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.