mary had been born the youngest of ten in 1912 in Tong, a village on the
Isle of Lewis in the Outer Hebrides, located forty miles off the northwest
coast of Scotland; her childhood had been bracketed by two global tragedies,
the latter of which also deeply affected her future husband: World War I and
the Spanish flu epidemic. Lewis had lost a disproportionate percentage of its
male population during the war, and in a cruel twist of fate, two months after
the armistice was signed in November 1918, a ship carrying soldiers home to
the island from the mainland crashed into rocks just a few yards offshore in
the early hours of January 1, 1919. More than 200 soldiers of the
approximately 280 on board died in the brutally cold waters less than a mile
from the safety of Stornoway Harbor. Much of the island’s young adult male
population was lost. Any young woman hoping to find a husband would have
better luck elsewhere.
Mary, one of six daughters, was encouraged to journey to America, where
the opportunities were greater and the men more plentiful.
In early May 1930, in a classic example of “chain migration,” Mary
boarded the RMS Transylvania in order to join two of her sisters who had
already settled in the United States. Despite her status as a domestic servant,
as a white Anglo-Saxon, Mary would have been allowed into the country
even under her son’s draconian new immigration rules introduced nearly
ninety years later. She turned eighteen the day before her arrival in New York
and met Fred not long after.
Fred and Mary were married on a Saturday in January 1936. After a
reception at the Carlyle Hotel in Manhattan, they honeymooned in Atlantic
City for one night. On Monday morning, Fred was back at his Brooklyn
The couple moved into their first house on Wareham Road, just down the
street from the house on Devonshire Road that Fred had shared with his
mother. In those early years, Mary was still in awe of her head-spinning
change in fortune, both financial and social. Instead of being the live-in help,
she had live-in help; instead of competing for limited resources, she was the
woman of the house. With free time to volunteer and money with which to
shop, she never looked back, which perhaps explains why she was quick to
judge others who came from similar circumstances. She and Fred put
together an entirely conventional life with strictly drawn roles for husband
and wife. He ran his business, which kept him in Brooklyn ten, sometimes
twelve hours a day, six days a week. She ran the house, but he ruled it—and,
at least in the beginning, so did his mother. Elizabeth was an intimidating
mother-in-law who, during the first few years of her son’s marriage, made
sure that Mary understood who was really in charge: she wore white gloves
when she visited, putting Mary on notice regarding the expectations she had
for her daughter-in-law’s housekeeping, which must have felt like a not-sosubtle mockery of her recent employment.
Despite Elizabeth’s hazing, those early years were a time of great energy
and possibility for Fred and Mary. Fred whistled his way down the stairs on
his way to work, and when he returned home in the evening, he whistled his
way up to his room, where he changed into a clean shirt before dinner.
Mary and Fred hadn’t discussed baby names, so when their first child, a
daughter, was born, they named her Maryanne, combining Mary’s first and
middle names. The couple’s first son was born a year and a half later, on
October 14, 1938, and named after his father—with one small change: Fred,
Sr.’s, middle name was Christ, his mother’s maiden name; his boy would be
named Frederick Crist. Everybody except his father would call him Freddy.
It seems as though Fred mapped out his son’s future before he was even
born. Although he would feel the burdens of the expectations placed upon
him when he grew older, Freddy benefited early on from his status in a way
Maryanne and the other children would not. After all, he had a special place
in his father’s plans: he would be the means through which the Trump empire
expanded and thrived in perpetuity.
Three and a half years passed before Mary gave birth to another child.
Shortly before the arrival of Elizabeth, Fred left for an extended period to
work in Virginia Beach. A housing shortage, the result of service members’
returning from World War II, created an opportunity for him to build
apartments for navy personnel and their families. Fred had had time to
sharpen his skills and gain the reputation that got him the work because while
other eligible men had enlisted, he had chosen not to serve, following in his
Through his growing experience with building many houses
simultaneously and his inherent skill at using local media to his own ends,
Fred was introduced to well-connected politicians and learned through them
how to call in favors at the right time, and, most important, chase government
money. The lure in Virginia Beach, where Fred learned the advantage of
building his real estate empire with government handouts, was the generous
funding made available by the Federal Housing Administration (FHA).
Founded in 1934 by President Franklin D. Roosevelt, the FHA seems to have
strayed far from its original mandate by the time Fred began taking advantage
of its largesse. Its chief purpose had been to ensure that enough affordable
housing was being built for the country’s constantly growing population.
After World War II, the FHA seemed equally concerned with enriching
developers such as Fred Trump.
The project in Virginia was also a chance to hone the expertise he’d begun
to acquire in Brooklyn: building larger-scale projects as quickly, efficiently,
and cheaply as possible while still managing to make them attractive to
renters. When the commute back and forth to Queens became too
inconvenient, Fred moved the entire family to Virginia Beach when Elizabeth
was still an infant.
From Mary’s perspective, other than finding herself in an unfamiliar
environment, things were much the same in Virginia as they had been in
Jamaica Estates. Fred worked long hours, leaving her alone with three
children under the age of six. Their social life revolved around people he
worked with or people whose services he needed. In 1944, when the FHA
funding that had been financing Fred’s projects dried up, the family returned
to New York.
Once back in Jamaica Estates, Mary suffered a miscarriage, a serious
medical event from which it took her months to recover fully. Doctors
warned her against further pregnancies, but Mary found herself expecting
again a year later. The miscarriage created large age gaps between the older
and younger children, with Elizabeth floating in the middle, almost four years
younger or older than her two closest siblings. Maryanne and Freddy were so
much older than the youngest children that it was almost as if they belonged
to two different generations.
Donald, the couple’s fourth child and second son, was born in 1946, just
as Fred began plans for the new family house. He purchased a half-acre lot
directly behind the Wareham Road house situated on a hill overlooking
Midland Parkway, a wide tree-lined thoroughfare that runs through the entire
neighborhood. When the kids found out about the impending move, they
joked that they didn’t need to hire a moving truck; they could just roll their
belongings down the hill.
At more than four thousand square feet, the House was the most
impressive residence on the block but still smaller and less grand than many
of the mansions that dominated the hills in the northern part of the
neighborhood. Set at the top of a rise, the House cast shadows in the
afternoon over the wide flagstone steps that led from the sidewalk to the front
door, an entrance we used only on special occasions. The lawn jockeys, racist
reminders of the Jim Crow era, were first painted pink and then replaced with
flowers. The faux coat of arms on the pediment over the front door remained.
Although Queens would eventually be one of the most diverse places on
the planet, in the 1940s, when my grandfather bought the land and built the
imposing redbrick Georgian colonial with the twenty-foot columns, the
borough was 95 percent white. The upper-middle-class neighborhood of
Jamaica Estates was even whiter. When the first Italian American family
moved to the neighborhood in the 1950s, Fred was scandalized.
In 1947, Fred embarked on the most important large-scale project of his
career up until that point: Shore Haven, a proposed complex in Bensonhurst,
Brooklyn, comprising thirty-two six-story buildings and a shopping center
spread over more than thirty acres. The draw this time was the $9 million in
FHA funds that would be paid to Fred directly, just as Donald would later
capitalize on tax breaks lavished on him by both the city and the state. Fred
had previously described the type of people renting the 2,201 apartments as
“unwholesome,” the implication being that upstanding people lived only in
the single-family dwellings that had been his early specialty. But $9 million
can be very persuasive. Around that time, when it became clear that Fred’s
fortune would only continue to grow, he and his mother set up trust funds for
his children that would shield the money from taxation.
Though an iron-fisted autocrat at home and in his office, Fred had become
expert at gaining access to and kowtowing to more powerful and betterconnected men. I don’t know how he acquired the skill, but he would later
pass it on to Donald. Over time, he developed ties to leaders of the Brooklyn
Democratic Party, the New York State political machine, and the federal
government, many of whom were major players in the real estate industry. If
getting funding meant sucking up to the local politicos who held the FHA
purse strings, so be it. He joined an exclusive beach club on the south shore
of Long Island and later North Hills Country Club, both of which he
considered excellent places to entertain, impress, and rub elbows with the
men best positioned to funnel government funds his way, much as Donald
would do at Le Club in New York in the 1970s and at golf clubs everywhere.
As Donald was later alleged to do with Trump Tower and his casinos in
Atlantic City, Fred was said to have worked discreetly with the Mob in order
to keep the peace. When he got the green light for another development—
Beach Haven, a forty-acre, twenty-three-building complex in Coney Island
that would net him $16 million in FHA funding—it was clear that his strategy
of building on the taxpayer’s dime was a winner.
Though Fred’s business was built on the back of government financing, he
loathed paying taxes and would do anything to avoid doing so. At the height
of his empire’s expansions, he never spent a dime he didn’t have to, and he
never acquired debt, an imperative that did not extend to his sons. Bound by
the scarcity mentality that had been shaped by World War I and the
Depression, Fred owned his properties free and clear. The profits his
company generated from rents were enormous. In relation to his net worth,
Fred, whose children said he was “tighter than a duck’s ass,” lived a
relatively modest life. Despite the piano lessons and private summer camps—
of a piece with his notion of what was expected for a man of his station in life
—his two oldest children grew up feeling “white poor.” Maryanne and
Freddy walked the fifteen minutes to Public School 131, and when they
wanted to go into the city, as everyone in the outer boroughs of New York
refers to Manhattan, they took the subway from 169th Street. Of course, they
weren’t poor—and aside from some early struggles after his father’s death,
Fred never had been, either.
Fred’s wealth afforded him the opportunity to live anywhere, but he would
spend most of his adult life less than twenty minutes from where he had
grown up. With the exception of a few weekends in Cuba with Mary in the
early days of their marriage, he never left the country. After he completed the
project in Virginia, he rarely even left New York City.
His business empire, though large and lucrative, was equally provincial.
The number of buildings he came to own exceeded four dozen, but the
buildings themselves had relatively few floors and were uniformly utilitarian.
His holdings remained almost exclusively in Brooklyn and Queens. The glitz,
glamour, and diversity of Manhattan might as well have been on another
continent as far as he was concerned, and in those early years, it seemed just
as far out of reach.
By the time the family moved into the House, everybody in the
neighborhood knew who Fred Trump was, and Mary embraced her role as the
wife of a rich, influential businessman. She became heavily involved in
charity work, including at the Women’s Auxiliary at Jamaica Hospital and
the Jamaica Day Nursery, chairing luncheons and attending black-tie fundraisers.
No matter how great the couple’s success, there remained for both Fred
and Mary a tension between their aspirations and their instincts. In Mary’s
case it was likely the result of a childhood marked by scarcity if not outright
deprivation and in Fred’s a caution deriving from the massive loss of life,
including his father’s, during the Spanish flu and World War I, as well as the
economic uncertainty his family had experienced after his father’s death.
Despite the millions of dollars pouring in from Trump Management every
year, Fred still couldn’t resist picking up unused nails or reverse engineering
a cheaper pesticide. Despite the ease with which Mary took to her new status
and the perks that went along with it, including a live-in housekeeper, she
spent most of her time in the House, sewing, cooking, and doing laundry. It
was as if neither of them could quite figure out how to reconcile what they
could possibly have and what they would actually allow themselves.
Although frugal, Fred was neither modest nor humble. Early in his career, he
had lied about his age in order to appear more precocious. He had had a
propensity for showmanship, and he often trafficked in hyperbole—
everything was “great,” “fantastic,” and “perfect.” He inundated local
newspapers with press releases about his newly completed homes and gave
numerous interviews extolling the virtues of his properties. He plastered
south Brooklyn with ads and hired a barge covered with ads to float just off
the shoreline. But he wasn’t nearly as good at it as Donald would come to be.
He could handle interacting one on one and currying favor with his politically
connected betters, but speaking in front of large groups or navigating
television interviews was beyond him. He took a Dale Carnegie public
speaking course, but he was so bad at it that even his usually obedient
children teased him about it. Just as some people have a face for radio, Fred
had a level of social confidence made for back rooms and print media. That
fact would figure significantly in his later support of his second son at the
expense of his first.
When Fred heard about Norman Vincent Peale in the 1950s, Peale’s
shallow message of self-sufficiency appealed to him enormously. The pastor
of Marble Collegiate Church in midtown Manhattan, Peale was very fond of
successful businessmen. “Being a merchant isn’t getting money,” he wrote.
“Being a merchant is serving the people.” Peale was a charlatan, but he was a
charlatan who headed up a rich and powerful church, and he had a message to
sell. Fred wasn’t a reader, but it was impossible not to know about Peale’s
wildly popular bestseller, The Power of Positive Thinking. The title alone was
enough for Fred, and he decided to join Marble Collegiate although he and
his family rarely attended.
Fred already had a positive attitude and unbounded faith in himself.
Although he could be serious and formal, or dismissive to people such as his
children’s friends, who were of no interest to him, he smiled easily, even
when he was telling somebody he or she was nasty, and was usually in a
good mood. He had reason to be; he was in control of everything in his
world. With the exception of his father’s death, the course of his life had been
fairly smooth and full of supportive family and colleagues. Since his early
days building garages, his success had been on an almost constantly upward
trajectory. He worked hard, but unlike most people who work hard, he was
rewarded with government grants, the almost limitless help of highly
connected cronies, and immensely good fortune. Fred didn’t need to read The
Power of Positive Thinking in order to co-opt, for his own purposes, the most
superficial and self-serving aspects of Peale’s message.
Anticipating the prosperity gospel, Peale’s doctrine proclaimed that you
need only self-confidence in order to prosper in the way God wants you to.
“[O]bstacles are simply not permitted to destroy your happiness and wellbeing. You need be defeated only if you are willing to be,” Peale wrote. That
view neatly confirmed what Fred already thought: he was rich because he
deserved to be. “Believe in yourself! Have faith in your abilities!… A sense
of inferiority and inadequacy interferes with the attainment of your hopes, but
self-confidence leads to self-realization and successful achievement.” Selfdoubt wasn’t part of Fred’s makeup, and he never considered the possibility
of his own defeat. As Peale also wrote, “It is appalling to realize the number
of pathetic people who are hampered and made miserable by the malady
popularly called the inferiority complex.”
Peale’s proto–prosperity gospel actually complemented the scarcity
mentality Fred continued to cling to. For him, it was not “the more you have,
the more you can give.” It was “the more you have, the more you have.”
Financial worth was the same as self-worth, monetary value was human
value. The more Fred Trump had, the better he was. If he gave something to
someone else, that person would be worth more and he less. He would pass
that attitude on to Donald in spades.
The First Son
Freddy’s status as the oldest son in the family had gone from protecting him
from Fred’s worst impulses as a parent to being an immense and stressful
burden. As he got older, he became torn between the responsibility that his
father had placed on him and his natural inclination to live life his own way.
Fred wasn’t torn at all: his son should be spending time at the Trump
Management office on Avenue Z, not with his friends out on Peconic Bay,
where he learned to love boating, fishing, and waterskiing. By the time
Freddy was a teenager, he knew what his future held and he knew what his
father expected of him. He also knew that he wasn’t measuring up. His
friends noticed that their usually laid-back and fun-loving friend became
anxious and self-conscious around Fred, whom Freddy and his friends called
“the Old Man.” Solidly built and standing six feet one, Fred was an imposing
figure with hair slicked back from a receding hairline who rarely wore
anything but a well-tailored three-piece suit. He was stiff and formal around
kids, he never played ball or games of any kind with them, and it seemed as if
he had never been young.
If the boys were tossing a ball around in the basement, the sound of the
garage door opening was enough to cause Freddy to freeze. “Stop! My dad’s
home.” When Fred came into the room, the boys had the impulse to stand and
“So what’s this?” he’d ask as he shook each boy’s hand.
“Nothing, Dad,” Freddy would say. “Everybody’s getting ready to leave
Freddy remained quiet and on high alert as long as the Old Man was
In his early teens, Freddy started lying to his father about his life outside
the House to avoid the mockery or disapproval he knew the truth would bring
down on him. He lied about what he and friends got up to after school. He
lied about smoking—a habit Maryanne had introduced him to when he was
twelve and she was thirteen—telling his father that he was going around the
corner to help his best friend, Billy Drake, walk a nonexistent dog. Fred, for
instance, wasn’t going to find out that Freddy and his buddy Homer from St.
Paul’s School had stolen a hearse for a joyride. Before returning the vehicle
to the funeral home, Freddy pulled into a gas station to fill up the tank. As he
got out of the car and walked toward the pump, Homer, who was lying down
in the back to see what it was like, sat up. A man at the pump across from
them, thinking he’d just seen a corpse rising from the dead, screamed, and
Freddy and Homer laughed until they cried. Freddy lived for that kind of
prank, but he regaled his brothers and sisters with his exploits only if their
father wasn’t home.
For some of the Trump kids, lying was a way of life, and for Fred’s oldest
son, lying was defensive—not simply a way to circumvent his father’s
disapproval or to avoid punishment, as it was for the others, but a way to
survive. Maryanne, for instance, never went against her father, perhaps out of
fear of an ordinary punishment such as being grounded or sent to her room.
For Donald, lying was primarily a mode of self-aggrandizement meant to
convince other people he was better than he actually was. For Freddy, the
consequences of going against his father were different not only in degree but
in kind, so lying became his only defense against his father’s attempts to
suppress his natural sense of humor, sense of adventure, and sensitivity.
Peale’s ideas about inferiority complexes helped shape Fred’s harsh
judgments about Freddy, while also allowing him to evade taking
responsibility for any of his children. Weakness was perhaps the greatest sin
of all, and Fred worried that Freddy was more like his own brother, John, the
MIT professor: soft and, though not unambitious, interested in the wrong
things, such as engineering and physics, which Fred found esoteric and
unimportant. Such softness was unthinkable in his namesake, and by the time
the family had moved into the House when Freddy was ten, Fred had already
determined to toughen him up. Like most people who aren’t paying attention
to where they’re going, however, he overcorrected.
“That’s stupid,” Fred said whenever Freddy expressed a desire to get a pet
or played a practical joke. “What do you want to do that for?” Fred said with
such contempt in his voice that it made Freddy flinch, which only annoyed
Fred more. Fred hated it when his oldest son screwed up or failed to intuit
what was required of him, but he hated it even more when, after being taken
to task, Freddy apologized. “Sorry, Dad,” Fred would mock him. Fred
wanted his oldest son to be a “killer” in his parlance (for what reason it’s
impossible to say—collecting rent in Coney Island wasn’t exactly a high-risk
endeavor in the 1950s), and he was temperamentally the opposite of that.
Being a killer was really code for being invulnerable. Although Fred
didn’t seem to feel anything about his father’s death, the suddenness of it had
taken him by surprise and knocked him off balance. Years later, when
discussing it, he said, “Then he died. Just like that. It just didn’t seem real. I
wasn’t that upset. You know how kids are. But I got upset watching my
mother crying and being so sad. It was seeing her that made me feel bad, not
my own feelings about what had happened.”
The loss, in other words, had made him feel vulnerable, not because of his
own feelings but because of his mother’s feelings, which he likely felt were
being imposed on him, especially as he did not share them. That imposition
must have been very painful. In that moment, he wasn’t the center of the
universe, and that was unacceptable. Going forward, he refused to
acknowledge or feel loss. (I never heard him or anyone else in my family
speak about my great-grandfather.) As far as Fred was concerned, he was
able to move on because nothing particularly important had been lost.
Subscribing as Fred did to Norman Vincent Peale’s ideas about human
failings, he didn’t grasp that by ridiculing and questioning Freddy, he was
creating a situation in which low self-esteem was almost inevitable. Fred was
simultaneously telling his son that he had to be an unqualified success and
that he never could be. So Freddy existed in a system that was all
punishment, no reward. The other children, especially Donald, couldn’t have
helped but notice.
The situation was somewhat different for Donald. With the benefit of a
seven-and-a-half-year age difference, he had plenty of time to learn from
watching Fred humiliate his older brother and Freddy’s resulting shame. The
lesson he learned, at its simplest, was that it was wrong to be like Freddy:
Fred didn’t respect his oldest son, so neither would Donald. Fred thought
Freddy was weak, and therefore so did Donald. It would take a long time
before the two brothers, in very different ways, came to adapt themselves to
the truth of this.
It’s difficult to understand what goes on in any family—perhaps hardest of
all for the people in it. Regardless of how a parent treats a child, it’s almost
impossible for that child to believe that parent means them any harm. It was
easier for Freddy to think that his father had his son’s best interests at heart
and that he, Freddy, was the problem. In other words, protecting his love for
his father was more important than protecting himself from his father’s
abuse. Donald would have taken his father’s treatment of his brother at face
value: “Dad’s not trying to hurt Freddy. He’s only trying to teach us how to
be real men. And Freddy’s failing.”
Abuse can be quiet and insidious just as often as, or even more often than,
it is loud and violent. As far as I know, my grandfather wasn’t a physically
violent man or even a particularly angry one. He didn’t have to be; he
expected to get what he wanted and almost always did. It wasn’t his inability
to fix his oldest son that infuriated him, it was the fact that Freddy simply
wasn’t what he wanted him to be. Fred dismantled his oldest son by
devaluing and degrading every aspect of his personality and his natural
abilities until all that was left was self-recrimination and a desperate need to
please a man who had no use for him.
The only reason Donald escaped the same fate is that his personality
served his father’s purpose. That’s what sociopaths do: they co-opt others and
use them toward their own ends—ruthlessly and efficiently, with no tolerance
for dissent or resistance. Fred destroyed Donald, too, but not by snuffing him
out as he did Freddy; instead, he short-circuited Donald’s ability to develop
and experience the entire spectrum of human emotion. By limiting Donald’s
access to his own feelings and rendering many of them unacceptable, Fred
perverted his son’s perception of the world and damaged his ability to live in
it. His capacity to be his own person, rather than an extension of his father’s
ambitions, became severely limited. The implications of that limitation
became clearer when Donald entered school. Neither of his parents had
interacted with him in a way that helped him make sense of his world, which
contributed to his inability to get along with other people and remained a
constant buffer between him and his siblings. It also made reading social cues
extremely difficult, if not impossible, for him—a problem he has to this day.
Ideally, the rules at home reflect the rules of society, so when children go
out into the world, they generally know how to behave. When kids go to
school, they’re supposed to know that they shouldn’t take other children’s
toys and they’re not supposed to hit or tease other children. Donald didn’t
understand any of that because the rules in the House, at least as they applied
to the boys—be tough at all costs, lying is okay, admitting you’re wrong or
apologizing is weakness—clashed with the rules he encountered at school.
Fred’s fundamental beliefs about how the world worked—in life, there can be
only one winner and everybody else is a loser (an idea that essentially
precluded the ability to share) and kindness is weakness—were clear. Donald
knew, because he had seen it with Freddy, that failure to comply with his
father’s rules was punished by severe and often public humiliation, so he
continued to adhere to them even outside his father’s purview. Not
surprisingly, his understanding of “right” and “wrong” would clash with the
lessons taught in most elementary schools.
Donald’s growing arrogance, in part a defense against his feelings of
abandonment and an antidote to his lack of self-esteem, served as a protective
cover for his deepening insecurities. As a result, he was able to keep most
people at arm’s length. It was easier for him that way. Life in the House made
all the children in one way or another uncomfortable with emotions—either
expressing them or being confronted with them. It was probably worse for the
boys, for whom the acceptable range of human feeling was extremely narrow.
(I never saw any man in my family cry or express affection for one another in
any way other than the handshake that opened and closed any encounter.)
Getting close to other children or authority figures may have felt like a
dangerous betrayal of his father. Nonetheless, Donald’s displays of
confidence, his belief that society’s rules didn’t apply to him, and his
exaggerated display of self-worth drew some people to him. A large minority
of people still confuse his arrogance for strength, his false bravado for
accomplishment, and his superficial interest in them for charisma.
Donald had discovered early on how easy it was to get under Robert’s pale
skin and push him past his limits; it was a game he never tired of playing.
Nobody else would have bothered—Robert was so skinny and quiet that there
was no sport in tormenting him—but Donald enjoyed flexing his power, even
if only over his younger, smaller, and even thinner-skinned brother. Once, out
of frustration and helplessness, Robert kicked a hole in their bathroom door,
which got him into trouble despite the fact that Donald had driven him to it.
When his mother told Donald to stop, he didn’t; when Maryanne and Freddy
told him to stop, he didn’t.
One Christmas the boys received three Tonka trucks, which soon became
Robert’s favorite toys. As soon as Donald figured that out, he started hiding
them from his little brother and pretending he had no idea where they were.
The last time it happened, when Robert’s tantrum spiraled out of control,
Donald threatened to dismantle the trucks in front of him if he didn’t stop
crying. Desperate to save them, Robert ran to his mother. Mary’s solution
was to hide the trucks in the attic, effectively punishing Robert, who’d done
nothing wrong, and leaving Donald feeling invincible. He wasn’t yet being
rewarded for selfishness, obstinacy, or cruelty, but he wasn’t being punished
for those flaws, either.
Mary remained a bystander. She didn’t intervene in the moment and didn’t
comfort her son, acting as if it weren’t her place to do so. Even for the 1950s,
the family was split deeply along gender lines. Despite the fact that Fred’s
mother had been his partner—she had literally started his business—it’s clear
that Fred and his wife were never partners. The girls were her purview, the
boys his. When Mary made her annual trip home to the Isle of Lewis, only
Maryanne and Elizabeth accompanied her. Mary cooked the boys’ meals and
laundered their clothes but didn’t feel that it was her place to guide them. She
rarely interacted with the boys’ friends, and her relationships with her sons,
already marred by their early experiences with her, became increasingly
When Freddy, at fourteen, dumped a bowl of mashed potatoes on his thenseven-year-old brother’s head, it wounded Donald’s pride so deeply that he’d
still be bothered by it when Maryanne brought it up in her toast at the White
House birthday dinner in 2017. The incident wasn’t a big deal—or it
shouldn’t have been. Donald had been tormenting Robert, again, and nobody
could get him to stop. Even at seven, he felt no need to listen to his mother,
who, having failed to heal the rift between them after her illness, he treated
with contempt. Finally, Robert’s crying and Donald’s needling became too
much, and in a moment of improvised expedience that would become family
legend, Freddy picked up the first thing at hand that wouldn’t cause any real
damage: the bowl of mashed potatoes.
Everybody laughed, and they couldn’t stop laughing. And they were
laughing at Donald. It was the first time Donald had been humiliated by
someone he even then believed to be beneath him. He hadn’t understood that
humiliation was a weapon that could be wielded by only one person in a
fight. That Freddy, of all people, could drag him into a world where
humiliation could happen to him made it so much worse. From then on, he
would never allow himself to feel that feeling again. From then on, he would
wield the weapon, never be at the sharp end of it.
The Great I-Am
By the time Maryanne left for Mount Holyoke and, a couple of years later,
Freddy for Lehigh University, Donald had already had plenty of experience
watching his older brother struggle with, and largely fail to meet, their
father’s expectations. They were vague, of course. Fred had the
authoritarian’s habit of assuming that his underlings knew what to do without
being told. Generally, the only way to know if you were doing something
right was if you didn’t get dressed down for it.
But it was one thing for Donald to stay out of his father’s crosshairs and
another to get into his good graces. Toward that end, Donald all but
eradicated any qualities he might have shared with his older brother. Except
for the occasional fishing trip with Freddy and his friends, Donald would
become a creature of country clubs and offices, golf being the only thing on
which he and his father differed. He would also double down on the
behaviors he had thus far gotten away with: bullying, pointing the finger,
refusing to take responsibility, and disregarding authority. He says that he
“pushed back” against his father and Fred “respected” that. The truth is, he
was able to push back against his father because Fred let him. When he was
very young, Fred’s attention was not trained on him; his focus was elsewhere
—on his business and his oldest son, that’s it. Eventually, when Donald went
away to military school at thirteen, Fred began to admire Donald’s disregard
of authority. Although a strict parent in general, Fred accepted Donald’s
arrogance and bullying—after he actually started to notice them—because he
identified with the impulses.
Encouraged by his father, Donald eventually started to believe his own
hype. By the time he was twelve, the right side of his mouth was curled up in
an almost perpetual sneer of self-conscious superiority, and Freddy had
dubbed him “the Great I-Am,” echoing a passage from Exodus he’d learned
in Sunday school in which God first reveals himself to Moses.
Because of the disastrous circumstances in which he was raised, Donald
knew intuitively, based on plenty of experience, that he would never be
comforted or soothed, especially when he most needed to be. There was no
point, then, in acting needy. And whether he knew it on any level or not,
neither of his parents was ever going to see him for who he truly was or
might have been—Mary was too depleted and Fred was interested only in
whichever of his sons could be of most use—so he became whatever was
most expedient. The rigid personality he developed as a result was a suit of
armor that often protected him against pain and loss. But it also kept him
from figuring out how to trust people enough to get close to them.
Freddy was terrified to ask Fred for anything. Donald had seen the results
of that reticence. Whenever Freddy deviated even slightly from Fred’s often
unspoken expectations, he ended up humiliated or shamed. Donald would try
something different: he chose instead to ingratiate himself with their father by
smashing through every barrier his older brother never dared test. He knew
exactly how to play it: when Freddy flinched, Donald shrugged. He took
what he wanted without asking for permission not because he was brave but
because he was afraid not to. Whether Donald understood the underlying
message or not, Fred did: in family, as in life, there could be only one winner;
everybody else had to lose. Freddy kept trying and failing to do the right
thing; Donald began to realize that there was nothing he could do wrong, so
he stopped trying to do anything “right.” He became bolder and more
aggressive because he was rarely challenged or held to account by the only
person in the world who mattered—his father. Fred liked his killer attitude,
even if it manifested as bad behavior.
Every one of Donald’s transgressions became an audition for his father’s
favor, as if he were saying “See, Dad, I’m the tough one. I’m the killer.” He
kept piling on because there wasn’t any resistance—until there was. But it
didn’t come from his father.
Though Donald’s behavior didn’t bother Fred—given his long hours at the
office, he wasn’t often around to witness much of what happened at home—it
drove his mother to distraction. Mary couldn’t control him at all, and Donald
disobeyed her at every turn. Any attempt at discipline by her was rebuffed.
He talked back. He couldn’t ever admit he was wrong; he contradicted her
even when she was right; and he refused to back down. He tormented his
little brother and stole his toys. He refused to do his chores or anything else
he was told to do. Perhaps worst of all to a fastidious woman like her, he was
a slob who refused to pick up after himself no matter how much she
threatened him. “Wait until your father comes home” had been an effective
threat with Freddy, but to Donald it was a joke that his father seemed to be in
Finally, by 1959, Donald’s misbehavior—fighting, bullying, arguing with
teachers—had gone too far. Kew-Forest had reached its limits. Fred’s being
on the school’s board of trustees cut two ways: on the one hand, Donald’s
behavior had been overlooked longer than it otherwise might have; on the
other, it caused Fred some inconvenience. Name-calling and teasing kids too
young to fight back had escalated into physical altercations. Fred didn’t mind
Donald’s acting out, but it had become intrusive and time consuming for him.
When one of his fellow board members at Kew-Forest recommended sending
Donald to New York Military Academy as a way to rein him in, Fred went
along with it. Throwing him in with military instructors and upperclassmen
who wouldn’t put up with his shit might toughen up Fred’s burgeoning
protégé even more. Fred had more important things to do than deal with
I don’t know if Mary had any say in the final decision, but she didn’t fight
for her son to stay home, either, a failure Donald couldn’t help but notice. It
must have felt like a replay of all the times she’d abandoned him in the past.
Over Donald’s objections, he was enrolled at NYMA, a private boys’
boarding school sixty miles north of New York City. The other kids in the
family referred to NYMA as a “reform school”—it wasn’t prestigious like St.
Paul’s, which Freddy had attended. Nobody sent their sons to NYMA for a
better education, and Donald understood it rightly as a punishment.
When Freddy found out, he told his friends with some bewilderment,
“Yeah, they can’t control him.” It didn’t really make any sense. His father
always seemed to be in control of everybody. What Freddy didn’t understand
was that their father wasn’t interested in Donald the same way he was
interested in him. If Fred had tried to discipline Donald, he would have been
disciplined, but before Donald was sent away, Fred just wasn’t interested
enough to bother with Donald or the other three children.
Parents always have different effects on their children, no matter the
dynamics of the family, but for the Trump children, the effects of Fred and
Mary’s particular pathologies on their offspring were extreme. As the five, at
different times and in different ways, got ready to go out in the world, their
disadvantages were already apparent:
Maryanne, the firstborn, was saddled with being a smart, ambitious girl in
a misogynistic family. She was the oldest, but because she was a girl, Freddy,
the oldest boy, got all of her father’s attention. She was left to align herself
with her mother, who had no power in the house. As a result, after having her
heart broken when she was rejected by the Dartmouth home economics
program, she settled for Mount Holyoke College, a “virtual nunnery,” as she
put it. Ultimately, she did what she believed she was supposed to do because
she thought her father cared.
Freddy’s problem was his failure to be a different person entirely.
Elizabeth’s problem was her family’s indifference. She was not just the
middle child (and a girl) but separated by her brothers on either side by an
age gap of three or four years. Shy and timid as an adolescent, she didn’t
speak much, having learned the lesson that neither of her parents was really
listening. Still she remained devoted to them until well into middle age,
returning to the House every weekend, still hoping for “Poppy’s” attention.
Donald’s problem was that the combative, rigid persona he developed in
order to shield him from the terror of his early abandonment, along with his
having been made to witness his father’s abuse of Freddy, cut him off from
real human connection.
Robert’s problem was that he was the youngest, an afterthought.
Nothing Maryanne, Elizabeth, or Robert did would gain Fred’s approval;
they were of no interest to him. Like planets orbiting a particularly large sun,
the five of them were kept apart by the force of his will, even as they moved
along the paths he set for them.
Freddy’s plans for the future still entailed becoming his father’s right-hand
man at Trump Management, but the first time Freddy took off from the
airstrip of the Slatington Flying Club behind the controls of a Cessna 170 in
1961, his perspective shifted.
As long as he fulfilled the requirements of his business major and kept his
grades up, he could fly, pledge a fraternity, and join the US Air Force
Reserve Officer Training Corps (ROTC). On a lark, Freddy chose Sigma
Alpha Mu, a historically Jewish fraternity. Whether it was a conscious rebuke
of his father, who frequently used phrases such as “Jew me down,” Freddy’s
fraternity brothers eventually became some of his best friends. Joining ROTC
served another purpose entirely. Freddy craved discipline that made sense.
He thrived in ROTC’s transparent system of achievement and reward. If you
did what you were told, your obedience was recognized. If you met or
exceeded expectations, you were rewarded. If you made a mistake or failed to
follow an order, you received discipline that was commensurate with the
infraction. He loved the hierarchy; he loved the uniforms; he loved the
medals that were clear symbols of accomplishment. When you are wearing a
uniform, other people can easily identify who you are and what you’ve
accomplished, and you are acknowledged accordingly. It was the opposite of
life with Fred Trump, by whom good work was expected but never
acknowledged; only mistakes were called out and punished.
Getting his pilot’s license made sense in the same way ROTC did: you log
a certain number of hours, you get certified on particular instruments, you get
a license. His flying lessons eventually became his number one priority. Just
as with boating, he took flying very seriously and began skipping card games
with his fraternity brothers to study or log another hour at the flight school.
But it wasn’t just the pleasure of finding something he excelled at, it was the
joy of total freedom, which he’d never before experienced.
In the summer, Freddy worked for Fred, as usual, but on weekends he took
his friends out east on a boat he’d bought in high school to fish and water-ski.
On occasion Mary asked Freddy to take Donald with him. “Sorry, guys,”
he’d say to his friends, “but I have to bring my pain-in-the-ass little brother
along.” Donald was probably as enthusiastic as Freddy was reluctant.
Whatever their father thought about his older brother, Freddy’s friends
clearly loved him and always had a good time—a reality that contradicted
what Donald had been brought up to believe.
In August 1958, before the beginning of his junior year, Freddy and Billy
Drake flew down to Nassau in the Bahamas for a short vacation before school
started up again. The two of them chartered a boat and spent their days
fishing and exploring the island. One evening back at their hotel, while they
sat at the pool bar, Freddy met a pretty, petite blonde named Linda Clapp.
Two years later, he would marry her.
That September, Donald arrived at NYMA. He went from a world in which
he could do as he pleased to one in which he faced punishment for not
making his bed and got slammed against the wall by upperclassmen for no
particular reason. Perhaps because of having lost his own father at twelve,
Fred recognized his son’s isolation and visited almost every weekend
between the time Donald started as an eighth grader and the time he
graduated in 1964. That somewhat mitigated Donald’s sense of abandonment
and grievance and gave him his first glimmer that he had a connection with
his father that his older brother did not. Donald’s mother went occasionally
but for the most part was relieved to have him gone.
Though he hadn’t wanted to attend NYMA, certain things made sense for
Donald there, just as ROTC had for Freddy. There was structure, and there
were consequences to his actions. There was a logical system of punishment
and reward. At the same time, though, life at NYMA reinforced one of Fred’s
lessons: the person with the power (no matter how arbitrarily that power was
conferred or attained) got to decide what was right and wrong. Anything that
helped you maintain power was by definition right, even if it wasn’t always
NYMA also reinforced Donald’s aversion to vulnerability, which is
essential for tapping into love and creativity because it can also expose us to
shame, something he could not tolerate. By necessity he had to improve his
impulse control, not only to avoid punishment but to help him get away with
transgressions that required a little more finesse.
Freddy’s senior year was one of the best and most productive years of his
whole life. The BA in business was the least of it. He’d been made president
of Sigma Alpha Mu, and he completed ROTC and would enter the Air Force
National Guard as a second lieutenant after graduation. Most important, he
became a fully licensed commercial pilot, although he had no intention of
using the license; he was going to work with his dad in Brooklyn with every
intention of someday taking over.
