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.