Freddy’s senior year was one of the best and most productive years of his whole life. The BA in business was the least of it. He’d been made president of Sigma Alpha Mu, and he completed ROTC and would enter the Air Force National Guard as a second lieutenant after graduation. Most important, he became a fully licensed commercial pilot, although he had no intention of using the license; he was going to work with his dad in Brooklyn with every intention of someday taking over.

By the time Freddy joined Trump Management in the summer of 1960, Fred’s company comprised more than forty buildings and complexes, with thousands of units, spread across Brooklyn and Queens. Fred had been taking his oldest son to construction sites for years; his largest developments, including Shore Haven and Beach Haven in Brooklyn, as well as smaller projects closer to home in Jamaica Estates, had all been built while Freddy was growing up in the 1940s and 1950s. During those visits, the importance of cost cutting (if it’s cheaper, do it yourself; if not, outsource it) and cost saving (red bricks were a penny cheaper than white bricks) were drilled into him. Fred also dragged him to meetings of the Brooklyn Democratic Party and political fund-raisers, making sure he got to know the most important and influential politicos in the city.

Now a full-time employee, Freddy started accompanying his father on rounds to the buildings, checking in with the superintendents, and overseeing repairs. Being in the field was better than being in the former dentist office where my grandfather’s business was located on Avenue Z in South Brooklyn, with its cramped quarters and dim lighting. Though Fred’s business was raking in millions of dollars a year, he still dealt directly with tenants when he believed the circumstances warranted doing so. If, for example, a tenant complained a little too loudly or frequently, Fred paid him or her a visit, knowing his reputation preceded him. On occasion he took Freddy along to demonstrate how to handle such situations.

When one tenant repeatedly called the office to report a lack of heat, Fred paid him a visit. After knocking on the door, he removed his suit jacket, something he usually did only right before getting into bed. Once inside the apartment, which was indeed cold, he rolled up his shirtsleeves (again, something he rarely did) and told his tenant that he didn’t know what they were complaining about. “It’s like the tropics in here,” he told them.

Freddy began checking in for his National Guard duty. One weekend a month he had to report to the Armory in Manhattan. Fred didn’t comment on those weekend absences, but he was annoyed by the two weeks a year Freddy had to take off in order to report to Fort Drum in upstate New York. For Fred, who had no use for military service, it was a waste of his employee’s time.

One evening after a long day in Brooklyn, Freddy got a phone call from Linda. They hadn’t spoken for more than a year. She told him that she’d become a stewardess for National Airlines and was flying out of Idlewild Airport (now John F. Kennedy International Airport). She remembered that Freddy had mentioned that his dad owned a couple of apartment buildings in Queens, and she wondered if he could help her find a place not too far from the airport. Fred had several buildings in Jamaica only a fifteen-minute bus ride from Idlewild. They found a studio at the Saxony on Highland Avenue right next to a nine-acre wooded park with a large pond in the middle of it. She moved in right away. Soon she and Freddy were dating.

A year later, in August 1961, Freddy took Linda for dinner at their favorite restaurant in Manhattan. During cocktails, he sneaked an engagement ring into Linda’s glass and proposed. After dinner, they drove to Jamaica Estates to tell his parents. Fred and Mary took the news… calmly.

Based on Linda’s modest upbringing (her father was a truck driver, and later her parents ran a clam shack near the beach in Florida) and her perceived lack of sophistication and education, they assumed that she must be a gold digger. But it was a fundamental and deliberate misunderstanding that failed to acknowledge reality; Linda probably had no idea just how wealthy her future father-in-law was. And if Linda was a gold digger, she was an exceptionally bad one.

Given her own very modest upbringing in Scotland, my grandmother could have been my mother’s ally, but when Mary MacLeod had reached the top of the ladder, she had pulled it up after her. As for Fred, he simply did not like her. In any case, she was Freddy’s choice, so she was suspect.

Meanwhile, the rules for stewardesses at the time were very strict: you could be suspended for letting your hair get too long or putting on weight, and you could not continue to work if you married. After her last flight in January 1962, a couple of weeks before the wedding, Linda would have no independent income.

Because Linda’s mother was confined to a wheelchair due to her advanced rheumatoid arthritis, they decided to have the wedding in Florida. A simple cocktail reception would take place at Pier Sixty-Six Hotel & Marina on the Inland Waterway in Fort Lauderdale after the church ceremony. Fred and Mary weren’t pleased, but since they didn’t offer to help financially, they had little say. Neither Elizabeth, who was at college in Virginia, nor Donald, who was still at NYMA, attended. The Trumps settled for hosting a reception in New York after the couple returned from their honeymoon.