By the time Freddy joined Trump Management in the summer of 1960,
Fred’s company comprised more than forty buildings and complexes, with
thousands of units, spread across Brooklyn and Queens. Fred had been taking
his oldest son to construction sites for years; his largest developments,
including Shore Haven and Beach Haven in Brooklyn, as well as smaller
projects closer to home in Jamaica Estates, had all been built while Freddy
was growing up in the 1940s and 1950s. During those visits, the importance
of cost cutting (if it’s cheaper, do it yourself; if not, outsource it) and cost
saving (red bricks were a penny cheaper than white bricks) were drilled into
him. Fred also dragged him to meetings of the Brooklyn Democratic Party
and political fund-raisers, making sure he got to know the most important and
influential politicos in the city.
Now a full-time employee, Freddy started accompanying his father on
rounds to the buildings, checking in with the superintendents, and overseeing
repairs. Being in the field was better than being in the former dentist office
where my grandfather’s business was located on Avenue Z in South
Brooklyn, with its cramped quarters and dim lighting. Though Fred’s
business was raking in millions of dollars a year, he still dealt directly with
tenants when he believed the circumstances warranted doing so. If, for
example, a tenant complained a little too loudly or frequently, Fred paid him
or her a visit, knowing his reputation preceded him. On occasion he took
Freddy along to demonstrate how to handle such situations.
When one tenant repeatedly called the office to report a lack of heat, Fred
paid him a visit. After knocking on the door, he removed his suit jacket,
something he usually did only right before getting into bed. Once inside the
apartment, which was indeed cold, he rolled up his shirtsleeves (again,
something he rarely did) and told his tenant that he didn’t know what they
were complaining about. “It’s like the tropics in here,” he told them.
Freddy began checking in for his National Guard duty. One weekend a month
he had to report to the Armory in Manhattan. Fred didn’t comment on those
weekend absences, but he was annoyed by the two weeks a year Freddy had
to take off in order to report to Fort Drum in upstate New York. For Fred,
who had no use for military service, it was a waste of his employee’s time.
One evening after a long day in Brooklyn, Freddy got a phone call from
Linda. They hadn’t spoken for more than a year. She told him that she’d
become a stewardess for National Airlines and was flying out of Idlewild
Airport (now John F. Kennedy International Airport). She remembered that
Freddy had mentioned that his dad owned a couple of apartment buildings in
Queens, and she wondered if he could help her find a place not too far from
the airport. Fred had several buildings in Jamaica only a fifteen-minute bus
ride from Idlewild. They found a studio at the Saxony on Highland Avenue
right next to a nine-acre wooded park with a large pond in the middle of it.
She moved in right away. Soon she and Freddy were dating.
A year later, in August 1961, Freddy took Linda for dinner at their favorite
restaurant in Manhattan. During cocktails, he sneaked an engagement ring
into Linda’s glass and proposed. After dinner, they drove to Jamaica Estates
to tell his parents. Fred and Mary took the news… calmly.
Based on Linda’s modest upbringing (her father was a truck driver, and
later her parents ran a clam shack near the beach in Florida) and her
perceived lack of sophistication and education, they assumed that she must be
a gold digger. But it was a fundamental and deliberate misunderstanding that
failed to acknowledge reality; Linda probably had no idea just how wealthy
her future father-in-law was. And if Linda was a gold digger, she was an
exceptionally bad one.
Given her own very modest upbringing in Scotland, my grandmother
could have been my mother’s ally, but when Mary MacLeod had reached the
top of the ladder, she had pulled it up after her. As for Fred, he simply did not
like her. In any case, she was Freddy’s choice, so she was suspect.
Meanwhile, the rules for stewardesses at the time were very strict: you
could be suspended for letting your hair get too long or putting on weight,
and you could not continue to work if you married. After her last flight in
January 1962, a couple of weeks before the wedding, Linda would have no
Because Linda’s mother was confined to a wheelchair due to her advanced
rheumatoid arthritis, they decided to have the wedding in Florida. A simple
cocktail reception would take place at Pier Sixty-Six Hotel & Marina on the
Inland Waterway in Fort Lauderdale after the church ceremony. Fred and
Mary weren’t pleased, but since they didn’t offer to help financially, they had
little say. Neither Elizabeth, who was at college in Virginia, nor Donald, who
was still at NYMA, attended. The Trumps settled for hosting a reception in
New York after the couple returned from their honeymoon.
Trump Village in Coney Island—the largest Trump Management project
to date—was slated to break ground in 1963, and Freddy would be assisting
in the preparations. Fred expected him to take an apartment in one of his
Brooklyn buildings so he could be close at hand to manage any problems that
cropped up, but Freddy and Linda moved instead into a one-bedroom in the
city on East 56th Street between First Avenue and Sutton Place. They bought
a poodle, the first pet Freddy had ever had, and a few months later Linda was
That November, Frederick Crist Trump, III, was born. A month later,
Freddy bought his first plane—a Piper Comanche 180. He and Linda flew it
down to Fort Lauderdale right after Christmas to show it—and their new son
—off to Linda’s parents. Her father, Mike, who often parked near the runway
of the Fort Lauderdale Airport to watch planes take off and land, couldn’t
have been more impressed.
During one of the weekly dinners Freddy and Linda had with Maryanne
and her husband, David Desmond, whom she had married in 1960, Freddy
told them about the plane, adding “Don’t tell Dad. He wouldn’t get it.”
In September 1963, they moved into the Highlander, one of Fred’s Jamaica
buildings, down the block from where Linda had lived when she had first
moved to town three years earlier—a stepping-stone to a house on Long
Island. The Highlander was typical of Fred’s buildings, having a grand
entrance to distract from the substandard rental units. The lobby had a large
sunken space with a formal sitting area blocked off by velvet ropes and
stanchions on one side and on the other a huge display of oversized tropical
plants. Between them, large floor-to-ceiling plate-glass windows looked out
onto a wide expanse of flagstones and brick steps on either side curving up to
the sidewalk. On either side of the steps was more extravagant foliage,
towering oak trees and exotic plants with enormous dark green leaves—
another Fred Trump touch. The building stood at the top of a hill on Highland
Avenue, essentially the dividing line that ran through Jamaica: the north side
had a more suburban feel and was predominantly white; the south side was
urban and predominantly black. The front and back doors of the building
gave onto two different worlds. Freddy and Linda took a two-bedroom
apartment on the southeast corner of the ninth and top floor overlooking the
park and Jamaica High School in the distance on one side and south Jamaica
on the other.
Freddy worried at first that being the landlord’s on-site son, as well as an
employee of the company that owned the building, would give people an
open invitation to bother him at all hours. But the building was less than
fifteen years old, and the superintendent made sure the other tenants left him
Not long after the move, Freddy told Linda he wanted to become a
professional pilot. After three years at Trump Management he found the work
a grind. Almost from the beginning, his father had frozen him out of the dayto-day operations of the Trump Village development; instead he’d been
relegated to handling tenants’ complaints and overseeing maintenance
Being a pilot would give him a chance to do something he loved while
making a good living. Before the dawn of the jet age in the early 1960s, there
had been a seven-year hiring freeze on commercial pilots. With the
introduction of the Boeing 707 and Douglas DC-8 into airline fleets,
however, air travel exploded. Pan Am launched overseas flights in 1958 and
loaned its jets to National for domestic routes. The following year, TWA,
American, Delta, and United were all using jets, which, larger, more
powerful, and safer to fly than their turboprop predecessors, could carry more
passengers greater distances.
With the expansion in air service came a demand for qualified pilots who
already had the skills necessary to train quickly on the new jets. TWA was
the last airline to embrace the 707, and it was under a lot of pressure to catch
up. At Idlewild and at MacArthur Airport, where Freddy kept his Comanche,
the walls were plastered with notices about the need for fresh blood in
Linda said no. Having been a stewardess, she knew what pilots got up to
during their layovers. For the time being, Freddy agreed to shelve the idea
and make the best of life at Trump Management.
But the situation with his father deteriorated. When Freddy approached
him with ideas for innovations, Fred shot him down. When he asked for more
responsibility, Fred brushed him off.
Trying to prove he could make executive decisions, Freddy placed a
window order for one of the older buildings. When Fred found out, he was
furious. “You should have slapped a goddamn coat of paint on them instead
of wasting my money!” he shouted while the employees looked on. “Donald
is worth ten of you. He never would have done anything so stupid.” Donald
was still in high school at the time.
It was one thing for his father to humiliate him in front of his siblings, but
the people in that office weren’t Freddy’s peers. Someday, presumably, he
would be their boss. For his nascent authority to be undermined so publicly
felt like a body blow.
When he got home that night, he told Linda how trapped he felt and
confessed that he’d never been happy working for his father. It wasn’t at all
what he had expected, and for the first time it occurred to him that Trump
Management might be a dead end for him. “I’m applying to TWA, Linda. I
have to.” He wasn’t asking anymore. Fred might cut him off, but Freddy was
willing to risk losing his inheritance. Pilots, especially pilots working for
TWA, had good benefits and job security. He would be able to support his
young family on his own, and he would be his own man.
When Freddy told his father that he was leaving Trump Management to
become a commercial pilot, Fred was stunned. It was a betrayal, and he had
no intention of letting his oldest son forget it.
Expecting to Fly
Only the best pilots were assigned to fly the coveted Boston–Los Angeles
route. And in May 1964, Freddy was on his first official flight as a
professional pilot from Boston’s Logan Airport to LAX—less than six
months after he’d applied for a spot in that year’s first training class.
What Freddy achieved in the cockpit made him unique in the Trump
family. None of Fred’s other children would accomplish so much entirely on
their own. Maryanne came closest, putting herself through law school in the
early 1970s and, over the course of nine years, compiling a solid record as a
prosecutor. Her eventual appointment to the federal appeals court, however,
was possible because Donald used his connections to do her a favor. For
decades Elizabeth worked in the same job at Chase Manhattan Bank that Fred
had arranged for her. Donald was enabled from the beginning, every one of
his projects funded and supported by Fred and then by myriad other enablers
right up to the present. Other than a brief stint at a New York securities firm
after graduating from college, Robert worked for Donald and then his father.
Even Fred was not entirely self-made, since his mother had started the
business that would become Trump Management.
Freddy had put himself through flight school in college, defied his father
(which he would spend the rest of his life paying for), and had no support
from, as well as the active contempt of, his family. Obstacles aside, he had
been determined to apply to TWA as many times as necessary. He made it on
the first try.
In the 1950s and ’60s, the vast majority of incoming pilots had received
their training in the military; a typical training class had twenty students: four
from the air force, four from the navy, four from the army, four from the
marines, and four civilians. At twenty-five years old, Freddy was one of
twelve men accepted into the airline’s first 1964 pilots’ class. Ten of them
had received their training in the military. When you consider that there were
no flight simulators and all the training was done in the air, the achievement
was all the more staggering. Freddy was finally reaping the rewards of all of
those hours he’d logged at the airfield while his fraternity brothers were
In those days, air travel was at the height of its glamour, and at the
forefront of that trend was Howard Hughes’s Trans World Airlines, the
favorite of the Hollywood glitterati. TWA provided limousines to the gossip
columnists Hedda Hopper and Louella Parsons to ferry them to and from the
airport; the resulting publicity made everyone want to fly TWA. One of the
largest carriers in the world, TWA flew both domestically and internationally.
The captain was God and treated accordingly, and thanks to Hughes’s
penchant for beautiful women, the stewardesses all looked like movie stars.
The reactions pilots got from passengers as they walked through the
terminal, the admiring stares, the requests for autographs, were all new to
Freddy and a welcome change from Trump Management, where he had
struggled and failed to gain respect. The gleaming airports stood in stark
contrast to the dark, unwelcoming office and dirty construction sites he’d left
behind in New York. In place of bulldozers and backhoes, rows of 707s and
DC-8s glimmered on the tarmac. Instead of having all of his decisions
second-guessed and criticized by his father, on the flight deck Freddy had the
Freddy moved his young family to Marblehead, a small harbor town forty
minutes northeast of Boston’s Logan Airport on the Massachusetts coast.
They rented a ramshackle cottage set among an eclectic mix of houses that
circled the village green not far from the sprawling harbor, where Freddy
kept his “yacht,” a beat-up Boston Whaler.
May in Marblehead was idyllic. Freddy loved the flying. There was a lot
of socializing, with barbecues and deep-sea fishing excursions. Almost every
weekend, friends came up from New York to visit them. After a month,
though, Freddy started to struggle with the schedule. He was often at loose
ends when he wasn’t in the cockpit. Linda noticed that he started drinking
more than everyone else—something that had never been a problem before.
Her husband didn’t confide in Linda anymore, wanting perhaps to shield
her, so she wasn’t privy to the details of the conversation he’d had with Fred
back in December. Linda didn’t know about the constant barrage of abuse
Freddy was receiving from his father in New York through letters and phone
calls. But his friends knew. Freddy told them, with a note of disbelief in his
voice, that the old man was embarrassed to have a “bus driver in the sky” for
a son. It didn’t take much for his father to convince him that choosing to
leave Trump Management meant choosing failure. The most crucial thing
that Linda didn’t fully grasp—and to be fair, Freddy probably didn’t grasp it,
either—was how much Fred Trump’s opinion mattered to his son.
One night, after returning from his most recent rotation, Freddy seemed
particularly on edge. Over dinner, he said, “We need to get a divorce.”
Linda was shocked. Her husband was under more stress than usual, but
she thought it might be the result of his being responsible for the lives of
more than two hundred people every time he flew.
“Freddy, what are you talking about?”
“It’s not working out, Linda. I don’t see how we can keep going.”
“You’re not even here half the time,” she said, mystified by his outburst.
“We have a baby. How can you say that?”
Freddy stood up and poured himself a drink. “Forget it,” he said, and left
They never renewed that conversation, and after a few days, they
continued on as though nothing unusual had happened.
In June Donald, then eighteen and freshly graduated from the military
academy, and Robert, sixteen, still a student at Freddy’s alma mater, St.
Paul’s, drove up to Marblehead for a visit, arriving in Donald’s new sports
car, a high school graduation present from his parents—a step up from the
luggage Freddy had received when he had graduated from college.
Freddy was anxious about seeing them. None of his siblings had ever been
up in a plane with him or expressed any interest in his new career. He hoped
that maybe, if he could let his brothers into his world, he’d find an ally;
having even one person in his family who believed in him might bolster his
waning strength to withstand his father’s disapproval.
At the time of the visit, Donald was at a crossroads. When Freddy had
announced he was stepping away from Trump Management in December
1963, Donald had been caught flat-footed. His brother’s decision had come at
the end of the first semester of Donald’s senior year, and since his name
wasn’t Fred, he had no idea what his future role in the company might be,
although he did plan to work there in some capacity. Because of that
uncertainty, he hadn’t adequately prepared for his future beyond high school.
When he graduated from New York Military Academy that spring, he had not
yet been accepted into college. He asked Maryanne to help him find a spot at
a local school when he got back home.
Freddy and Linda had a barbecue for lunch, during which Donald told
them he was going to Chicago with their dad to “help” him with a
development he was considering. Freddy’s relief was palpable. Maybe Fred
was beginning to accept the new reality and had decided to take Donald on as
his heir apparent.
Later in the afternoon, Freddy took the boys out on his “yacht” to do some
Despite Freddy’s best attempts to teach his brother the basics of the sport,
Donald had never gotten the hang of it. Donald had still been at NYMA the
last time they’d been on a boat together, along with Billy and a couple of
Freddy’s fraternity brothers. When one of them had tried to show Donald
how to hold the pole properly, Donald had pulled away and said, “I know
what I’m doing.”
“Yeah, buddy. And you’re doing it really badly.” The rest of the guys had
laughed. Donald had thrown his pole onto the deck and stalked off toward the
bow. He had been so angry, he wasn’t paying attention to where he was
walking, and Freddy had worried that he might walk right off the boat.
Donald’s fishing skills hadn’t improved in the interim.
When the three brothers returned from the harbor, Linda was preparing
dinner. As soon as they came into the house, she could sense the tension.
Something had shifted. Freddy’s good mood had been replaced by a quiet,
barely contained anger. Freddy didn’t often lose his temper, not then, and she
took it as a bad sign. He poured himself a drink. Another bad sign.
Even before they sat down for dinner, Donald started in on his older
brother. “You know, Dad’s really sick of you wasting your life,” he declared,
as though he’d suddenly remembered why he was there.
“I don’t need you to tell me what Dad thinks,” said Freddy, who already
knew his father’s opinions all too well.
“He says he’s embarrassed by you.”
“I don’t get why you care,” Freddy replied. “You want to work with Dad,
go ahead. I’m not interested.”
“Freddy,” he said, “Dad’s right about you: you’re nothing but a glorified
bus driver.” Donald may not have understood the origin of their father’s
contempt for Freddy and his decision to become a professional pilot, but he
had the bully’s unerring instinct for finding the most effective way to
undermine an adversary.
Freddy understood that his brothers had been sent to deliver their father’s
message in person—or at least Donald had. But hearing Fred’s belittling
words come out of his little brother’s mouth broke his spirit.
Linda overheard the exchange and came into the living room from the
kitchen in time to see Freddy’s face drained of all color. She slammed the
plate she was holding onto the table and screamed at her brother-in-law,
“You should just keep your mouth shut, Donald! Do you know how hard he’s
had to work? You have no idea what you’re talking about!”
Freddy didn’t speak to either of his brothers for the remainder of that
night, and they left for New York the next morning, a day earlier than
Freddy’s drinking worsened.
In July, TWA offered him a promotion. The airline wanted to send him to
their facility in Kansas City to train him on the new 727s it was introducing
to the fleet. He declined, even though Linda reminded him that he never
would have disregarded an order from one of his superiors in the National
Guard. He told management that having signed a yearlong lease for a
furnished house in Marblehead only two months earlier, he couldn’t justify
uprooting his young family again. In truth, Freddy had begun to suspect that
his dream was coming to an end. He was losing hope that his father would
accept him as a professional pilot, and without that acceptance he probably
couldn’t continue. He had spent his entire life up until he had left Trump
Management trying his best to become the person his father wanted him to
be. When those attempts had repeatedly ended in failure, he had hoped that in
the course of fulfilling his own dream that his father would come to accept
him for who he really was. He had spent his childhood navigating the
minefield of his father’s conditional acceptance, and he knew all too well that
there was only one way to receive it—by being someone he wasn’t—and he
would never be able to pull that off. His father’s approval still mattered more
than anything else. Fred was, and always had been, the ultimate arbiter of his
children’s worth (which is why, even late into her seventies, my aunt
Maryanne continued to yearn for her long-dead father’s praise).
When TWA later offered Freddy the opportunity to fly out of Idlewild, he
jumped at the chance, thinking it might be a way to salvage the situation. The
move made no sense from a practical perspective, since he’d have to
commute from Marblehead to New York every three or four days. Worse, it
put him into closer proximity to Fred. But maybe for Freddy that was the
point. Even if he couldn’t get Fred’s approval, it might be easier to convince
his father that flying was what he should be doing if he could see it up close.
In between flights, Freddy took fellow pilots back to the House to meet his
family, hoping Fred might be impressed. It was a desperate move, but Freddy
In the end, it made no difference. Fred could never get past the betrayal.
Although Freddy had joined ROTC and a fraternity and the flying club,
things his father would have disdained but probably didn’t know about, those
activities hadn’t altered his plan to work for his father to ensure that the
empire would survive in perpetuity. From Fred’s perspective, Freddy’s
leaving Trump Management must have felt like an act of blatant disrespect.
Ironically, it was the kind of boldness Fred had wanted to instill in his son,
but it had been squandered on the wrong ambition. Instead, Fred felt that
Freddy’s unprecedented move undermined his authority and diminished
Fred’s sense that he was in control of everything, including the course of his
A few weeks after the boys’ visit, a summer storm thundered over
Marblehead Harbor. Linda was standing in the living room ironing Freddy’s
white uniform shirts when the phone rang. As soon as she heard her
husband’s voice, she knew something was wrong. He had quit his job at
TWA, he told her. The three of them needed to move back to New York as
soon as possible. Linda was stunned. That Freddy would give up everything
he’d worked for after only four months made no sense at all.
In fact, TWA had given him an ultimatum: if he resigned, he could keep
his license; otherwise, it would be forced to fire him as a result of his serious
alcohol problem. If Freddy got fired, he’d likely never be able to fly again.
He chose the first option, and with that their life in Marblehead was over. Just
after Labor Day, the three of them moved back to the corner apartment on the
ninth floor of the Highlander in Jamaica.
But Freddy hadn’t entirely given up on a flying career. Maybe, he thought,
if he started with smaller airlines with smaller planes and shorter, less
stressful routes, he could work his way back up. While Linda and Fritz settled
in, Freddy went to Utica, a small city in upstate New York, to work for
Piedmont Airlines, which flew commuter routes in the northeast. That job
lasted less than a month.
He moved to Oklahoma and flew for another local airline. He was there
when Fritz celebrated his second birthday. By December, he was back in
Queens. His drinking was out of control, and he knew that he could no longer
hack it as a pilot. The only self-made man in the family, Freddy was being
slowly, inexorably dismantled.
Less than a year after it had begun, Freddy’s flying career was over. With no
other options, he found himself standing in front of his father, who sat in his
usual spot on the love seat in the library while his oldest son asked for a job
that he didn’t want and Fred didn’t think he could do.
Fred reluctantly agreed, making it clear that he was doing his son a favor.
And then one more glimmer of hope emerged. In February 1965, Fred
acquired the site of Steeplechase Park, one of three iconic amusement parks
in Coney Island that had been in operation since around the turn of the
twentieth century. Steeplechase had outlived its two rivals by decades:
Dreamland had been destroyed by fire in 1911, and Luna Park, also struck by
fires, had closed in 1944. Fred owned a building complex and shopping area
named after Luna Park not far from the original site. Steeplechase continued
operations until 1964. The Tilyou family had owned the park from the
beginning, but several factors—including high crime and increasing
competition for entertainment dollars—had persuaded them to sell the
property. Fred, who had known that Steeplechase might become available for
development, set his sights on its acquisition. The plan would be another
residential development in the style of Trump Village, but a significant hurdle
would need to be overcome: changing current zoning laws from public use to
private construction. While he waited for the opportunity to present itself,
Fred began to lobby his old cronies for their support and started drafting his
He dangled the possibility of Freddy’s involvement in the ambitious
project, and his oldest son, frantic to improve his position and put TWA
behind him, jumped at the opportunity. He suspected it might be his last
chance to prove himself to the old man.
By then Linda was six months pregnant with me.
The Wrong Side of the Tracks
Since September 1964, Donald had been living at the House and commuting
thirty minutes to Fordham University in the Bronx, his attendance at which
he’d avoid mentioning in the years to come. Going from the regimented life
at New York Military Academy to the relatively relaxed structure of college
was a tough transition for Donald, who often found himself at loose ends and
spent time strutting around the neighborhood looking for girls to flirt with.
One afternoon he came across Annamaria, Billy Drake’s girlfriend, standing
in the driveway watching her father wash the family car. Donald knew who
she was, but they’d never spoken before. Annamaria knew all about Donald
from Freddy. As the two of them were chatting, she mentioned that she had
gone to a boarding school near New York Military Academy.
“Which one?” he asked.
When she told him, he looked at her for a second and then said, “I’m so
disappointed that you went to that school.”
Annamaria, who was three years older than Donald, said, “Who are you to
be disappointed in me?” That ended the conversation. His idea of flirting was
to insult her and act superior. It struck her as juvenile, as if he were a second
grader who expressed his affection for a girl by pulling her hair.
With Freddy’s apparent fall from grace, Donald saw an opportunity to take
his place as their father’s right-hand man at Trump Management. Having
learned his lesson to be the best—even if in ways his father hadn’t intended
—Donald was determined to secure a degree commensurate with his new
ambitions even if it only secured him bragging rights. Fred knew nothing
about the relative merits of one college over another—neither he nor my
grandmother had gone to college—so the Trump kids were essentially on
their own when it came to applying to schools. Aware of the Wharton
School’s reputation, Donald set his sights on the University of Pennsylvania.
Unfortunately, even though Maryanne had been doing his homework for him,
she couldn’t take his tests, and Donald worried that his grade point average,
which put him far from the top of his class, would scuttle his efforts to get
accepted. To hedge his bets he enlisted Joe Shapiro, a smart kid with a
reputation for being a good test taker, to take his SATs for him. That was
much easier to pull off in the days before photo IDs and computerized
records. Donald, who never lacked for funds, paid his buddy well. Not
leaving anything to chance, he also asked Freddy to speak with James Nolan,
a friend from St. Paul’s, who happened to work in Penn’s admissions office.
Maybe Nolan would be willing to put in a good word for Freddy’s little
Freddy was happy to help, but he had an ulterior motive: though he never
saw Donald as competition or thought he was out to replace him, he also
didn’t like to be around his increasingly insufferable younger sibling. It
would be a relief to have Donald out of the way.
In the end, all of Donald’s machinations may not have even been
necessary. In those days, Penn was much less selective than it is now,
accepting half or more of those who applied. In any case, Donald got what he
wanted. In the fall of 1966, his junior year, he would transfer from Fordham
to the University of Pennsylvania.
My grandfather completed the purchase of Steeplechase Park for $2.5 million
in July 1965, a couple of months after I was born; a year later, Trump
Management was still struggling to get the approvals and zoning it needed to
move ahead. They were also battling public opposition to the project.
Freddy told his friends that nothing had changed since his previous stint at
Trump Management. Fred’s constant micromanaging and lack of respect for
his son made what could have been an exciting challenge a grim, joyless
exercise. Failure, it went without saying, would have been a disaster. Freddy
still believed, though, that if he had a hand in pulling the development off,
he’d be on a much better footing with his father.
That summer my parents rented a cottage in Montauk from Memorial Day
through Labor Day so Dad could escape the pressure cooker in Brooklyn.
Mom planned to stay with me and Fritz full-time, and Dad would fly back
and forth on the weekends. The recently renamed JFK was a fifteen-minute
drive from the Trump Management office, and Montauk Airport, really just a
small airstrip in an open field, was right across the street from the cottage,
making it an easy commute. Freddy’s favorite thing to do was still fly his
friends to Montauk and take them out on the water.
By the time the summer was over, my grandfather’s plans for Steeplechase
were in peril, and he knew it. Fred had been counting on his longtime
connections to the Brooklyn Democratic machine, which had eased the way
for so many of his developments in the past. By the mid-1960s, however, his
political cronies were falling out of power, and it soon became clear that he
wasn’t going to get the rezoning he needed. Nevertheless, he made Freddy
responsible for the near impossible: making Steeplechase a success.
Time was running out. Suddenly, my father, at twenty-eight, had a more
public role, giving press conferences and arranging photo ops. In one picture,
my dad, thin in his trench coat, stands in the foreground of a warehouse,
empty and cavernous, staring into the vast space, looking small and utterly
In a last-ditch effort to circumvent a push by local residents to have
Steeplechase declared a landmark, which would have halted the development
and scuttled his plans, Fred decided to host an event at the Pavilion of Fun,
built in 1907. The purpose was to celebrate the park’s demolition—in other
words, he would destroy what the community was trying to save before
landmark status could be secured. He had my father give a press conference
in order to announce the plan, making him the face of the controversy. The
extravaganza featured models in bathing suits. Guests were invited to throw
bricks (available for purchase) through the iconic window featuring an
enormous image of the park’s mascot, Tilly, and his wide, toothy smile. In a
photograph my grandfather holds a sledgehammer while grinning at a bikiniclad woman.
The entire spectacle was a disaster. Sentiment, nostalgia, and community
were concepts my grandfather didn’t understand, but when those windows
were broken, even he must have conceded to himself that he’d gone too far.
Due to local rebellion against his project, he was unable to secure the zoning
change he needed and was forced to back out of the Steeplechase
The venture exposed his waning ability to move the ball down the field.
Fred’s power was largely derived from his connections. In the early to mid1960s, there was a significant changing of the guard in New York City
politics, and, as many of his old connections and cronies were losing their
own power and places, Fred was being passed by. He would never again
pursue an original construction project. Trump Village, completed in 1964,
would be the last complex ever built by Trump Management.
Unable to accept responsibility, much as Donald would later be, Fred
blamed Freddy for the failure of Steeplechase. Eventually, Freddy blamed
It didn’t help that Donald drove back to the House from Philadelphia
almost every weekend. It turned out that he wasn’t any more comfortable at
Penn than he had been at Fordham. The work didn’t interest him, and it’s
possible that he suddenly found himself a small fish in a big pond. In the
1960s, NYMA had been at the height of its enrollment—a little over five
hundred students in grades eight through twelve—but Penn had several
thousand when he attended. At the military academy, Donald had survived
the first couple of years as an underclassman by using the considerable skills
he’d acquired growing up in the family house: his ability to feign indifference
in the face of pain and disappointment, to withstand the abuse of the bigger,
older boys. He hadn’t been a great student, but he’d had a certain charm, a
way of getting others to go along with him that, back then, wasn’t entirely
grounded in cruelty. In high school Donald had been a decent athlete, a guy
some people found attractive with his blue eyes and blond hair and his
swagger. He had all the confidence of a bully who knows he’s always going
to get what he wants and never has to fight for it. By the time he was a senior,
he had enough cachet with his fellow students that they chose him to lead the
NYMA contingent in the New York City Columbus Day Parade. He didn’t
foresee any such success at Penn and saw no reason to spend any more time
there than he had to. The prestige of the degree was what really mattered
During the most crucial juncture of the Steeplechase deal, its unraveling,
and its aftermath, Donald did a fair amount of armchair quarterbacking.
Freddy, who had never developed the armor that might have helped him
withstand his father’s mockery and humiliation, was particularly sensitive to
being dressed down in front of his siblings. When they were younger, Donald
had been both a bystander and collateral damage. Now that he was older, he
felt increasingly confident that Freddy’s continuing loss of their father’s
esteem would be to his benefit, so he often watched silently or joined in.
My father and grandfather were conducting a Steeplechase postmortem in
the breakfast room that, on Fred’s side, was acrimonious and accusatory and,
on Freddy’s, was defensive and remorseful. Donald casually said to his
brother, as though completely unaware of the effect his words would have,
“Maybe you could have kept your head in the game if you didn’t fly out to
Montauk every weekend.”
Freddy’s siblings knew that their father had always disapproved of what
was now merely Freddy’s hobby. There was a tacit agreement that they
wouldn’t talk about the planes or the boats in front of the Old Man. Fred’s
reaction to Donald’s revelation proved the point when he said to Freddy, “Get
rid of it.” The next week, the plane was gone.
Fred made Freddy miserable, but Freddy’s need for his father’s approval
seemed to intensify after Marblehead and even more after the demise of
Steeplechase. He’d do whatever his father told him to do in the hope of
gaining his acceptance. Whether he realized it consciously or not, it would
never be granted.
When they first moved into the Highlander, Freddy and Linda had been
concerned that the other tenants would bother the landlord’s son with their
complaints. Now they found themselves at the bottom of the list when they
The windows in my parents’ ninth-floor corner bedroom offered
expansive southern and eastern views, but they were also vulnerable to strong
gusts of wind. In addition, the Highlander had built-in air conditioners in
every room that hadn’t been installed properly, so condensation accumulated
between the drywall and outer bricks whenever the AC was running. Over
time, the built-up moisture seeped into the drywall, softening it. By
December, the wall around the unit in my parents’ bedroom had deteriorated
so badly that a frigid draft constantly blew into the room. My mother tried to
cover the wall around the air conditioner with plastic sheeting, but the arctic
air continued to pour in. Even with the heat blasting, their bedroom was
always bitterly cold. The superintendent at the Highlander never responded to
their request to have a maintenance crew sent up, and the wall was never
New Year’s Eve 1967 was particularly inclement, but despite the rain and
wind, my parents drove out east to celebrate with friends at Gurney’s Inn in
Montauk. By the time they were ready to drive back to Jamaica in the early
hours of New Year’s Day, the weather had turned even colder and the steady
rain had become a downpour. When Freddy went outside to warm up the car,
the battery was dead. Dressed only in his shirtsleeves, he got drenched trying
to get the car to start. By the time he and Linda returned to the apartment and
their windblown bedroom, he was sick.
Between the stress of the last two years and his heavy drinking and
smoking (by then he averaged two packs of cigarettes a day), Freddy was in
bad shape to begin with. His cold rapidly worsened, and after a few days he
wasn’t getting any better as he shivered, wrapped in a blanket, unable to
escape the drafts. Linda repeatedly called the superintendent but got no
response. Finally she called her father-in-law. “Please, Dad,” she begged,
“there must be someone who can fix this. Maybe from another building in
Jamaica Estates or Brooklyn? Freddy is so sick.” My grandfather suggested
that she speak to the Highlander super again; there was nothing he could do.
Because for so long their life had been lived in the confines of Fred
Trump’s domain, it didn’t occur to either one of them to hire a handyman
who wasn’t on Fred Trump’s payroll. That wasn’t how it worked in the
family; Fred’s permission was sought whether it was needed or not. The wall
was never fixed.
A week after New Year’s, Linda’s father called to tell her that her mother
had had a stroke. My mom didn’t want to leave my father, but her mother’s
condition was serious, and she needed to fly down to Fort Lauderdale as soon
as she could arrange child care.
Not long after, Gam called my mother to tell her that Freddy was in
Jamaica Hospital with lobar pneumonia. Linda immediately got onto a plane
and took a taxi straight to the hospital as soon as she landed.
My father was still in the hospital on January 20, 1967, their fifth wedding
anniversary. Undeterred by his poor health and worsening alcoholism, my
mother sneaked a bottle of champagne and a couple of glasses into his room.
Regardless of what was happening around them or what state her husband
was in, they were determined to celebrate.
Dad had been home from the hospital for only a few weeks when Linda
got a call from her father. Her mother was doing better after her stroke, he
told her, but he hated leaving her at the mercy of nurses while he put in full
days at the quarry. The stress of work, the expense of his wife’s care, and his
constant worry about her were taking their toll on both of them. “I’m at the
end of my rope,” he said. “I don’t see how we can continue.”
Although Linda didn’t know exactly what her father was implying, he
sounded so distraught she was afraid he meant that both he and her mother
would be better off dead and, out of desperation, might do something about
it. When she told Freddy about her parents’ precarious situation, he told her
not to worry and called his father-in-law to tell him he was going to help out.
“Quit your job, Mike. Take care of Mom.” Money wasn’t an issue, at least
not then, but Freddy wasn’t sure how his father would react when he told
“Of course,” Fred said. “That’s what you do for family.”
My grandfather believed that in the same way he believed it was
appropriate to send your kids to college or join a country club: even if it was
of no interest to him or wasn’t particularly important to him, it was simply
“what you do.”
After the Steeplechase deal collapsed, there was less for Freddy to do at
Trump Management. He and Linda had been planning to buy a house since
my brother had been born, and now, with extra time on his hands, they started
to look for one. It didn’t take long for them to find a perfect four-bedroom on
a half-acre lot in Brookville, a beautiful, affluent town on Long Island. The
move would add at least half an hour to Dad’s commute, but a change of
scenery and the freedom of being out of his father’s building would do him
some good. He assured the real estate agent that he could meet the asking
price and getting a mortgage would be no problem.
When the bank called a few days later to tell him his mortgage application
had been rejected, Freddy was stunned. With the exception of his one year
with TWA, he’d been working for his father for almost six years. He was still
an executive at Trump Management, which brought in tens of millions of
dollars a year free and clear. In 1967, the company was worth approximately
$100 million. Freddy made a decent living, he didn’t have many expenses,
and there was a trust fund and a (fast dwindling) stock portfolio. The most
plausible explanation was that Fred, still burned by what he considered his
son’s betrayal and reeling from the failure of Steeplechase, had intervened in
some way to prevent the transaction. My grandfather had prominent contacts
and enormous accounts at Chase, Manufacturer’s Hanover Trust, and the
other biggest banks in the city, so not only could he guarantee that Freddy
would get a mortgage, he could just as easily make sure he didn’t. Our family
was effectively trapped in that run-down apartment in Jamaica.
When June rolled around, my father was more than ready to spend the
summer in Montauk again. My parents rented the same cottage, and with
funds he raised by selling some of his blue-chip stocks, Dad bought a
Chrisovich 33, which, with its sixteen-foot tuna tower, was much more suited
to handle the kind of deep-sea fishing he loved. He also bought another plane,
this time a Cessna 206 Stationair, which had a more powerful engine and a
larger seating capacity than the Piper Comanche.
But the new toys weren’t just for recreation. Dad had a plan. After
Steeplechase, he had been increasingly sidelined at Trump Management, so
he came up with the idea of chartering both the boat and the plane to create
another source of income. If it worked out, he might be able to free himself
from Trump Management after all. He hired a full-time captain to run the
boat charters, but on the weekends, when doing so would have been the most
lucrative, he had the captain drive him and his friends around instead.
When Linda joined them on the boat, she noticed that Freddy always
drank more than everybody else, just as he had in Marblehead, which spurred
increasingly intense fights between them. The increasing frequency with
which Freddy flew under the influence was alarming, and as the summer of
1967 proceeded, Linda became reluctant to get onto the plane with him. The
unraveling continued. By September, Dad realized that his plan wasn’t going
to work. He sold the boat, and when Fred found out about the plane, he got
rid of that, too.
At twenty-nine years old, my father was running out of things to lose.
A Zero-Sum Game
I woke up to the sound of Dad’s laughter. I had no sense of the time. My
room was very dark, and the hallway light glared bright and incongruous
under my door. I slipped out of bed. I was two and a half, and my five-yearold brother was sleeping far away on the opposite end of the apartment. I
went alone to see what was going on.
My parents’ room was next to mine, and its door was standing wide open.
