The son of Donald and Ivana Trump, Don Jr. spent his childhood in a pink marble palace at Trump Tower, where he was raised by two Irish nannies. He was just 12 when his parents' marriage imploded and the intimate details of their separation became tabloid fodder. (Don recalls seeing Marla Maples' famous quote on the front page of the Post, "Best Sex I Ever Had," on the way to school.) He was soon shipped off to boarding school, returning to New York on vacations and dividing his time between his mom and dad's homes. After high school, Don headed off to his dad's alma mater, Penn, where he soon developed a rep as a party boy who liked to drink and occasionally fight. After college and a "year off," which he spent skiing/boozing in Aspen, Don returned to New York and took a job with his father, natch.
These days Don is an executive vice president at the Trump Organization. Whether Don Jr. actually turns up at work every day isn't entirely clear, but he's taken credit for overseeing the refurbishment of the old Delmonico Hotel at 502 Park Avenue and launching the Trump International Hotel and Tower in Chicago and Trump Soho condo/hotel. He also pops up to dispense invaluable pearls of wisdom on The Apprentice along with his sister Ivanka.
In 2005, Don married model Vanessa Haydon at Mar-a-Lago, his father's estate in Florida. The couple has three children, a daughter named Kai and a two sons named Donald J. Trump III and Tristan. [Image via Getty]