Vanessa Trump's High School Sweetheart Was in a Violent Gang, Alleges She Helped Him Deliver Weed
A former member of the violent street gang the Latin Kings claims in a bombshell interview that he was Vanessa Trump‘s “first love” in high school — and that she allegedly helped him deliver marijuana, drove him to gang meetings, and visited him in prison before eventually leaving him for Leonardo DiCaprio.
Valentin Rivera opened up about his rough and rocky past with Vanessa, now 40, in a new interview with the New York Post‘s Page Six amid the former model’s highly publicized split from President Trump‘s eldest son, Donald Trump Jr.
Rivera alleged to the outlet that while Vanessa (then Vanessa Haydon) was in high school at the elite Upper West Side Dwight prep school, she drove her then-boyfriend to gang meetings on the weekends and helped him deliver weed to friends in her stepfather’s convertible — which allegedly had an illegal gun in the trunk.
Vanessa’s lawyer did not immediately respond to PEOPLE’s request for comment.
A rep for Vanessa told Page Six, “Vanessa is a devoted mother of five amazing children. This is nothing more than an attempt to sensationalize over 20-year-old ‘stories’ from high school for clickbait.”
Rivera says he began dating Vanessa when they were both around 15, after he had already served a stint in a juvenile detention center for fighting with neighborhood kids.
A year later, Rivera was arrested for assault and sentenced to 1 1/3 to four years in prison, according to Page Six. Vanessa visited Rivera on Rikers Island before he was transferred to an upstate maximum-security youth prison, he says, recalling how “she was heartbroken that I was being taken away.”
“The first time [she came to visit], she was upset — she cried a little bit — but after a while, we get used to things. She only came to visit me twice because her mother forbid her from coming to visit me.”
In the upstate prison, Rivera was indoctrinated into the Latin Kings, a notorious Hispanic street gang that was formed in Chicago in the 1940s. The now-national gang is known for brutal tactics including intimidation, violence and murder.
Rivera says he and Vanessa stayed in touch while he was in prison, and after a 16-month sentence, “I came home [to New York City], I was a full-blown Latin King, and now I came home to a whole nation of Latin Kings.”
“[Vanessa] was worried in the beginning,” Rivera told Page Six, “but after I guess seeing the power of who I became, she was cool with it.” Rivera said he and Vanessa were deeply in love at the time and talked about one day getting married and having children. She once told Rivera that she wanted to have five children — which she eventually did with Trump Jr. (The estranged couple are parents to Kai Madison, 10, Donald III, 9, Tristan, 6, Spencer, 5, and Chloe, 3.)
Rivera said Vanessa regularly drove him to gang meetings and became “fascinated” with street life: “She liked that type of environment — being around gang members and stuff.”
Rivera said the lifestyle began to rub off on Vanessa and claims she “got into a couple of little catfights.”
“She was pretty jealous,” he said, “as far as other girls and stuff, she let it be known that I was her man.”
Before Vanessa filed for divorce from Trump Jr. in March after 12 years of marriage, she discovered in 2012 that her husband had allegedly been having an affair with former Celebrity Apprentice star Aubrey O’Day. A friend of O’Day’s told Page Six that Vanessa “went gangster” on O’Day at the time. Trump Jr. has neither confirmed nor denied the affair.
Rivera and Vanessa’s five-year relationship ended in 1998 when he learned from a New York Post report that Vanessa had allegedly been cheating on him with Leonardo DiCaprio. New York magazine also reported at the time that Vanessa Haydon, then a 20-year-old Wilhelmina model, was seen “nuzzling Leo at that premiere party at Moomba” for the movie Two Girls and a Guy.
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DiCaprio’s publicist at the time, Cindy Guagenti, told New York magazine, “He never dated her.”
An unnamed Dwight school classmate of Vanessa’s described her to New York magazine at the time as “an ill thug” and added that “she went out with this Latin King for like three years.”
Since his time with Vanessa, Rivera has served various prison sentences for assault, weapons offenses and negligent homicide, according to Page Six. In 2013, he became “inactive” in the Latin Kings and says he’s since turned his life around.
Rivera said he wasn’t happy to see Vanessa move on with Trump Jr. but added, “I’m happy for her that she has five beautiful children and she’s doing well.”