All of the lights were on. I stopped at the threshold. Dad had his back to the
chest of drawers, and Mom, sitting on the bed directly across from him, was
leaning away, one hand held up, the other supporting her weight on the
mattress. I didn’t immediately know what I was looking at. Dad was aiming a
rifle at her, the .22 he kept on his boat to shoot sharks—and he kept laughing.
Mom begged him to stop. He raised the gun until it was pointing at her
face. She lifted her left arm higher and screamed again, more loudly. Dad
seemed to find it funny. I turned and ran back to bed.
My mother corralled my brother and me into the car and took us to a friend’s
house for the night. Eventually my father tracked us down. He barely
remembered what he’d done, but he promised my mother it would never
happen again. He was waiting for us when we returned to the apartment the
next day, and they agreed to try to work things out.
But they kept going through the motions of their day-to-day lives without
acknowledging the problems in their marriage. Nothing was going to get
better. Things weren’t even going to stay the same.
Less than two miles away, in another one of my grandfather’s buildings,
Maryanne was in trouble. Her husband, David, had lost his Jaguar dealership
a couple of years earlier and still didn’t have a job. Anybody who was paying
attention would have realized that all was not well, but Maryanne’s siblings
and their friends thought David Desmond was a joke—rotund and harmless.
Freddy had never understood the marriage or taken his brother-in-law
Maryanne had been twenty-two when she had met David. A graduate
student at Columbia studying public policy, she had planned to get a PhD,
but, wanting to avoid the shame of being called an old maid by her family
(Freddy included), she had accepted David’s proposal and dropped out of
school after getting her master’s degree.
The initial problem was that David, a Catholic, insisted that Maryanne
convert. Not wanting to provoke her father’s anger or hurt her mother’s
feelings, she was terrified to ask for their blessing.
When she finally did, Fred said, “Do whatever you want to do.”
She explained how very, very sorry she was to disappoint them.
“Maryanne, I couldn’t care less. You’re going to be his wife.”
Gam didn’t say anything at all, and that was that.
David liked to tell Maryanne that his name would be known far beyond
the reach of the Trumps. Although well educated, he didn’t have any obvious
skills to back up his ambition. Even so, he remained convinced that he’d find
a way to succeed beyond his dreams and “show them.” Like Ralph Kramden
without the charm, kindness, or steady job with benefits, his “next big thing,”
just like the car dealership, always failed or never materialized at all. It
wasn’t long into the marriage before David started drinking.
The Desmonds lived rent free in a Trump apartment and enjoyed the same
medical insurance everyone in the family received through Trump
Management, but free rent and medical insurance didn’t put food on the
table, and they had no income.
The biggest mystery, however, was why Maryanne was so financially
dependent on her incompetent husband, just as it was a mystery that
Elizabeth lived in a gloomy one-bedroom apartment next to the 59th Street
Bridge and Freddy couldn’t buy a house and his planes, boats, and luxury
cars kept disappearing. My grandfather and great-grandmother had set up
trust funds for all of Fred’s children in the 1940s. Whether or not Maryanne
was entitled to the principal yet, the trusts must have generated interest. But
the three oldest children had been trained not to ask for anything ever, and if
my grandfather was the trustee of those trusts, they were trapped in their
financial circumstances. Asking for help meant you were weak or greedy or
seeking advantage over someone who needed nothing from you in return,
although an exception was made for Donald. It was so frowned upon that
Maryanne, Freddy, and Elizabeth, in different ways, all suffered from totally
After a few years of her husband’s continued unemployment, Maryanne
was at the end of her rope. She approached her mother, but in a way that
didn’t arouse suspicion. “Mom, I need some change for the laundry,” she
would say casually whenever she went to the House. She thought nobody
knew how bad it was. For Fred, once his daughter was married, she wasn’t
his concern, but my grandmother knew. She didn’t ask questions, either
because she didn’t want to pry or because she wanted Maryanne to have her
“pride,” and handed her daughter a Crisco can filled with dimes and quarters
that came from the washers and dryers that she’d retrieved from my
grandfather’s buildings. Every few days, Gam made the rounds in Brooklyn
and Queens, driving her pink Cadillac convertible and wearing her fox fur
stole to collect the coins. As my aunt would later concede, in a family of
already tremendous wealth, those Crisco cans saved her life; without them
she wouldn’t have been able to feed herself or her son, David, Jr.
At the very least, Maryanne should have been able to buy groceries
without having to ask my grandmother, no matter how obliquely. But no
matter how dire their situation, the three oldest Trump children couldn’t get
anybody in their family to help them in any substantive way. After a while
there seemed to be no point in trying at all. Elizabeth simply accepted her lot.
Dad eventually came to believe it was what he deserved. Maryanne
convinced herself that not asking for or receiving help was a badge of honor.
Their fear of my grandfather was so deeply ingrained that they no longer
even recognized it for what it was.
The situation with David Desmond eventually became untenable. He
couldn’t get a job, and his drinking worsened. Desperate but being very
careful not to seem as if she were asking for anything, Maryanne hinted to
her father that David would love a place at Trump Management. My
grandfather didn’t ask if there was a problem. He gave his son-in-law a job as
a parking lot attendant at one of his buildings in Jamaica Estates.
Donald graduated from the University of Pennsylvania in the spring of 1968
and went straight to work at Trump Management. From his first day on the
job, my twenty-two-year-old uncle was given more respect and perks and
paid more money than my father ever had been.
Almost immediately, my grandfather appointed Donald vice president of
several companies that fell under the Trump Management umbrella, named
him “manager” of a building he didn’t actually have to manage, gave him
“consulting” fees, and “hired” him as a banker.
The reasoning for that was twofold: First, it was an easy way to put
Freddy in his place while signaling to the other employees that they were
expected to defer to Donald. Second, it helped consolidate Donald’s de facto
position as heir apparent.
Donald secured his father’s attention in a way nobody else did. None of
Freddy’s friends could understand why Donald was, in Fred’s eyes, “the cat’s
meow.” But after the summers and weekends Donald spent working for his
father and visiting construction sites, Fred exposed his younger son to the ins
and outs of the real estate business. Donald discovered he had a taste for the
seamier side of dealing with contractors and navigating the political and
financial power structures that undergirded the world of New York City real
estate. Father and son could discuss the business and local politics and gossip
endlessly even if the rest of us in the cheap seats had no idea what they were
talking about. Not only did Fred and Donald share traits and dislikes, they
had the ease of equals, something Freddy could never achieve with his father.
Freddy had a wider view of the world than his brother or father did. Unlike
Donald, he had belonged to organizations and groups in college that had
exposed him to other people’s points of view. In the National Guard and as a
pilot at TWA, he had seen the best and brightest, career professionals who
believed there was a greater good, that there were things more important than
money, such as expertise, dedication, loyalty. They understood that life
wasn’t a zero-sum game. But that was part of my dad’s problem. Donald was
as narrow and provincial and egotistical as their father. But he also had a
confidence and brazenness that Fred envied and his older brother lacked,
qualities that Fred planned to turn to his advantage.
Donald’s bid to replace my father at Trump Management was off to a strong
start, but he was still at loose ends at home. Robert was at Boston University,
which enabled him to avoid service in Vietnam, and Donald and Elizabeth
didn’t socialize with each other. Freddy did his best to include his little
brother in whatever he and his friends got up to, but it rarely went well. They
were a laid-back group who loved flying out east with Freddy to fish and
water-ski. They found Donald’s lack of humor and self-importance offputting. Though they tried for Freddy’s sake to welcome his little brother,
they didn’t like him.
Toward the end of Donald’s first year at Trump Management, the tension
between him and Freddy was becoming noticeable. Though Freddy tried to
leave it at the office, Donald never let anything go. Despite that, when Billy
Drake’s girlfriend, Annamaria, was having a dinner party, Freddy asked if he
could invite his brother.
The evening didn’t go much better than Donald’s attempted flirtation in
the driveway years earlier. Shortly after the brothers arrived, raised voices
drew Annamaria from the kitchen, where she was preparing dinner. She
found Donald standing inches away from his brother, flushed and pointing
his finger in Freddy’s face. Donald looked as though he were about to hit
Freddy, so Annamaria pushed herself between the two very tall men.
Freddy took a step back and said through clenched teeth, “Donald, get out
Donald seemed stunned, then stormed away, saying, “Fine! You eat the
girl’s roast beef!” as he slammed the door on his way out.
“Idiot!” Annamaria called after him. She turned back to Freddy and asked,
“What was that about?”
Shaken, Freddy simply said, “Work stuff.” And they left it at that.
Things weren’t getting any better at the Highlander, either. Despite my
mother’s fear of snakes, Dad brought home a ball python one day and put the
tank into the den, forcing my mother to pass by it any time she needed to do
laundry, go into my brother’s room, or leave the apartment. Their fights
escalated after that gratuitous bit of cruelty, and by 1970 my mother had had
all she could take. She asked Dad to leave. When he came back unannounced
a couple of weeks later and let himself in, she called my grandfather and
insisted that the locks be changed. For once, Fred didn’t object; he didn’t ask
any questions, and he didn’t blame her. He simply told her that he would take
care of it, and he did.
Dad never lived with us again.
My mother called Matthew Tosti, one of my grandfather’s attorneys, to tell
him she wanted a divorce. Mr. Tosti and his partner, Irwin Durben, had been
doing work for my grandfather since the 1950s. Even before my parents
separated, Mr. Tosti had been my mother’s main contact for anything having
to do with me, my brother, or money. He became her confidant; in the bleak
landscape of the Trump family, he stood out as a warm and supportive ally,
and she considered him a friend.
As genuinely kind as Mr. Tosti may have been, he also knew on which
side his bread was buttered. Despite the fact that my mother had her own
counsel, the divorce agreement might as well have been dictated by my
grandfather. He knew that his daughter-in-law had no idea how much money
my father’s family had or what his future prospects, as the son of an
exceedingly wealthy man, might be.
My mother received $100 a week in alimony plus $50 a week for child
support. At the time, those weren’t insignificant sums, especially considering
that the big expenses, such as school, camp tuition, and medical insurance,
were taken care of separately. My father was also responsible for paying the
rent. Because my grandfather owned the building we lived in, it was only $90
a month. (I learned many years later that my brother and I each owned 10
percent of the Highlander, so in retrospect, charging us rent at all seems
excessive.) Dad’s rent obligation was capped at $250, which limited our
ability to move if we ever wanted to relocate to a better apartment or
neighborhood. My father, the scion of a family that at the time was worth
well over a hundred million dollars, agreed to pay for private school and
college. But Mr. Tosti had to approve our vacations. There were no marital
assets to split, so my mother’s total net worth was the $600 she got every
month, an amount that wouldn’t change over the next decade. After expenses,
there was barely enough left over for Mom to contribute to her annual
Christmas fund, let alone save up to buy a house.
My mother got full custody of me and my brother, as was customary at the
time, but visitation rights weren’t specified: “Mr. Trump shall be free to see
[the children], on reasonable notice, at all reasonable times.” In the vast
majority of cases, visitation meant having the kids every other weekend and
one night a week for dinner. That’s eventually what my parents’ arrangement
evolved into, but at the beginning there were no formal rules.
The Steeplechase development was permanently blocked in 1969, but
eventually the city purchased the land back from my grandfather. He walked
away with $1.3 million in profit for having done nothing but ruin a beloved
city landmark. My dad was left with nothing but the blame.
When Freddy (in 1960) and Donald (in 1968) joined Trump Management,
each had a similar expectation: to become his father’s right-hand man and
then succeed him. They had, at different times and in different ways, been
groomed to fit the part, never lacking for funds to buy expensive clothes and
luxury cars. The similarities ended there.
Freddy quickly found that his father was unwilling to make room for him
or delegate him any but the most mundane tasks, a problem that came to a
head at the height of the construction at Trump Village. Feeling trapped,
unappreciated, and miserable, he left to find his success elsewhere. At age
twenty-five, he was a professional pilot, flying 707s for TWA and supporting
his young family. That would turn out to be the pinnacle of Freddy’s personal
and professional life. At twenty-six and back at Trump Management, the
chimerical chance for rehabilitation ostensibly offered to him at Steeplechase
evaporated, and his prospects were at an end.
By 1971, my dad had been working for my grandfather, with the exception
of his ten months as a pilot, for eleven years. Nonetheless, Fred promoted
Donald, then only twenty-four, to the position of president of Trump
Management. He’d been on the job for only three years and had very little
experience and even fewer qualifications, but Fred didn’t seem to mind.
The truth was, Fred Trump didn’t need either one of his sons at Trump
Management. He promoted himself to CEO, but nothing about his job
description changed: he was a landlord. Fred hadn’t been a developer since
the failure of Steeplechase six years earlier, so Donald’s role as president
remained amorphous. In the early 1970s, with New York City on the brink of
economic collapse, the federal government was cutting back on the FHA (in
large part because of the cost of the Vietnam War), so no more FHA funding
was available to Fred. Mitchell-Lama, a New York State–sponsored program
to provide affordable housing that funded Trump Village, also ground to a
As a business move, promoting Donald was pointless. What exactly was
he being promoted to do? My grandfather had no development projects, the
political power structure he’d depended on for decades was unraveling, and
New York City was in dire financial straits. The main purpose of the
promotion was to punish and shame Freddy. It was the latest in a long line of
such punishments, but it was almost certainly the worst, especially given the
context in which it happened.
Fred was determined to find a role for Donald. He had begun to realize
that although his middle son didn’t have the temperament for the day-to-day
attention to detail that was required to run his business, he had something
more valuable: bold ideas and the chutzpah to realize them. Fred had long
harbored aspirations to expand his empire across the river into Manhattan, the
Holy Grail of New York City real estate developers. His early career had
demonstrated that he had a knack for self-promotion, dissembling, and
hyperbole. But as the first-generation son of German immigrants, Fred had
English as his second language and he needed to improve his communication
skills—he had taken the Dale Carnegie course for a reason, and it wasn’t to
boost his self-confidence. But the course had been a failure. And there was
another obstacle, perhaps even more difficult to overcome: Fred’s mother, as
forward thinking as she had been in some ways, was generally very austere
and traditional. It was okay for her son to be successful and rich. It was not
okay for him to show off.
Donald had no such restraint. He hated Brooklyn as much as Freddy did
but for very different reasons—the bleak working-class smallness of it, the
lack of “potential.” He couldn’t get out of there fast enough. Trump
Management was located on Avenue Z, right in the middle of Beach Haven
in South Brooklyn, one of my grandfather’s largest apartment complexes. He
hadn’t made many alterations. The narrow outer office was crammed with too
many desks, and the small windows admitted little light. If Donald had
thought of the surrounding buildings and complexes in terms of number of
units, the value of the ground leases, and the sheer volume of income that
poured into Trump Management every month, he would have recognized the
huge opportunity. Instead, whenever he stood outside the office and surveyed
the utilitarian sameness of Beach Haven, he must have felt suffocated by the
sense that it was all beneath him. A future in Brooklyn wasn’t what he
wanted for himself, and he was determined to get out as quickly as possible.
Besides being driven around Manhattan by a chauffeur whose salary his
father’s company paid, in a Cadillac his father’s company leased to “scope
out properties,” Donald’s job description seems to have included lying about
his “accomplishments” and allegedly refusing to rent apartments to black
people (which would become the subject of a Justice Department lawsuit
accusing my grandfather and Donald of discrimination).
Donald dedicated a significant portion of his time to crafting an image for
himself among the Manhattan circles he was desperate to join. Having grown
up a member of the first television generation, he had spent hours watching
the medium, the episodic nature of which appealed to him. That helped shape
the slick, superficial image he would come to both represent and embody. His
comfort with portraying that image, along with his father’s favor and the
material security his father’s wealth afforded him, gave him the unearned
confidence to pull off what even at the beginning was a charade: selling
himself not just as a rich playboy but as a brilliant, self-made businessman.
In those early days, that expensive endeavor was being enthusiastically, if
clandestinely, funded by my grandfather. Fred didn’t immediately realize the
scope of Donald’s limitations and had no idea that he was essentially
promoting a fiction, but Donald was happy to spend his father’s money either
way. For his part, Fred was determined to keep money pouring into his son’s
pocket. In the late 1960s, for example, Fred developed a high-rise for the
elderly in New Jersey, a project that was in part an exercise in how to get
government subsidies (Fred received a $7.8 million, practically interest-free
loan to cover 90 percent of the cost of the project’s construction) and in part
an example of how far he was willing to go to enrich his second son.
Although Donald put no money toward the development costs of the
building, he received consulting fees, and he was paid to manage the
property, a job for which there were already full-time employees on site. That
one project alone netted Donald tens of thousands of dollars a year despite his
having done essentially nothing and having risked nothing to develop,
advance, or manage it.
In a similar sleight of hand, Fred bought Swifton Gardens, an FHA project
originally costing $10 million to build, at auction for $5.6 million. In
addition, he secured a $5.7 million mortgage, which also covered the cost of
upgrades and repairs, essentially paying zero dollars for the buildings. When
he later sold the property for $6.75 million, Donald got all of the credit and
took most of the profits.
My dad’s dream of flying had been taken away from him, and he had now
lost his birthright. He was no longer a husband; he barely saw his kids. He
had no idea what was left for him or what he was going to do next. He did
know that the only way for him to retain any self-respect was to walk away
from Trump Management, this time for good.
Dad’s first apartment after he moved out of the Highlander was a studio in
the basement of a brick row house on a quiet, shady street in Sunnyside,
Queens. He was thirty-two years old and had never lived on his own.
The first thing we saw when we walked through the door was a tank
holding two garter snakes and a terrarium with a ball python.
Another tank stocked with goldfish, and another with a few mice
scrambling around in the straw, were set up on stands to the left of the
snakes. I knew what the mice were for.
In addition to a fold-out couch, a small kitchen table with a couple of
cheap chairs, and the TV, there were two more terrariums housing an iguana
and a tortoise. We called them Tomato and Izzy.
Dad seemed proud of his new place, and he kept adding to the menagerie.
On one visit, he took us down to the boiler room and led us to a cardboard
box with six ducklings inside. The landlord had let him set up some heat
lamps, creating a makeshift incubator. They were so tiny that we had to feed
them with an eyedropper.
“Just give it a quarter of a turn on the mental carburetor,” my grandfather said
to my father, as if that were all it would take for his son to stop drinking. As
if it were just a matter of willpower. They were in the library, but for once
they sat across from each other—not equals exactly, never equals—but as
two people who had a problem to solve, even though they might never agree
on the solution. Although the medical view of alcoholism and addiction had
changed drastically in the previous few decades, public perception hadn’t
evolved much. Despite treatment programs such as Alcoholics Anonymous,
which had been around since 1935, the stigma attached to addicts and
“Just make up your mind, Fred,” my grandfather said, offering a useless
platitude that Norman Vincent Peale would have approved of. The closest
thing Fred had to a philosophy was the prosperity gospel, which he used like
a blunt instrument and an escape hatch, and it had never harmed any of his
children more than it did right then.
“That’s like telling me to make up my mind to give up cancer,” Dad said.
He was right, but my grandfather wholeheartedly embraced the “blame the
victim” mentality that was still pervasive and couldn’t make that leap.
“I need to beat this, Dad. I don’t think I can do it by myself. I know I
Instead of asking “What can I do for you?” Fred said, “What do you want
Freddy had no idea where to start.
My grandfather had never been sick a day in his life; he had never missed
a day of work; he had never been sidelined by depression or anxiety or
heartbreak, not even when his wife was near death. He appeared to have no
vulnerabilities at all and therefore couldn’t recognize or sanction them in
He had never handled Gam’s injuries and illnesses well. Whenever Gam
was suffering, my grandfather would say something like “Everything’s great.
Right, Toots? You just have to think positive,” and then leave the room as
quickly as possible, leaving her alone to deal with her pain.
Sometimes Gam forced herself to say, “Yes, Fred.” Usually she said
nothing, clenched her jaw, and struggled to keep from crying. My
grandfather’s relentless insistence that everything was “great” left no room
for any other feelings.
We were told that Dad was sick and would be in the hospital for a few weeks.
We were also told that he had to give up his apartment—apparently the
landlord wanted to rent the place to somebody else. Fritz and I went to pack
up clothes, games, and other odds and ends we’d left behind, and when we
arrived, the place was almost completely empty. The tanks were gone, the
snakes were gone. I never found out what happened to them.
When Dad returned from wherever he had been—the hospital or rehab—
he moved into my grandparents’ attic. It was a temporary arrangement, and
no effort was made to turn it into a proper living space. All of the storage
boxes and old toys—including the vintage fire engine, crane, and dump truck
my grandmother had hidden there all those years ago—had simply been
pushed to one end of the attic and a cot set up in the cleared space at the
other. Dad put his portable six-inch black-and-white television on his old
National Guard trunk beneath the dormered window.
When Fritz and I visited him, we camped out on the floor next to his cot,
and the three of us watched an endless stream of old movies such as Tora!
Tora! Tora! and It’s a Mad, Mad, Mad, Mad World. When he was well
enough to come downstairs, Dad joined us on Sundays for the weekly Abbott
and Costello movie on WPIX.
After a month or two, my grandfather told Dad there was a vacancy in
Sunnyside Towers, a building my grandfather had bought in 1968—a onebedroom apartment on the top floor.
As Dad was preparing to move to Sunnyside, Maryanne, with the help of a
$600 loan, was getting ready to start her studies at Hofstra Law School.
Although not her first choice, Hofstra was only a ten-minute drive from
Jamaica Estates—close enough that she could still take my cousin David to
school in the morning and pick him up in the afternoon. Going back to school
was a long-deferred dream. She also hoped that becoming a lawyer would
give her the financial wherewithal to leave her husband someday. Their
situation had become increasingly dire over the years. The parking lot
attendant job that his father-in-law had given him was a humiliation from
which he hadn’t recovered. Over the years, David had lashed out at his wife
from time to time, particularly when he was drunk.
Maryanne’s move toward independence sent her husband even further
over the edge, and after she returned home from her first day at law school,
her husband, in a fit of rage, threw their thirteen-year-old son out of the
apartment. Maryanne took him to the House, and they spent the night there.
David Desmond, Sr., cleaned out their meager joint savings account and left
When the whole family was together, we spent most of our time in the
library, a room without books until Donald’s ghostwritten The Art of the Deal
was published in 1987. The bookshelves were used instead to display
wedding photos and portraits. The wall across from the bay window
overlooking the backyard was dominated by a studio portrait of the five
siblings taken when they were adults that had replaced an earlier version of
the five in similar poses taken when Freddy was fourteen. The only nonstudio
photographs in the room were a black-and-white shot of my grandmother,
looking regal and condescending in her hat and fur stole as she and my aunts,
young girls at the time, descended the air stairs to the tarmac in Stornoway on
the Isle of Lewis, where Gam had been born, and one of Donald in his New
York Military Academy dress uniform leading the school contingent in the
New York City Columbus Day Parade. There were two love seats
upholstered in dark-blue-and-green vinyl against the walls and one large
chair in front of the TV, a spot the kids fought over regularly. My
grandfather, dressed in his three-piece suit and tie, sat on the love seat nearest
the heavy pine phone table by the door, his feet planted squarely on the
Every Saturday, if we weren’t in Sunnyside with Dad, Fritz and I rode our
bikes down Highland Avenue and along the back streets of Jamaica Estates to
the House to hang out with our cousin David—or rather, Fritz and David
hung out and I followed them around, trying to keep up.
Gam sat with Maryanne and Elizabeth whenever they visited at a small
sky blue Formica table with stainless steel edging that looked as though it
came straight out of a 1950s malt shop. Just past it, there was a dark pantry
the size of a walk-in closet with a little desk where Gam kept her shopping
lists, receipts, and bills. Marie, the long-suffering housekeeper, often hid
there, listening to her portable radio, and on rainy or cold days when David,
Fritz, and I were confined to the House, we drove her crazy. On the other side
of the pantry, a swinging door led to the dining room. We used the loop that
ran from the back door hallway past the kitchen, through the foyer, around to
the dining room, through the pantry, and back to the kitchen as our personal
racetrack, chasing one another, wiping out, screaming, gaining speed, one of
us invariably banging into a piece of furniture. Between the refrigerator and
the pantry doorway, Gam generally gave us free rein, but when she was in the
kitchen, she would lose her patience and yell at us to stop. She threatened us
with the wooden spoon if we ignored her—the sound of the drawer opening
was enough to give us pause. But if we were stupid enough to keep running
around her and making a racket, the spoon came out, and whoever was
closest at hand got whacked. Liz did her part to slow us down by grabbing
our hair as we passed by.
After that Fritz, David, and I usually ran to the basement—adults passed
through only on their way to the laundry room or the garage, so we were free
to be loud and to kick around the soccer ball or take turns riding up and down
on (or fighting over) Gam’s electric stair lift. We spent most of our time in
the open space at the far end with all the lights on. With the exception of my
grandfather’s life-sized wooden Indian chief statues that were lined up
against the far wall like sarcophagi, it was a pretty typical basement: drop
ceiling with fluorescent lighting, white-and-black linoleum tile, and an old
upright piano that stood largely ignored because it was so badly out of tune it
wasn’t even worth playing. Donald’s marching hat with the huge plume that
he had worn during color guard at NYMA sat on top of it. Sometimes I put it
on, though it slid down to the bridge of my nose, and fastened the strap
beneath my chin.
When I was down there by myself, the basement—half illuminated, the
wooden Indians standing sentinel in the shadows—became a weirdly exotic
space. Across from the stairs, a huge mahogany bar, fully stocked with
barstools, dusty glasses, and a working sink but no alcohol, had been built in
the corner—an anomaly in a house built by a man who didn’t drink. A large
oil painting of a black singer with beautiful, full lips and generous, swaying
hips hung on the wall behind it. Wearing a curve-hugging gold-and-yellow
dress with ruffles, she stood at the microphone, mouth open, hand extended.
A jazz band made up entirely of black men dressed in white dinner jackets
and black bow ties played behind her. The brasses glowed, the woodwinds
glistened. The clarinetist, a sparkle in his eyes, looked straight out at me. I
would stand behind the bar, towel slung over my shoulder, whipping up
drinks for my imaginary customers. Or I would sit on one of the barstools,
the only patron, dreaming myself inside that painting.
Our uncle Rob, who wasn’t that much older than we were and seemed
more like a sibling than an uncle, played soccer with us in the backyard
whenever he came out from the city. We played hard and on hot days made
frequent trips to the kitchen for a can of Coke or a grape juice. Rob would
often grab a block of Philadelphia cream cheese; leaning against the
refrigerator, he’d peel back the foil and eat the cream cheese as if it were a
candy bar, then wash it down with soda.
Rob was a very good soccer player, and I tried to keep up with the boys,
but it sometimes felt as though he used me for target practice.
When Donald was at the House, we mostly threw a baseball or football
around. He had played baseball at New York Military Academy and was
even less likely to pull his punches than Rob; he saw no reason to throw the
ball any more gently just because his niece and nephews were six or nine or
eleven. When I did manage to catch the ball he threw at me, the report of it
against my leather glove reverberated off the brick retaining wall like a shot.
Even with little kids, Donald had to be the winner.
Only the most dedicated optimist could have lived in Sunnyside Towers
without losing hope. There was no doorman, and the plastic plants and
flowers that filled the two large planters on either side of the plexiglass front
door were perpetually coated in a thin film of dust. Our sixth-floor hallway
reeked of stale cigarette smoke. The dank carpet was a soulless shade of seal
grey. The indifferent overhead lighting hid nothing.
The height of my father’s lifestyle had been when he and my mom had
lived in their one-bedroom near Sutton Place right after they were married.
During that year, they had spent their evenings going to the Copacabana with
friends and flying to Bimini on weekends. It had been all downhill from
there, a trajectory that mirrored that of Donald, whose own lifestyle became
more extravagant as the years passed. Donald had already been living in
Manhattan when he married Ivana. After the wedding, they lived in a twobedroom apartment on Fifth Avenue, then in an eight-bedroom apartment
also on Fifth Avenue. Within five years they were living in the $10 million
penthouse triplex in Trump Tower, all while Donald was still effectively on
my grandfather’s payroll.
My grandfather created Midland Associates in the 1960s to benefit his
children, each of whom was given 15 percent ownership in eight buildings,
one of which was Sunnyside Towers. The express purpose of this apparently
quasi-legal, if not outright fraudulent, transfer of wealth was to avoid paying
the lion’s share of the gift taxes that would have been assessed if it had been
an aboveboard transaction. I don’t know if Dad knew that he owned part of
the building he now lived in, but in 1973 his share of it would have been
worth about $380,000, or $2.2 million in today’s dollars. He seemed to have
no apparent access to any of the money—his boats and planes were gone; his
Mustang and Jaguar were gone. He still had his FCT vanity plates, but now
they were attached to a beat-up Ford LTD. Whatever wealth my father had
was by then entirely theoretical. Either his access to his trust funds had been
blocked, or he had stopped thinking he had any right to his own money.
Thwarted one way or the other, he was at his father’s mercy.
Dad and I were watching a Mets game on television when the intercom
buzzed. Dad looked surprised and went to answer. I didn’t hear who was
calling from the lobby, but I heard my father say “Shit” under his breath.
We’d been having a laid-back afternoon, but Dad seemed tense now.
“Donald’s coming up for a couple of minutes,” he told me.
“No idea.” He seemed annoyed, which was unusual for him.
Dad tucked his shirt in and opened the door as soon as the bell rang. He
took a couple of steps back to let his brother pass. Donald was wearing a
three-piece suit and shiny shoes and carrying a thick manila envelope
wrapped with several wide rubber bands. He walked into the living room.
“Hi, Honeybunch,” he said when he saw me.
I waved at him.
Donald turned back to my dad and said, “Jesus, Freddy,” as he looked
around disdainfully. My father let it slide. Donald tossed the envelope onto
the coffee table and said, “Dad needs you to sign these and then bring them to
“Yeah. Why? You busy?”
“You take it to him.”
“I can’t. I’m on my way to the city to look at some properties that are in
foreclosure. It’s a fantastic time to take advantage of losers who bought at the
height of the market.”
Freddy never would have dared develop his own projects outside of
Brooklyn. A few years earlier on a weekend trip to the Poconos, as he and
Linda had driven past row after row of condemned buildings on either side of
the Cross Bronx Expressway, she’d pointed out that he could start his own
business and renovate buildings in the Bronx.
“No way I could go against Dad,” Freddy had said. “It’s all about
Brooklyn for him. He’d never go for it.”
Now Donald looked out the window and said, “Dad’s going to need
somebody in Brooklyn. You should go back.”
“And do what, exactly?” Dad scoffed.
“I don’t know. Whatever you used to do.”
“I had your job.”
In the uncomfortable silence, Donald looked at his watch. “My driver’s
waiting downstairs. Get this to Dad by four o’clock, okay?”
After Donald left, Dad sat on the couch next to me and lit a cigarette. “So,
kiddo,” he said, “want to take a ride to Brooklyn?”
When we visited the office, Dad made the rounds on his way to Amy
Luerssen, my grandfather’s secretary and gatekeeper (and also my
godmother), whose desk stood right outside of her boss’s door. Aunt Amy
clearly adored the man she called “my Freddy.”
My grandfather’s private office was a square room with low lighting, its
walls covered with plaques and framed certificates, a lot of wooden busts of
Indian chiefs in full headdress scattered about. I sat behind his desk and
chose from what seemed an endless supply of blue Flair markers and the
same thick pads of cheap scratch paper he had at the House, writing notes and
drawing until it was time to go to lunch. When I was left alone, I spun wildly
in his chair.
My grandfather always took us to eat at Gargiulo’s, a formal restaurant
with crisp cloth napkins and tablecloths where he went almost every day. The
deferential waiters knew him, always called him “Mr. Trump,” pulled out his
chair, and generally fussed over him throughout the meal. It was better when
Aunt Amy or somebody else from the office joined us because it took the
pressure off Dad; he and my grandfather had little left to say to each other. It
didn’t happen often that Donald was at the office at the same time we were,
but it was much worse when we crossed paths. He acted as though he owned
the place, which my grandfather seemed not only to encourage but to enjoy.
My grandfather was transformed in Donald’s presence.
In 1973, the Department of Justice Civil Rights Division sued Donald and my
grandfather for violating the 1968 Fair Housing Act by refusing to rent to die
Schwarze, as my grandfather put it. It was one of the largest federal housing
discrimination suits ever brought, and the notorious attorney Roy Cohn
offered to help. Donald and Cohn had crossed paths at Le Club, a swanky
members-only restaurant and disco on East 55th Street that was frequented by
Vanderbilts and Kennedys, an array of international celebrities, and minor
royalty. Cohn was more than a decade removed from his disastrous
involvement in Joseph McCarthy’s failed anti-Communist crusade. He’d
been forced to resign from his position as the senator’s chief counsel, but not
until he’d wrecked the lives and careers of dozens of men because of their
alleged homosexuality and/or ties to communism.
Like many men of his vicious temperament and with his influential
connections, Cohn was subject to no rules. Embraced by a certain segment of
the New York elite and hired by a diverse pool of clients such as Rupert
Murdoch, John Gotti, Alan Dershowitz, and the Roman Catholic Archdiocese
of New York, Cohn entered private practice back in New York City, where
he’d grown up. Over the ensuing years, he became very rich, very successful,
and very powerful.
Though Cohn was flashy where Fred was conservative and loud where
Fred was taciturn, the differences between them were really of degree, not
kind. Cohn’s cruelty and hypocrisy were more public, but Fred had, in the
intimate context of his family, also mastered those arts. Fred had also primed
Donald to be drawn to men such as Cohn, as he would later be drawn to
authoritarians such as Vladimir Putin and Kim Jong-un or anyone else, really,
with a willingness to flatter and the power to enrich him.
Cohn recommended that Trump Management file a countersuit against the
Justice Department for $100 million over what he alleged were the
government’s false and misleading statements about his clients. The
maneuver was simultaneously absurd, flashy, and effective, at least in terms
of the publicity it garnered; it was the first time that Donald, at twenty-seven,
had landed on a newspaper’s front page. And although the countersuit would
be tossed out of court, Trump Management settled the case. There was no
admission of wrongdoing, but they did have to change their rental practices to
avoid discrimination. Even so, both Cohn and Donald considered it a win
because of all the press coverage.
When Donald hitched his fortunes to the likes of Roy Cohn, the only
things he had going for him were Fred’s largesse and a carefully cultivated
but delusional belief in his own brilliance and superiority. Ironically, the
defenses he had developed as a young child to protect himself against the
indifference, fear, and neglect that had defined his early years, along with his
being forced to watch the abuse of Freddy, primed him to develop what his
older brother clearly lacked: the ability to be the “killer” and proxy his father
There’s no way to know precisely when Fred started to notice Donald, but
I suspect it was after he shipped his son off to military school. Donald
seemed amenable to his father’s exhortations to be tough, a “killer,” and he
proved his worth by bragging about the random beatings he received from the
upperclassmen or pretending not to care about his exile from home. Fred’s
growing confidence in Donald created a bond between them and an
unshakable self-confidence in Donald. After all, the most important person in
the family, the only one whose opinion mattered, was finally showing him
favor. And unlike Freddy, the attention Donald received from his father was
After college, when Donald was finally out in the world using his father’s
connections to make more connections and using his father’s money to create
his image as a burgeoning Master of the Universe, Fred knew that anything
his son got credit for would redound to his own benefit. After all, if Donald
was embraced as an up-and-coming dealmaker, that was entirely to the credit
of Fred Trump—even if Fred was the only person who knew it.
In interviews in the early 1980s, Fred claimed that Donald’s success had
far exceeded his own. “I gave Donald free rein,” he said. “He has great
visions, and everything he touches seems to turn to gold. Donald is the
smartest person I know.” None of that was true, and Fred must have known
that a decade before he said it.
After Steeplechase, Fred had lost a lot of ground. If he wanted to expand
the reach of his empire, he would need a new playing field and a surrogate.
He needed Donald to go out in the world and create the brand. It hadn’t taken
Fred long to realize that his profligate middle son wasn’t suited to the
unglamorous, tightly budgeted, and highly regimented routine of running
rental properties. But with his father’s backing, maybe he could use his
hubris and shamelessness to make the push into Manhattan. Fred wasn’t
living vicariously; he was intimately involved in all aspects of Donald’s early
forays into the Manhattan market, getting things done behind the scenes
while Donald played to the crowd up front. Fred made it possible for Donald
to play a role that fulfilled his own desire for recognition while allowing his
son to garner the reputation as a Manhattan developer that Fred had always
aspired to. Fred would never get the public recognition, but it was enough for
him to know that the opportunities Donald had to make his mark and promote
himself would never have materialized without him. The success and the
acclaim were due to Fred and his vast wealth. Any story about Donald was
really a story about Fred. Fred also knew that if that secret was uncovered,
the ruse would fall apart. In retrospect, Fred was the puppeteer, but he
couldn’t be seen to be pulling his son’s strings. It’s not that Fred was
overlooking Donald’s incompetence as a businessman; he knew he had more
than enough talent in that arena for both of them. Fred was willing to stake
millions of dollars on his son because he believed he could leverage the skills
Donald did have—as a savant of self-promotion, shameless liar, marketer,
and builder of brands—to achieve the one thing that had always eluded him:
a level of fame that matched his ego and satisfied his ambition in a way
money alone never could.
When things turned south in the late 1980s, Fred could no longer separate
himself from his son’s brutal ineptitude; the father had no choice but to stay
invested. His monster had been set free. All he could do was mitigate the
damage, keep the cash flowing, and find somebody else to blame.
Over the next two years, Dad became more taciturn, more grim, and, if
possible, thinner. The apartment in Sunnyside Towers was grey—grey
because of the northwest exposure, grey from the unending clouds of
cigarette smoke, grey because of his terrible moods. There were mornings
when he barely managed to get out of bed, let alone spend a whole day with
us. Sometimes he was hungover; sometimes it was his depression, which
grew heavier. If we didn’t have anything scheduled, Dad often made an
excuse to leave us alone, saying he had to work or run an errand for Gam.
