NEW YORK, NY - DECEMBER 11: Vanessa Haydon attends the Z100's iHeartRadio Jingle Ball 2015 at Madison Square Garden on December 11, 2015 in New York City.  (Photo by Jim Spellman/WireImage)
The Stunning Transformation Of Vanessa Trump
Lifestyle - News
Privileged Upbringing
Vanessa Trump, born Vanessa Haydon, grew up in luxury on Manhattan's Upper East Side. Vanessa attended the expensive Dwight School across town and went to high-profile parties with her nanny, where she rubbed shoulders with models, while her parents — a modeling agency owner and a celebrity attorney — went to work.
High School Years
According to former classmates, Vanessa was rather wild in her youth and reportedly dated gang member Valentin Rivera, who has served several prison stints for a range of crimes. Rivera said that the teenage Trump helped him deliver weed and that they even stayed together when he was sent to juvenile prison.
Dating DiCaprio
Surprisingly, Rivera says that it wasn't his gang activity and his trouble with the law but the rumors of her dating film star Leonardo DiCaprio that ended his relationship with Vanessa. While the relationship was never confirmed, it was circulated enough for Page Six to run a story on the alleged new couple.
Princess Vanessa
After the rumored relationship between Vanessa and Rivera ended, Vanessa was said to have moved on to Prince Khalid bin Bandar bin Sultan Al Saud. A source told Page Six that they planned to marry and were living together, but the prince broke up with her and returned home to Saudi Arabia following the 9/11 attacks.
Like many of the women in the Trump family, Vanessa is a former model who began modeling as a child and was signed to Wilhelmina. While the fact that her mother ran a modeling agency may have helped ease her way into the industry, Vanessa's good looks and long legs ensured she found steady work.