A father of five, Donald Jr. was 12 years old when Ivana and Donald Sr. divorced. Unlike his younger siblings, he was old enough to understand what the nasty divorce headlines meant — his classmates were, too.
As a child he was extremely close to his maternal grandfather, Milos, who passed away in 1990. The two would spend a couple of weeks every summer hunting and fishing in a town outside of Prague (Ivana is Czechoslovakian). The fast-talking Donald Jr. is fluent in Czech and named one of his sons Tristan Milos, after his grandfather.
After boarding school (Pennsylvania's prestigious Hill School), he followed in his father's footsteps — as most of the Trump kids have — to The Wharton School of the University of Pennsylvania, where he earned his bachelor’s degree in finance and real estate.
In 2001, a year after he graduated from college, Donald Jr. went to work for his dad for the second time. (The first time was when he was 13 and earning minimum wage plus tips as a dock attendant at Trump Castle.) Now an executive vice president at The Trump Organization, he cut his teeth with the development of Trump Place at West Side Yards and has gone on to spearhead projects in Chicago, Las Vegas, Scotland, and India.
Thanks to a fix-up from his dad, he met his wife, Vanessa, at a fashion show. He caught a lot of heat for proposing to her in front of a jewelry store with a bunch of photographers standing by. The rumor-mill called it a publicity stunt and claimed he'd gotten the $100,000 ring on trade. But as the happy couple has welcomed five children in the past seven years, that news story has long since been buried.