For Donald Trump, Lessons From a Brother’s Suffering

One evening in the 1960s, Donald J. 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. “There was a lot of combustion.”

For Mr. 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, Mr. 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.

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