Fred Trump Jr. (1938-1981)

Being his father's eldest son, and for whom he was named, he was expected to join and eventually take over the family real estate business. However, he wasn't interested in that path and instead he became an airline pilot. His father reportedly viewed his chosen career as disappointing and not a "real" job, although unlike his younger brother, Donald, Fred Jr. always remained financially solvent. After returning to New York to have open heart surgery at 38, he was unable to continue as a pilot and recuperated at his parents' home, after which he worked as a maintenance worker for the Trump properties. But the rift between the two Freds had created significant family tension and already struggling with alcoholism Fred Jr.'s health problems led to his early death at age 42 from an alcohol-related heart attack. He and his wife had two children: Mary, an academic who wrote the much-publicized book Too Much and Never Enough: How My Family Created the World's Most Dangerous Man.; and Fred, an advocate for the disabled who wrote All in the Family: The Trumps & How We Got This Way.