Vanessa Trump's gangster high school boyfriend says they used to deliver weed together and that she cheated on him with Leonardo DiCaprio

  • Donald Trump Jr.’s estranged wife Vanessa was the “first love” of a gang member in high school, according to an exclusive interview with Page Six.
  • Valentin Rivera says the pair dated for five years, and that they broke up when she cheated on him with actor Leonardo DiCaprio.

Vanessa Trump, estranged wife of Donald Trump, Jr., dated a member of a violent street gang in high school, Page Six reported on Tuesday.

Trump, a former model who was linked to Leonardo DiCaprio in 1997, dated Valentin Rivera, a member of the Latin Kings gang, after meeting in the fifth grade then reuniting when they were both 15, he told The New York Post’s gossip site. Her reps didn’t respond to Page Six’s request for comment.

While she was still Vanessa Haydon, Trump was reportedly a regular at Rikers Island after Rivera was convicted for assault before her mother forbid her from visiting, he said.

Raised on New York’s Upper East Side, Trump, whom Rivera called his “first love”, apparently fit in with Rivera’s fellow gang members, as Rivera said, “she was fascinated. We were kids. She liked the street life at the time.”

Rivera said Trump, who attended the now $US46,750 per year Dwight School, would drive him to his gang meetings on the Lower East Side and to drop off weed in her stepfather’s convertible. Her stepfather, Charles Haydon, was a high-powered lawyer.

The two dated for five years, Rivera said – until Trump, at that point a model, cheated on him with DiCaprio. Rivera said he found out when Page Six reported the two were spotted together in 1998.

Though he doesn’t support President Donald Trump, Rivera told Page Six he is “happy for her that she has five beautiful children and she’s doing well.”

Trump filed for divorce from Donald Jr. in March, and his alleged affair with singer Aubrey O’Day became public shortly thereafter.

Read the full Page Six report here ยป

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