Trump Village in Coney Island—the largest Trump Management project to date—was slated to break ground in 1963, and Freddy would be assisting in the preparations. Fred expected him to take an apartment in one of his Brooklyn buildings so he could be close at hand to manage any problems that cropped up, but Freddy and Linda moved instead into a one-bedroom in the city on East 56th Street between First Avenue and Sutton Place. They bought a poodle, the first pet Freddy had ever had, and a few months later Linda was pregnant.

That November, Frederick Crist Trump, III, was born. A month later, Freddy bought his first plane—a Piper Comanche 180. He and Linda flew it down to Fort Lauderdale right after Christmas to show it—and their new son—off to Linda’s parents. Her father, Mike, who often parked near the runway of the Fort Lauderdale Airport to watch planes take off and land, couldn’t have been more impressed.

During one of the weekly dinners Freddy and Linda had with Maryanne and her husband, David Desmond, whom she had married in 1960, Freddy told them about the plane, adding “Don’t tell Dad. He wouldn’t get it.”

In September 1963, they moved into the Highlander, one of Fred’s Jamaica buildings, down the block from where Linda had lived when she had first moved to town three years earlier—a stepping-stone to a house on Long Island. The Highlander was typical of Fred’s buildings, having a grand entrance to distract from the substandard rental units. The lobby had a large sunken space with a formal sitting area blocked off by velvet ropes and stanchions on one side and on the other a huge display of oversized tropical plants. Between them, large floor-to-ceiling plate-glass windows looked out onto a wide expanse of flagstones and brick steps on either side curving up to the sidewalk. On either side of the steps was more extravagant foliage, towering oak trees and exotic plants with enormous dark green leaves—another Fred Trump touch. The building stood at the top of a hill on Highland Avenue, essentially the dividing line that ran through Jamaica: the north side had a more suburban feel and was predominantly white; the south side was urban and predominantly black. The front and back doors of the building gave onto two different worlds. Freddy and Linda took a two-bedroom apartment on the southeast corner of the ninth and top floor overlooking the park and Jamaica High School in the distance on one side and south Jamaica on the other.

Freddy worried at first that being the landlord’s on-site son, as well as an employee of the company that owned the building, would give people an open invitation to bother him at all hours. But the building was less than fifteen years old, and the superintendent made sure the other tenants left him alone.

Not long after the move, Freddy told Linda he wanted to become a professional pilot. After three years at Trump Management he found the work a grind. Almost from the beginning, his father had frozen him out of the day-to-day operations of the Trump Village development; instead he’d been relegated to handling tenants’ complaints and overseeing maintenance projects.

Being a pilot would give him a chance to do something he loved while making a good living. Before the dawn of the jet age in the early 1960s, there had been a seven-year hiring freeze on commercial pilots. With the introduction of the Boeing 707 and Douglas DC-8 into airline fleets, however, air travel exploded. Pan Am launched overseas flights in 1958 and loaned its jets to National for domestic routes. The following year, TWA, American, Delta, and United were all using jets, which, larger, more powerful, and safer to fly than their turboprop predecessors, could carry more passengers greater distances.

With the expansion in air service came a demand for qualified pilots who already had the skills necessary to train quickly on the new jets. TWA was the last airline to embrace the 707, and it was under a lot of pressure to catch up. At Idlewild and at MacArthur Airport, where Freddy kept his Comanche, the walls were plastered with notices about the need for fresh blood in commercial cockpits.

Linda said no. Having been a stewardess, she knew what pilots got up to during their layovers. For the time being, Freddy agreed to shelve the idea and make the best of life at Trump Management.

But the situation with his father deteriorated. When Freddy approached him with ideas for innovations, Fred shot him down. When he asked for more responsibility, Fred brushed him off.

Trying to prove he could make executive decisions, Freddy placed a window order for one of the older buildings. When Fred found out, he was furious. “You should have slapped a goddamn coat of paint on them instead of wasting my money!” he shouted while the employees looked on. “Donald is worth ten of you. He never would have done anything so stupid.” Donald was still in high school at the time.

It was one thing for his father to humiliate him in front of his siblings, but the people in that office weren’t Freddy’s peers. Someday, presumably, he would be their boss. For his nascent authority to be undermined so publicly felt like a body blow.

When he got home that night, he told Linda how trapped he felt and confessed that he’d never been happy working for his father. It wasn’t at all what he had expected, and for the first time it occurred to him that Trump Management might be a dead end for him. “I’m applying to TWA, Linda. I have to.” He wasn’t asking anymore. Fred might cut him off, but Freddy was willing to risk losing his inheritance. Pilots, especially pilots working for TWA, had good benefits and job security. He would be able to support his young family on his own, and he would be his own man.

When Freddy told his father that he was leaving Trump Management to become a commercial pilot, Fred was stunned. It was a betrayal, and he had no intention of letting his oldest son forget it.