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. Nonetheless, the rift between the two Freds created significant family tension and already struggling with alcoholism this only exacerbated Fred Jr.'s problems which ultimately 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.