Once Dad told us he had a job managing paperboys. I’d briefly had a
paper route, and as far as I could tell that meant he was the guy who handed
out the papers to the delivery kids from the trunk of his car, then collected the
cash from them when they’d finished their routes. He told me once that he
made $100 a day, which seemed like an enormous sum to me.
One evening, we were at the apartment having dinner with Dad’s
girlfriend, Johanna. I preferred it when she wasn’t there; something about her
was off-putting. She didn’t connect—or even try to—with me and Fritz. It
was bad enough that she said things such as “Freddy, light me a fag,”
considering she wasn’t British, but Dad started saying them, too.
We’d just finished eating when I started to recount the adventures I’d had
with my mother at the bank that afternoon. While she had waited in the very
long line, I had stood at one of the counters and filled out deposit slips with
all sorts of aliases and wild sums of money I planned to withdraw in order to
fund various schemes. I could barely contain how funny I thought the whole
thing was. But as I told them about the secret identities, the secret
withdrawals of cash, and my fiendish plots to disperse them, Dad got a wary
look in his eyes.
“Does Mr. Tosti know about this?” he asked.
If I’d been paying closer attention, I might have known to stop, but I
thought he was kidding, so I kept telling my story.
Dad got increasingly agitated, leaned forward, and pointed his finger at
me. “What did you do?” As moody as my father could be, I’d rarely seen him
so angry, and I’d almost never heard him raise his voice. I was confused and
tried to retrace my narrative back to the point where he had started to think
I’d done something wrong. But there was no such point, and my explanation
about what had really happened only agitated him further.
“If Mr. Tosti finds out about this, I’m going to be in trouble with your
Johanna put her hand on Dad’s arm, as if to draw his attention away from
me. “Freddy,” she said, “it’s nothing.”
“What do you mean ‘nothing’? This is really goddamn serious.”
I flinched at the curse word.
At that point both Johanna and I knew there was no talking him down. He
was drunk and trapped in some old narrative. I tried to explain it to him, to
steady him, but he was too far gone. And I was only eight.
In the summer of 1975, Donald gave a press conference during which he
presented a rendering of the architect’s plans for the Grand Hyatt, as if he’d
already won the contract to replace the old Commodore Hotel next door to
Grand Central Terminal on 42nd Street. The media printed his claims as fact.
That same summer, just before Fritz and I were scheduled to leave for
camp, Dad had told Mom that he had some news. She invited him to dinner. I
answered the door when Dad rang the bell. He was wearing what he almost
always wore—black slacks and a white dress shirt—but his clothes were
crisp and his hair was slicked back. I had never seen him look so handsome.
While Mom tossed the salad, Dad grilled the steak on our small terrace.
When the food was ready, we sat at the small table next to the terrace,
propping the door open so the mild summer breeze could blow in. We drank
water and iced tea.
“I’m moving to West Palm Beach at the end of the summer,” he told us. “I
found a great apartment on the Intracoastal with a dock in the back.” He
already had a boat picked out, and when we visited, he’d take us fishing and
waterskiing. As he spoke, he seemed happy and confident—and relieved. All
of us knew it was the right decision; for the first time in a very long time, we
I sat at the dining room table with the shoe in front of me, trying to figure out
what the point of it was. I had looked through the remaining boxes under the
tree, thinking that perhaps the shoe’s twin had been wrapped separately, but
no, there was just the one—a gold lamé shoe with a four-inch heel filled with
hard candy. Both the individual candies and the shoe itself were wrapped in
cellophane. Where had this thing come from? I wondered. Had it been a door
prize or a party favor from a luncheon?
Donald came through the pantry from the kitchen. As he passed me, he
asked, “What’s that?”
“It’s a present from you.”
“Really?” He looked at it for a second. “Ivana!” he shouted into the foyer.
She was standing on the other side of the Christmas tree near the living room.
“What is it, Donald?”
“This is great.” He pointed at the shoe, and she smiled. Maybe he thought
it was real gold.
It had all started in 1977 with a three-pack of Bloomie’s underwear, retail
$12, my very first Christmas present from Donald and his new wife, Ivana.
That same year, they had given Fritz a leather-bound journal. It looked as
though it were meant for somebody older, but it was really nice, and I felt a
bit slighted until we realized that it was two years out of date. At least the
underwear wouldn’t expire.
On holidays, Donald and Ivana pulled up to the House in either an
expensive sports car or a chauffeur-driven limo that was even longer than my
grandfather’s. They swept into the foyer like socialites, Ivana in her furs and
silk and outrageous hair and makeup, Donald in his expensive three-piece
suits and shiny shoes, everyone else looking conservative and unfashionable
I grew up thinking that Donald had struck out on his own and singlehandedly built the business that had turned my family name into a brand and
that my grandfather, provincial and miserly, cared only about making and
keeping money. On both counts, the truth was vastly different. A New York
Times article published on October 2, 2018, that uncovered the vast amounts
of alleged fraud and quasi-legal and illegal activities my family had engaged
in over the course of several decades included this paragraph:
Fred Trump and his companies also began extending large loans and
lines of credit to Donald Trump. Those loans dwarfed what the other
Trumps got, the flow so constant at times that it was as if Donald
Trump had his own Money Store. Consider 1979, when he borrowed
$1.5 million in January, $65,000 in February, $122,000 in March,
$150,000 in April, $192,000 in May, $226,000 in June, $2.4 million in
July and $40,000 in August, according to records filed with New Jersey
In 1976, when Roy Cohn suggested that Donald and Ivana sign a
prenuptial agreement, the terms set for Ivana’s compensation were based on
Fred’s wealth because at the time Donald’s father was his only source of
income. I heard from my grandmother that, in addition to alimony and child
support as well as the condo, the prenup, at Ivana’s insistence, included a
“rainy day” fund of $150,000. My parents’ divorce agreement had also been
based on my grandfather’s wealth, but Ivana’s $150,000 bonus was worth
almost twenty-one years of the $600-per-month checks my mother received
for child support and alimony.
Before Ivana, there had always been a sameness to the holidays that made
them blur together. Christmas when I was five was indistinguishable from
Christmas when I was eleven. The routine never varied. We’d enter the
House through the front door at 1:00 p.m., dozens of packages in tow,
handshakes and air kisses all around, then gather in the living room for
shrimp cocktail. Like the front door, we used the living room only twice a
year. Dad came and went, but I have no recollection of his being there one
way or another.
Thanksgiving and Christmas dinners were identical, although one
Christmas, Gam had the temerity to make roast beef instead of turkey. It was
a meal everybody liked, but Donald and Robert were pissed off. Gam spent
the whole meal with her head bowed, hands in her lap. Just when you thought
the subject was dropped for good, one of them would say some version of
“Jesus, Mom, I can’t believe you didn’t make turkey.”
Once Ivana became a part of the family, she joined Donald at the power
center of the table, where he sat at my grandfather’s right hand, his only
equal. The people nearest to them (Maryanne and Robert and Ivana) formed a
claque with one mission: to prop Donald up, follow his lead in conversation,
and defer to him as though nobody was as important as he was. I think that
initially, it was simply an expedient—Maryanne and Robert had learned early
on that there was no point in contradicting their father’s obvious preference.
“I never challenged my father,” Maryanne said. “Ever.” It was easier to go
along for the ride. Donald’s chiefs of staff are prime examples of this
phenomenon. John Kelly, at least for a while, and Mick Mulvaney, without
any reservations at all, would behave the same way—until they were ousted
for not being sufficiently “loyal.” That’s how it always works with the
sycophants. First they remain silent no matter what outrages are committed;
then they make themselves complicit by not acting. Ultimately, they find they
are expendable when Donald needs a scapegoat.
Over time, the discrepancy between Fred’s treatment of Donald and his
other children became painfully clear. It was simpler for Rob and Maryanne
to toe the party line in the hope that they wouldn’t get treated any worse,
which seems to be the same calculation Republicans in Congress make every
day now. They also knew what had happened to my father when he failed to
meet Fred’s expectations. The rest of us at the other end of the table were
superfluous; our job was to fill the cheap seats.
A year after the gold lamé shoe, the gift basket I received from Donald
and Ivana hit the trifecta: it was an obvious regift, it was useless, and it
demonstrated Ivana’s penchant for cellophane. After unwrapping it, I noticed,
among the tin of gourmet sardines, the box of table water crackers, the jar of
vermouth-packed olives, and a salami, a circular indentation in the tissue
paper that filled the bottom of the basket where another jar had once been.
My cousin David walked by and, pointing at the empty space, asked, “What
“I have no idea. Something that goes with these, I guess,” I said, holding
up the box of crackers.
“Probably caviar,” he said, laughing. I shrugged, having no idea what
I grabbed the basket handle and walked toward the pile of presents I’d
stacked next to the stairs. I passed Ivana and my grandmother on the way,
lifted the basket, said, “Thanks, Ivana,” and put it on the floor.
“Is that yours?”
At first I thought she was talking about the gift basket, but she was
referring to the copy of Omni magazine that was sitting on top of the stack of
gifts I’d already opened. Omni, a magazine of science and science fiction that
had launched in October of that year, was my new obsession. I had just
picked up the December issue and brought it with me to the House in the
hope that between shrimp cocktail and dinner I’d have a chance to finish
“Bob, the publisher, is a friend of mine.”
“No way! I love this magazine.”
“I’ll introduce you. You’ll come into the city and meet him.”
It wasn’t quite as seismic as being told I was going to meet Isaac Asimov,
but it was pretty close. “Wow. Thanks.”
I filled a plate and went upstairs to my dad’s room, where he’d been all
day, too sick to join us. He was sitting up, listening to his portable radio. I
handed the plate to him, but he put it on the small bedside table, not
interested. I told him about Ivana’s generous offer.
“Wait a second; who does she want to introduce you to?”
I would never forget the name. I’d looked at the magazine’s masthead
right after speaking to Ivana, and there he was: Bob Guccione, Publisher.
“You’re going to meet the guy who publishes Penthouse?” Even at
thirteen I knew what Penthouse was. There was no way we could be talking
about the same person. Dad chuckled and said, “I don’t think that’s such a
good idea.” And all of a sudden, neither did I.
It was impossible to laugh about the presents my mother received. Why she
was still expected to attend family holidays years after her divorce from my
father was a mystery, but why she went was an even bigger mystery. Clearly,
the Trumps didn’t want her there any more than she wanted to be there. Some
of the presents they gave her were nice enough, but they always came from
lesser stores than the gifts for Ivana and Robert’s wife, Blaine. Worse, many
of them had clearly been regifted. A handbag she got from Ivana one year
bore a luxury brand but contained a used Kleenex.
After dinner and the opening of presents, we split up—some of us went to
the kitchen, some to the backyard, and the rest of us to the library, where I sat
on the floor near the door with my legs crossed. From a distance I watched
whatever Godzilla movie or football game Donald and Rob happened to have
on. After a while, I noticed my mother wasn’t around. I didn’t worry at first,
but when she didn’t return, I went to look for her. I checked the kitchen but
found only my grandmother and aunts. I went out to the backyard, where my
brother and David were throwing a football around. When I asked Fritz
where she was, he said, “I have no idea,” clearly not interested. With time, I
would know where to find her without needing to ask, but the first few times
I felt panic.
Mom was in the dining room, sitting alone at the table. By then the
sideboard had been cleared, and the only evidence of the meal was a few
stray cloth napkins on the floor. I stood in the doorway, hoping she would
notice me and that my presence would set her back into motion. I was afraid
to say anything, not wanting to disturb her. While the clatter of dishes and
talk about leftovers and ice cream cake filtered out from the kitchen, I
approached the mahogany table in the fading afternoon light. The chandelier
had been extinguished, but I wished it had been even darker so that I didn’t
have to see my mother’s face, how stricken she looked.
Careful not to touch her, I sat in the chair next to her. There was no
comfort I could give or take except in solidarity.
Eight months before the gift of underwear, Donald and Ivana were married at
Marble Collegiate Church and held their reception at the 21 Club. Mom,
Fritz, and I were relegated to the cousins’ table, and Dad wasn’t there. The lie
the family told was that Dad had been asked to be Donald’s best man and his
MC at the reception (a role Joey Bishop actually filled) but the family had
decided he needed to stay in Florida in order to take care of Uncle Vic,
Gam’s brother-in-law. The truth was, my grandfather simply didn’t want him
at the wedding and he had been told not to come.
While Donald was cruising Manhattan looking for foreclosures, I was losing
tens of thousands of dollars almost every week. On Fridays after school, I
went to a friend’s house and we played our version of Monopoly: double
houses and hotels, double the money. Our sessions were marathons spanning
the entire weekend. One game could last anywhere from thirty minutes to
several hours. The only constant in all of that gaming was my performance: I
lost every single time I played.
In order to give me a fighting chance (and my friend something of a
challenge), I was allowed to borrow increasingly huge sums of money from
the bank and eventually from my opponent. We kept a running total of my
enormous debt by writing the sums I owed in long columns of numbers on
the inside of the cover.
Despite my terminally poor performance, I never once changed my
strategy; I bought every Atlantic City property I landed on and put houses
and hotels on my properties even when I had no chance of recouping my
investment. I doubled and tripled down no matter how badly I was losing. It
was a great joke between me and my friends that I, the granddaughter and
niece of real estate tycoons, was terrible at real estate. It turned out that
Donald and I had something in common after all.
Since my father’s death, Donald has suggested that “they” (meaning he
and my grandfather) should have “let” Freddy do what he loved and excelled
at (flying) rather than force him to do something he hated and was bad at
(real estate). But there’s no evidence to suggest that my father lacked the
skills to run Trump Management, just as there is none to suggest that Donald
One night in 1978, Dad woke up in his West Palm Beach apartment with
excruciating stomach pains. He managed to drag himself to his car and drove
to the emergency room. He later told Mom that when he had gotten to the
hospital, he hadn’t gone in right away. He had stayed in his car, wondering if
he should bother. Perhaps it would be simpler, he had thought, if it just
ended. The only thing that had forced him to get help was the thought of me
Dad was very sick and was transferred to a Miami hospital, where the
doctors diagnosed him with a heart defect that required surgery. Fred told
Maryanne to fly to Florida, get him out of the hospital, and bring him back to
New York. It would be my father’s last trip north. After three years in
Florida, he was going home.
In New York, doctors discovered that Dad had a faulty mitral valve and
his heart had become dangerously enlarged. He needed to undergo an
experimental procedure to replace it with a healthy valve from a pig’s heart.
When Mom and I got to the House to see Dad the day before his surgery,
Elizabeth was already there, sitting with him in his tiny childhood bedroom,
which we called “the Cell.” He lay in his cot, and I kissed him on the cheek
but didn’t sit next to him for fear of breaking him. I’d seen Dad sick before—
with pneumonia, with jaundice, with drunkenness, with despair—but his
condition now was shocking. Not yet forty, he looked like a worn-out eightyyear-old man. He told us about the procedure and the pig valve, and Mom
said, “Freddy, it’s a good thing you’re not kosher.” We all laughed.
It was a long recovery, and Dad stayed at the House to recuperate. A year
after the surgery, he was better than he had been, but he would never be well
enough to live on his own again. Part of the obstacle to that may have been
financial. He started working for my grandfather again but this time on a
maintenance crew. It wasn’t surprising that apart from a few stints in rehab to
dry out, he had never stopped drinking. He told me once that one of his
doctors had warned him, “If you have another drink, it’s going to kill you.”
Even open-heart surgery wasn’t enough to stop him.
That Thanksgiving, Dad joined us for the first time since he’d moved back
to New York. He sat with me at Gam’s end of the table, pale and thin as a
Halfway through the meal, Gam started choking. “You okay, Mom?” Dad
asked. Nobody else seemed to notice. As she continued to struggle, a couple
of people at the other end of the table looked up to see what was going on but
then looked down at their plates and continued eating.
“Come on,” Dad said as he put a hand under Gam’s elbow and gently
helped her to her feet. He led her to the kitchen, where we heard some
shuffling and the distressing sound of my grandmother’s grunts as Dad
performed the Heimlich maneuver; he’d learned it when he had been a
volunteer ambulance driver in the late 1960s and early ’70s.
When they returned, there was a desultory round of applause. “Good job,
Freddy,” Rob said, as if my father had just killed a mosquito.
Donald was becoming a constant presence even when he wasn’t in the House.
Every time my father wanted to go to the kitchen or back to his room, he had
to pass through the gauntlet of magazine covers and newspaper articles that
littered the breakfast room table. Ever since the 1973 lawsuit, Donald had
been a staple of the New York tabloids, and my grandfather had collected
every single article that mentioned his name.
The Grand Hyatt deal Donald was working on when Dad moved back to the
House was merely a more complex version of the 1972 partnership my
grandfather had formed with Donald in New Jersey. The Grand Hyatt was
initially made possible because of my grandfather’s association with New
York City mayor Abe Beame. Fred also contributed generously to both the
mayor’s and Governor Hugh Carey’s campaigns. Louise Sunshine, Carey’s
fund-raiser, helped pull the deal together. In order to seal it, Beame offered
him a $10-million-a-year tax abatement that would remain in place for forty
years. When the demolition of the Commodore Hotel began, the New York
press, taking Donald at his word, consistently presented the deal as something
Donald had accomplished single-handedly.
Perhaps to bridge the gap that had widened between us since he’d moved
back to New York, Dad told me he wanted to throw me a Sweet Sixteen party
in May 1981. The Grand Hyatt had had its grand opening a few months
earlier, and Dad said he’d ask Donald if we could use one of the smaller
ballrooms. Donald, who seemed eager for the chance to show off his new
project to the family, readily agreed and even offered him a discount.
Dad told my grandfather about the plans for the party a few days later
when the three of us were in the breakfast room, the ubiquitous clippings
covering the table. “Fred,” he said angrily, “Donald’s busy, he doesn’t need
The subtext was clear: Donald is important, and he’s doing important
things; you’re not.
I don’t know how the situation got resolved, but Dad eventually pulled it
off. I was going to have my party.
Most of my guests had arrived and I was standing with a small group of
friends when Donald made his entrance. He walked over to us, and instead of
saying hello, he spread his arms and said, “Isn’t this great?”
We all agreed that it was, indeed, great. I thanked him again for letting us
use the hotel, then introduced him to everybody.
“So what’d you think of that lobby? Fantastic, right?”
“Fantastic,” I said. My friends nodded.
“Nobody else could have pulled this off. Just look at those windows.”
I worried that he might tell us how great the bathroom tiles were next, but
he saw my grandparents, shook my hand, kissed me on the cheek, said,
“Have fun, Honeybunch,” and walked over to them. My dad was sitting a
couple of tables away from them, by himself.
When I turned back to my friends, they were staring at me.
“What the hell was that?” one of them asked.
In the summer of 1981, Maryanne drove my father to the Carrier Clinic in
Belle Mead, New Jersey, about half an hour from the Bedminster property
that Donald would later turn into a golf course. Dad went through the thirtyday program, but he did it reluctantly. At the end of his stay, Maryanne and
her second husband, John Barry, picked him up and brought him back to the
House, arguably the worst place he could be. When she checked on him the
next day, Dad had already started drinking again.
Freddy had lost his home and family, his profession, much of his
willpower, and most of his friends. Eventually his parents were the only
people left to take care of him. And they resented it. In the end, Freddy’s very
existence infuriated his father.
Fred’s treatment of my father had always served as an object lesson to his
other children—a warning. In the end, though, the control became something
much different. Fred wielded the complete power of the torturer, but he was
ultimately as trapped in the circumstance of Freddy’s growing dependence
due to his alcoholism and declining health as Freddy was tied to him. Fred
had no imagination and no ability to see a way beyond the circumstances he
was essentially responsible for having created. The situation was proof that
his power had limits.
After I got home from summer camp that August, I announced that I wanted
to go to boarding school. I explained to Dad that after ten years at KewForest, the same extremely small school my aunts and uncles had gone to, I
was feeling hemmed in and bored. I wanted more of a challenge, a place with
a campus, better sports facilities, more opportunities. Dad warned me about
the dangers of becoming a small fish in a big pond, but I think he understood
that although my stated reasons were all true, I also needed to get away.
The problem was that I had only three weeks to figure out where I wanted
to go, fill out applications, and get accepted. Over the last two weeks of
August 1981, my mother and I visited almost every boarding school in
Connecticut and Massachusetts.
While I waited for the results, we needed to get permission from my
grandfather, or at least that’s what Dad said.
The two of us stood in front of my grandfather’s usual spot on the love
seat, and Dad explained what I wanted to do. “What does she want to do that
for?” my grandfather asked, as if I weren’t standing right in front of him.
“Kew-Forest is fine.” He’d been on the board there for almost thirty years.
“It’s just time for a change. Come on, Pop. It’ll be good for her.”
My grandfather complained about the extra expense, even though the
money would come from my father’s trust fund and wouldn’t affect him at
all, and he reiterated his belief in the superiority of Kew-Forest. But Dad
didn’t back down.
I don’t think my grandfather really cared where I went to school, but I was
grateful that Dad had stood by my side once again.
The day before heading to boarding school, I left the apartment at the
Highlander and rode my bike to my grandparents’ house. I coasted down the
driveway, propped my bike against the high brick wall next to the garage,
then climbed the stairs to the path leading to the back door.
The backyard was quiet in the early-September afternoon. I jumped up the
two steps to the cement patio and rang the doorbell. There was no outdoor
furniture, just an empty slab. The only person who’d ever used it when we
were younger was my uncle Rob. At one time there had been a couple of
wrought-iron chairs out there, and when he was home for the weekend, he’d
pull them together, and, using one as a footrest, he’d slather himself with
baby oil and prop his folding aluminum tanning reflector under his chin.
Minutes passed. I was about to press the doorbell again when my
grandmother finally answered the door. She seemed surprised to see me. I
pulled the screen door toward me to enter, but Gam remained in the doorway.
“Hi, Gam. I’m here to see Dad.”
Gam stood there wiping her hands on her apron, tense, as if I’d just caught
her at something. I reminded her that I was leaving for school the next day.
She was quite tall, and with her blond hair swept up and pinned tightly
behind her head, she looked more severe than usual. She didn’t move to let
“Your father’s not home,” she said. “I don’t know when he’ll be back.”
I was confused. I knew my father had wanted to see me off—we’d talked
about it only a few days before. I assumed that he had forgotten I was coming
by. In the last year, he’d often forgotten when we had plans. I wasn’t
surprised, exactly, but something about it still didn’t seem right. Directly
above where my grandmother and I stood, the sound of a radio came through
the open window of my father’s bedroom.
I shrugged at Gam, pretending not to care. “Okay, then, I guess tell him to
call me later.” I moved toward her for a hug, and she put her arms around me
stiffly. When I turned to leave, I heard the door close. I walked down the path
and down the stairs to the driveway, got on my bike, and rode home. I left for
school the next day. Dad never called me.
I was watching a movie in the brand-new auditorium of the Ethel Walker
School when the projector went dark and the lights came up. The students
were there to watch The Other Side of the Mountain, an uplifting story about
an Olympic skier who becomes paralyzed in a skiing accident. Instead, The
Other Side of Midnight—a decidedly different kind of movie with an early
rape scene—had been ordered. The faculty were in a bit of a tumult trying to
figure out what to do next, while we students thought it was hysterical.
As I sat talking and laughing with some kids from my dorm, I saw Diane
Dunn, a phys ed teacher, making her way through the crowd. Dunn was also
a counselor at the sailing camp I went to every summer, so I’d known her
since I was a little kid. To everyone else at Walker’s, she was Miss Dunn,
which I found impossible to wrap my head around. At camp she was Dunn
and I was Trump, and that’s what we continued to call each other. She was
largely responsible for my having decided to go to this boarding school, and
after I had been there for only two weeks, she was still the only person I
When she waved me over, I smiled and said, “Hey, Dunn.”
“Trump, you need to call home,” she said. She had a piece of paper in her
fist but didn’t give it to me. She looked flustered.
“You need to call your mother.”
“Yes. If she isn’t home, call your grandparents.” She was speaking to me
as if she’d memorized the lines.
It was almost 10:00 p.m., and I had never called my grandparents so late,
but my dad and grandmother were both in the hospital pretty frequently—
Dad due to his years of heavy drinking and smoking, and Gam’s tendency to
break bones fairly often because of her osteoporosis. So I wasn’t really
worried—or, rather, I didn’t think it was anything more serious than usual.
My dorm was adjacent to the auditorium, so I went outside, crossed the
oval lawn between them, and climbed the two flights of stairs to my floor.
The pay phone hung on the stairwell wall on the landing right next to the
I placed a collect call to my mother, but there was no answer, so I dialed
the House. Gam answered and accepted the charges—so the emergency
wasn’t about her. After a quick, muffled “Hello,” she immediately handed the
phone to my grandfather.
“Yes,” he said, brisk and businesslike as usual. For a moment, it was easy
to believe that there had been a mistake, that nothing was really wrong. But
then something had been urgent enough for me to be pulled out of the
auditorium. I had also seen the way Dunn’s eyes had widened in panic as she
looked for me in the auditorium. It would only occur to me much later that
she already knew.
“What’s the matter?” I asked.
“Your mother just left,” he said. “She should be home in a few minutes.” I
could picture him in the poorly lit library standing next to the telephone table
wearing his starched white shirt, red tie, and navy blue three-piece suit,
impatient to be done with me.
“But what’s wrong?”
“Your father has been taken to the hospital, but it’s nothing to worry
about,” he said as though reporting the weather.
I could have hung up then. I could have gone back to trying to fit in with
my new classmates at my new school.
“Is it his heart?” It was unheard of for me—for anyone but Donald—to
challenge my grandfather in any way, but there was obviously a reason I’d
been told to call.
“Then it’s serious.”
“Yes, I would say it’s serious.” There was a pause during which, perhaps,
he was deciding whether to tell me the truth. “Go to sleep,” he said finally.
“Call your mother in the morning.” He hung up.
I stood there in the stairwell with the phone in my hand, not knowing quite
what to do. A door slammed on the floor above me. Footsteps followed,
growing louder. A couple of students passed me on their way to the first
floor. I put the receiver back into the cradle, picked it up, and tried my mother
This time she answered the phone.
“Mom, I just spoke to Grandpa. He told me Dad’s in the hospital, but he
wouldn’t tell me what’s going on. Is he okay?”
“He had a heart attack,” my mother said.
From the moment she spoke, time took on a different quality. Or maybe it
was the next moment, which I don’t remember, and the effect of the shock
was retroactive. Either way, my mother kept talking but I didn’t hear any of
the words she said. As far as I could tell, there was no gap in the
conversation, but part of it never existed for me.
“He had a heart attack?” I said, echoing the last words I’d heard, as if I
hadn’t missed something crucial.
“Oh, Mary, he’s dead.” My mother started to cry. “I really did love him
once,” she said.
As my mother continued to speak, I slid down the wall until I was sitting
on the floor of the landing. I dropped the phone, let it hang on its cord, and
Sometime in the afternoon of Saturday, September 26, 1981, one of my
grandparents called an ambulance. I didn’t know it then, but my father had
been critically ill for three weeks. It was the first time anybody had called for
My grandmother had been a regular at Jamaica Hospital and Booth
Memorial Hospital and Medical Center. My dad, too, had been admitted to
Jamaica a few times. All of my grandparents’ children had been born there,
so the family had a long-standing relationship with the staff and
administration. My grandparents had donated millions of dollars to Jamaica
in particular, and in 1975 the Trump Pavilion for Nursing and Rehabilitation
had been named for my grandmother. As for Booth Memorial, my
grandmother was heavily involved with the Salvation Army volunteers there
—and it was also where I’d spent much of my childhood because of my
severe asthma. A single phone call would have guaranteed the best treatment
for their son at either facility. No call was made. The ambulance took my
father to the Queens Hospital Center in Jamaica. No one went with him.
After the ambulance left, my grandparents called their other four children,
but only Donald and Elizabeth could be reached. By the time they arrived in
the late afternoon, the information coming from the hospital made it clear that
my father’s situation was grave. Still nobody went.
Donald called my mother to let her know what was going on but kept
getting a busy signal. He got in touch with our superintendent and told him to
buzz her on the intercom.
Mom immediately called the House.
“The doctors think Freddy probably won’t make it, Linda,” Donald told
her. My mother had had no idea that Dad was even sick.
“Would it be all right if I came to the House so I can be there if there’s any
news?” She didn’t want to be alone.
When my mother arrived a short time later, my grandparents were sitting
alone by the phone in the library; Donald and Elizabeth had gone to the
While Mom sat with my grandparents, nobody said much. A couple of
hours later, Donald and Elizabeth returned. When they were told there was no
news, Donald left, and Elizabeth, nearing forty, made a cup of tea and went
upstairs to her room. As my mother was getting ready to leave, the phone
rang. It was the hospital. Dad had been pronounced dead at 9:20 p.m. He was
Nobody thought to come get me from school, but arrangements were made
for me to take a bus the next morning. Dunn drove me to the Greyhound
station in Hartford, where I boarded a bus bound for the Port Authority Bus
Terminal in Manhattan. After picking me up in the city, my mother, brother,
and I drove to the House, where the rest of the family was already gathered in
the breakfast room to discuss the funeral arrangements. Maryanne and her
son, my cousin David, were there; my uncle Robert and Blaine; and Donald,
Ivana, almost eight months pregnant with Ivanka, and their three-year-old
son, Donny. Nobody said much to my mother, brother, or me. There were
some attempts at forced heartiness, mostly by Rob, but they didn’t land well
and soon stopped. My grandfather and Maryanne spoke in hushed tones. My
grandmother fretted about what she was going to wear to the wake; my
grandfather had picked out a black pantsuit for her, and she wasn’t pleased.
In the afternoon, we drove over to R. Stutzmann & Son Funeral Home, a
small place in Queens Village about ten minutes from the House, for a
private viewing. Before going into the main room, where the coffin was
already perched on its stand, I asked my uncle Robert if I could discuss
something with him. I pulled him into a small alcove down the hall from the
visitation room. “I want to see Dad’s body.” I saw no reason not to be direct.
I didn’t have a lot of time.
“You can’t, Mary. It’s impossible.”
“Rob, it’s important.” It wasn’t for religious reasons or because I thought
that was how things were done; I had never been to a funeral before and
knew nothing about protocol. Although I knew I needed to see my father, I
couldn’t articulate why. How could I say, “I don’t believe he’s dead. There’s
no reason for me to believe that. I didn’t even know he was sick”? I could
only say, “I need to see him.”
Rob paused and finally said, “No, Honeybunch. Your dad is being
cremated, and his body hasn’t been prepared. It would be terrible for that to
be the last memory you have of him.”
“It doesn’t matter.” I felt desperate in a way I didn’t understand. Rob
looked down at me and then turned to leave. I stepped in front of him.
He paused again, then began walking down the hall. “Come on,” he said.
“We should go in.”
On Monday, in between the two sessions of the wake, the family went
back to the House for lunch. On the way, Donald and Ivana had gone to the
supermarket and picked up large quantities of prepackaged cold cuts that
Maryanne and Elizabeth laid out on the breakfast room table and we ate or
ignored in relative silence.
I had no appetite and wasn’t part of the conversation, so I left the breakfast
room to wander around the house, as I’d used to do when I was younger. I
walked to the back stairs across from the library doorway and caught a
glimpse of Donald holding the telephone in his hand. I don’t know if he had
just finished a call or was about to make one, but when he noticed me
standing in the hallway, he returned the handset to the cradle. Neither one of
us spoke. I hadn’t seen Donald since Mother’s Day, which we had celebrated
at North Hills, my grandparents’ country club on Long Island. I didn’t expect
tears from anybody except my grandmother, but Donald, and particularly my
grandfather, seemed to be taking my dad’s death in stride. “Hey, Donald.”
“What’s up, Honeybunch?” I sometimes wondered if either of my uncles
actually knew my name.
“Dad’s going to be cremated, right?” I had known for years that that was
what Dad wanted. He had felt so strongly about not being buried that it was
one of the first things he had told my mother after they were married. His
insistence upon it bordered upon an obsession, which was why I had known
about it before I turned ten.
“And then what? He’s not going to be buried, is he?”
A look of impatience crossed his face. It was clear he didn’t want to be
having that conversation. “I think he is.”
“You know that makes no sense, right?”
“That’s what Dad wants.” He picked up the phone. When he noticed I
wasn’t moving, he shrugged and started to dial.
I turned to climb the back stairway. On one end of the long second-floor
hallway was Elizabeth’s corner room with Maryanne’s on the other side of
their joint bathroom; on the other, Donald and Robert’s shared bedroom was
outfitted with blue-and-gold bedspreads and matching window treatments.
My grandparents’ much larger master bedroom stood right next to theirs and
included Gam’s separate dressing room with mirrored walls. In the middle of
the hallway was the Cell. Dad’s cot had been stripped, exposing the thin
mattress. His portable radio was still on the small bedside table. The door to
the closet was ajar, and I saw a couple of white button-down shirts hanging
askew on wire hangers. Even on such a sunny day, the only window let in
little light, and the room looked austere in the shadows. I thought I should go
in, but there was nothing for me there. I went back downstairs.
The wake fell on the first night of Rosh Hashanah, but many of Dad’s
fraternity brothers still came. His friend Stu, who had often attended dinner
parties and charity events at Jamaica Hospital with his wife, Judy, probably
knew my family better than any of Dad’s friends other than Billy Drake. Stu
saw my grandfather standing alone in the back of the room, and he walked
over to pay his respects. The two men shook hands and, after offering his
condolences, Stu said, “It looks like real estate isn’t doing so well. I hope
Donald’s okay. I see him in the news a lot, and it looks like he owes the
banks a lot of money.”
Fred put his arm around his dead son’s friend and said with a smile,
“Stuart, don’t worry about Donald. He’s going to be just fine.” Donald wasn’t
My brother gave the only eulogy (or, at least, the only one I remember),
written on a sheet of loose-leaf paper, probably on the plane ride from
Orlando, where he was a sophomore at Rollins College. He reminisced about
the good times he and Dad had had together, most of which had occurred
before I had been old enough to remember them, but he refused to shy away
from the fundamental reality of my father’s life. At one point he referred to
Dad as the black sheep of the family, and there were audible gasps from the
guests. I felt a thrill of recognition and a sense of vindication—at long last.
My brother, who had always been so much better at negotiating the family
than I was, had dared tell the truth. I admired his honesty but also felt jealous
that he seemed to have so many more good memories of my father than I did.
As the wake drew to a close, I watched as people began to line up, walk
past the coffin, pause with eyes closed, hands clasped—sometimes kneeling
on a low cushioned bench that seemed to have been put there for the purpose
—and then move on.
When my aunt Elizabeth’s turn came, she began to sob uncontrollably. In
the midst of all that stoicism, her display of emotion was jarring, and people
looked at her with muted alarm. But no one approached her. She placed her
hands on the coffin and slid to her knees. Her body was shaking so badly that
she lost her balance and fell sideways to the floor. I watched her fall. She lay
there as if she had no idea where she was or what she was doing and
continued to cry. Donald and Robert finally came from the back of the room,
where they’d been talking to my grandfather, who stayed where he was.
My uncles lifted Elizabeth from the floor. She limped between them as
they pulled her from the room.
I approached the coffin eventually, tentatively. It seemed impossibly
small, and I thought that there must have been a mistake. There was no way
my father, at six feet two, could have fit inside that box. I ignored the bench
and remained on my feet. I bowed my head, concentrating hard on one of the
coffin’s brass fixtures. Nothing came to me.
“Hi, Dad,” I finally said under my breath. I wracked my brains as I stood
there looking down, until it occurred to me that I might be standing at the
wrong end of the coffin, that the conversation I was trying to have with my
father was being directed at his feet. Mortified, I took a step back and
returned to my friends.
There was no church ceremony. The coffin was transferred to the
crematorium, and we met briefly in the chapel next door—oddly sundrenched and bright—where a minister of no specified denomination
demonstrated both his utter lack of knowledge of my father and the fact that
nobody in the family had bothered to educate him about the man he was soon
to consign to the flames.
When the business of the funeral was complete, the family planned to take
a drive to the All Faiths Cemetery in Middle Village where the family plot
was; my grandfather’s parents, Friedrich and Elizabeth Trump, were the only
occupants at the time. I later learned that over the preceding two days, my
mother and my brother and I had separately pleaded with different members
of the family to allow my father’s ashes to be spread over the waters of the
Before we left the chapel, I caught up with my grandfather to make one
final plea. “Grandpa,” I said, “we can’t bury Dad’s ashes.”
“That’s not your decision to make.”
He started to walk away, but I grabbed his sleeve, knowing it would be my
last chance. “Wasn’t it his?” I asked. “He wanted to be cremated because he
didn’t want to be buried. Please, let us take his ashes out to Montauk.”
As soon as the words came out of my mouth, I realized that I’d made a
critical mistake. My grandfather realized it, too. He associated Montauk with
my father’s frivolous hobbies, such as boating and fishing, activities that had
distracted him from the serious business of real estate.
“Montauk,” he repeated, almost smiling. “That’s not going to happen. Get
in the car.”
Sunlight glinted off the marble and granite grave markers as our
grandfather, his light blue eyes squinting beneath his enormous eyebrows at
the brightness of the day, explained that the tombstone, which was already
inscribed with his mother’s and father’s names, would be removed
temporarily so my father’s name and dates could be added. As he spoke, he
spread his hands wide, like a used-car salesman, bouncing on the balls of his
feet, almost jaunty, knowing he was in the presence of a rube.
My grandfather followed the letter of the law and then did what he
wanted. After my father was cremated, they put his ashes into a metal box
and buried them in the ground.
Dad’s death certificate, dated September 29, 1981, states that he died of
natural causes. I don’t know how that is possible at forty-two. There was no
will. If he had anything to leave—books, photographs, his old 78s, his ROTC
and National Guard medals—I don’t know. My brother got Dad’s Timex. I
didn’t get anything.
