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.