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For Trump, lessons from a brother's suffering

Donald Trump was eight years younger than his alcoholic brother, Freddy, who died in 1981.
Donald Trump was eight years younger than his alcoholic brother, Freddy, who died in 1981.
Published Jan. 3, 2016

NEW YORK — One evening in the 1960s, Donald Trump, still in college but eager to make it big, met his older brother, Freddy, for dinner in a Queens apartment complex built by their father.

Things went bad fast.

As Freddy, a fun-loving airline pilot with a gift for imitating W.C. Fields, joked with his best friend at the table, his younger brother grew impatient. Grow up, get serious and make something of yourself in the family business, Donald scolded.

"Donald put Freddy down quite a bit," said Annamaria Schifano, then the girlfriend of Freddy's best friend, who was at the dinner and recalled Donald's tendency to pick fights and storm out.

For Trump, a presidential candidate whose appeal is predicated on an aura of toughness, personal achievement and perpetual success, the story of Freddy, a handsome, gregarious and self-destructive figure who died as an alcoholic in 1981 at the age of 43, is bleak and seldom told.

In a telephone interview last week, Trump said he had learned by watching his brother how bad choices could drag down even those who seemed destined to rise. Seeing his brother suffering led him to avoid ever trying alcohol or cigarettes, he said.

But the painful case of Freddy Trump, eight years his brother's senior and once the heir apparent to their father's real estate empire, also serves as an example of the dangers of failing to conform in a family dominated by a driven, perfectionist patriarch and an aggressive younger brother. In the upwardly mobile Trump family, Donald was the second and favorite son, the one who got into the University of Pennsylvania's Wharton School, relished the combat of New York real estate and ultimately made the Trump name an international brand. Freddy was the disappointment, who lacked the killer instinct and drifted from his father's ambitions.

Freddy, as he was known, "was caught sort of in the middle as somebody who didn't really love it, and only because he didn't really love it, he wasn't particularly good at it," Donald Trump said. "My father had great confidence in me, which maybe even put pressure on Fred."

Asked whether Freddy's experience in the family business, which friends described as miserable, contributed to the drinking that ultimately killed him, Trump said: "I hope not. I hope not."

From the beginning, Freddy stood out as different from his authoritarian, workaholic father. As Fred Sr. became one of the master builders of the New York boroughs, his mischievous son drank Cokes, and eventually beers, with friends in the family recreation room. Less quick-witted than his older sister, Maryanne Trump Barry, now a federal judge, he was also more welcoming of outsiders than his father.

When Schifano moved to Jamaica Estates, Queens, the wealthy enclave where the Trumps lived, Freddy confided to her that his parents had panicked because, as Italians, the Schifanos were "the first ethnic family to move into the neighborhood." But Freddy was less concerned with ethnic distinctions. When he enrolled at Lehigh University in Pennsylvania, the boy with blond hair who had attended an Episcopalian boys' preparatory school on Long Island joined a Jewish fraternity.

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"It may have been Freddy's first attempt to make his own statement to his father," said his best friend at Lehigh, Bruce Turry, who, like several other former fraternity brothers, remembered Freddy claiming that his father, the son of German immigrants, was Jewish. (He was not.) "Freddy was a classic illustration of someone who had a father complex."

Freddy developed his passion for aviation at Lehigh's flying club. But as his 1960 graduation neared, his father began building Trump Village, an enormous development on Coney Island and the first to bear the family name. Freddy was eager to make his mark.

"He was going to make the Trump name known," as his father dreamed, Turry said.

It didn't work out. While working on Trump Village, Freddy was berated by his father for installing expensive new windows instead of repairing old ones. Donald Trump said that their father "could be unyielding," and that Freddy had struggled with his abundant criticism and stinginess with praise.

"For me, it worked very well," Trump said. "For Fred, it wasn't something that was going to work."

As Freddy stumbled, Trump said, "I watched him. And I learned from him."

Freddy left real estate to pursue his passion for flying, working for Trans World Airlines, which gave him some good years.

But as he reached his mid 20s, he began drinking heavily.

Trump said he had eventually come to recognize that his brother was a talented pilot and belonged in the clouds, not amid bricks and mortar. But by the time Donald had graduated from college in 1968 and had begun ascending at Trump headquarters on Coney Island, Freddy's drinking was out of control.

Schifano recalled that the last time she saw Freddy, one night in the late 1960s, he looked gaunt. Even though she prepared his favorite food, roast beef, he barely ate.

The years that followed were unkind. He got divorced, quit flying because he knew his drinking presented a danger and failed at commercial fishing in Florida. By the late 1970s, he was living back in his parents' house in Jamaica Estates, working on one of his father's maintenance crews.

By then, Donald had broken into the Manhattan real estate market and the city's celebrity culture.

In 1977, Donald asked Freddy to be the best man at his first wedding, to the Czech model Ivana Winklmayr, an honor Donald said he hoped would be "a good thing for him." But the drinking continued, and four years later, Freddy was dead.

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