The House seemed to grow colder as I got older. The first Thanksgiving after
Dad died, the House felt colder still.
After dinner, Rob walked over and put his hand on my shoulder. He
pointed to my new cousin, Ivanka, asleep in her crib. “See, that’s how it
works.” I understood the point he was trying to make, but it felt as though it
was on the tip of his tongue to say, “Out with the old, in with the new.” At
least he had tried. Fred and Donald didn’t act as if anything was different.
Their son and brother was dead, but they discussed New York politics and
deals and ugly women, just as they always had.
When Fritz and I were home for Christmas vacation, we met with Irwin
Durben, one of my grandfather’s lawyers and, after Matthew Tosti died, my
mother’s main contact, in order to go over the details of my father’s estate. I
was shocked to find out that he had one. I thought he’d died virtually
penniless. But apparently there were trust funds that had been set up by my
grandfather and great-grandmother, such as the one that had paid for
boarding school, that I didn’t know about at the time. They were to be split
between me and my brother and kept in trust until we turned thirty. The
people appointed to manage those trust funds and to protect our long-term
financial interests were Irwin Durben, my aunt Maryanne, and my uncles
Donald and Robert. Although Irwin was the point man—it was he we had to
call or meet with if we had a question or a problem or any unforeseen
financial needs—Donald was the ultimate arbiter of approval and the
cosigner of all checks.
Stacks of documents covered Irwin’s desk. He sat in his chair behind them
and began to explain what, exactly, we were about to sign. Before we got
very far, Fritz interrupted him and said, “Mary and I talked about this earlier,
and first we need to make sure that Mom will be taken care of.”
“Of course,” Irwin said. Then over the next two hours he methodically
went through every piece of paper. The actual amount of money my father
had left wasn’t clear to me. The trusts were complex financial arrangements
(at least to a sixteen-year-old), and there was what seemed to be a huge tax
burden. After explaining each document’s significance, Irwin pushed it
across the desk for us to sign.
When he finished, he asked if we had any questions.
“No,” Fritz said.
I shook my head. I hadn’t understood a thing Irwin had said.
Smoke and Mirrors
The Art of the Bailout
“MARY TRUMP MUGGED” the New York tabloids, subtle as ever, blared in
100-point font the day after Halloween 1991. Even though I already knew
what had happened, it was jarring to see the headlines as I passed news
kiosks on my way to the subway.
My grandmother hadn’t just been mugged, though. The kid who’d grabbed
her purse in the grocery store parking lot as she loaded shopping bags into
her Rolls-Royce had slammed her head against the car with such force that
her brain had hemorrhaged, and she had lost some sight and hearing. When
she hit the pavement, her pelvis fractured in several places and ribs broke,
injuries that were no doubt more dangerous than they might have been if she
hadn’t had severe osteoporosis. By the time she arrived at Booth Memorial
Hospital, her condition was grave, and we weren’t sure if she was going to
It wasn’t until she was moved out of the intensive care unit and into a
private room that her progress became visible, and it was weeks more before
her pain became bearable. When her appetite started to come back, I took her
whatever she wanted. One day she was drinking the butterscotch milkshake
I’d picked up on the way when Donald showed up.
He said hello to us both and kissed her quickly. “Mom, you look great.”
“She’s doing much better,” I said. He sat in a chair next to the bed and put
a foot up on the edge of the bed frame.
“Mary’s been visiting me every day,” Gam said, smiling at me.
He turned to me. “Must be nice to have so much free time.”
I looked at Gam. She rolled her eyes, and I tried not to laugh.
“How are you, sweetheart?” Gam asked him.
“Don’t ask.” He seemed annoyed.
Gam asked him about his kids, if anything was new with him and Ivana.
He didn’t have much to say; clearly bored, he left after ten minutes or so.
Gam glanced at the door to make sure he was gone. “Somebody’s cranky.”
Now I did laugh. “To be fair, he’s having a tough time,” I said. In the last
twelve months, the Taj Mahal, his favorite Atlantic City casino, had declared
bankruptcy just a little over a year after it had opened; his marriage was a
disaster, thanks in part to his very public affair with Marla Maples; the banks
had put him on an allowance; and the paperback version of his second book,
Surviving at the Top, had been published under the title The Art of Survival.
Despite the fact that he’d brought it all on himself, he seemed put upon rather
than humbled or humiliated.
“Poor Donald,” Gam mocked. She seemed almost giddy, and I thought the
hospital staff might need to cut back on her pain meds. “He was always like
this. I shouldn’t say it, but when he went to the Military Academy, I was so
relieved. He didn’t listen to anyone, especially me, and he tormented Robert.
And, oh, Mary! He was such a slob. At school he got medals for neatness,
then when he came home, he was still a slob!”
“What did you do?”
“What could I do? He never listened to me. And your grandfather didn’t
care.” She shook her head. “Donald got away with murder.”
That surprised me. I had always assumed my grandfather was a
taskmaster. “That doesn’t sound like him.”
At the time, my grandfather was at the Hospital for Special Surgery in
Manhattan getting a hip replacement. I think he had only ever been in the
hospital once, when he’d had a tumor on his neck near his right ear removed
in 1989. I don’t know if the timing of his hip surgery was a coincidence or if
it had been scheduled after Gam was admitted so she wouldn’t have to deal
with him while she recovered. His mental state had been deteriorating for
some time and while he was in the hospital had definitely taken a turn for the
worse. A few times, late at night, the nurses found him trying to leave
wearing only boxer shorts. He told them he was going to find Mrs. Trump.
Gam seemed pretty happy not to be found.
Donald’s perceived success with the Grand Hyatt in 1980 had paved the way
for Trump Tower, which had opened to great fanfare in 1983. From his
reportedly abysmal treatment of the undocumented workers who built it to
the alleged Mob involvement, the project was steeped in controversy. The
affronts culminated in the destruction of the beautiful Art Deco limestone
reliefs on the facade of the Bonwit Teller building, which he razed to make
room for his. Donald had promised those historically significant artifacts to
the Metropolitan Museum of Art. Realizing that removing them in one piece
would cost money and slow down construction, he instead ordered that they
be destroyed. When confronted with that breach of trust and taste, he
shrugged it off, declaring the sculptures to be “without artistic merit,” as if he
knew better than the considered assessment of experts. Over time that attitude
—that he knew better—would become even more entrenched: as his
knowledge base has decreased (particularly in areas of governing), his claims
to know everything have increased in direct proportion to his insecurity,
which is where we are now.
The real reason Donald’s first two projects were acquired and developed
relatively smoothly was in large part because of Fred’s expertise as a
developer and dealmaker. Neither would have been possible without his
contacts, influence, approval, money, knowledge, and, maybe most
important, endorsement of Donald.
Before that point, Donald had relied entirely on Fred’s money and
influence—although he never acknowledged it and publicly credited his own
wealth and savvy for his success. The media were more than happy to go
along without question, and the banks followed suit when Donald started to
pursue the idea of becoming a casino operator in New Jersey, which in 1977
had legalized gambling in Atlantic City in an effort to save the flailing
seaside resort town. If my grandfather’s opinion had carried any weight with
him, Donald would never have invested in Atlantic City. Manhattan was
worth the risk, as far as Fred was concerned, but in Atlantic City he would
have nothing except money and advice to offer—no political clout or
knowledge of the industry to draw on. By then Fred’s influence over him was
waning, and in 1982 Donald applied for his gaming license.
While her brother was casting about for investment opportunities,
Maryanne, who had been an assistant district attorney in New Jersey since the
mid-1970s, asked Donald if he would ask Roy Cohn to do him a favor. Cohn
had enough clout with the Reagan administration that he was given access to
AZT, an experimental AIDS treatment, as well as influence over judicial
appointments. Conveniently, a seat was open in the US District Court for the
District of New Jersey. Maryanne thought it would be a great fit, and Donald
thought it might be useful to have a close relative on the bench in a state in
which he planned to do a lot of business. Cohn gave Attorney General Ed
Meese a call, and Maryanne was nominated in September and confirmed in
In yet another sign of Fred’s waning influence, Donald had purchased a $300
million–plus casino that would become Trump’s Castle sight unseen in 1985,
only a year after he had bought Harrah’s, which became Trump Plaza. For
Donald, too much of a good thing was a better thing; Atlantic City had
unlimited potential, he believed, so two casinos were better than one. By then
Donald’s ventures already carried billions of dollars of debt (by 1990, his
personal obligation would balloon to $975 million). Even so, that same year
he bought Mar-a-Lago for $8 million. In 1988, he’d bought a yacht for $29
million and then, in 1989, the Eastern Air Lines Shuttle for $365 million. In
1990, he’d had to issue almost $700 million in junk bonds, carrying a 14
percent interest rate, just to finish construction on his third casino, the Taj
Mahal. It seemed as if the sheer volume of purchases, the price tags of the
acquisitions, and the audacity of the transactions kept everybody, including
the banks, from paying attention to his fast-accumulating debt and
questionable business acumen.
Back then, Donald’s favorite color scheme was red, black, and gold, so
Atlantic City’s cheap glitz appealed to him almost as much as the allure of
easy money. The house always wins, after all, and it was a good bet that
anybody who could afford the buy-in would do well there. Atlantic City was
completely outside of Fred’s purview, which also appealed to Donald. Setting
aside the massive monetary investments made by Fred and others, operating a
casino, unlike the Grand Hyatt and Trump Tower, which were development
projects that were ultimately managed by other entities, would be an ongoing
business. As such, it would have been Donald’s first opportunity to succeed
independently of his father.
Having his own casino provided Donald an outsize canvas; he could tailor
that entire world to his specifications. And if one casino was good, two would
be better and three even better than that. Of course, his casinos were
competing with one another and eventually would be cannibalizing one
another’s profits. As absurd as it was, there was a certain logic to his wanting
more—after all, it had worked for his father. But Donald didn’t understand,
and refused to learn, that owning and running casinos were vastly different
from owning and running rental properties in Brooklyn, from the business
model and the market to the customer base and the calculus involved.
Because he couldn’t see that glaring distinction, it was easy for him to
believe that more was better in Atlantic City, just as it had been for my
grandfather in New York’s outer boroughs. If one casino was a cash cow,
three would be a herd of them. He would do with casinos what Fred had done
with his apartment buildings.
The only part of the scenario that defies explanation is the fact that the
banks and investors in his first two casinos didn’t object more strenuously to
his opening a third, which would cut into their own bottom lines. It made
even less sense that he could find anybody interested in investing in it. Even a
casual glance at the numbers—not least, the debt service—should have
scared the most reckless lender away. In the late 1980s, nobody said no to
Donald, thereby legitimizing another misguided project that had the ancillary
benefit of bolstering the ego of a man who had no way of making it succeed.
In August of that year, Surviving at the Top was published, and within
weeks it would become clear that the book’s subject matter and timing were
bad enough to qualify as parody.
In June 1990, Donald missed a $43 million payment for Trump’s Castle.
Six months later, my grandfather sent his chauffeur with more than $3
million in cash to purchase chips at the Castle. In other words, he bought the
chips with no intention of gambling with them; his driver simply put them in
a briefcase and left the casino. Even that wasn’t enough. The next day, my
grandfather wired another $150,000 to the Castle, presumably for more chips.
Although those maneuvers helped temporarily, they resulted in my
grandfather’s having to pay a $30,000 fine for violating a gaming
commission rule prohibiting unauthorized financial sources from lending
money to casinos. If he wanted to continue lending Donald money to keep his
casinos afloat (which he did), he would also be required to get a gaming
license in New Jersey. But it was too late. Donald might have controlled 30
percent of Atlantic City’s market share, but the Taj was making it impossible
for his two other casinos to make money (the Plaza and Castle lost a
combined $58 million the year the Taj opened), the three properties carried
$94 million in annual debt, and the Taj alone needed to pull in more than $1
million a day to break even.
The banks were bleeding money. Just as the Taj was opening, Donald and
his lenders were meeting to try to figure out how to rein in and manage his
spending. The possibility of more defaults and bankruptcies still loomed, and
a solution had to be found that would protect Donald’s image, which, in turn,
would protect the banks’ money. Without the veneer of success and
confidence he projected (and had projected for him), the bankers feared that
his properties, already in trouble, would lose even more value. His last name
was the draw: without the name there would be no new gamblers or tenants
or people willing to buy bonds and hence no new revenue.
In addition to fronting Donald the money to cover his businesses’
operating expenses, the banks reached an agreement with him in May 1990 to
put him on a $450,000-a-month allowance—that is, almost $5.5 million a
year for having failed miserably. That money was just for personal expenses:
the Trump Tower triplex apartment, the private jet, the mortgage on Mar-aLago. In order to sell his image, Donald needed to be able to continue living
the lifestyle that bolstered it.
In order for the banks to keep tabs on him, Donald had to meet with them
every Friday to report on his expenditures as well as progress he’d made
selling assets such as the yacht. In May 1990, there was no denying how dire
the situation was. As much as Donald complained to Robert that the banks
were “killing” him, the truth was that he was beholden to them in a way he
had never been to his father: he had never been on a leash before, let alone a
short one, and it chafed. He was legally obligated to pay the banks back, and
if he didn’t, there would be consequences. At least there should have been.
Despite the restrictions, Donald continued spending cash he didn’t have,
including $250,000 for Marla’s engagement ring and $10 million to Ivana as
part of their divorce settlement. I don’t think it ever occurred to him that he
couldn’t spend whatever he wanted no matter what the circumstances. The
banks admonished him for betraying their agreement, but they never took any
action against him, which just reinforced his belief that he could do whatever
he wanted, as he almost always had.
In a way, you can’t really blame Donald. In Atlantic City, he had become
unmoored from his need for his father’s approval or permission. He no longer
needed to talk himself up; his exaggerated assessment of himself was
simultaneously fueled and validated by banks that were throwing hundreds of
millions of dollars at him and a media that lavished him with attention and
unwarranted praise. The two combined rendered him blind to how dire his
situation was. My grandfather’s myths about Donald were now being
reinforced by the world at large.
Regardless of who was disseminating them, however, they were still
myths. Donald was, in essence, still Fred’s construct. Now he belonged to the
banks and the media. He was both enabled by and dependent upon them, just
as he had been upon Fred. He had a streak of superficial charm, even
charisma, that sucked certain people in. When his ability to charm hit a wall,
he deployed another “business strategy”: throwing tantrums during which he
threatened to bankrupt or otherwise ruin anybody who failed to let him have
what he wanted. Either way, he won.
Donald was successful because he was a success. That was a premise that
ignored one fundamental reality: he had not achieved and could not achieve
what he was being credited with. Despite that, his ego, now unleashed, had to
be fed continually, not just by his family but by all who encountered it.
New York’s elite would never accept him as anything but the court jester
from Queens, but they also validated his pretensions and grandiose selfimage by inviting him to their parties and allowing him to frequent their
haunts (such as Le Club). The more New Yorkers wanted spectacle, the more
willing the media were to provide it—even at the expense of more important
and substantive stories. Why bore them with hard-to-follow articles about his
convoluted bank transactions? The distractions and sleights of hand benefited
Donald enormously while giving him exactly what he wanted: the ongoing
adulation of media that focused on his salacious divorce and alleged sexual
prowess. If the media could deny reality, so could he.
By some miracle, I had gotten into Tufts University after boarding school,
and despite dropping out the second semester of my freshman year, I
graduated in 1989. A year later, just before my grandfather’s modest
purchase of $3.15 million worth of casino chips, I entered the graduate
program in English and comparative literature at Columbia University.
Two months after the semester started, my apartment was burgled. All of
my electronics, including my typewriter, which was essential for school, were
taken. When I called Irwin to see if I could get an advance on my allowance,
he refused. My grandfather thought I should get a job, he told me.
The next time I visited my grandmother at the House, I explained the
situation to her, and she offered to write me a check. “It’s okay, Gam. I only
have to wait a couple of weeks.”
“Mary,” she said, “never reject a gift of money.” She wrote me the check,
and I was able to buy a typewriter later that week.
I soon got an angry call from Irwin. “Did you ask your grandmother for
“Not exactly,” I said. “I told her I got robbed, and she helped me out.”
While going through the canceled checks of all of his personal and
business accounts, as well as my grandmother’s, as he did at the end of every
month, my grandfather had discovered the check my grandmother had written
to me, and he was furious.
“You need to be careful,” Irwin warned me. “Your grandfather often
speaks of disowning you.”
I got another call from Irwin a few weeks later. My grandfather was angry
with me again, this time because he didn’t like the signature with which I
endorsed my checks.
“Irwin, you’ve got to be kidding.”
“I’m not. He hates the fact that it’s illegible.”
“It’s a signature.”
He paused and softened his tone. “Change it. Mary, you’ve got to play the
game. Your grandfather thinks you’re being selfish, and there may be nothing
left by the time you turn thirty.” But I never understood what he meant by
“the game”—it was my family, not a bureaucracy.
“I don’t see what I’m doing wrong. I’m getting a master’s degree at an Ivy
“He doesn’t care.”
“Does Donald know about this?”
“He’s my trustee. What does he have to say?”
“Donald?” Irwin laughed dismissively. “Nothing.”
My grandfather hadn’t yet been diagnosed with Alzheimer’s disease, but
he’d been struggling with dementia for a while by then, so I didn’t take the
threats too seriously. I did, however, change my signature.
Everyone in my family experienced a strange combination of privilege and
neglect. Although I had all of the material things I needed—and luxuries such
as private schools and summer camp—there was a purposely built-in idea of
uncertainty that any of it would last. By the same token, there was the
sometimes dispiriting and sometimes devastating sense that nothing any of us
did really mattered or, worse, that we didn’t matter—only Donald did.
Trump Management, which Donald often referred to as a “two-bit operation,”
was doing fairly well. Fred paid himself more than $109 million between
1988 and 1993 and had tens of millions more in the bank. The Trump
Organization, the company Donald ostensibly ran, was, however, in
increasingly serious trouble.
Reduced to a monthly allowance—that a family of four could have lived
on comfortably for ten years but still an allowance—and shut out by the
banks, which finally refused to lend him more money, Donald fully believed
that whatever was happening to him was the result of the economy, the poor
treatment he received from the banks, and bad luck.
Nothing was ever fair to him. That struck a chord in Fred, who nursed his
own grievances and also never took responsibility for anything other than his
successes. Donald’s talent for deflecting responsibility while projecting
blame onto others came straight from his father’s playbook. Even with the
untold millions of dollars Fred spent, he couldn’t prevent Donald’s failures,
but he could certainly find a scapegoat, just as he had always done when his
missteps and poor judgment caught up with him, as when he blamed Freddy
for the failure of Steeplechase. Donald knew that taking responsibility for
your failures, which obviously meant acknowledging failure, was not
something Fred admired; he’d seen where it had gotten Freddy.
It’s very possible that back in the late 1960s and early ’70s, Fred didn’t
know just how deep Donald’s ineptitude ran. Acknowledging weakness of
any kind in the son on whom he had staked the future of his empire and for
whom he had sacrificed Freddy would have been nearly impossible. It was
much easier to convince himself that Donald’s talents were wasted in the
backwater of Brooklyn; he simply needed a bigger pond in which to make a
As the Commodore Hotel slowly transformed into the Grand Hyatt, Fred
was so blinded by the success with which Donald manipulated and debased
every part of the process in order to get his way that he seemed to forget how
vital his own connections, knowledge, and skills were; neither the Hyatt nor
Trump Tower would have seen the light of day without them. Even Fred’s
head must have been turned by all of the attention Donald generated for two
projects that, if developed by anybody else, would have been considered
fairly commonplace occurrences in Manhattan.
Fred had known all along what games Donald was playing, because he’d
taught Donald how to play them. Working the refs, lying, cheating—as far as
Fred was concerned, those were all legitimate business tactics. The most
effective game for both father and son was the shell game. While Fred kept
churning out projects and solidifying his status as a “postwar master builder,”
he was fattening his wallet with taxpayer money by skimming off the top and
allegedly committing so much tax fraud that four of his children would
continue to benefit from it for decades. While the rubes focused on the
salacious details Donald kept generating for the tabloids, he was building a
reputation for success based on bad loans, bad investments, and worse
judgment. The difference between the two, however, is that despite his
dishonesty and lack of integrity, Fred actually ran a solid, income-generating
business, while Donald had only his ability to spin and his father’s money to
prop up an illusion.
Once Donald moved into Atlantic City, there was no longer any denying
that he wasn’t just ill-suited to the day-to-day grind of running a few dozen
middle-class rental properties in the outer boroughs, he was ill-suited to
running any kind of business at all—even one that ostensibly played to his
strengths of self-promotion and self-aggrandizement and his taste for glitz.
When Fred bragged about Donald’s brilliance and claimed that his son’s
success had far outpaced his own, he must have known that not a word of it
was true; he was too smart and too good at arithmetic to think otherwise: the
numbers simply didn’t add up. But the fact that Fred continued to prop
Donald up despite the wisdom of continuing to do so suggests that something
else was going on.
Because Fred did deny the reality on the ground in Atlantic City. He had
already shown himself impervious to facts that didn’t fit his narrative, so he
blamed the banks and the economy and the casino industry just as
vociferously as his son did. Fred had become so invested in the fantasy of
Donald’s success that he and Donald were inextricably linked. Facing reality
would have required acknowledging his own responsibility, which he would
never do. He had gone all in, and although any rational person would have
folded, Fred was determined to double down.
There was still plenty of publicity to turn Fred’s head, and thanks to the
banks that father and son maligned, the extraordinary financial reversal didn’t
put a dent in Donald’s lifestyle. Finally, there was the slow-rolling toll that
his as-yet-undiagnosed Alzheimer’s was beginning to take on his executive
functioning. Already susceptible to believing the best of his worst son, it
became easier over time for him to confuse the hype about Donald with
As usual, the lesson Donald learned was the one that supported his
preexisting assumption: no matter what happens, no matter how much
damage he leaves in his wake, he will be okay. Knowing ahead of time that
you’re going to be bailed out if you fail renders the narrative leading up to
that moment meaningless. Claim that a failure is a tremendous victory, and
the shameless grandiosity will retroactively make it so. That guaranteed that
Donald would never change, even if he were capable of changing, because he
simply didn’t need to. It also guaranteed a cascade of increasingly
consequential failures that would ultimately render all of us collateral
As the bankruptcies and embarrassments mounted, Donald was confronted
for the first time with the limits of his ability to talk or threaten his way out of
a problem. Always adept at finding an escape hatch, he seems to have come
up with a plan to betray his father and steal vast sums of money from his
siblings. He secretly approached two of my grandfather’s longest-serving
employees, Irwin Durben, his lawyer, and Jack Mitnick, his accountant, and
enlisted them to draft a codicil to my grandfather’s will that would put
Donald in complete control of Fred’s estate, including the empire and all its
holdings, after he died. Maryanne, Elizabeth, and Robert would effectively be
at Donald’s financial mercy, dependent on his approval for the smallest
As Gam later told Maryanne, when Irwin and Jack went to the House to
have Fred sign the codicil, they presented the document as if it had been
Fred’s idea all along. My grandfather, who was having one of his more lucid
days, sensed that something was not right, although he couldn’t say exactly
what. He angrily refused to sign. After Irwin and Jack left, Fred conveyed his
concerns to his wife. My grandmother immediately called her oldest child to
explain what had happened as best she could. In short, she said, “it simply
didn’t pass the smell test.”
Maryanne, with her background as a prosecutor, had limited knowledge of
trusts and estates. She asked her husband, John Barry, a well-known and
respected attorney in New Jersey, to recommend someone who could help,
and he asked one of his colleagues to look into the situation. It didn’t take
long for Donald’s scheme to be uncovered. As a result, my grandfather’s
entire will was rewritten, replacing one he had written in 1984, and
Maryanne, Donald, and Robert were all named as executors. In addition, a
new standard was put into place: whatever Fred gave Donald, he would have
to give an equal amount to each of the other three children.
Maryanne would say years later, “We would have been penniless.
Elizabeth would have been begging on a street corner. We would have had to
beg Donald if we wanted a cup of coffee.” It was “sheer luck” that they had
stopped the scheme. Yet the siblings still got together every holiday as
though nothing had happened.
Donald’s attempt to wrest control of Fred’s estate away from him was the
logical outcome of Fred’s leading his son to believe that he was the only
person who mattered. Donald had been given more of everything; he had
been invested in; elevated to the detriment of Maryanne, Elizabeth, and
Robert (and even his mother) and at the expense of Freddy. In Donald’s
mind, the success and reputation of the entire family rested on his shoulders.
Given that, it makes sense in the end that he would feel he deserved not just
more than his fair share but everything.
I was standing at the window of my studio apartment looking at the rush-hour
traffic clogging the 59th Street Bridge when Donald called me from his
plane, not a usual occurrence.
“The dean of students at Tufts sent me a letter you wrote.”
It took me a minute to realize what he was talking about. One of my
professors had been up for tenure, and before I graduated, I had written a
letter in support of him. That had been four years earlier, and I’d forgotten all
“The letter was to show me how great you thought Tufts was. It was a
“I’m sorry. That was rude of him.”
“No, it’s a fantastic letter.”
The point of the conversation was eluding me. Then Donald said, apropos
of nothing as far as I could tell, “Do you want to write my next book? The
publisher wants me to get started, and I thought it would be a great
opportunity for you. It’ll be fun.”
“That sounds incredible,” I said. And it did. I heard the plane engine rev in
the background and remembered where he was. “Where are you going,
“Heading back from Vegas. Call Rhona tomorrow.” Rhona Graff was his
executive assistant at the Trump Organization.
“I will. Thanks, Donald.”
It wasn’t until later, when I reread the letter, that I understood why Donald
thought it would be a good idea to hire me—not because it was “fantastic”
but because it demonstrated that I was really good at making other people
look really good.
A few days later, I was given my own desk in the back office of the
Trump Organization. A nondescript, open space with drop ceilings,
fluorescent lighting, and huge steel filing cabinets lining the walls, it had a lot
more in common with the utilitarian office of Trump Management on Avenue
Z than the gold-and-glass walls lined with magazine covers featuring
Donald’s face that greeted guests out front.
I spent the first week on the job familiarizing myself with the people who
worked there and the filing system. (To my surprise, there was a folder with
my name on it containing a single sheet of paper—a handwritten letter I had
sent to Donald my junior year in high school. I’d asked if he could get me a
pair of tickets to a Rolling Stones concert. He couldn’t.) I kept to myself for
the most part, but whenever I had a question, Ernie East, one of Donald’s
vice presidents and a very nice man, helped me out. He suggested documents
that might be useful, and on occasion he’d put some file folders on my desk
that he thought might help. The problem was that I didn’t really know what
the book was supposed to be about beyond its broad theme, which I cleverly
deduced from its working title, The Art of the Comeback.
I hadn’t read either of Donald’s other two books, but I knew a bit about
them. The Art of the Deal, as far as I understood it, had been meant to present
Donald as a serious real estate developer. The book’s ghostwriter, Tony
Schwartz, had done a good job—which he has long since regretted—of
making his subject sound coherent, as if Donald had actually espoused a fully
realized business philosophy that he understood and lived by.
After the embarrassment of the poorly timed publication of Surviving at
the Top, I assumed that Donald wanted a return to the relative seriousness of
its predecessor. I set about trying to explain how, under the most adverse
circumstances, he had emerged from the depths, victorious and more
successful than he had ever been. There wasn’t much evidence to support that
narrative—he was about to experience his fourth bankruptcy filing with the
Plaza Hotel—but I had to try.
Every morning on the way to my desk, I stopped by to see Donald in the
hope that he’d have time to sit down with me for an interview. I figured that
would be the best way to find out what he had done and how he had done it.
His perspective was everything, and I needed the stories in his own words.
He was usually on a call, which he’d put on speaker as soon as I sat down.
The calls, as far as I could tell, were almost never about business. The person
on the other end, who had no idea he or she was on speaker, was looking for
gossip or for Donald’s opinion about women or a new club that had opened.
Sometimes he was being asked for a favor. Often the conversation was about
golf. Whenever anything outrageously sycophantic, salacious, or stupid was
said, Donald smirked and pointed to the speakerphone as if to say, “What an
When he wasn’t on a call, I’d find him going through the newspaper
clippings that were collected for him daily. Every article was about him or at
least mentioned him. He showed them to me, something he did with most
visitors. Depending on the content of the article, he sometimes wrote on it
with a blue Flair felt-tip marker, just like the one my grandfather used, and
sent it back to the reporter. After he finished writing, he’d hold up the
clipping and ask for my opinion of what he considered his witty remarks.
That did not help me with my research.
A few weeks after Donald hired me, I still hadn’t gotten paid. When I
brought it up to him, he pretended at first not to understand what I was
talking about. I pointed out that I needed an advance so I could at least buy a
computer and a printer—I was still writing on the same electric typewriter I’d
bought with Gam’s help in grad school. He said he thought that was the
publisher’s problem. “Can you talk to Random House?”
I didn’t realize it at the time, but Donald’s editor had no idea he’d hired
One night, as I sat at home trying to figure out how to piece together
something vaguely interesting out of the uninteresting documents I’d been
poring over, Donald called. “When you come to the office tomorrow,
Rhona’s going to have some pages for you. I’ve been working on material for
the book. It’s really good.” He sounded excited.
Finally I might have something to work with, some idea about how to
organize this thing. I still didn’t know what he thought about his “comeback,”
how he ran his business, or even what role he played in the deals he was
The next day, Rhona handed me a manila envelope containing about ten
typewritten pages, as promised. I took it to my desk and began to read. When
I finished, I wasn’t sure what to think. It was clearly a transcript of a
recording Donald had made, which explained its stream-of-consciousness
quality. It was an aggrieved compendium of women he had expected to date
but who, having refused him, were suddenly the worst, ugliest, and fattest
slobs he’d ever met. The biggest takeaways were that Madonna chewed gum
in a way Donald found unattractive and that Katarina Witt, a German
Olympic figure skater who had won two gold medals and four world
championships, had big calves.
I stopped asking him for an interview.
From time to time, Donald asked about my mother. He hadn’t seen her in
four years, ever since Ivana and Blaine had given Gam an ultimatum just
before Thanksgiving: either Linda came to the House for the holidays, or they
did. They found their not-exactly sister-in-law too quiet and depressed, and
they just couldn’t have a good time with her there. My mother had been in
the Trump family since 1961, and though I never understood why my
grandfather required her presence at holidays after my parents divorced, she
always went. More than twenty-five years later, my grandmother chose Ivana
and Blaine, without factoring in how the decision might affect me and my
Now Donald said, “I think we made a big mistake continuing to support
your mother. It might have been better if we’d cut her off after a couple of
years and she had to stand on her own two feet.”
The idea that anyone else was entitled to money or support he or she
wasn’t obviously earning was impossible for Donald and my grandfather to
fathom. Nothing my mother had received as the former wife of the oldest son
of a very wealthy family, who had raised two of Fred and Mary Trump’s
grandchildren almost single-handedly, had come from my grandfather, and it
certainly hadn’t come from Donald, yet they both acted as if it did.
Donald probably thought he was being kind. There used to be a spark of
that in him. He did once give me $100 to get my car out of impound. And
after my father died, Donald was the only member of my family, other than
my grandmother, who included me in anything. But his kindness had become
so warped over time—through lack of use and Fred’s discouragement—that
what he considered kindness would have been practically unrecognizable to
the rest of us. I didn’t know it at the time, but when we had that conversation,
Donald was still receiving his $450,000 allowance from the banks every
One morning as I sat across from Donald at his desk going over the details of
our trip to Mar-a-Lago (Donald thought it would help me with the book if I
saw his Palm Beach mansion firsthand) the phone rang. It was Philip
As they chatted, Donald suddenly seemed to get an idea. He put the phone
on speaker. “Philip!” he said. “You have to talk to my niece. She’s writing
my next book. You can tell her all about the Taj.”
I introduced myself, and Philip suggested I come to his house in
Connecticut the following week to discuss the book.
After Donald finished the call, he said to me, “That’ll be fantastic. Philip
is a great guy. I hired him to design the porta-co-share for the Taj Mahal. It’s
tremendous—I’d never seen anything like it.”
After we finished discussing the logistics of our trip to Florida, I left the
office and headed to the library. I had no idea who Philip Johnson was, and
I’d never heard of a “porta-co-share.”
In the limo on the way to the airport the following day, I told Donald that
I’d arranged to meet Johnson at his home, which I’d learned at the library
was the very famous Glass House that he, a very famous architect, had
designed. I had also discovered that the thing Johnson had designed for the
Taj—what Donald called a porta-co-share—was a porte cochere, basically a
large carport. I understood why Donald had wanted Johnson to be involved in
the project; he wasn’t just famous, he also traveled in the kind of circles
Donald aspired to. I didn’t, however, understand why Johnson would bother
designing the Taj’s carport. It was a very small-scale project that seemed not
worth his while.
When Donald picked up a copy of the New York Post less than ten minutes
into the car ride, I knew he had no intention of giving me information for the
book. I’d begun to suspect that he’d hired me without consulting his
publisher because he didn’t want to be micromanaged by the people there. It
would also be a lot easier to put off his niece, who wasn’t under contract and
was barely getting paid, than a professional writer, who would most likely
have a significant stake in the success of the book. But we were about to be
trapped together on a plane for two hours, so I hoped he might talk to me
When we got into the cabin of the jet that was waiting for us on the
tarmac, Donald spread out his arms and asked, “So what do you think?”
“It’s great, Donald.” I knew the drill.
As soon as we reached cruising altitude and we could unbuckle our seat
belts, one of his bodyguards handed him a huge stack of mail after setting a
glass of Diet Coke next to him. I watched as he opened one envelope after
another, then, after examining the contents for a few seconds, threw them and
the envelope onto the floor. When a large pile accumulated, the same guy
would reappear, pick up the wastepaper, and throw it into the garbage. That
happened over and over again. I moved to another seat so I didn’t have to
The staff were waiting as the car pulled up to the entrance at Mar-a-Lago.
Donald went off with his butler, and I introduced myself to everybody else.
The fifty-eight-bedroom mansion with thirty-three bathrooms outfitted with
fixtures plated in gold and an eighteen-hundred-square-foot living room that
sported forty-two-foot ceilings was as garish and uncomfortable as I’d
Dinner that evening was just me, Donald, and Marla. She and I had met a
few times before, but we had never had a chance to get to know each other
one on one. I found her friendly, and Donald seemed relaxed with her. She
was just two years older than I was and about as different from Ivana as a
human being could be. Marla was down to earth and soft spoken where Ivana
was all flash, arrogance, and spite.
The next day, I spent the morning exploring the property. There were no
other guests, so the entire place felt empty and strangely quiet. I talked to the
butler to see if he had any interesting stories, got to know some of the other
guys who worked there, and then took a quick swim before lunch, which was
scheduled for 1:00 p.m. As formal as Mar-a-Lago was in some ways, it was
also much more casual than our usual family gathering places, so I felt
comfortable wearing a bathing suit and a pair of shorts to lunch, which was
being served on the patio.
Donald, who was wearing golf clothes, looked up at me as I approached as
if he’d never really seen me before. “Holy shit, Mary. You’re stacked.”
“Donald!” Marla said in mock horror, slapping him lightly on the arm.
I was twenty-nine and not easily embarrassed, but my face reddened, and I
suddenly felt self-conscious. I pulled my towel around my shoulders. It
occurred to me that nobody in my family, outside of my parents and brother,
had ever seen me in a bathing suit. Unfortunately for the book, that was about
the only interesting thing that happened during my entire visit to Palm Beach.
Back in New York, Donald finally got sick of my asking him to sit for an
interview and handed me a list of names. “Talk to these people.” Included
were the presidents of his casinos and Maryanne’s husband, John. Although
that was potentially helpful, he didn’t seem to understand that writing the
book without any input from him would be close to impossible.
I met with all the presidents of the casinos. Not surprisingly, a lot of their
answers were canned, and I realized that they weren’t going to give me dirt
on what was happening in their boss’s business at the height of the chaos and
dysfunction. The trips weren’t a total waste of time; I’d never been down
there before, and at least I got a sense of the place.
My meeting with John Barry was even less productive than the trips to
“What can you tell me?” I asked him.
He rolled his eyes.
Finally Donald told me his editor wanted to meet with me. A lunch was
set up, and I arrived at the restaurant thinking he and I were going to be
discussing next steps. It was an expensive “in” place in Midtown, and we
were seated at a small, cramped table near the kitchen.
With very little preliminary conversation, the editor told me that Random
House wanted Donald to hire someone with more experience.
“I’ve been working on this for a while,” I said, “and I think I’ve made
some progress. The problem is, I can’t get Donald to sit down with me for an
“You can’t expect to play a Mozart concerto the first time you sit down at
a piano,” the editor said, as if I’d just learned the alphabet the day before.
“Donald told me he likes what I’ve done so far,” I said.
The editor looked at me as if I’d just proved his point for him. “Donald
hasn’t read any of it,” he said.
I stopped at the office the next day to clear out my desk and hand over
anything that might be useful to my eventual replacement. I wasn’t upset. I
didn’t even mind that Donald had had somebody else fire me. The project
had hit a wall. Besides, after all of the time I had spent in his office, I still had
no idea what he actually did.
Nightfall Does Not Come at Once
We were sitting at the same table at Mar-a-Lago where I’d had lunch with
Donald and Marla a couple of years earlier. The family had started going
there for Easter. My grandfather turned to my grandmother, pointed to me,
smiled, and asked, “Who is this nice lady?”
He turned to me. “Aren’t you a nice lady.”
“Thank you, Grandpa,” I said.
Gam seemed upset. I told her not to worry. I’d already seen people my
grandfather had known for decades erased from his memory: his youngest
grandchildren, his driver. His new nickname for me stuck, and he called me
“nice lady” until his final illness. He said it gently and with apparent
kindness; he was very sweet to me after he’d forgotten who I was.
