PART TWO. CHAPTER FIVE

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.

During the most crucial juncture of the Steeplechase deal, its unraveling, and its aftermath, Donald did a fair amount of armchair quarterbacking. Freddy, who had never developed the armor that might have helped him withstand his father’s mockery and humiliation, was particularly sensitive to being dressed down in front of his siblings. When they were younger, Donald had been both a bystander and collateral damage. Now that he was older, he felt increasingly confident that Freddy’s continuing loss of their father’s esteem would be to his benefit, so he often watched silently or joined in.

My father and grandfather were conducting a Steeplechase postmortem in the breakfast room that, on Fred’s side, was acrimonious and accusatory and, on Freddy’s, was defensive and remorseful. Donald casually said to his brother, as though completely unaware of the effect his words would have, “Maybe you could have kept your head in the game if you didn’t fly out to Montauk every weekend. ”

Freddy’s siblings knew that their father had always disapproved of what was now merely Freddy’s hobby. There was a tacit agreement that they wouldn’t talk about the planes or the boats in front of the Old Man. Fred’s reaction to Donald’s revelation proved the point when he said to Freddy, “Get rid of it. ” The next week, the plane was gone.

Fred made Freddy miserable, but Freddy’s need for his father’s approval seemed to intensify after Marblehead and even more after the demise of Steeplechase. He’d do whatever his father told him to do in the hope of gaining his acceptance. Whether he realized it consciously or not, it would never be granted.

When they first moved into the Highlander, Freddy and Linda had been concerned that the other tenants would bother the landlord’s son with their complaints. Now they found themselves at the bottom of the list when they needed repairs.

The windows in my parents’ ninth-floor corner bedroom offered expansive southern and eastern views, but they were also vulnerable to strong gusts of wind. In addition, the Highlander had built-in air conditioners in every room that hadn’t been installed properly, so condensation accumulated between the drywall and outer bricks whenever the AC was running. Over time, the built-up moisture seeped into the drywall, softening it. By December, the wall around the unit in my parents’ bedroom had deteriorated so badly that a frigid draft constantly blew into the room. My mother tried to cover the wall around the air conditioner with plastic sheeting, but the arctic air continued to pour in. Even with the heat blasting, their bedroom was always bitterly cold. The superintendent at the Highlander never responded to their request to have a maintenance crew sent up, and the wall was never repaired.

New Year’s Eve 1967 was particularly inclement, but despite the rain and wind, my parents drove out east to celebrate with friends at Gurney’s Inn in Montauk. By the time they were ready to drive back to Jamaica in the early hours of New Year’s Day, the weather had turned even colder and the steady rain had become a downpour. When Freddy went outside to warm up the car, the battery was dead. Dressed only in his shirtsleeves, he got drenched trying to get the car to start. By the time he and Linda returned to the apartment and their windblown bedroom, he was sick.

Between the stress of the last two years and his heavy drinking and smoking (by then he averaged two packs of cigarettes a day), Freddy was in bad shape to begin with. His cold rapidly worsened, and after a few days he wasn’t getting any better as he shivered, wrapped in a blanket, unable to escape the drafts. Linda repeatedly called the superintendent but got no response. Finally she called her father-in-law. “Please, Dad, ” she begged, “there must be someone who can fix this. Maybe from another building in Jamaica Estates or Brooklyn? Freddy is so sick. ” My grandfather suggested that she speak to the Highlander super again; there was nothing he could do.

Because for so long their life had been lived in the confines of Fred Trump’s domain, it didn’t occur to either one of them to hire a handyman who wasn’t on Fred Trump’s payroll. That wasn’t how it worked in the family; Fred’s permission was sought whether it was needed or not. The wall was never fixed.

A week after New Year’s, Linda’s father called to tell her that her mother had had a stroke. My mom didn’t want to leave my father, but her mother’s condition was serious, and she needed to fly down to Fort Lauderdale as soon as she could arrange child care.

Not long after, Gam called my mother to tell her that Freddy was in Jamaica Hospital with lobar pneumonia. Linda immediately got onto a plane and took a taxi straight to the hospital as soon as she landed.

