For my daughter, Avary, and my dad

Prologue

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 black-and-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 life-sized 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 happened.

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 years.

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’ birthdays.”

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 emphatically.

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.”

I agreed.

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 asked.

“Well,” Maryanne said, as dry as the Sahara, “he has had five bankruptcies.”

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 family.”

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!”

PART ONE

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 his daughter.

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 Kew-Forest, 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 make it.”

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 long-term 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 empathy.

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 motherless.

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 unsupported.

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 wrath.

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 Fred’s abuse.

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, stopped eating.

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.

CHAPTER TWO

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 salute him.

“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 soon.”

Freddy remained quiet and on high alert as long as the Old Man was home.

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 distant.

When Freddy, at fourteen, dumped a bowl of mashed potatoes on his then-seven-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.

CHAPTER THREE

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 on.

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 Donald.

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 fair.

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.

CHAPTER FOUR

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 partying.

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 controls.

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 the room.

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 fishing.

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 planned.

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 was desperate.

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 son’s life.

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 proposal.

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.

PART TWO

The Wrong Side of the Tracks

CHAPTER FIVE

Grounded

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 brother.

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 lost.

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 bikini-clad 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 development.

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 mid-1960s, 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 himself.

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 anyway.

CHAPTER SIX

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-year-old 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 seriously.

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 avoidable deprivation.

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 off-putting. 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 of here.”

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.

CHAPTER SEVEN

Parallel Lines

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 halt.

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 addiction persisted.

“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 can’t.”

Instead of asking “What can I do for you?” Fred said, “What do you want from me?”

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 other people.

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 one-bedroom 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 town.

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 ground.

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.

CHAPTER EIGHT

Escape Velocity

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. “Ivana!”

“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 by comparison.

I grew up thinking that Donald had struck out on his own and single-handedly 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 casino regulators.

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 was that?”

“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 caviar was.

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 reading it.

“Oh, yeah.”

“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 had them.

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 and Fritz.

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 eighty-year-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 specter.

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 this bullshit.”

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 thirty-day 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 Kew-Forest, 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.”

PART THREE

Smoke and Mirrors

CHAPTER NINE

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 make it.

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 October.

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-a-Lago. 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.

CHAPTER TEN

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-a-Lago 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 you?”

Her eyes watered as if somebody had slapped her. “Dad,” she said gently, “it’s Maryanne.”

“Okay, Maryanne.” He smiled, but the name didn’t mean anything to him anymore.

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 use.

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.

CHAPTER ELEVEN

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 her funeral.

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 burial.

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 grandchildren.”

“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 second.”

“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 remained noncommittal.

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 afternoon.

“Is there anything you guys can do, Rob?” I asked.

“Sign the will, and we’ll see.”

“Really?”

“Your father’s dead,” he said.

“I know he’s dead, Rob. But we’re not.” I was so sick of having that conversation.

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 anything.”

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.

CHAPTER TWELVE

The Debacle

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 self-worth 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 his life.

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 judge.

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.

PART FOUR

The Worst Investment Ever Made

CHAPTER THIRTEEN

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 shoulders.

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 my grandfather.

“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 us.”

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 one-third 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 anytime.”

“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.

CHAPTER FOURTEEN

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 powerful men.

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 his “greatness.”

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 bidding.

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 pointed questions.

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-and-diming 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.

EPILOGUE

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 people.

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 worst-case 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 J. Trump.

“Everything’s great. Right, Toots?”

Acknowledgments

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.

• 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
• Omni, 109–10
• 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
• Penthouse, 110
• 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
• Politico, 189
• 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
• Russia, 8
• 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
• Trump, Donald:
  • 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, 196–99, 201
  • 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
• White House:
  • 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