“Come on, Pop.” Rob took a step, but my grandfather didn’t move. He
looked around at the crowds of people at a gala thrown in my grandparents’
honor, and his eyes glazed over with a look of sheer panic, as if he suddenly
had no idea who anybody was or what he was doing there. Up until then, I
had only seen my grandfather look contemptuous, annoyed, angry, amused,
and self-satisfied. The look of fear was new and alarming. The only other
time I had seen my grandfather look unsettled at all was on the one occasion
Donald had taken him to play golf—a hobby that Donald spent an inordinate
amount of time on but that Fred, who had no use for pastimes, never
complained about. I was at the House when they came back from the course,
and I almost didn’t recognize him. They were both wearing golf clothes—my
grandfather in light blue pants, a white cardigan, and matching white shoes. It
was the first time I’d ever seen my grandfather wearing something other than
a suit. I’d never seen him look so uncomfortable and self-conscious before.
Soon he’d go from habitually misplacing things and forgetting a word or a
conversation here and there to forgetting familiar faces. You could measure
your worth in my grandfather’s eyes by how long he remembered you. I
don’t know if he remembered Dad, because I never once heard him mention
my father in the years after his death.
Maryanne made sure my cousin David, by then a clinical psychologist,
accompanied my grandfather to all of his appointments for checkups and
neurological exams in a concerted effort to cement him in my grandfather’s
memory, but it didn’t take long before my grandfather simply referred to
David as “the doctor.”
I was standing with Maryanne and my grandfather by the pool at Mar-aLago when he pointed to me and said to his daughter, “Isn’t she a nice lady?”
A year or so had passed since he’d first given me the sobriquet.
“Yes, Dad,” Maryanne said. She smiled wearily.
He looked at her carefully and, almost as an afterthought, asked, “Who are
Her eyes watered as if somebody had slapped her. “Dad,” she said gently,
“Okay, Maryanne.” He smiled, but the name didn’t mean anything to him
He never forgot Donald.
Rob, who’d left his position as president of Trump’s Castle (of the infamous
$3.15 million chip bailout) under a cloud, had sat in for my grandfather at
Trump Management during his 1991 hospitalization and never left. It was a
good gig for Robert. In addition to the millions of dollars a year he got
simply by virtue of the fact that he was one of Fred’s living children, he was
also paid half a million dollars a year to do a job that required little skill or
effort. It was the position for which Freddy and then Donald had been
groomed—and had rejected, each in his own way.
Fred still went to the office every day and sat behind his desk until it was
time to go home, but Rob was actually, if not nominally, in charge of the
well-oiled, self-sustaining machine he often referred to as a “cash cow.”
My grandfather was having a bad day. Most of us were gathered in the library
when he came down the stairs, his mustache and eyebrows freshly dyed and
his wig askew but impeccably dressed in his three-piece suit.
The hair color and wig were recent innovations. My grandfather had
always been vain about his appearance and bemoaned his receding hairline.
Now his full head of hair gave him a slightly shaggy appearance. Nobody
said much about the wig, but the hair dye caused considerable consternation
in the family, especially when we were going out in public. My grandfather
often left the cheap drugstore dye on too long, turning his eyebrows and
mustache a jarring shade of magenta. When he joined us in the library,
obviously proud of what he’d done, Gam said, “Oh, for God’s sake, Fred.”
“Jesus Christ, Dad!” Donald yelled at him.
“For fuck’s sake,” Rob swore under his breath.
Maryanne, touching his arm, said, “Dad, you can’t do that again.”
He was standing by his love seat when I came into the library.
“Hello,” he said
“Hi, Grandpa. How are you?”
He looked at me and reached for his wallet, so thick with bills I was
constantly surprised that it fit in his pocket. He carried a wallet-sized
photograph of a half-naked woman in his billfold, and for a second I was
worried that he planned to show it to me, as he had when I was twelve.
“Look at this,” he had said, sliding the picture out of its slot. A heavily
made-up woman, who couldn’t have been more than eighteen and might have
been younger, smiled innocently at the camera, her hands holding up her
naked breasts. Donald had been looking over my grandfather’s shoulder. I
hadn’t known what to say and had looked at him for some indication of how I
should respond, but he’d merely leered at the picture.
“What do you think about that?” My grandfather had chuckled. I never
heard him laugh. I don’t think he ever did. He usually expressed amusement
by saying “Ha!” and then sneering.
Now, instead of a picture, my grandfather pulled out a hundred-dollar bill
and asked, “Can I buy your hair?”
That was something he’d ask me every time I saw him when I was
growing up. I laughed. “Sorry, Grandpa. I need to hang on to it.”
Elizabeth walked over carrying a small box in one hand. She looped an
arm around my grandfather’s elbow and leaned against him. He looked ahead
blankly, disengaged his arm, and left the room.
Shortly after, Donald came in with his kids and Rob’s stepson. With the
exception of Eric, they were all teenagers, the boys tall and chubby and
wearing suits. Donald went to sit on the chair by the TV, and Ivanka climbed
on his lap. The boys started wrestling. Donald watched the action from his
chair, kissing Ivanka or pinching her cheek. Every once in a while, he’d stick
his foot out and kick whichever boy was being pinned to the floor. When they
had been younger, Donald had wrestled with them—a fight that had basically
consisted of his picking them up, throwing them on the ground, and kneeling
on them until they cried uncle. As soon as they had gotten big enough to fight
back in earnest, he had opted out.
When Liz and I were as far out of harm’s way as we could get, she held
the box out to me and said, “This is yours.”
We didn’t exchange gifts outside of Christmas, but I took the box from
her, curious, and opened it to find a vintage stainless-steel Timex with a
small, plain face and an olive green band.
“Somebody gave it to you for Christmas,” she said. “You were only ten,
and I thought you were too young to have something that nice. So I took it.”
She left the room to look for her father.
Later Donald and Rob huddled together in the breakfast room, their
shoulders close and their heads down. My grandfather stood nearby, leaning
forward almost on the tips of his toes, trying to hear what they were saying.
Fred said, “Donald, Donald.” When he didn’t respond, my grandfather
tugged on Donald’s sleeve.
“What, Dad?” he asked without turning around.
“Look at this,” Fred said. He held up a page that had been torn out of a
magazine, an ad for a limo similar to the one he already owned.
“What about it?”
“Can I get this?”
Donald took the page and handed it to Rob, who folded it in half and slid
it onto the table.
“Sure, Pop,” Rob said. Donald left the room. Whatever had once tied them
together, Fred’s remaining sons had given up all pretense of caring what their
father thought or wanted. Having served his father’s purpose, Donald now
treated him with contempt, as if his mental decline were somehow his own
fault. Fred had treated his oldest son and his alcoholism the same way, so
Donald’s attitude wasn’t surprising. It was jarring, though, to witness the
open contempt. As far as I knew at the time, Donald not only had been my
grandfather’s favorite, he had also seemed to be the only child of his that he
liked. I knew my grandfather could be cruel, but I thought the largest measure
of that cruelty was reserved for my father, who, to my shame, I thought had
probably deserved it. I didn’t know how lonely and frightening life in the
House had been at the time of my grandmother’s illness all those years ago. I
didn’t know that my grandfather hadn’t taken care of any of his children
during the year of Gam’s absence or that Donald had been particularly
vulnerable to that neglect. And far from supporting and nurturing my father
as he ventured out into the world with the sincere intent to be a success, Fred
was really only enabling Donald, waiting until he was old enough to be of
In 1994, I moved from my Upper East Side apartment to Garden City, a town
on Long Island only a fifteen-minute drive from the House. I would take
Gam to see her great-grandchildren, my brother’s daughter and son, driving
her in the red Rolls-Royce my grandfather had bought for her birthday a few
years earlier. Behind the large, loose walnut steering wheel, I felt so high up
that I could practically see the curvature of the earth. Sometimes Gam and I
chatted easily during the forty-five-minute drive, but more often she was
moody and taciturn. On days like that, the trip felt interminable. She
sometimes smelled strongly of vanilla even when she hadn’t been baking.
Other times, I would see her out of the corner of my eye surreptitiously slide
her hand into her purse and put something into her mouth.
Usually we sat in the library chatting. I was often there when Maryanne
made her daily phone call to check in. After answering, Gam covered the
receiver and said to me, “It’s Maryanne,” then, to her daughter, “Guess who’s
here? Mary.” She paused, I guess to give Maryanne a chance to say
something such as “Tell her I say hi,” but she never did.
Sometimes we went to eat at a local restaurant. One of Gam’s favorite
places to have lunch was the Sly Fox Inn, a low-key pub directly across the
street from the grocery store parking lot where she’d been mugged. We never
talked about Dad much, but one day she seemed particularly nostalgic. She
reminisced about the trouble he and Billy Drake used to get into, how easily
Dad had made her laugh. She went quiet after the waiter came to take our
plates. When he asked if we wanted the check Gam didn’t answer, so I
“Mary, he was so sick.”
“I know, Gam,” I said, assuming she meant his drinking.
“I didn’t know what to do.”
I thought she was going to cry and said, uselessly, “Gam, it’s okay.”
“Those last few weeks”—she took a deep breath—“he couldn’t get out of
“The day I came by—” I started to ask.
The waiter brought the check.
“Didn’t he go to the doctor?” I asked. “I mean, if he was that sick.”
“He felt so bad when he heard you’d come to see him.”
I waited for her to say something else, but Gam opened her purse. She
always paid for lunch. I drove her home in silence.
In 1987, I had spent my junior year abroad in Germany, a place for which
I had no affinity, but I’d thought it might please my grandfather since it was
the country of his parents’ birth. (It didn’t.) I had planned to come home for
Christmas, and I called my grandparents to ask if I could stay with them.
I’d stood at the pay phone in the hallway of my dorm with a handful of
five-mark coins and called the House. “Hi, Grandpa. It’s Mary,” I’d said
when he answered.
“Yes,” he had replied.
I explained why I was calling.
“Why can’t you stay with your mother?” he had asked.
“I’m allergic to the cats, and I’m afraid I might have an asthma attack.”
“Then tell her to get rid of the cats.”
It was so much easier being the “nice lady” now.
I saw firsthand how difficult living with my grandfather had become for
Gam. My grandfather’s odd behavior had started with small things, such as
hiding her checkbook. When she confronted him, he accused her of trying to
bankrupt him. When she tried to reason with him, he became enraged,
leaving her feeling shaken and unsafe. He worried constantly about money,
terrified that his fortune was disappearing. My grandfather had never been
poor a day in his life, but poverty became his sole preoccupation; he was
tortured by the prospect of it.
My grandfather’s moods eventually evened out, and the problem for Gam
became the repetition. After getting home from the office in the evening, he’d
go upstairs to change, often coming back downstairs wearing a fresh dress
shirt and tie but no pants, just his boxers, socks, and dress shoes. “So how is
everybody? Okay? Okay. Good night, Toots,” he’d say, and head back
upstairs, only to descend again a few minutes later.
One evening as Gam and I sat together in the library, my grandfather came
in and asked, “Hey, Toots, what’s for dinner?”
After she answered, he walked out. A few moments later, he returned.
“What’s for dinner?” She answered again. He left and returned ten, twelve,
fifteen times. With decreasing amounts of patience, she told him “Roast beef
and potatoes” every time.
Eventually she lashed out at him. “For God’s sake, Fred, stop it! I’ve
already told you.”
“Okay, okay, Toots,” he said with a nervous laugh, hands raised against
her as he bounced up on his toes. “Well, that’s that,” he said, tucking his
thumbs under his suspenders, as though we had just finished a conversation.
The gestures were the same as they’d always been, but the glint in his eyes
had become dully benign.
He left the room, only to wander in a few minutes later to ask, “What’s for
Gam pulled me onto the porch—an uninviting square of cement on the
side of the House just off the library that decades earlier had been used for
family barbecues. It had been so long neglected that I often forgot it existed.
“I swear, Mary,” she told me, “he’s going to drive me mad.” The chairs
that had been left out there and long forgotten were so littered with twigs and
dead leaves that we remained standing.
“You need to get help,” I said. “You should talk to someone.”
“I can’t leave him.” She was close to tears.
“I would have liked to go home again,” she once told me wistfully. I
didn’t understand why she couldn’t go back to Scotland, but she adamantly
refused to do anything that might look selfish.
On weekends, if they weren’t at Mar-a-Lago, my grandparents would
drive to one of their other children’s country homes: Robert’s in Millbrook,
New York; Elizabeth’s in Southampton; or Maryanne’s in Sparta, New
Jersey. They would plan to spend the night, and my grandmother would look
forward to a quiet, relaxing weekend with other people. As soon as they
arrived at their destination, my grandfather would ask if they could go home.
He wouldn’t relent until Gam gave up and they got back into the car. The
idea of a weekend (or day) retreat had been for Gam’s benefit, a chance for
her to get out of the House and have company. Eventually the visits became
just another form of torture. Like so much else in the family that didn’t make
sense, they continued doing it anyway.
Gam was in the hospital again. I don’t remember what she’d broken, but after
the hospital stay, she had the option of going to a rehab facility or having a
physical therapist sent to her home. She opted for the rehab facility.
“Anything to avoid going back to the House,” she told me.
It was better that way. After the mugging, she had had to sleep in a
hospital bed in the library for weeks. My grandfather, who’d recovered very
well from his hip surgery, hadn’t had much to say in the way of
commiseration or comfort.
“Everything’s great. Right, Toots?” he’d say.
In 1998, we celebrated Father’s Day at Donald’s apartment at Trump Tower
for the first time. It had become too difficult for my grandfather to be in
public, so our traditional trip to Peter Luger in Brooklyn was out of the
question. It was a family custom to go there twice a year, on Father’s Day
and my grandfather’s birthday.
Peter Luger was a deeply strange, very expensive restaurant that charged
extra for bad service and accepted only cash, check, or a Peter Luger charge
card (which my grandfather possessed). The menu was limited, and whether
you asked for them or not, huge platters of sliced beefsteak tomatoes and
white onions arrived, accompanied by tiny ceramic dishes of hash fries and
creamed spinach that usually went untouched. A side of beef was brought out
on trays, punctuated with little plastic cows in varying shades ranging from
red (still mooing) and pink (almost able to crawl across the table) to—
actually, I don’t know. All of our little cows were red and pink. Most of us
ordered Cokes, which were served in six-ounce bottles; because of the
legendarily bad service, that meant at the end of the evening the table was
littered with the wreckage of a couple of cow carcasses, dozens of Coke
bottles, and plates full of food nobody in my family ever ate.
The meal wasn’t over until my grandfather had sucked the marrow out of
the bones, which, given his mustache, was a sight to behold.
Since I’d stopped eating meat in college, dinner at Peter Luger had
become a challenge. I’d once made the mistake of ordering salmon, which
took up half the table and tasted about as good as you might expect salmon
from a steak house would taste. Eventually my meal consisted of Coke, the
little potatoes, and an iceberg wedge salad.
I wouldn’t miss the rude waiters, but I hoped there would at least be
something for me to eat at Donald’s.
I made the mistake of arriving at the penthouse early and alone. Although
Donald and Marla were still married, she was already a distant memory,
replaced by his new girlfriend, Melania, a twenty-eight-year-old Slovenian
model whom I’d never met. They sat on an uncomfortable-looking love seat
in the foyer, a large, undefined space. Everything was marble, gold leaf,
mirrored walls, white walls, and frescoes. I’m not sure how he managed it,
but Donald’s apartment felt even colder and less like a home than the House
Melania was five years younger than I was. She sat slightly sideways next
to Donald with her ankles crossed. I was struck by how smooth she looked.
After Robert and Blaine had met her for the first time, Rob told me that
Melania had barely spoken throughout the entire meal.
“Maybe her English isn’t very good,” I said.
“No,” he scoffed. “She knows what she’s there for.” Clearly it wasn’t for
her sparkling conversation.
As soon as I sat down, Donald started telling Melania about the time he’d
hired me to write The Art of the Comeback and then launched into his version
of my “back from the brink” redemption story. He thought it was something
we had in common: we’d both hit rock bottom and then somehow clawed our
way back to the top (in his case) or just back (in mine).
“You dropped out of college, right?”
“Yes, Donald, I did.” It was exactly how I wanted to be introduced to
someone I’d never met. I was also surprised he even knew about it
“It was really bad for a while—and then she started doing drugs.”
“Whoa,” I said, holding up my hands.
“Really?” said Melania, suddenly interested.
“No, no, no. I’ve never done drugs in my life.”
He slid me a look and smiled. He was embellishing the story for effect,
and he knew I knew it. “She was a total disaster,” he said, smiling more
Donald loved comeback stories, and he understood that the deeper the hole
you crawled out of, the better billing your triumphant comeback would get.
Which was exactly how he experienced his own journey. By conflating my
dropping out of college and his hiring me to write his book (while throwing
in a fictional drug addiction), he concocted a better story that somehow had
him playing the role of my savior. Of course, between my dropping out of
school and his hiring me, I’d dropped back into school, graduated, and gotten
a master’s degree—all without taking any drugs at all. There was no point in
setting the record straight, however; there never was with him. The story was
for his benefit as much as anybody else’s, and by the time the doorbell rang,
he probably already believed his version of events. When the three of us rose
to greet the new guests, I realized that Melania had said only one word during
our time together.
On June 11, 1999, Fritz called to tell me our grandfather had been taken to
Long Island Jewish Medical Center, another Queens hospital my
grandparents had patronized in recent years. He said it was likely the end.
I drove the ten minutes from my house and found that the room was
already full. Gam sat in the only chair near the bed; Elizabeth stood next to
her, holding my grandfather’s hand.
After saying hello, I stood by the window next to Robert’s wife, Blaine.
She said, “We’re supposed to be in London with Prince Charles.” I realized
she was talking to me—something she rarely did.
“Oh,” I said.
“He invited us to one of his polo matches. I can’t believe we had to
cancel.” She sounded exasperated and made no effort to lower her voice.
I could have topped that story. In a week I was supposed to be getting
married on a beach in Maui. Nobody in the family knew; they’d always been
spectacularly uninterested in my personal life (when necessary, I asked a guy
friend to accompany me to any family occasion that required a plus one) and
never asked about my boyfriends or relationships.
A couple of years earlier, Gam and I had been talking about Princess
Diana’s funeral, and when she had said with some vehemence, “It’s a
disgrace they’re letting that little faggot Elton John sing at the service,” I’d
realized it was better that she didn’t know I was living with and engaged to a
Seeing how serious my grandfather’s condition was, I had a terrible
feeling that when I got home, I’d have to break the news to my fiancée that,
after months of planning and overcoming several logistical nightmares, our
mostly secret wedding would have to be postponed.
I noticed a hush in the room, as if everybody had run out of small talk at
the same time. We were reduced for the moment to listening to my
grandfather’s uneven breathing: a ragged, uncertain inhalation, followed by
an unnatural pause for longer than seemed safe until finally he exhaled.
The Only Currency
Fred Trump died on June 25, 1999. The following day, his obituary was
published in the New York Times under the banner “Fred C. Trump, Postwar
Master Builder of Housing for Middle Class, Dies at 93.” The obituary writer
made a point of contrasting Fred’s status as “a self-made man” with “his
flamboyant son Donald.” My grandfather’s propensity for picking up unused
nails at his construction sites to hand back to his carpenters the next day was
noted before the details of his birth. The Times also repeated the family line
that Donald had built his own business with minimal help from my
grandfather—“a small amount of money”—a statement that the paper itself
would refute twenty years later.
We sat in the library, each with our own copy of the Times. Robert was
raked over the coals by his siblings for having told the Times that my
grandfather’s estate was worth between $250 million and $300 million.
“Never, never give them numbers,” Maryanne lectured him, as if he were a
stupid kid. He stood there shamefaced, cracking his knuckles and bouncing
on the balls of his feet, just as my grandfather used to do, as if suddenly
imagining the ensuing tax bill. The valuation was absurdly low—eventually
we would learn that the empire was probably worth four times that—but
Maryanne and Donald would never have admitted that it was even that much.
Later we stood upstairs in the Madison Room at the Frank E. Campbell
Funeral Chapel on Manhattan’s Upper East Side, the most exclusive and
expensive bereavement services provider in the city, smiling and shaking
hands as a seemingly endless line of visitors passed through.
Overall, more than eight hundred people moved through the rooms. Some
were there to pay their respects, including rival real estate developers such as
Sam LeFrak, New York governor George Pataki, former Senator Al
D’Amato, and comedian and future Celebrity Apprentice contestant Joan
Rivers. The rest were most likely there to catch a glimpse of Donald.
On the day of the funeral, Marble Collegiate Church was filled to capacity.
During the service, from beginning to end, everyone had a role to play. It was
all extremely well choreographed. Elizabeth read my grandfather’s “favorite
poem,” and the rest of the siblings gave eulogies, as did my brother, who
spoke on behalf of my dad, and my cousin David, who represented the
grandchildren. Mostly they told stories about my grandfather, although my
brother was the only one who came close to humanizing him. For the most
part, in ways both oblique and direct, the emphasis was on my grandfather’s
material success, his “killer” instinct, and his talent for saving a buck. Donald
was the only one to deviate from the script. In a cringe-inducing turn, his
eulogy devolved into a paean to his own greatness. It was so embarrassing
that Maryanne later told her son not to allow any of her siblings to speak at
Rudolph Giuliani, New York City’s mayor at the time, also spoke.
When the service was over, the six oldest grandchildren (Tiffany was too
young) accompanied the casket to the hearse as honorary pallbearers, which
meant, as was often the case in our family, that others did the heavy lifting
while we got the credit.
All of the streets from Fifth Avenue and 45th Street to the Midtown
Tunnel more than sixteen blocks away had been closed to cars and
pedestrians, so our motorcade, with a police escort, slid easily out of the city.
It was a quick trip to All Faiths Cemetery in Middle Village, Queens, for the
We drove back to the city just as quickly, but with less fanfare, for lunch
at Donald’s apartment. Afterward, I accompanied my grandmother back to
the House. The two of us sat in the library and chatted for a while. She
seemed tired but relieved. It had been a very long day; a very long few years,
actually. Other than the live-in maid, who was asleep upstairs, it was just the
two of us. I was supposed to be on my honeymoon. I stayed with her until she
was ready to go to bed.
When she said she was ready for bed, I asked her if she wanted me to stay
or if there was anything I could get for her before I left.
“No, dear, I’m fine.”
I bent over to kiss her cheek. She smelled like vanilla. “You are my
favorite person,” I told her. It wasn’t true, but I said it because I loved her. I
said it, too, because nobody else had bothered to stay with her after her
husband of sixty-three years had been put in the ground.
“Good,” she replied. “I should be.”
And then I left her alone in that large, quiet, empty house.
Two weeks after my grandfather’s funeral, I was home when a DHL truck
pulled up and delivered a yellow envelope containing a copy of my
grandfather’s will. I read through it twice to be sure I hadn’t misunderstood
anything. I had promised my brother I’d call him as soon as I knew anything,
but I was reluctant to do so. Fritz and Lisa’s third child, William, had been
born hours after my grandfather’s funeral. Twenty-four hours after that, he’d
begun having seizures. He had been in the neonatal intensive care unit ever
since. They had two young children at home, and Fritz had to work. I had no
idea how they were managing all of it.
I hated to be the bearer of more bad news, but he needed to know.
I called him.
“So what’s the deal?” he asked.
“Nothing,” I told him. “We got nothing,”
A few days later, I got a call from Rob. As far as I could remember, he had
only ever called me before to let me know when Gam was in the hospital. He
acted as if everything were fine. If I signed off on the will, he implied,
everything would be great. And he did need my signature in order for the will
to be released for probate. Though it’s true that my grandfather disinherited
me and my brother—that is, instead of splitting what would have been my
father’s 20 percent share of his estate between me and my brother, he had
divided it evenly among his four other children—we were included in a
bequest made separately to all of the grandchildren, an amount that proved to
be less than a tenth of 1 percent of what my aunts and uncles had inherited. In
the context of the entire estate it was a very small amount of money, and it
must have infuriated Robert that it gave me and Fritz the power to hold up the
distribution of the assets.
Days passed, and I couldn’t bring myself to sign. In the breadth and
concision of its cruelty, the will was a stunning document that very much
resembled my parents’ divorce agreement.
For a while, Robert called me every day. Maryanne and Donald had
assigned him to be the point person; Donald didn’t want to be bothered, and
Maryanne’s husband, John, had been diagnosed with esophageal cancer, and
his prognosis was not good.
“Cash in your chips, Honeybunch,” Rob said repeatedly, as if that would
make me forget what was in the will. No matter how many times he said it,
though, my brother and I had agreed not to sign anything until we had some
idea of what our options were.
Eventually Rob began to lose patience. Fritz and I were holding
everything up; the will couldn’t go to probate until all of the beneficiaries had
signed off. When I told Rob that Fritz and I weren’t yet willing to take that
step, he suggested we get together to discuss it.
At our first meeting, when we asked Rob to explain why my grandfather
had done what he had, Rob said, “Listen, your grandfather didn’t give a shit
about you. And not just you, he didn’t give a shit about any of his
“We’re being treated worse because our father died,” I said.
“No, not at all.”
When we pointed out that our cousins would still benefit from what their
parents were getting from my grandfather, Rob said, “Any of them could be
disowned at any time. Donny was going to join the army or some bullshit like
that, and Donald and Ivana told him if he did, they’d disown him in a
“Our father didn’t have that luxury,” I said.
Rob sat back. I could see him trying to recalibrate. “It’s pretty simple,” he
said. “As far as your grandfather was concerned, dead is dead. He only cared
about his living children.”
I wanted to point out that my grandfather hadn’t cared about Rob, either,
but Fritz intervened. “Rob,” he said, “this just isn’t fair.”
I lost track of how many meetings the three of us had between July and
October 1999. There was a brief respite in September while I was in Hawaii
for my postponed wedding and honeymoon.
At the very beginning of our discussions, Fritz, Robert, and I agreed that
we would leave Gam out of it. I assumed she had no idea how we’d been
treated in my grandfather’s will and saw no reason to upset her. Hopefully we
would be able to resolve everything, and she’d never have to know there had
been a problem at all. I spoke to her every day while I was away and, once
back in New York, resumed my visits to her. The negotiations, if they could
even be called that, also resumed. There was a numbing sameness to our
conversations. No matter what Fritz and I said, Rob came back with his
clichés and canned responses. We remained at a standstill.
I asked him about Midland Associates, the management company my
grandfather had set up decades earlier in order to avoid paying certain taxes
and benefit his children. Midland owned a group of seven buildings
(including Sunnyside Towers and the Highlander) that were referred to in my
family as “the mini-empire.” I knew very little about it—none of my trustees
had ever explained what role it played or how money was generated—but I
received a check every few months. We wanted to know how or if my
grandfather’s death would affect the partnership going forward.
We weren’t asking for a specific dollar amount or a percentage of the
estate, just some assurance that the assets we already had would be secure in
the future and if, given the family’s enormous wealth, there was anything
they could see their way clear to doing as far as my grandfather’s estate was
concerned. As the executors and, along with Elizabeth, sole beneficiaries,
Maryanne, Donald, and Robert had a wide latitude in that area, but Rob
At our final meeting, in the bar of the Drake Hotel on 56th Street and Park
Avenue, it was clear that Robert had begun to understand that we weren’t
going to back down. Prior to that, despite the unpleasant things he’d been
saying to us, he had maintained an affable “Hey, kids, I’m just the
messenger” attitude. That day he reminded us, once again, that my
grandfather had hated our mother and had been afraid his money would fall
into her hands.
That was laughable, because for more than twenty-five years my mother
had lived according to the terms the Trumps had set, following their
directions to the letter. She had lived in the same poorly maintained
apartment in Jamaica, Queens; her alimony and child support payments had
rarely been increased, yet she had never asked for more.
Finally, Fred had disowned us because he could. The people who’d been
assigned to protect us, at least financially, were our trustees—Maryanne,
Donald, Robert, and Irwin Durben—but they apparently had little interest in
protecting us, especially at their own expense.
Rob leaned forward, suddenly serious. “Listen, if you don’t sign this will,
if you think of suing us, we will bankrupt Midland Associates and you will be
paying taxes on money you don’t have for the rest of your lives.”
There was nothing left to say after that. Either Fritz and I gave in, or we
fought. Neither option was a good one.
We consulted with Irwin, who felt like the only ally we had left. He was
incensed about how poorly our grandfather had treated us in the will. When
we told him how Robert had responded when asked about Midland
Associates and our share in other Trump entities, he said, “Your share of the
ground leases under Shore Haven and Beach Haven alone are priceless. If
they’re not going to do anything for you, you’re going to have to sue them.”
I had no idea what a ground lease was, let alone that I had a share in two
of them, but I knew what priceless meant. And I trusted Irwin. Based on his
recommendation, Fritz and I made a decision.
After all those months, William was still in the hospital, and Fritz and Lisa
were feeling overwhelmed. I told him I’d take care of it and called Rob that
“Is there anything you guys can do, Rob?” I asked.
“Sign the will, and we’ll see.”
“Your father’s dead,” he said.
“I know he’s dead, Rob. But we’re not.” I was so sick of having that
He paused. “Maryanne, Donald, and I are simply following Dad’s wishes.
Your grandfather didn’t want you or Fritz, or especially your mother, to get
I took a deep breath. “This is going nowhere,” I said. “Fritz and I are
going to hire an attorney.”
As if a switch had been flipped, Robert screamed, “You do whatever the
fuck you need to do!” and slammed the phone down.
The next day, there was a message from Gam on my answering machine
when I got home. “Mary, it’s your grandmother,” she said tersely. She never
referred to herself that way. It was always “Gam.”
I called her back right away.
“Your uncle Robert tells me you and your brother are suing for twenty
percent of your grandfather’s estate.”
I felt blindsided and said nothing right away. Obviously Rob had broken
our agreement and told my grandmother his version of what we’d been
discussing. But the other thing that held me up was that my grandmother
spoke as if our getting what would have been my father’s share of the estate
was somehow wrong and unseemly. I was confused—about loyalty, about
love, about the limits of both. I’d thought I was part of the family. I’d gotten
it all wrong.
“Gam, we haven’t asked for anything. I don’t know what Rob told you,
but we’re not suing anybody.”
“You’d better not be.”
“We’re just trying to figure this out, that’s all.”
“Do you know what your father was worth when he died?” she said. “A
whole lot of nothing.”
There was a pause and then a click. She’d hung up on me.
I sat there with the phone in my hand, not knowing what to do next. It was
one of those moments that changes everything—both what came before and
what will come after—and it was too big to process.
I called my brother, and as soon as I heard his voice, I burst into tears.
He called Gam to see if he could explain what we were really asking for,
but they had basically the same conversation. Her parting shot to him was
slightly different, though: “When your father died, he didn’t have two nickels
to rub together.” In the world of my family, that was the only thing that
mattered. If your only currency is money, that’s the only lens through which
you determine worth; somebody who has accomplished in that context as
little as my father was worth nothing—even if he happened to be your son.
Further, if my father died penniless, his children weren’t entitled to anything.
My grandfather had every right to change his will as he saw fit. My aunts
and uncles had every right to follow his instructions to the letter, despite the
fact that none of them deserved their share of Fred’s fortune any more than
my father did. If not for an accident of birth, none of them would have been a
multimillionaire. Prosecutors and federal judges don’t typically have $20
million cottages in Palm Beach. Executive assistants don’t have weekend
homes in Southampton. (Although, to be fair, Maryanne and Elizabeth were
the only two of the siblings, other than my father, to work outside of the
family business.) Still, they acted as if they had earned every penny of my
grandfather’s wealth and that money was so tied up in their sense of selfworth that letting any of it go was not an option.
On Irwin’s advice we approached Jack Barnosky, a partner at Farrell Fritz,
the largest law firm in Nassau County. Jack, a pompous, self-satisfied man,
agreed to take us on as clients. His strategy was to prove that my
grandfather’s 1990 will should be overturned: Fred Trump had not been of
sound mind at the time the will was signed, and he had been under the undue
influence of his children.
Less than a week after we served the executors, Jack received a letter from
Lou Laurino, a short, wiry pit bull of a lawyer who was representing my
grandfather’s estate. The medical insurance that had been provided to us by
Trump Management since we were born had been revoked. Everyone in the
Trump family was covered by it. My brother depended upon this insurance to
pay for my nephew’s crushing medical expenses. When William had first
fallen ill, Robert had promised Fritz that they would take care of everything;
he should just send the bills to the office.
Taking away our insurance didn’t benefit them at all; it was merely a way
to cause us more pain and make us more desperate. William was out of the
hospital by then, but he was still susceptible to seizures, which more than
once had put him in a state of cardiac arrest so severe that he would not have
survived without CPR. He still required round-the-clock nursing care.
The family all knew this, but none of them objected, not even my
grandmother, who was as aware as anybody that her own desperately ill
great-grandchild would probably need expensive medical care for the rest of
Fritz and I had no choice but to launch another lawsuit to make them
reinstate William’s medical insurance. The suit required depositions and
affidavits from the doctors and nurses responsible for William’s care. It was
time consuming and stressful and culminated in an appearance in front of a
Laurino defended the cancellation of the insurance by first claiming that
we had no right to expect the insurance in perpetuity. It was, rather, a gift that
had been bestowed upon us out of the goodness of my grandfather’s heart. He
also downplayed William’s condition, insisting that the round-the-clock
nurses who attended to William and had saved his life more than once were
overpriced babysitters. If Fritz and Lisa were worried that their infant son
might have another seizure, he said, they should just learn CPR.
The depositions did nothing to help us. I couldn’t believe what a terrible
interlocutor Jack was. He failed to follow up and went off on tangents.
Despite the fact that Fritz and I had prepared long lists of questions for him,
he rarely, if ever, referred to them. Robert, much more detached than the last
time I’d spoken to him, reiterated my grandfather’s hatred of my mother as
his central justification for the disinheritance; Maryanne angrily referred to
me and my brother as “absentee grandchildren.” I thought of all the times she
had called the House when I was visiting my grandmother; now I understood
why she’d never told my grandmother to say hi. My grandfather, she said,
had been furious with us because we had never spent time with our
grandmother, completely ignoring the history of the last decade. Apparently,
my grandfather had also hated that Fritz never wore a tie and I, as a teenager,
had dressed in baggy sweaters and jeans. When he was deposed, Donald
didn’t know or couldn’t remember anything, a kind of strategic forgetfulness
he has employed many times to evade blame or scrutiny. All three of them
claimed in their sworn depositions that my grandfather had been “sharp as a
tack” until just before he died.
During that time, my aunt Elizabeth ran into a family friend, who later
relayed the exchange to my brother. “Can you believe what Fritz and Mary
are doing?” she asked him. “All they care about is the money.” Of course
wills are about money, but in a family that has only one currency, wills are
also about love. I thought Liz might have understood that. She had no power.
Her opinion about the situation wouldn’t have mattered to anybody but me
and my brother, but it still hurt that she was toeing the party line. Even a
silent, powerless ally would have been better than none at all.
After almost two years, with legal bills piling up and having made no
progress on any kind of settlement, we had to decide whether to take our
family to court. William’s condition remained serious, and a trial would have
taken the kind of energy and focus my brother didn’t have. Reluctantly, we
decided to settle.
Maryanne, Donald, and Robert refused to settle unless we agreed to let
them buy our shares of the assets we’d inherited from our father—his 20
percent of the mini-empire and the “priceless” ground leases.
My aunts and uncles submitted a property valuation to Jack Barnosky,
and, using their figures, he and Lou Laurino arrived at a settlement figure that
was likely based on suspect numbers. Jack told us that, short of a trial, it was
the best we could expect. “We know they’re lying,” he said, “but it’s ‘He
said, she said.’ Besides, your grandfather’s estate is only worth around thirty
million dollars.” That was only a tenth of the estimate Robert had given the
New York Times in 1999, which itself would turn out to be only 25 percent of
the estate’s actual value.
Fred no doubt believed that my dad had been given the same tools, the
same advantages, and the same opportunities as Donald had. If Freddy had
thrown them all away, that wasn’t his father’s fault. If, despite them, my dad
had continued to be a terrible provider, my brother and I should consider
ourselves lucky that there were trust funds our father couldn’t squander when
he was alive. Whatever happened to us after that had nothing to do with Fred
Trump. He had done his part; we had no right to expect more.
While the lawsuits were still in progress, I received word that, after a brief
illness, Gam had died on August 7, 2000, at Long Island Jewish Medical
Center, just as my grandfather had. She was eighty-eight.
If I had known she was sick, I think I would have tried to see her, but the
fact that she hadn’t asked to see me clarified just how easy it had been for us
to let each other go. We had never spoken after that last phone conversation,
just as I had not spoken again to Robert, Donald, Maryanne, or Elizabeth. It
had never occurred to me to try.
Fritz and I decided to attend Gam’s funeral, but, knowing we were
unwelcome, we stood in one of the overflow rooms at the back of Marble
Collegiate Church. Along with a couple of Donald’s security guards, we
watched the service on a closed-circuit monitor.
The eulogies were remarkable only for what was not said. There was a lot
of speculation about my grandparents’ reunion in Heaven, but my father,
their oldest son, who had been dead for almost twenty-seven years, was not
mentioned at all. He didn’t even appear in my grandmother’s obituary.
I received a copy of Gam’s will a few weeks after she died. It was a
carbon copy of my grandfather’s, with one exception: my brother and I had
been removed from the section outlining the bequests for her grandchildren.
My father and his entire line had now been effectively erased.
The Worst Investment Ever Made
The Political Is Personal
Nearly a decade would pass before I saw my family again, in October 2009
at my cousin Ivanka’s wedding to Jared Kushner. I had no idea why I’d
received the invitation—which was printed on the same heavy-gauge
stationery favored by the Trump Organization.
