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.