"It is rare for Trump to express regret or admit mistakes. But he said his brother’s short, tragic life scarred him like no other event..."

"... and he said he remains haunted by watching Fred Jr.’s handsome features fade.... Freddy, as everyone called him, was the firstborn son, so he was given the name of his father. His friends said in interviews that he was the opposite of Donald Trump — soft-spoken, playful, and often joking.... Fred Jr. saw flying as an honorable profession, his friends said. He applied to be trained as a pilot for TWA and passed a rigorous set of requirements to enroll in a 1964 class of about a dozen students. He flew for a number of months as a secondary pilot. 'What he loved doing was flying airplanes,' Donald Trump said. 'I remember being at the house and other pilots from TWA would come to the house and they’d come to work with Fred because he was a very natural talent.' Three pilots who trained with Fred Jr. said in interviews that they saw signs of his alcoholism emerging. The pilots said they didn’t know anything about the pressure Trump was under from his family to join the business, but they said he clearly was under stress that he could not handle.... [O]ne of Fred Jr.’s friends, Annamaria Forcier, who as a teenager in 1958 moved to the Queens neighborhood where the Trump family lived, thought Fred Jr. left TWA because of the pressure from the family. 'My impression of it was that he was basically forced to go work for the family firm,' she said. 'There was a lot of tension between not only the old man but also between him and Donald. There was a lot of tension because they didn’t want him to be an airline pilot.'"

From "Trump pressured his alcoholic brother about his career. Now he has regrets" by Michael Kranish (WaPo). Donald Trump is quoted saying to his brother, “Come on, Freddy, what are you doing? You’re wasting your time." And we're told that their father, Fred Sr., said that to be an airline pilot is to be "a chauffeur in the sky."