As the limo I’d taken from my home on Long Island approached the
clubhouse at Donald’s golf club in Bedminster, New Jersey, which looked
eerily like the House, I was unsure what to expect. Ushers handed out black
shawls, which made me feel a little less exposed as I wrapped one around my
The outdoor ceremony took place beneath a large white tent. Gilt chairs
were lined up in rows on either side of a gilt-trimmed runway carpet. The
traditional Jewish chuppah, covered in white roses, was about the size of my
house. Donald stood awkwardly in a yarmulke. Before the vows, Jared’s
father, Charles, who’d been released from prison three years earlier, rose to
tell us that when Jared had first introduced him to Ivanka, he had thought she
would never be good enough to join his family. It was only after she had
committed to converting to Judaism and worked hard to make it happen that
he had begun to think she might be worthy of them after all. Considering that
Charles had been convicted of hiring a prostitute to seduce his brother-in-law,
taping their illicit encounter, and then sending the recording to his sister at his
nephew’s engagement party, I found his condescension a bit out of line. After
the ceremony, my brother, my sister-in-law, and I entered the clubhouse.
As I walked down the hallway, I saw my uncle Rob. My last exchange
with him had been when he’d hung up on me in 1999 after I had told him that
Fritz and I were hiring a lawyer to contest my grandfather’s will. As I
approached him now, he surprised me by breaking into a smile. He put his
hand out, then leaned down—he was much taller than I was even in my heels
—shook my hand, and kissed me on the cheek, the typical Trump greeting.
“Honeybunch! How are you?” he said brightly. Before I could answer, he
said, “You know, I’ve been thinking that the statute of limitations on family
estrangement has passed.” Then, bouncing on the balls of his feet, he
smacked a closed fist into his open palm in a not-quite-accurate imitation of
“That sounds good to me,” I said. We spent a couple of minutes
exchanging pleasantries. When we were done, I walked up the stairs to the
cocktail reception, where I spotted Donald speaking to somebody I
recognized—a mayor or a governor—although I can’t recall who it was.
“Hi, Donald,” I said, as I walked toward them.
“Mary! You look great.” He shook my hand and kissed my cheek, as Rob
had. “It’s good to see you.”
“It’s good to see you, too.” It was a relief to discover that things between
us were pleasant and civil. Having established that, I gave way to the next
person in the lengthening line of people, some of them waiting to
congratulate the father of the bride. But The Apprentice had just concluded its
eighth season, so it’s just as likely that many of them were simply there for
the photo op. “Have fun,” he called after me as I walked away.
The reception was being held in an enormous ballroom quite a distance
from the hors d’oeuvres. Along the way I saw my aunt Liz in the distance,
chasing after her husband. I caught her eye and waved. She waved back and
said, “Hi, sweetie pie.” But she didn’t stop, and that was the last I saw of her.
I walked past voluminous bunting and the highly polished dance floor and
finally found my place at the second cousins’ table on the periphery of the
ballroom. In the distance I could hear the occasional thwap of rotors as
helicopters landed and took off.
After the first course had been served, I decided to find Maryanne. As I
wound my way through the tables, Donald took to the stage to give his toast.
If I hadn’t known who he was talking about, I would have thought he was
toasting his secretary’s daughter.
I spotted Maryanne and paused. Fritz and I would not have been invited to
Ivanka’s wedding without Maryanne’s approval. She didn’t see me until I
was standing right in front of her.
“Hi, Aunt Maryanne.”
It took her a few seconds to realize who I was. “Mary.” She didn’t smile.
“How are you?” she asked, her expression rigid.
“Everything’s great. My daughter just turned eight, and—”
“I didn’t know you had a daughter.”
Of course she didn’t know I had a daughter or that I was raising her with
the woman I’d married after my grandfather’s funeral and then divorced or
that I had recently received my doctorate in clinical psychology. But she
acted as if her lack of such knowledge was an insult to her. The rest of our
brief conversation was equally tense. She mentioned that Ivana had missed
Ivanka’s wedding shower but said, sotto voce, that she couldn’t discuss why.
I retreated to my table, and when I realized the vegetarian meal I’d ordered
had not arrived, I ordered a martini in its stead. The olives would suffice.
Sometime later, I saw Maryanne, looking determined, head toward us as if
on a mission. She walked straight up to my brother and said, “We need to talk
about the elephant in the room.” Then, gesturing to include me, “The three of
A few weeks after Ivanka and Jared’s wedding, Fritz and I met with
Maryanne and Robert at her apartment on the Upper East Side. It wasn’t clear
to me why Rob was there, but I thought perhaps he planned to make good on
his claim that the “statute of limitations” on family estrangement had passed.
I took it as a good sign, but as the afternoon wore on, I became less sure. We
didn’t discuss anything that seemed pertinent. As we sat in the living room
with its spectacular view of Central Park and the Metropolitan Museum of
Art, Maryanne made passing references to “the debacle,” as she called the
lawsuit, but nobody else seemed eager to go down that road.
Rob leaned forward in his chair, and I hoped finally we were going to start
dealing with the so-called elephant in the room. Instead he told a story.
Ten years earlier, Rob had still been working for Donald in Atlantic City
when Donald’s financial situation was dire. His investors were getting
hammered, the banks were after him, and his personal life was in shambles.
When things were at their worst, Donald had called Rob with a request.
“Listen, Rob, I don’t know how this is all going to end,” he had said. “But
it’s tough, and I might drop dead of a heart attack. If anything happens to me,
I want you to make sure Marla will be okay.”
“Sure, Donald. Just tell me what you want me to do.”
“Get her ten million dollars.”
I thought, Holy shit, that’s a lot of money! at the same moment that Rob
said, “What a cheap bastard.”
Rob laughed at the memory as I sat there stunned, wondering how much
money those people had. Last I’d heard, $10 million would have been onethird of my grandfather’s entire estate.
“Around the same time, Donald called to tell me I was one of his three
favorite people,” Maryanne said. “Apparently he forgot he had three
children.” (Tiffany and Barron were still to come.)
We never met with Rob again, but Fritz and I, separately and together, had
lunch occasionally with Maryanne. For the first time in my life, I got to know
my aunt. Not since I’d spent time with Donald while I was writing his book
had I felt a little bit as though I were part of the family.
A couple of months after my aunts’ April 2017 birthday party, I was in my
living room lacing up my sneakers when the front doorbell rang. I don’t
know why I answered it. I almost never did. Seventy-five percent of the time
it was a Jehovah’s Witness or Mormon missionaries. The rest of the time, it
was somebody wanting me to sign a petition.
When I opened the door, the only thing that registered was that the woman
standing there, with her shock of curly blond hair and dark-rimmed glasses,
was someone I didn’t know. Her khakis, button-down shirt, and messenger
bag placed her out of Rockville Centre.
“Hi. My name is Susanne Craig. I’m a reporter for the New York Times.”
Journalists had stopped contacting me a long time before. With the
exception of David Corn from Mother Jones and somebody from Frontline,
the only other person to leave a message before the election had been from
Inside Edition. Nothing I had to say about my uncle would have mattered
before November 2016; why would anybody want to hear from me now?
The futility of it annoyed me, so I said, “It is so not cool that you’re
showing up at my house.”
“I understand. I’m sorry. But we’re working on a very important story
about your family’s finances, and we think you could really help us.”
“I can’t talk to you.”
“At least take my card. If you change your mind, you can call me
“I don’t talk to reporters,” I said. I took her card anyway.
A few weeks later, I fractured the fifth metatarsal of my left foot. For the next
four months, I was a prisoner in my home, my foot elevated at all times as I
sat on the couch.
I received a letter from Susanne Craig reiterating her belief that I had
documents that could help “rewrite the history of the President of the United
States,” as she put it. I ignored the letter. But she persisted.
After a month of sitting on the couch, scrolling through Twitter with the
news constantly on in the background, I watched in real time as Donald
shredded norms, endangered alliances, and trod upon the vulnerable. The
only thing about it that surprised me was the increasing number of people
willing to enable him.
As I watched our democracy disintegrating and people’s lives unraveling
because of my uncle’s policies, I kept thinking about Susanne Craig’s letter. I
found her business card and called her. I told her that I wanted to help but I
no longer had any documents relating to our lawsuit years before.
“Jack Barnosky might still have them,” she said.
Ten days later I was on my way to his office.
The headquarters of Farrell Fritz was located in one of two oblong
buildings sheathed in blue glass. Bitterly cold air pushed between them
across the wide-open space of the enormous parking lot. It’s impossible to
park anywhere near the entrance, so after I found a spot, it took me ten
minutes to get to the lobby on my crutches. I negotiated the escalator and the
marble floors very carefully.
By the time I arrived at my destination, I was tired and overheated. Thirty
banker’s boxes lined two walls and filled a bookshelf. The room’s only other
contents were a desk and a chair. Jack’s secretary had kindly put out a pad of
paper, a pen, and some paper clips. I dropped my bags, leaned my crutches
against the wall, and half fell into the desk chair. None of the boxes was
labeled; I had no idea where to start.
It took me about an hour to familiarize myself with the contents of the
boxes and compile a list, which required wheeling around the room on my
chair and lifting boxes onto the desk while standing on one leg. When Jack
stopped by, I was flushed and soaking wet. He reminded me that I couldn’t
take any documents out of the room. “They belong to your brother, too, and I
need his permission,” which wasn’t at all true.
When he turned to leave, I called after him, “Jack, wait a second. Can you
remind me why we decided to settle the lawsuit?”
“Well, you were getting concerned about the costs, and, as you know, we
don’t take cases on contingency. Although we knew they were lying to us, it
was ‘He said, she said.’ Besides, your grandfather’s estate was only worth
thirty million dollars.” It was almost word for word what he’d told me when I
had last seen him almost twenty years earlier.
“Ah, okay. Thanks.” I was holding in my hands documents that proved the
estate had actually been worth close to a billion dollars when he died; I just
didn’t know it yet.
After I was sure he had gone, I grabbed copies of my grandfather’s wills,
floppy disks with all of the depositions from the lawsuit, and some of my
grandfather’s bank records—all of which I was legally entitled to as part of
the lawsuit—and stuffed them into my bags.
Sue came by my house the next day to pick up the documents and drop off
a burner phone so we could communicate more securely going forward. We
weren’t taking any chances.
On my third trip to Farrell Fritz, I methodically went through every box
and discovered that there were two copies of everything. I mentioned the fact
to Jack’s secretary and suggested that it obviated the need to get my brother’s
permission, which was a relief since I didn’t want to involve him. I would
leave a set of documents for him in the unlikely event he ever wanted one.
I was just beginning to look for the list of material the Times wanted when
I got a message from Jack: I could take whatever I wanted, as long as I left a
copy. I hadn’t been prepared for that. In fact, I had plans to meet Sue and her
colleagues Russ Buettner and David Barstow (the other two journalists
working on the story) at my house at 1:00 with whatever I’d managed to
smuggle out. I texted Sue with the news that I’d be late.
At 3:00, I drove to the loading dock beneath the building, and nineteen
boxes were loaded into the back of the borrowed truck I was driving since I
couldn’t work the clutch in my own car.
It was just beginning to get dark when I pulled into my driveway. The
three reporters were waiting for me in David’s white SUV, which sported a
pair of reindeer antlers and a huge red nose wired to the grill. When I showed
them the boxes, there were hugs all around. It was the happiest I’d felt in
When Sue, Russ, and David left, I was exhausted and relieved. It had been
a head-spinning few weeks. I hadn’t fully grasped how much of a risk I was
taking. If anybody in my family found out what I was doing, there would be
repercussions—I knew how vindictive they were—but there was no way to
gauge how serious the consequences might be. Anything would pale in
comparison to what they’d already done. I finally felt as though I might be
able to make a difference after all.
In the past, there had been nothing I could do that would be significant
enough, so I hadn’t tried very hard. Because being good or doing good didn’t
count for much; whatever you did had to be extraordinary. You couldn’t just
be a prosecutor; you had to be the best prosecutor in the country, you had to
be a federal judge. You couldn’t just fly planes; you had to be a professional
pilot for a major carrier at the dawn of the jet age. For a long time, I blamed
my grandfather for my feeling this way. But none of us realized that the
expectation of being “the best” in my grandfather’s view had applied only to
my father (who had failed) and Donald (who had wildly exceeded Fred’s
When I finally realized that my grandfather didn’t care what I
accomplished or contributed and that my own unrealistic expectations were
paralyzing me, I still felt that only a grand gesture would set it right. It wasn’t
enough for me to volunteer at an organization helping Syrian refugees; I had
to take Donald down.
After the election, Donald called his big sister, ostensibly to find out how he
was doing. Of course, he thought he already knew the answer; otherwise he
wouldn’t have made the call in the first place. He merely wanted her to
confirm very strongly that he was doing a fantastic job.
When she said, “Not that good,” Donald immediately went on offense.
“That’s nasty,” he said. She could see the sneer on his face. Then,
seemingly apropos of nothing, he asked her, “Maryanne, where would you be
without me?” It was a smug reference to the fact that Maryanne owed her
first federal judgeship to Donald because Roy Cohn had done him (and her) a
favor all those years ago.
My aunt has always insisted that she’d earned her position on the bench
entirely on her own merits, and she shot back at him, “If you say that one
more time, I will level you.”
But it was an empty threat. Although Maryanne had prided herself on
being the only person on the planet Donald ever listened to, those days were
long past, which was illustrated not long after, in June 2018. On the eve of
Donald’s first summit with North Korean dictator Kim Jong-un, Maryanne
called the White House and left a message with his secretary: “Tell him his
older sister called with a little sisterly advice. Prepare. Learn from those who
know what they are doing. Stay away from Dennis Rodman. And leave his
Twitter at home.”
He ignored all of it. The Politico headline the following day read “Trump
Says Kim Meeting Will Be About ‘Attitude,’ Not Prep Work.” If Maryanne
had ever had any sway over her little brother, it was gone now. Aside from
the requisite birthday call, they didn’t speak much after that.
While they were working on the article, the Times reporters invited me to join
them for a tour of my grandfather’s properties. On the morning of January 10,
2018, they picked me up in David’s SUV, still adorned with its antlers and
red nose, at the Jamaica train station. We started at the Highlander, where I’d
grown up, and over the course of the day we traversed snow drifts and
patches of ice in an effort to visit as much of the Trump empire as possible.
After nine hours we still hadn’t managed to see all of it. I had traded in my
crutches for a cane by then but was still exhausted, mentally and physically,
when I got home. I tried to make sense of what I’d seen. I’d always known
that my grandfather owned buildings, but I’d had no idea just how many.
More disturbing, my father had apparently owned 20 percent of some of the
buildings I’d never heard of before.
On October 2, 2018, the New York Times published an almost 14,000-
word article, the longest in its history, revealing the long litany of potentially
fraudulent and criminal activities my grandfather, aunts, and uncles had
Through the extraordinary reporting of the Times team, I learned more
about my family’s finances than I’d ever known.
Donald’s lawyer, Charles J. Harder, predictably denied the allegations,
saying: “The New York Times’s allegations of fraud and tax evasion are 100
percent false, and highly defamatory. There was no fraud or tax evasion by
anyone.” But the investigative reporters laid out a devastating case. Over the
course of Fred’s life, he and my grandmother had transferred hundreds of
millions of dollars to their children. While my grandfather was alive, Donald
alone had received the equivalent of $413 million, much of it through
questionable means: loans that he had never repaid, investments in properties
that had never matured; essentially gifts that had never been taxed. That did
not include the $170 million he had received through the sale of my
grandfather’s empire. The amounts of money the article mentioned were
mind-boggling, and the four siblings had benefited for decades. Dad had
clearly shared in the wealth early in his life, but he had had nothing left to
show for it by the time he was thirty. I have no idea what happened to his
In 1992, only two years after Donald’s attempt to attach the codicil to my
grandfather’s will, effectively cutting his siblings out, the four of them
suddenly needed one another: after a lifetime of their father’s playing them
off against one another, they finally had a common purpose—to protect their
inheritance from the government. Fred had refused to heed his lawyers’
advice to cede control of his empire to his children before his death in order
to minimize estate taxes. That meant that Maryanne, Elizabeth, Donald, and
Robert would be responsible for potentially hundreds of millions of dollars of
estate taxes. In addition to dozens of buildings, my grandfather had amassed
extraordinary sums of cash. His properties carried no debt and brought in
millions of dollars every year. The siblings’ solution was to establish All
County Building Supply & Maintenance. At that point, my grandfather was
effectively sidelined by his increasing dementia—not that he would have
objected to their scheme. And since my father was long gone, Maryanne,
Donald, and Robert could do whatever they wanted; they were our trustees,
but there was no one to force them to fulfill their obligations to Fritz and me,
and they could easily keep us out of the loop.
My aunts and uncles detested paying taxes almost as much as their father
did, and it seemed the main purpose of All County was to siphon money from
Trump Management through large gifts disguised as “legitimate business
transactions,” according to the article. The ruse was so effective that, when
Fred died in 1999, he had only $1.9 million in cash and no assets larger than
a $10.3 million IOU from Donald. After Gam’s death the following year, the
combined value of my grandparents’ estate was said to be just $51.8 million,
a laughable assertion, especially since the siblings sold the empire for more
than $700 million four years later.
My grandfather’s investment in Donald had been extremely successful in the
short term. He had strategically deployed millions of dollars, and often tens
of millions of dollars, at key moments in Donald’s “career.” Sometimes the
funds had supported the image and the lifestyle that came with it; sometimes
they had bought Donald access and favors. With increasing frequency, they
had bailed him out. In that way, Fred purchased the ability to bask in
Donald’s reflected glory, satisfied with the knowledge that none of it would
have been possible without his expertise and largesse. In the long run,
however, my grandfather, who had one wish—that his empire survive in
Whenever my brother and I met with Robert to discuss my grandfather’s
estate, he was emphatic about honoring my grandfather’s wish that we get
nothing. When it came to their own benefit, however, the four surviving
Trump siblings had no compunction about doing the one thing my
grandfather least would have wanted: when Donald announced his desire to
sell, nobody put up a fight.
In 2004, the vast majority of the empire my grandfather had spent more
than seven decades building was sold to a single buyer, Ruby Schron, for
$705.6 million. The banks financing the sale for Schron had assigned a value
of almost $1 billion to the properties, so in one fell swoop my uncle Donald,
the master dealmaker, left almost $300 million on the table.
Selling the estate in bulk was a strategic disaster. The smartest thing
would have been to keep Trump Management intact. With practically no
effort on their part, the four siblings could have earned $5 million to $10
million a year each. But Donald needed a much bigger infusion of cash. Such
a paltry sum—even if it came to him annually—wasn’t going to cut it.
They could also have sold the buildings and complexes individually. That
would have added substantially to the selling price. That process, though,
would have been a lengthy one. Donald, whose Atlantic City creditors were
nipping at his heels, didn’t want to wait. Besides, it would have been almost
impossible to keep the news of dozens of sales a secret. They needed to
complete the sale in one transaction, as quickly and as quietly as possible.
They succeeded on that score. It may be the only one of Donald’s real
estate deals that received no press attention. Whatever objections Maryanne,
Elizabeth, and Robert might have had, they kept to themselves. Even now
Maryanne, almost ten years older, smarter, and more accomplished than the
second youngest Trump child, deferred to him. “Donald always got his way,”
she said. Besides, none of them could risk waiting; they all knew where the
bodies were buried because they had buried them together in All County.
Split four ways, they each got approximately $170 million. For Donald, it
still wasn’t enough. Maybe it wasn’t for any of them. Nothing ever was.
When I visited Maryanne in September 2018, less than a month before the
article was published, she mentioned that she had been contacted by David
Barstow. My cousin David, who had tracked my grandfather’s old accountant
Jack Mitnick, now ninety-one, to a nursing home somewhere in Florida,
believed he must have been the source of the exposé. Maryanne brushed the
whole thing off and suggested that the article was merely about the 1990
codicil controversy. If she did speak to Barstow, though, she must have
known the extent of what they were looking into—All County, the potential
tax fraud—but she seemed unfazed by it. I wondered, now for completely
different reasons, why she and Robert hadn’t tried everything in their power
to dissuade Donald from running for president. They couldn’t possibly have
thought that he (and by extension they) would continue to escape scrutiny.
I met with Maryanne again shortly after the article ran. She denied all of it.
She was just a “girl,” after all. When a piece of paper requiring her signature
had been put in front of her, she’d signed it, no questions asked. “This article
goes back sixty years. You know that’s before I was a judge,” she said, as if
the investigation had also ended sixty years before. She seemed unconcerned
that there would be any repercussions. Although a court inquiry had been
opened into her alleged conduct, all she had had to do to put an end to it was
retire, which she did, thereby retaining her $200,000-a-year pension.
In the interim, she had transferred her suspicion from the geriatric Jack
Mitnick to her first cousin John Walter, my grandfather’s sister Elizabeth’s
son, who had died that January. I marveled at the ease with which Maryanne
jumped to that conclusion. John had worked for and with my grandfather for
decades, had benefited enormously from his uncle’s wealth, had been heavily
involved in All County, and, as far as I knew, had always been very loyal. I
thought it strange she would implicate him—although her suspicions of him
worked in my favor. What I didn’t know at the time was that John’s obituary
had neglected to mention Donald. John had always been interested in Trump
family history and boastful of his connection with Trump Management, so
that was a remarkable omission.
More surprising, though, was the fact that Maryanne didn’t seem to think
that I would find anything in the article disturbing—as if she, too, had come
to believe a version of events that obliterated the truth and rewrote history. It
didn’t occur to her that the revelations would affect me in any way.
In fact, the vast amounts of money the siblings had possibly stolen made
their fight with us over my grandfather’s will and their drastic devaluation of
our partnership share (which I now understood for the first time) seem
pathologically petty and their treatment of my nephew vis-à-vis our medical
insurance even more cruel.
A Civil Servant in Public Housing
There is a through line from the House to the Trump Tower triplex to the
West Wing, just as there is from Trump Management to the Trump
Organization to the Oval Office. The first are essentially controlled
environments in which Donald’s material needs have always been taken care
of; the second, a series of sinecures in which the work was done by others
and Donald never needed to acquire expertise in order to attain or retain
power (which partly explains his disdain for the expertise of others). All of
this has protected Donald from his own failures while allowing him to
believe himself a success.
Donald was to my grandfather what the border wall has been for Donald: a
vanity project funded at the expense of more worthy pursuits. Fred didn’t
groom Donald to succeed him; when he was in his right mind, he wouldn’t
trust Trump Management to anybody. Instead, he used Donald, despite his
failures and poor judgment, as the public face of his own thwarted ambition.
Fred kept propping up Donald’s false sense of accomplishment until the only
asset Donald had was the ease with which he could be duped by more
There was a long line of people willing to take advantage of him. In the
1980s, New York journalists and gossip columnists discovered that Donald
couldn’t distinguish between mockery and flattery and used his
shamelessness to sell papers. That image, and the weakness of the man it
represented, were precisely what appealed to Mark Burnett. By 2004, when
The Apprentice first aired, Donald’s finances were a mess (even with his
$170 million cut of my grandfather’s estate when he and his siblings sold the
properties), and his own “empire” consisted of increasingly desperate
branding opportunities such as Trump Steaks, Trump Vodka, and Trump
University. That made him an easy target for Burnett. Both Donald and the
viewers were the butt of the joke that was The Apprentice, which, despite all
evidence to the contrary, presented him as a legitimately successful tycoon.
For the first forty years of his real estate career, my grandfather never
acquired debt. In the 1970s and ’80s, however, all of that changed as
Donald’s ambitions grew larger and his missteps became more frequent. Far
from expanding his father’s empire, everything Donald did after Trump
Tower (which, along with his first project, the Grand Hyatt, could never have
been accomplished without Fred’s money and influence) chipped away at the
empire’s value. By the late 1980s, the Trump Organization seemed to be in
the business of losing money, as Donald siphoned untold millions away from
Trump Management in order to support the growing myth of himself as a real
estate phenom and master dealmaker.
Ironically, as Donald’s failures in real estate grew, so did my grandfather’s
need for him to appear successful. Fred surrounded Donald with people who
knew what they were doing while giving him the credit; who propped him up
and lied for him; who knew how the family business worked.
The more money my grandfather threw at Donald, the more confidence
Donald had, which led him to pursue bigger and riskier projects, which led to
greater failures, forcing Fred to step in with more help. By continuing to
enable Donald, my grandfather kept making him worse: more needy for
media attention and free money, more self-aggrandizing and delusional about
Although bailing out Donald was originally Fred’s exclusive domain, it
didn’t take long for the banks to become partners in the project. At first,
taken in by what they believed to be Donald’s ruthless efficiency and ability
to get a job done, they were operating in good faith. As the bankruptcies piled
up and the bills for the reckless purchases came due, the loans continued but
now as a means to maintain the illusion of success that had fooled them in the
first place. It’s understandable that Donald increasingly felt he had the upper
hand, even if he didn’t. He was completely unaware that other people were
using him for their own ends and believed that he was in control. Fred, the
banks, and the media gave him more leeway in order to get him to do their
In the very early stages of his attempts to take over the Commodore Hotel,
Donald held a press conference presenting his involvement in the project as a
fait accompli. He lied about transactions that hadn’t taken place, inserting
himself in a way that made it difficult for him to be removed. He and Fred
then used this gambit to leverage his newly inflated reputation in the New
York press—and many millions of dollars of my grandfather’s money—to
get enormous tax abatements for his next development, Trump Tower.
In Donald’s mind, he has accomplished everything on his own merits,
cheating notwithstanding. How many interviews has he given in which he
offers the obvious falsehood that his father loaned him a mere million dollars
that he had to pay back but he was otherwise solely responsible for his
success? It’s easy to understand why he would believe this. Nobody has
failed upward as consistently and spectacularly as the ostensible leader of the
shrinking free world.
Donald today is much as he was at three years old: incapable of growing,
learning, or evolving, unable to regulate his emotions, moderate his
responses, or take in and synthesize information.
Donald’s need for affirmation is so great that he doesn’t seem to notice
that the largest group of his supporters are people he wouldn’t condescend to
be seen with outside of a rally. His deep-seated insecurities have created in
him a black hole of need that constantly requires the light of compliments
that disappears as soon as he’s soaked it in. Nothing is ever enough. This is
far beyond garden-variety narcissism; Donald is not simply weak, his ego is a
fragile thing that must be bolstered every moment because he knows deep
down that he is nothing of what he claims to be. He knows he has never been
loved. So he must draw you in if he can by getting you to assent to even the
most seemingly insignificant thing: “Isn’t this plane great?” “Yes, Donald,
this plane is great.” It would be rude to begrudge him that small concession.
Then he makes his vulnerabilities and insecurities your responsibility: you
must assuage them, you must take care of him. Failing to do so leaves a
vacuum that is unbearable for him to withstand for long. If you’re someone
who cares about his approval, you’ll say anything to retain it. He has suffered
mightily, and if you aren’t doing all you can to alleviate that suffering, you
should suffer, too.
From his childhood in the House to his early forays into the New York real
estate world and high society until today, Donald’s aberrant behavior has
been consistently normalized by others. When he hit the New York real estate
scene, he was touted as a brash, self-made dealmaker. “Brash” was applied to
him as a compliment (used to imply self-assertiveness more than rudeness or
arrogance), and he was neither self-made nor a good dealmaker. But that was
how it started—with his misuse of language and the media’s failure to ask
His real skills (self-aggrandizement, lying, and sleight of hand) were
interpreted as strengths unique to his brand of success. By perpetuating his
version of the story he wanted told about his wealth and his subsequent
“successes,” our family and then many others started the process of
normalizing Donald. His hiring (and treatment) of undocumented workers
and his refusal to pay contractors for completed work were assumed to be the
cost of doing business. Treating people with disrespect and nickel-anddiming them made him look tough.
Those misrepresentations must have seemed harmless at the time—a way
to sell more copies of the New York Post or increase the viewership of Inside
Edition—but each transgression inevitably led to another, more serious one.
The idea that his tactics were legitimate calculations instead of unethical cons
was yet another aspect of the myth that he and my grandfather had been
constructing for decades.
Though Donald’s fundamental nature hasn’t changed, since his
inauguration the amount of stress he’s under has changed dramatically. It’s
not the stress of the job, because he isn’t doing the job—unless watching TV
and tweeting insults count. It’s the effort to keep the rest of us distracted from
the fact that he knows nothing—about politics, civics, or simple human
decency—that requires an enormous amount of work. For decades, he has
gotten publicity, good and bad, but he’s rarely been subjected to close
scrutiny, and he’s never had to face significant opposition. His entire sense of
himself and the world is being questioned.
Donald’s problems are accumulating because the maneuvering required to
solve them, or to pretend they don’t exist, has become more complicated,
requiring many more people to execute the cover-ups. Donald is completely
unprepared to solve his own problems or adequately cover his tracks. After
all, the systems were set up in the first place to protect him from his own
weaknesses, not help him negotiate the wider world.
The walls of his very expensive and well-guarded padded cell are starting
to disintegrate. The people with access to him are weaker than Donald is,
more craven, but just as desperate. Their futures are directly dependent on his
success and favor. They either fail to see or refuse to believe that their fate
will be the same as that of anyone who pledged loyalty to him in the past.
There seems to be an endless number of people willing to join the claque that
protects Donald from his own inadequacies while perpetuating his unfounded
belief in himself. Although more powerful people put Donald into the
institutions that have shielded him since the very beginning, it’s people
weaker than he is who are keeping him there.
When Donald became a serious contender for the Republican Party
nomination and then the nominee, the national media treated his pathologies
(his mendacity, his delusional grandiosity), as well as his racism and
misogyny, as if they were entertaining idiosyncrasies beneath which lurked
maturity and seriousness of purpose. Over time, the vast bulk of the
Republican Party—from the extreme Right to the so-called moderates—
either embraced him or, in order to use his weakness and malleability to their
own advantage, looked the other way.
After the election, Vladimir Putin, Kim Jong-un, and Mitch McConnell,
all of whom bear more than a passing psychological resemblance to Fred,
recognized in a way others should have but did not that Donald’s checkered
personal history and his unique personality flaws make him extremely
vulnerable to manipulation by smarter, more powerful men. His pathologies
have rendered him so simple-minded that it takes nothing more than
repeating to him the things he says to and about himself dozens of times a
day—he’s the smartest, the greatest, the best—to get him to do whatever they
want, whether it’s imprisoning children in concentration camps, betraying
allies, implementing economy-crushing tax cuts, or degrading every
institution that’s contributed to the United States’ rise and the flourishing of
In an article for The Atlantic, Adam Serwer wrote that, for Donald, the
cruelty is the point. For Fred, that was entirely true. One of the few pleasures
my grandfather had, aside from making money, was humiliating others.
Convinced of his rightness in all situations, buoyed by his stunning success
and a belief in his superiority, he had to punish any challenge to his authority
swiftly and decisively and put the challenger in his place. That was
effectively what happened when Fred promoted Donald over Freddy to be
president of Trump Management.
Unlike my grandfather, Donald has always struggled for legitimacy—as
an adequate replacement for Freddy, as a Manhattan real estate developer or
casino tycoon, and now as the occupant of the Oval Office who can never
escape the taint of being utterly without qualification or the sense that his
“win” was illegitimate. Over Donald’s lifetime, as his failures mounted
despite my grandfather’s repeated—and extravagant—interventions, his
struggle for legitimacy, which could never be won, turned into a scheme to
make sure nobody found out that he’s never been legitimate at all. This has
never been more true than it is now, and it is exactly the conundrum our
country finds itself in: the government as it is currently constituted, including
the executive branch, half of Congress, and the majority of the Supreme
Court, is entirely in the service of protecting Donald’s ego; that has become
almost its entire purpose.
His cruelty serves, in part, as a means to distract both us and himself from
the true extent of his failures. The more egregious his failures become, the
more egregious his cruelty becomes. Who can pay attention to the children
he’s kidnapped and put into concentration camps on the Mexican border
when he’s threatening to out whistleblowers, coercing senators to acquit him
in the face of overwhelming evidence of guilt, and pardoning Navy SEAL
Eddie Gallagher, who’d been accused of war crimes and convicted of posing
for a picture with a corpse, all within the same month? If he can keep fortyseven thousand spinning plates in the air, nobody can focus on any one of
them. So there’s that: it’s just a distraction.
His cruelty is also an exercise of his power, such as it is. He has always
wielded it against people who are weaker than he is or who are constrained
by their duty or dependence from fighting back. Employees and political
appointees can’t fight back when he attacks them in his Twitter feed because
to do so would risk their jobs or their reputations. Freddy couldn’t retaliate
when his little brother mocked his passion for flying because of his filial
responsibility and his decency, just as governors in blue states, desperate to
get adequate help for their citizens during the COVID-19 crisis, are
constrained from calling out Donald’s incompetence for fear he would
withhold ventilators and other supplies needed in order to save lives. Donald
learned a long time ago how to pick his targets.
Donald continues to exist in the dark space between the fear of indifference
and the fear of failure that led to his brother’s destruction. It took forty-two
years for the destruction to be completed, but the foundations were laid early
and played out before Donald’s eyes as he was experiencing his own trauma.
The combination of those two things—what he witnessed and what he
experienced—both isolated him and terrified him. The role that fear played in
his childhood and the role it plays now can’t be overstated. And the fact that
fear continues to be an overriding emotion for him speaks to the hell that
must have existed inside the House six decades ago.
Every time you hear Donald talking about how something is the greatest,
the best, the biggest, the most tremendous (the implication being that he
made them so), you have to remember that the man speaking is still, in
essential ways, the same little boy who is desperately worried that he, like his
older brother, is inadequate and that he, too, will be destroyed for his
inadequacy. At a very deep level, his bragging and false bravado are not
directed at the audience in front of him but at his audience of one: his longdead father.
Donald has always been able to get away with making blanket statements (“I
know more about [fill in the blank] than anybody, believe me” or the other
iteration, “Nobody knows more about [fill in the blank] than me”); he’s been
allowed to riff about nuclear weapons, trade with China, and other things
about which he knows nothing; he’s gone essentially unchallenged when
touting the efficacy of drugs for the treatment of COVID-19 that have not
been tested or engaging in an absurd, revisionist history in which he’s never
made a mistake and nothing is his fault.
It’s easy to sound coherent and somewhat knowledgeable when you
control the narrative and are never pressed to elaborate on your premise or
demonstrate that you actually understand the underlying facts. It is an
indictment (among many) of the media that none of that changed during the
campaign, when exposing Donald’s lies and outrageous claims might actually
have saved us from his presidency. On the few occasions he was asked about
his positions and policies (which for all intents and purposes don’t really
exist), he still wasn’t expected or required to make sense or demonstrate any
depth of understanding. Since the election, he’s figured out how to avoid
such questions completely; White House press briefings and formal news
conferences have been replaced with “chopper talk” during which he can
pretend he can’t hear any unwelcome questions over the noise of the
helicopter blades. In 2020, his pandemic “press briefings” quickly devolved
into mini–campaign rallies filled with self-congratulation, demagoguery, and
ring kissing. In them he has denied the unconscionable failures that have
already killed thousands, lied about the progress that’s being made, and
scapegoated the very people who are risking their lives to save us despite
being denied adequate protection and equipment by his administration. Even
as hundreds of thousands of Americans are sick and dying, he spins it as a
victory, as proof of his stunning leadership. And in the event that anybody
thinks he’s capable of being serious or somber, he’ll throw in a joke about
bedding models or lie about the size of his Facebook following for good
measure. Still the news networks refuse to pull away. The few journalists
who do challenge him, and even those who simply ask Donald for words of
comfort for a terrified nation, are derided and dismissed as “nasty.” The
through line from Donald’s early, destructive behavior that Fred actively
encouraged to the media’s unwillingness to challenge him and the
Republican Party’s willingness to turn a blind eye to the daily corruption he
has committed since January 20, 2017, have led to the impending collapse of
this once great nation’s economy, democracy, and health.
We must dispense with the idea of Donald’s “strategic brilliance” in
understanding the intersection of media and politics. He doesn’t have a
strategy; he never has. Despite the fluke that was his electoral advantage and
a “victory” that was at best suspect and at worst illegitimate, he never had his
finger on the pulse of the zeitgeist; his bluster and shamelessness just
happened to resonate with certain segments of the population. If what he was
doing during the 2016 campaign hadn’t worked, he would have kept doing it
anyway, because lying, playing to the lowest common denominator, cheating,
and sowing division are all he knows. He is as incapable of adjusting to
changing circumstances as he is of becoming “presidential.” He did tap into a
certain bigotry and inchoate rage, which he’s always been good at doing. The
full-page screed he paid to publish in the New York Times in 1989 calling for
the Central Park Five to be put to death wasn’t about his deep concern for the
rule of law; it was an easy opportunity for him to take on a deeply serious
topic that was very important to the city while sounding like an authority in
the influential and prestigious pages of the Gray Lady. It was unvarnished
racism meant to stir up racial animosity in a city already seething with it. All
five boys, Kevin Richardson, Antron McCray, Raymond Santana, Korey
Wise, and Yusef Salaam, were subsequently cleared, proven innocent via
incontrovertible DNA evidence. To this day, however, Donald insists that
they were guilty—yet another example of his inability to drop a preferred
narrative even when it’s contradicted by established fact.
Donald takes any rebuke as a challenge and doubles down on the behavior
that drew fire in the first place, as if the criticism is permission to do worse.
Fred came to appreciate Donald’s obstinacy because it signaled the kind of
toughness he sought in his sons. Fifty years later, people are literally dying
because of his catastrophic decisions and disastrous inaction. With millions
of lives at stake, he takes accusations about the federal government’s failure
to provide ventilators personally, threatening to withhold funding and
lifesaving equipment from states whose governors don’t pay sufficient
homage to him. That doesn’t surprise me. The deafening silence in response
to such a blatant display of sociopathic disregard for human life or the
consequences for one’s actions, on the other hand, fills me with despair and
reminds me that Donald isn’t really the problem after all.