My father was still in the hospital on January 20, 1967, their fifth wedding anniversary. Undeterred by his poor health and worsening alcoholism, my mother sneaked a bottle of champagne and a couple of glasses into his room. Regardless of what was happening around them or what state her husband was in, they were determined to celebrate.

Dad had been home from the hospital for only a few weeks when Linda got a call from her father. Her mother was doing better after her stroke, he told her, but he hated leaving her at the mercy of nurses while he put in full days at the quarry. The stress of work, the expense of his wife’s care, and his constant worry about her were taking their toll on both of them. “I’m at the end of my rope, ” he said. “I don’t see how we can continue. ”

Although Linda didn’t know exactly what her father was implying, he sounded so distraught she was afraid he meant that both he and her mother would be better off dead and, out of desperation, might do something about it. When she told Freddy about her parents’ precarious situation, he told her not to worry and called his father-in-law to tell him he was going to help out. “Quit your job, Mike. Take care of Mom. ” Money wasn’t an issue, at least not then, but Freddy wasn’t sure how his father would react when he told him.

“Of course, ” Fred said. “That’s what you do for family. ”

My grandfather believed that in the same way he believed it was appropriate to send your kids to college or join a country club: even if it was of no interest to him or wasn’t particularly important to him, it was simply “what you do. ”

After the Steeplechase deal collapsed, there was less for Freddy to do at Trump Management. He and Linda had been planning to buy a house since my brother had been born, and now, with extra time on his hands, they started to look for one. It didn’t take long for them to find a perfect four-bedroom on a half-acre lot in Brookville, a beautiful, affluent town on Long Island. The move would add at least half an hour to Dad’s commute, but a change of scenery and the freedom of being out of his father’s building would do him some good. He assured the real estate agent that he could meet the asking price and getting a mortgage would be no problem.

When the bank called a few days later to tell him his mortgage application had been rejected, Freddy was stunned. With the exception of his one year with TWA, he’d been working for his father for almost six years. He was still an executive at Trump Management, which brought in tens of millions of dollars a year free and clear. In 1967, the company was worth approximately $100 million. Freddy made a decent living, he didn’t have many expenses, and there was a trust fund and a (fast dwindling) stock portfolio. The most plausible explanation was that Fred, still burned by what he considered his son’s betrayal and reeling from the failure of Steeplechase, had intervened in some way to prevent the transaction. My grandfather had prominent contacts and enormous accounts at Chase, Manufacturer’s Hanover Trust, and the other biggest banks in the city, so not only could he guarantee that Freddy would get a mortgage, he could just as easily make sure he didn’t. Our family was effectively trapped in that run-down apartment in Jamaica.

When June rolled around, my father was more than ready to spend the summer in Montauk again. My parents rented the same cottage, and with funds he raised by selling some of his blue-chip stocks, Dad bought a Chrisovich 33, which, with its sixteen-foot tuna tower, was much more suited to handle the kind of deep-sea fishing he loved. He also bought another plane, this time a Cessna 206 Stationair, which had a more powerful engine and a larger seating capacity than the Piper Comanche.

But the new toys weren’t just for recreation. Dad had a plan. After Steeplechase, he had been increasingly sidelined at Trump Management, so he came up with the idea of chartering both the boat and the plane to create another source of income. If it worked out, he might be able to free himself from Trump Management after all. He hired a full-time captain to run the boat charters, but on the weekends, when doing so would have been the most lucrative, he had the captain drive him and his friends around instead.

When Linda joined them on the boat, she noticed that Freddy always drank more than everybody else, just as he had in Marblehead, which spurred increasingly intense fights between them. The increasing frequency with which Freddy flew under the influence was alarming, and as the summer of 1967 proceeded, Linda became reluctant to get onto the plane with him. The unraveling continued. By September, Dad realized that his plan wasn’t going to work. He sold the boat, and when Fred found out about the plane, he got rid of that, too.

At twenty-nine years old, my father was running out of things to lose.

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