When a younger son trumps the older

US Republican presidential candidate Donald Trump reacts to supporters at the start of a Trump for President campaign rally in Raleigh, North Carolina.
US Republican presidential candidate Donald Trump reacts to supporters at the start of a Trump for President campaign rally in Raleigh, North Carolina.PHOTO: REUTERS

Brother's self-destruction taught US presidential hopeful Donald Trump valuable lessons

NEW YORK • One evening in the 1960s, Donald Trump, still in college but eager to make it big, met his brother, Freddy, for dinner at an 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 Ms 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. "There was a lot of combustion."

For Mr Trump, a US presidential hopeful 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 recent telephone interview, Mr Trump said he had learnt by watching his brother and 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.


Donald put Freddy down quite a bit. There was a lot of combustion.

MS ANNAMARIA SCHIFANO, former girlfriend of Freddy's best friend, who recalled Donald's tendency to pick fights

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 favourite 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 so far from his father's ambitions that his children were largely cut out of the patriarch's will.

Freddy "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", Mr 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, Mr Trump said: "I hope not. I hope not."

From the very beginning, Freddy stood out as different from his authoritarian, workaholic father.

As Fred Senior became one of the master builders of the New York boroughs, his mischievous son drank Coke, 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 Ms Schifano moved to Jamaica Estates, the wealthy enclave in Queens 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 neighbourhood".

But Freddy was less concerned with ethnic distinctions. When he enrolled at Lehigh University in Pennsylvania, the blond boy who had attended an Episcopalian boys' preparatory school on Long Island joined a Jewish fraternity.

"It may have been Freddy's first attempt to make his own statement to his father," said his best friend at Lehigh, Mr 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," he said.

Ms Schifano recalled that the last time she saw Freddy, in the late 1960s, he looked gaunt. Even though she prepared his favourite 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 with one of his father's maintenance crews.

By then, Donald had broken into the Manhattan real estate market and the city's celebrity culture. A younger brother, Robert, had followed in Donald's footsteps, joining the family company and eventually becoming a top executive there.

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


A version of this article appeared in the print edition of The Straits Times on January 04, 2016, with the headline 'When a younger son trumps the older'. Print Edition | Subscribe