This is the end result of Donald’s having continually been given a pass
and rewarded not just for his failures but for his transgressions—against
tradition, against decency, against the law, and against fellow human beings.
His acquittal in the sham Senate impeachment trial was another such reward
for bad behavior.
The lies may become true in his mind as soon as he utters them, but
they’re still lies. It’s just another way for him to see what he can get away
with. And so far, he’s gotten away with everything.
The Tenth Circle
On November 9, 2016, my despair was triggered in part by the certainty that
Donald’s cruelty and incompetence would get people killed. My best guess at
the time was that that would occur through a disaster of his own making, such
as an avoidable war he either provoked or stumbled into. I couldn’t have
anticipated how many people would willingly enable his worst instincts,
which have resulted in government-sanctioned kidnapping of children,
detaining of refugees at the border, and betrayal of our allies, among other
atrocities. And I couldn’t have foreseen that a global pandemic would present
itself, allowing him to display his grotesque indifference to the lives of other
Donald’s initial response to COVID-19 underscores his need to minimize
negativity at all costs. Fear—the equivalent of weakness in our family—is as
unacceptable to him now as it was when he was three years old. When
Donald is in the most trouble, superlatives are no longer enough: both the
situation and his reactions to it must be unique, even if absurd or nonsensical.
On his watch, no hurricane has ever been as wet as Hurricane Maria.
“Nobody could have predicted” a pandemic that his own Department of
Health and Human Services was running simulations for just a few months
before COVID-19 struck in Washington state. Why does he do this? Fear.
Donald didn’t drag his feet in December 2019, in January, in February, in
March because of his narcissism; he did it because of his fear of appearing
weak or failing to project the message that everything was “great,”
“beautiful,” and “perfect.” The irony is that his failure to face the truth has
inevitably led to massive failure anyway. In this case, the lives of potentially
hundreds of thousands of people will be lost and the economy of the richest
country in history may well be destroyed. Donald will acknowledge none of
this, moving the goalposts to hide the evidence and convincing himself in the
process that he’s done a better job than anybody else could have if only a few
hundred thousand die instead of 2 million.
“Get even with people who have screwed you,” Donald has said, but often
the person he’s getting revenge on is somebody he screwed over first—such
as the contractors he’s refused to pay or the niece and nephew he refused to
protect. Even when he manages to hit his target, his aim is so bad that he
causes collateral damage. Andrew Cuomo, the governor of New York and
currently the de facto leader of the country’s COVID-19 response, has
committed not only the sin of insufficiently kissing Donald’s ass but the
ultimate sin of showing Donald up by being better and more competent, a
real leader who is respected and effective and admired. Donald can’t fight
back by shutting Cuomo up or reversing his decisions; having abdicated his
authority to lead a nationwide response, he no longer has the ability to
counter decisions made at the state level. Donald can insult Cuomo and
complain about him, but every day the governor’s real leadership further
reveals Donald as a petty, pathetic little man—ignorant, incapable, out of his
depth, and lost in his own delusional spin. What Donald can do in order to
offset the powerlessness and rage he feels is punish the rest of us. He’ll
withhold ventilators or steal supplies from states that have not groveled
sufficiently. If New York continues not to have enough equipment, Cuomo
will look bad, the rest of us be damned. Thankfully, Donald doesn’t have
many supporters in New York City, but even some of those will die because
of his craven need for “revenge.” What Donald thinks is justified retaliation
is, in this context, mass murder.
It would have been easy for Donald to be a hero. People who have hated
and criticized him would have forgiven or overlooked his endless stream of
appalling actions if he’d simply had somebody take the pandemic
preparedness manual down from the shelf where it was put after the Obama
administration gave it to him. If he’d alerted the appropriate agencies and
state governments at the first evidence the virus was highly contagious, had
extremely high mortality rates, and was not being contained. If he’d invoked
the Defense Production Act of 1950 to begin production of PPE, ventilators,
and other necessary equipment to prepare the country to deal with the worstcase scenario. If he’d allowed medical and scientific experts to give daily
press conferences during which facts were presented clearly and honestly. If
he’d ensured that there was a systematic, top-down approach and
coordination among all of the necessary agencies. Most of those tasks would
have required almost no effort on his part. All he would have had to do was
make a couple of phone calls, give a speech or two, then delegate everything
else. He might have been accused of being too cautious, but most of us would
have been safe and many more of us would have survived. Instead, states are
forced to buy vital supplies from private contractors; the federal government
commandeers those supplies, and then FEMA distributes them back to
private contractors, who then resell them.
While thousands of Americans die alone, Donald touts stock market gains.
As my father lay dying alone, Donald went to the movies. If he can in any
way profit from your death, he’ll facilitate it, and then he’ll ignore the fact
that you died.
Why did it take so long for Donald to act? Why didn’t he take the novel
coronavirus seriously? In part because, like my grandfather, he has no
imagination. The pandemic didn’t immediately have to do with him, and
managing the crisis in every moment doesn’t help him promote his preferred
narrative that no one has ever done a better job than he has.
As the pandemic moved into its third, then fourth month, and the death toll
continued its rise into the tens of thousands, the press started to comment on
Donald’s lack of empathy for those who have died and the families they leave
behind. The simple fact is that Donald is fundamentally incapable of
acknowledging the suffering of others. Telling the stories of those we’ve lost
would bore him. Acknowledging the victims of COVID-19 would be to
associate himself with their weakness, a trait his father taught him to despise.
Donald can no more advocate for the sick and dying than he could put
himself between his father and Freddy. Perhaps most crucially, for Donald
there is no value in empathy, no tangible upside to caring for other people.
David Corn wrote, “Everything is transactional for this poor broken human
being. Everything.” It is an epic tragedy of parental failure that my uncle does
not understand that he or anybody else has intrinsic worth.
In Donald’s mind, even acknowledging an inevitable threat would indicate
weakness. Taking responsibility would open him up to blame. Being a hero—
being good—is impossible for him.
The same could be said of his handling of the worst civil unrest since the
assassination of Martin Luther King, Jr. This is another crisis in which it
would have been so easy for Donald to triumph, but his ignorance
overwhelms his ability to turn to his advantage the third national catastrophe
to occur on his watch. An effective response would have entailed a call for
unity, but Donald requires division. It is the only way he knows how to
survive—my grandfather ensured that decades ago when he turned his
children against each other.
I can only imagine the envy with which Donald watched Derek Chauvin’s
casual cruelty and monstrous indifference as he murdered George Floyd;
hands in his pockets, his insouciant gaze aimed at the camera. I can only
imagine that Donald wishes it had been his knee on Floyd’s neck.
Instead, Donald withdraws to his comfort zones—Twitter, Fox News—
casting blame from afar, protected by a figurative or literal bunker. He rants
about the weakness of others even as he demonstrates his own. But he can
never escape the fact that he is and always will be a terrified little boy.
Donald’s monstrosity is the manifestation of the very weakness within him
that he’s been running from his entire life. For him, there has never been any
option but to be positive, to project strength, no matter how illusory, because
doing anything else carries a death sentence; my father’s short life is evidence
of that. The country is now suffering from the same toxic positivity that my
grandfather deployed specifically to drown out his ailing wife, torment his
dying son, and damage past healing the psyche of his favorite child, Donald
“Everything’s great. Right, Toots?”
At Simon and Schuster, thanks to Jon Karp, Eamon Dolan, Jessica Chin, Paul
Dippolito, Lynn Anderson, and Jackie Seow.
At WME thanks to Jay Mandel and Sian-Ashleigh Edwards.
Thank you also to Carolyn Levin for your thoughtful vetting; David Corn
at Mother Jones for your kindness; Darren Ankrom, fact-checker
extraordinaire; Stuart Oltchick for telling me about better days; Captain Jerry
Lawler for all of the wonderful TWA history; and Maryanne Trump Barry for
all of the enlightening information.
My appreciation to Denise Kemp for the solidarity with me; to my mother,
Linda Trump, for all of the great stories; Laura Schweers; Debbie R; Stefanie
B; and Jennifer T for your friendship and trust when I most needed them. Jill
and Mark Nass for helping us keep the tradition alive (JCE!).
To our beloved Trumpy, whom I miss every day.
I am deeply grateful to Ted Boutrous, for that first meeting and for
believing in the cause; Annie Champion for your generosity and friendship;
Pat Roth for your thoughtful feedback and for being in my life; Annamaria
Forcier for being such a good friend to my dad, I am so glad I found you;
Susanne Craig and Russ Buettner for their extraordinary journalism and
integrity, thank you for bringing me along for the ride. Sue, none of this
would have been possible without your persistence, courage, and
encouragement; Liz Stein for being on the journey with me and making this a
better book—and this a much more fun, less lonely experience than it might
have been (and, of course, for Baby Yoda); Eric Adler for being there for me
throughout, for your tireless feedback, and for having my back at the local
pawnbroker; and Alice Frankston for being involved from the very beginning
of this project, believing in it even when I didn’t, and reading every word
more times than I can count. I can’t wait for what comes next.
And finally, to my daughter, Avary, for being more patient and
understanding than any kid should have to be. I love you.
About the Author
© PETER SERLING
Mary L. Trump holds a PhD from the Derner Institute of Advanced
Psychological Studies and taught graduate courses in trauma,
psychopathology, and developmental psychology. She lives with her
daughter in New York.
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A note about the index: The pages referenced in this index refer to the page numbers in the print
edition. Clicking on a page number will take you to the ebook location that corresponds to the
beginning of that page in the print edition. For a comprehensive list of locations of any word or phrase,
use your reading system’s search function.
Access Hollywood, 10
Affordable Care Act, 15
Air Force National Guard, 53, 54–55, 65, 84
Air Force Reserve Officer Training Corps (ROTC), 51–52, 53, 66
air travel, 61
see also pilots
Alcoholics Anonymous, 92
All County Building Supply & Maintenance, 191–93
All Faiths Cemetery, 126, 166
Annamaria (girlfriend of Billy Drake), 71, 85
Apprentice, The, 11, 182, 196
Art of Survival, The (Surviving at the Top) (Trump), 132, 136, 146
Art of the Comeback, The (Trump), 145–49, 151–52, 162–63
Art of the Deal, The (Trump), 94–95, 146
Atlantic City, N.J., 35, 132, 134–37, 142, 151, 184, 192
attachment, 23, 25
Barnosky, Jack, 174–76, 186–87
Barr, William, 12
Barry, John, 115, 143–44, 151, 168
Barry, Maryanne Trump, 2, 5, 32, 33, 44, 45, 47, 50, 51, 56, 63, 65, 72, 81–83, 95, 108–9, 112, 115,
122, 128, 154, 155, 158, 161, 165, 173, 177, 183–84, 188–89, 193–94
birth of, 31
Catholic conversion of, 9, 81
childhood of, 24, 26, 28, 35, 40
deprivation of, 82–83
Donald and, 60
and Donald’s attempt to control Fred’s estate, 143–44
Donald’s presidential campaign and, 8–9, 10
family finances and, 190–93
father’s will and, 168, 170, 171, 173–76
law career of, 60, 94, 134, 143, 189, 193
marriage to David Desmond, 56, 81–83, 94
medical insurance and, 174
mother’s health problems and, 21–22, 24
New York Times exposé and, 193
retirement of, 193
and sale of father’s estate, 192–93, 196
son of (David Desmond, Jr.), 2, 28, 82, 95–96, 122, 154, 166, 193
at White House dinner, 1, 2, 4, 7
Barstow, David, 187–89, 193
Beach Haven, 25, 28, 35, 54, 90, 171
Beame, Abe, 114
Bedminster, N.J., 115, 181
Bishop, Joey, 111
Bonwit Teller, 133
Booth Memorial Hospital, 121, 131
Beach Haven in, 25, 28, 35, 54, 90, 171
Democratic Party in, 34, 54, 73
Donald’s view of, 89–90
Steeplechase Park in, 67–68, 72–76, 78–79, 87, 88, 89, 102, 141
Trump Village in, 56, 57, 68, 74, 88, 89
Buettner, Russ, 187, 188
Burnett, Mark, 11, 196
Carey, Hugh, 114
Carrier Clinic, 115
Celebrity Apprentice, The, 166
Central Park Five, 204
Charles, Prince, 164
Chase Manhattan Bank, 60
Chauvin, Derek, 210
child abuse, 26, 42
child development, 23
attachment in, 23, 25
Christmas, 106, 108–11
Clapp, Mike, 56, 77–78
Clinton, Hillary, 3, 9, 10, 15
Cohn, Roy, 100–101, 107, 134, 189
Columbia University, 139–40
Commodore Hotel, 105, 114, 141, 197
Beach Haven, 25, 28, 35, 54, 90, 171
Steeplechase Park, 67–68, 72–76, 78–79, 87, 88, 89, 102, 141
Trump Village, 56, 57, 68, 74, 88, 89
Corn, David, 185, 210
COVID-19 pandemic, 13–14, 201–2, 204, 207–10
Craig, Susanne, 185–88
Cuomo, Andrew, 208
Dale Carnegie courses, 37, 89
D’Amato, Al, 166
Defense Production Act, 209
Democratic Party, 34, 54, 73
Depression, Great, 35
Derner Institute of Advanced Psychological Studies, 12
Dershowitz, Alan, 101
Desmond, David, Jr., 2, 28, 82, 95–96, 122, 154, 166, 193
Desmond, David, Sr., 56, 81–83, 94
Diagnostic and Statistical Manual of Mental Disorders (DSM-5), 12
Diana, Princess, 164
Dixon, James, 22
Drake, Billy, 40, 52, 64, 71, 85, 124, 158
Dunn, Diane, 118–19, 122
Durben, Irwin, 85, 127, 128, 143, 170–71
East, Ernie, 145
Eastern Air Lines Shuttle, 134
election of 2016, 14–15, 204
empathy, 23, 24, 26, 209–10
Ethel Walker School, 116–20
E. Trump and Son, 28, 29–30, 45, 60
evangelical Christians, 9, 12
Fair Housing Act, 100
Falwell, Jerry, Jr., 9
Farrell Fritz, 174, 186–87
Federal Housing Administration (FHA), 32–35, 89, 91
Floyd, George, 210
Fordham University, 71, 72, 74
Fort Drum, 54–55
Fox News, 210–11
Frank E. Campbell Funeral Chapel, 165–66
Frankenstein (Shelley), 14
Gallagher, Eddie, 201
Germany, 28–29, 159
Giuliani, Rudolph, 166
Glass House, 149
Gotti, John, 101
Graff, Rhona, 14–15, 145, 147
Grand Hyatt New York, 105, 114–15, 133, 135, 136, 138, 141, 196
Grau, Elizabeth Trump, 1, 2, 9, 45, 50–51, 60, 84, 95, 96, 113, 161, 173, 177, 182–83
childhood of, 26, 28, 32, 33
deprivation of, 82–83
and Donald’s attempt to control Fred’s estate, 143–44
family finances and, 190, 192–93
father’s death and, 164
at father’s funeral, 166
father’s will and, 170, 173–76
Freddy’s death and, 121–23, 125
mother’s health problems and, 24
and sale of father’s estate, 192–93, 196
watch gift and, 156–57
Grau, James, 2
Great Depression, 35
Guccione, Bob, 109–10
Harder, Charles J., 190
health care, 15
Highlander, 57, 67, 76–77, 85, 86, 169, 189
Hofstra Law School, 94
Hopper, Hedda, 61
Hospital for Special Surgery, 132
House, the, 21, 27, 28, 33–34, 36, 41, 43, 44, 51, 66, 71, 74, 94–97, 127, 157, 158, 161, 162, 167, 175,
181, 195, 198, 202
basement of, 96–97
Christmas at, 106, 108–11
Freddy’s stay in attic of, 93–94
library of, 94–95
Mary, Fritz, and David at, as children, 95–96
wooden Indian statues in, 96
Hughes, Howard, 61
Inside Edition, 185, 198
Jamaica Estates, 33, 34, 54, 83, 95
Jamaica Hospital, 21, 77, 121, 124
Johanna (girlfriend of Freddy Trump), 104, 105
John, Elton, 164
Johnson, Philip, 149
Justice Department, 90, 100–101
Kelly, John, 108
Kew-Forest School, 22, 49, 116–17
Khan family, 10
Kid Rock, 8
Kim Jong-un, 101, 189, 200
King, Martin Luther, Jr., 210
Kovaleski, Serge, 9
Kushner, Charles, 181–82
Kushner, Jared, 4, 6, 7, 181–83
Laurino, Lou, 174–76
Le Club, 34, 100, 138
LeFrak, Sam, 166
Long Island Jewish Medical Center, 163, 176
Luerssen, Amy, 99–100
Mafia (Mob), 35, 133
Manhattan Psychiatric Center, 12
Maples, Marla, 132, 137, 150, 151, 162, 184
Mar-a-Lago, 134, 137, 148–51, 153, 154, 160
Marble Collegiate Church, 37, 111, 166, 177
Marblehead, Mass., 61–63, 65–67, 76
McCarthy, Joseph, 100
McCarthy, Kevin, 12
McConnell, Mitch, 12, 200
McCray, Antron, 204
media, 11, 114, 133–34, 138, 141, 195–98, 200, 203
Meese, Ed, 134
Metropolitan Museum of Art, 133, 184
Mexican border, 195, 201, 207
Midland Associates, 98, 169–71
Mitchell-Lama Housing Program, 89
Mitnick, Jack, 143, 193
Mob, the, 35, 133
Montauk Airport, 73
Mother Jones, 185
Mount Holyoke College, 50
Mulvaney, Mick, 108
Murdoch, Rupert, 101
Muslim travel ban, 15
National Guard, 53, 54–55, 65, 84
New York City, 208
economy in 1970s, 89
Fred Trump’s Manhattan aspirations, 89, 102–3
press in, 114, 131, 141, 195, 197
see also Brooklyn
New York Military Academy (NYMA), 47, 49–50, 52–53, 56, 63, 64, 71, 74–75, 95, 96, 97, 132
New York Post, 149, 198
New York Times, 9, 107, 165, 176, 204
exposé on Trump family finances in, 185–91, 193–94
Nolan, James, 72
Nugent, Ted, 8
Obama administration, 209
opioid crisis, 9
Palin, Sarah, 8
parenting and child development, 23
attachment in, 23, 25
Parsons, Louella, 61
Pataki, George, 166
Peale, Norman Vincent, 37–38, 40–41, 42, 92
Pence, Mike, 3, 4
Peter Luger Steak House, 161–62
Piedmont Airlines, 67
Pierce, Charles P., 14
pilots, 58, 59, 61
Freddy’s career, 52, 53, 56, 57–59, 60–68, 78, 84, 88
Pompeo, Mike, 12
Power of Positive Thinking, The (Peale), 37
presidential election of 2016, 14–15, 204
Putin, Vladimir, 8, 101, 200
Queens Hospital Center, 121
racism, 9, 15, 200, 204
housing discrimination lawsuit, 90, 100–101
Random House, 147, 151–52
Reagan, Ronald, 134
Republican National Convention, 10
Republican Party, 11–12, 109, 200, 203
Reserve Officer Training Corps (ROTC), 51–52, 53, 66
Richardson, Kevin, 204
Rivers, Joan, 166
Rodman, Dennis, 189
Roman Catholic Archdiocese of New York, 101
Roosevelt, Franklin D., 32
Ryan, Paul, 3
Salaam, Yusef, 204
Salvation Army, 121
Santana, Raymond, 204
Schron, Ruby, 192
Schumer, Chuck, 3
Schwartz, Tony, 146
Serwer, Adam, 200
Shapiro, Joe, 72
Shelley, Mary Wollstonecraft, 14
Shore Haven, 25, 28, 34, 54, 171
Sigma Alpha Mu, 51, 52, 53
Slatington Flying Club, 51
Sly Fox Inn, 158
sociopathy, 24, 26, 43
Spanish flu epidemic, 29, 30, 36
Steeplechase Park, 67–68, 72–76, 78–79, 87, 88, 89, 102, 141
Sunnyside Towers, 94, 97, 98, 103, 169
Sunshine, Louise, 114
Surviving at the Top (Trump), 132, 136, 146
Swifton Gardens, 91
Taj Mahal, 132, 135, 136, 149
Tosti, Matthew, 85–86, 104–5, 127
Trans World Airlines (TWA), 58, 59, 61, 65–68, 78, 84, 88
Trump, Barron, 184
Trump, Blaine, 110, 122, 148, 162, 164
Access Hollywood tape of, 10
The Apprentice, 11, 182, 196
The Art of the Comeback, 145–49, 151–52, 162–63
The Art of the Deal, 94–95, 146
authoritarian rulers and, 101
bankruptcies of, 9, 11, 132, 136, 143, 197
banks and investors and, 11, 124, 132, 134–38, 140, 142, 148, 184, 196–97
baseball playing of, 97
birth of, 33
Brooklyn as viewed by, 89–90
casinos of, 35, 132, 134–36, 142, 151, 201
The Celebrity Apprentice, 166
chiefs of staff of, 108
childhood of, 7, 11, 24–28, 42–46, 47–51, 101–2, 198, 202
childhood home of, see House, the
COVID-19 crisis and, 13–14, 201–2, 204, 207–10
cruelty of, 15, 45, 75, 200, 201, 207
debts of, 134–36
early forays into Manhattan market, 102–3
ego of, 17, 136, 138, 198, 201
elected president, 14–15, 204
empathy lacking in, 209–10
extravagant lifestyle and spending of, 98, 107, 136, 137, 142, 191
father and, 11, 25–27, 42, 43, 47–50, 52–53, 63, 72, 83–84, 100, 102–3, 108, 114, 115, 132, 133–
35, 137–38, 140–42, 144, 157–58, 188, 195, 202, 203, 204, 211
father’s estate sold by, 192–93, 196
father’s loans to, 107, 190, 197
father’s promotion to president of Trump Management, 88–90, 200
father’s role in real estate ventures of, 84, 91, 102–3, 107, 133, 134, 140–42, 191, 196–97
father’s will alteration attempted by, 143–44, 190, 193
father treated with contempt by, 157
on fishing outing, 64
at Fordham University, 71, 72, 74
Freddy and, 7, 45–46, 47, 48, 52, 63–65, 72, 75, 84–85, 98–99, 102, 201, 209
Freddy’s death and, 121–25, 127
gift-giving of, 106, 109
golf club of, 115, 181
golfing of, 154
housing discrimination lawsuit against, 90, 100–101
immigration and, 30
impeachment of, 205
income of, 91, 107, 190
Ivana’s divorce from, 137, 138
Ivana’s marriage to, 98, 111
Ivana’s prenuptial agreement with, 107
knowledge claims of, 133, 202–3
Linda and, 65, 148
lying of, 11–12, 14, 15, 40, 90, 103, 141, 197, 198, 200, 203, 205
Mar-a-Lago estate of, 134, 137, 148–51, 153, 154, 160
Mary enlisted as ghostwriter for book of, 145–49, 151–52, 162–63
Mary given gifts by, 106, 109
Mary story invented by, 163
Maryanne and, 60
media and, 11, 114, 133–34, 138, 141, 195–98, 200, 203
Mexican border and, 195, 201, 207
at military academy, 47, 49–50, 52–53, 56, 63, 64, 71, 74–75, 95, 96, 97, 132
money-oriented worldview of, 15–16, 38
mother and, 24, 25, 44, 45, 48–50
mother’s mugging and, 131–32
Muslim ban of, 15
narcissism of, 12, 198
pathologies of, 11–13, 200
powerful men and, 34, 101, 200
presidential campaign of, 9–11, 203, 204
presidential campaign announced by, 8–9, 11
press briefings of, 203
racism of, 9, 15, 300, 204
real estate career of, 1, 8–9, 11, 35, 84, 90–91, 102–3, 107, 111, 114–15, 133–38, 140–43, 192,
as reality television star, 8, 11, 182, 196
Robert and, 6–7, 44–45
at school, 43–44, 47, 49–50, 52–53, 56, 58, 63, 64, 71, 74–75, 95, 96, 97, 132
self-esteem of, 44
self-promotion and self-aggrandizement of, 90–91, 103, 137, 198
as shielded from reality, 13, 16, 199
“strategies” of, 17, 203–4
Surviving at the Top, 132, 136, 146
taxes and, 34
at University of Pennsylvania, 72, 74, 75, 83
White House dinner for family of, 1–8, 45
at Trump Management, 71–72, 83, 84, 88, 112, 155
as Trump Management president, 88–90, 200
Trump, Donald “Donny,” Jr., 4, 6, 7, 122, 169
Trump, Elizabeth (sister of Donald), see Grau, Elizabeth Trump
Trump, Elizabeth (sister of Fred), 29, 193
Trump, Elizabeth Christ (mother of Fred), 28, 29, 31, 34, 41, 89, 126
E. Trump and Son created by, 28, 29–30, 45, 60
Trump, Eric, 4, 7, 156
Trump, Frederick Christ “Fred” (father of Donald), 2, 9, 11, 12, 14, 15, 17, 28–32, 34, 39–44, 47, 51,
52, 60, 92–93, 140, 188, 200, 211
Cohn and, 100–101
cruelty of, 15, 157, 200
Dale Carnegie course taken by, 37, 89
death of, 10, 163–64, 165
dementia of, 133, 140, 142, 153–54, 157, 159–61, 174, 175, 191
dishonest business tactics of, 141–42
Donald and, 11, 25–27, 42, 43, 47–50, 52–53, 63, 72, 83–84, 100, 102–3, 108, 114, 115, 132, 133–
35, 137–38, 140–42, 144, 157–58, 188, 195, 202, 203, 204, 211
Donald loaned money by, 107, 190, 197
Donald promoted to president of Trump Management by, 88–90, 200
Donald’s attempt to control estate of, 143–44, 190, 193
Donald’s contempt for, 157
Donald’s real estate ventures and, 84, 91, 102–3, 107, 133, 134, 140–42, 191, 196–97
Donald’s sale of estate of, 192–93, 196
early life of, 29
elderly housing project of, 91
as father, 23–27, 39, 47–48, 50, 51, 157–58
father’s death and, 35, 36, 37, 41–42, 52–53
Federal Housing Administration and, 32–35, 89, 91
Freddy and, 31–32, 39–44, 47, 48, 50–53, 58, 59, 60–62, 64–67, 71, 75–76, 84, 88, 89, 98, 102,
109, 111, 116, 154, 157, 188, 200, 210, 211
Freddy’s alcoholism and, 92–93, 157
Freddy’s death and, 119–27
and Freddy’s divorce from Linda, 85, 86
Freddy’s mortgage application and, 78–79
funeral for, 165–67
golfing and, 154
hair of, 155, 156
hip surgery of, 132–33, 161
home of (the House), see House, the
housing discrimination lawsuit against, 90, 100–101
Linda and, 55, 56, 148, 170, 171, 175
Manhattan aspirations of, 89, 102–3
marriage of, 30–31
Maryanne and, 81, 82
Mary L. and, 3, 116–17, 139–40
Midland Associates created by, 98
money-oriented worldview of, 16, 38
New York Times exposé on finances of, 185–91, 193–94
obituary for, 165
office of, 100
Peale’s philosophy and, 37–38, 40–41, 42, 92
photograph of, 4, 5
photograph of woman carried by, 155–56
powerful men courted by, 34, 37
real estate career of, 24–25, 28–37, 45, 53–57, 60, 89, 102, 133, 141–42, 165, 190–92, 196; see
also Trump Management
sexist attitudes of, 3, 24
showmanship and hyperbole of, 36–37, 89
sociopathy of, 24, 26, 43
Steeplechase Park project of, 67–68, 72–76, 78–79, 87, 88, 89, 102, 141
Swifton Gardens acquired by, 91
taxes and, 35, 98, 141, 169, 190, 191
tenant dealings of, 54
Trump’s Castle and, 136
trust funds and building ownerships for family of, 82, 127–28, 169–71, 176
wealth of, 35, 55, 86, 90, 98, 103, 107, 133, 190–91
wife’s health emergency and, 21–22
will and estate of, 10–11, 59, 143–44, 165, 167–72, 173–77, 182, 184, 186–87, 190–94
wooden Indian statues of, 96, 100
Trump, Frederick Crist “Freddy” (brother of Donald), 2, 10–12, 15, 17, 25–28, 31–33, 39–46, 47, 50,
51, 60–68, 76–77, 79, 95, 97–98, 103–4, 108, 110, 116, 119, 144, 173, 176, 177, 201, 202, 211
alcoholism of, 9, 15, 62, 64–67, 76, 79, 92–93, 105, 113, 115–16, 119, 157
apartments of, 91–94, 97, 98, 103
birth of, 31
boat charter plan of, 79
boats and planes of, 56, 75, 79, 82, 98, 105
childhood of, 7, 35
David Desmond and, 81
death of, 2, 112, 119–27, 209
deprivation of, 82–83
Donald and, 7, 45–46, 47, 48, 52, 63–65, 72, 75, 84–85, 98–99, 102, 201, 209
and Donald’s marriage to Ivana, 111
father and, 31–32, 39–44, 47, 48, 50–53, 58, 59, 60–62, 64–67, 71, 75–76, 84, 88, 89, 98, 102, 109,
111, 116, 154, 157, 188, 200, 210, 211
father’s will and, 10–11, 59, 167–72, 176
fishing of, 63–64, 79, 84
Florida move of, 105, 112
flying and pilot career of, 52, 53, 56, 57–59, 60–68, 73, 75, 78, 79, 84, 88, 91, 112, 201
funeral for, 122–26
gun incident of, 80
heart surgery of, 112–13
Highlander apartment of, 57, 67, 76–77, 85, 86
Johanna and, 104, 105
Linda’s divorce conversation with, 62–63
Linda’s divorce from, 85–87, 91, 107, 110, 168
Linda’s marital problems with, 80–81, 85
Linda’s marriage to, 52, 55, 56
in Marblehead, 61–63, 65–67, 76
Mary’s banking story and, 104–5
Mary’s Sweet Sixteen party thrown by, 114–15
in mashed potatoes incident, 7, 45–46
money and estate of, 127–28, 172, 173, 190
mortgage application of, 78–79
mother and, 158–59
mother’s choking incident and, 113–14
mother’s health problems and, 24
mother’s will and, 177
in National Guard, 53, 54–55, 65, 84
pets of, 85, 92, 93
pneumonia contracted by, 77
in ROTC, 51–52, 53, 66
snakes of, 85, 92
Steeplechase project and, 73–76, 78–79, 87, 88, 141
Sunnyside Towers apartment of, 94, 97, 98, 103
at Trump Management, 53–59, 61–63, 65, 66, 73, 78, 79, 83, 84, 88, 89, 91, 112, 155, 200
Trump, Frederick Crist “Fritz,” III (nephew of Donald), 2, 28, 67, 73, 86, 93, 94, 105, 111, 112, 148,
163, 175, 177, 183–84
birth of, 56
Donald and Ivana’s gift for, 106
family finances and, 191–92, 194
father’s death and, 122, 124–27
father’s estate and, 127–28
grandfather’s will and, 167–71, 176, 182, 186, 187, 191–92, 194
grandmother’s will and, 177
at the House as a child, 95–96
medical insurance and, 174, 175, 194
son of (William), 167, 174, 175, 176, 194
wife of (Lisa), 2, 167, 171, 175
Trump, Friedrich (father of Fred), 28–29, 126
death of, 28, 35, 36, 37, 41–42, 52–53
Trump, Ivana, 106–10, 122, 123, 132, 148, 150, 169, 183
Donald’s divorce from, 137, 138
Donald’s marriage to, 98, 111
Donald’s prenuptial agreement with, 107
gift-giving of, 106, 109
Trump, Ivanka, 4, 6, 122, 127, 156
wedding of, 181–83
Trump, John, 41
Trump, Lara, 4, 7
Trump, Linda Clapp, 55–59, 62–68, 73, 78, 97–98, 99, 105, 112, 113, 127, 159
Donald and, 65, 148
father of, 56, 77–78
Fred and, 55, 56, 148, 170, 171, 175
Freddy’s death and, 119–22, 126, 128
Freddy’s divorce conversation with, 62–63
Freddy’s divorce from, 85–87, 91, 107, 110, 168
Freddy’s marital problems with, 80–81, 85
Freddy’s marriage to, 52, 55, 56
in gun incident, 80
Highlander apartment of, 57, 67, 76–77
mother’s stroke and, 77–78
snake and, 85
Tosti and, 85–86
Trump family holidays and, 110–11, 148
Trump, Lisa, 2, 167, 171, 175
Trump, Mary Anne MacLeod (mother of Donald), 2, 4, 33, 35, 36, 50, 52, 95, 96, 108, 117–18, 144,
155, 158–61, 167
charity work of, 36, 121
childhood of, 23, 30, 36, 55
choking incident of, 113–14
death of, 176–77, 191
Donald and, 24, 25, 44, 45, 48–50
and Donald’s attempt to control Fred’s estate, 143
family finances and, 190
Freddy and, 158–59
Freddy’s death and, 119, 121, 122
Fred’s death and, 164
Fred’s dementia and, 159–61
Fred’s marriage to, 30–31
Fred’s will and, 169, 171–72, 173
funeral for, 177
home of (the House), see House, the
illnesses and absence of, 12, 21–28, 33, 93, 119, 121, 131, 158, 161, 211
immigration to America, 30
Linda and, 55, 56, 148
Maryanne and, 81, 82
medical insurance and, 174
as mother, 23–27, 44, 45, 48–50
mugging and hospitalization of, 131–33, 161
neediness of, 23, 24
will of, 177
Trump, Mary L.:
apartment burgled, 139
banking story told to father by, 104–5
birth of, 68
at boarding school, 116–20, 138
career of, 12, 183
childhood of, 1, 10
at Columbia University, 139–40
daughter of, 183
Donald and Ivana’s gifts for, 106, 109
Donald’s story about, 163
family finances and, 191–92, 194
foot injury of, 185, 189
as ghostwriter for Donald’s book, 145–49, 151–52, 162–63
grandfather and, 3, 116–17, 139–40
grandfather’s billfold picture and, 155–56
grandfather’s will and, 10–11, 167–72, 173–77, 182, 186–87, 191–92, 194
grandmother’s will and, 177
grandmother visited in hospital by, 131–32
Mar-a-Lago visited by, 148–51
marriage of, 164, 169, 183
Monopoly played by, 111–12
name of, 1, 2
Sweet Sixteen party of, 114–15
at Tufts University, 3, 138, 144–45
watch given to, 156–57
at White House dinner, 1–8
Trump, Maryanne, see Barry, Maryanne Trump
Trump, Melania, 4, 162–63
Trump, Robert, 2, 6, 9, 51, 60, 63, 84, 97, 108–9, 110, 114, 117, 128, 132, 137, 153, 154, 155, 157,
160–61, 162, 165, 177, 182, 184
birth of, 21–22
childhood of, 24, 25, 26, 28
Donald and, 6–7, 44–45
and Donald’s attempt to control father’s estate, 143–44
family finances and, 190–93
father’s will and, 167–72, 175, 176, 191–92
Freddy’s death and, 122–23, 125, 127
Marla and, 184
and sale of father’s estate, 192–93, 196
at Trump Management, 154–55
William’s illness and, 174
Trump, Tiffany, 166, 184
Trump, William, 167, 174, 175, 176, 194
Trump and Son, 28, 29–30, 45, 60
Trump International Hotel, 1–2
Trump Management, 24, 36, 39, 51, 60, 73, 74, 81–82, 88–90, 112, 140, 145, 155, 194, 195
All County Building Supply & Maintenance and, 191–93
Beach Haven, 25, 28, 35, 54, 90, 171
David Desmond at, 83
Donald at, 71–72, 83, 84, 88, 112, 155
Donald promoted to president of, 88–90, 200
and Donald’s sale of father’s estate, 192
elderly housing project, 91
Freddy at, 53–59, 61–63, 65, 66, 73, 78, 79, 83, 84, 88, 89, 91, 112, 155, 200
housing discrimination lawsuit against, 90, 100–101
medical insurance and, 174
Robert at, 154–55
Shore Haven, 25, 28, 34, 54, 171
Steeplechase Park, 67–68, 72–76, 78–79, 87, 88, 89, 102, 141
Swifton Gardens, 91
Trump Village, 56, 57, 68, 74, 88, 89
Trump Organization, 140, 145, 181, 195, 196
Trump Plaza, 134, 136
Trump’s Castle, 134, 136, 154
Trump Steaks, 196
Trump Tower, 35, 98, 133, 135, 141, 161, 195, 196, 197
Trump University, 196
Trump Village, 56, 57, 68, 74, 88, 89
Trump Vodka, 196
Tufts University, 3, 138, 144–45
TWA (Trans World Airlines), 58, 59, 61, 65–68, 78, 84, 88
21 Club, 111
Twitter, 15, 186, 189, 199, 201, 210
University of Pennsylvania, 72, 74, 75, 83
Vietnam War, 84, 89
Virginia Beach, Va., 32–33
Walter, John, 193–94
Washington, George, 5
Wharton School, 72
Lincoln Bedroom, 5
Trump family dinner at, 1–8, 45
Wise, Korey, 204
Witt, Katarina, 147
World War I, 30, 35, 36
World War II, 32
First published in the United States by Simon & Schuster Inc., 2020
First published in Great Britain by Simon & Schuster UK Ltd, 2020
Copyright © Compson Enterprises LLC, 2020
The right of Mary L. Trump to be identified as the author of this work has been asserted in accordance
with the Copyright, Designs and Patents Act, 1988.
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The author and publishers have made all reasonable efforts to contact copyright-holders for permission,
and apologise for any omissions or errors in the form of credits given. Corrections may be made to
A CIP catalogue record for this book is available from the British Library
Hardback ISBN: 978-1-4711-9013-1
eBook ISBN: 978-1-4711-9015-5
Interior design by Paul Dippolito
Jacket photograph by Archivo GBB/Contrasto/Redux