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Vanessa Trump Once Dated A Violent Street Gang Member — Until She Cheated On Him With Leonardo DiCaprio

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Vanessa Trump Once Dated A Violent Street Gang Member — Until She Cheated On Him With Leonardo DiCaprio

Before she got married to (and then divorced from) Donald Trump Jr., Vanessa Trump dated a notorious gang member in high school, long before she became a part of the first family.

Who did Vanessa Trump date?

In 2018, a man named Valentin Rivera spoke out about being Trump’s high school sweetheart — and a member of the Latin Kings, a dangerous gang he joined while serving time in prison. 

In the interview, Trump’s former boyfriend opened up about their teenage relationship and run-ins with the law.

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The two met in the fifth grade. Rivera recalled already getting into trouble at a young age. 

“We was in the carnival in the school and I hit her with a water balloon, and she told on me. I went to the principal’s office,” Rivera revealed. “Then we parted ways until a couple of years later.”


A post shared by Donald Trump Jr. (@donaldjtrumpjr) on Dec 25, 2018 at 1:38pm PST

Trump and Rivera didn’t run into each other again until a house party in high school. She was 15 and noticed some kids were stealing things from the party. Rivera said she asked him to help her stop the thieves.

“They were stealing out the house and we searched them,” he said. “That’s how we started talking again.”

Rivera revealed how Trump would chauffeur him around in her stepfather’s car as he made his rounds delivering weed. They kept an illegal gun in the trunk of the convertible.

After a year of dating, Rivera began getting into trouble with the law. He was sentenced to one to four years in prison for assault, and Trump visited him twice before her parents decided it was best if she stopped seeing him.

“She was heartbroken that I was being taken away,” Rivera said. “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.”

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Trump kept in contact with Rivera while he was held in a maximum-security youth prison, where he was recruited into the Latin Kings. “A few fights, a few slashings, and my name was ready in the prison as a person who was a bad guy,” he said.

Once he completed his 16-month term, he returned to his girlfriend as a member of the prominently Hispanic gang that was founded in the 1940s. “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.”

He and Trump continued to date after his prison stint, and he became more and more involved with the gang. “[Vanessa] was worried in the beginning but after I guess seeing the power of who I became, she was cool with it,” Rivera said.

The Latin King expressed the love he and Trump shared in their youth. He said they had even discussed marriage and children, and said Trump enjoyed their lifestyle.

“She was fascinated,” Rivera explained. “We were kids. She liked the street life at the time. She liked that type of environment — being around gang members and stuff.”

According to Rivera, the uptown girl reveled in the attention she got from dating him, and even used her father’s status as a well-known lawyer to get them out of trouble. 

“If we got pulled over, the police would just let us go,” he said. “She’ll give up Charles’s information. Car’s registered to Charles Haydon. They’ll just cut us loose.”

Their relationship lasted for five years, but came to an abrupt end in 1998 when Rivera discovered Trump had cheated on him with Leonardo DiCaprio.

Since Rivera and Trump split, he has spent time behind bars for assault, weapons offenses, and negligent homicide. Rivera turned his life around after becoming “inactive” in the Latin Kings in 2013. He chauffeurs the elderly to medical appointments these days.

He's not bitter toward Vanessa, though he said he doesn’t care for the Trumps, saying, “I’m happy for her that she has five beautiful children and she’s doing well.”

At the time, a representative for Vanessa stated that, “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.”

Vanessa and Donald Jr. finalized their divorce in 2018. They had been married for 12 years.

In a joint statement at the time, they said, “We finalized our agreement at the end of last year. We are incredibly lucky to have five amazing children and are committed to raising them together. Our kids and their happiness will always be our first priority.”

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Sarah Gangraw writes about all things news, entertainment and crime. You can follow her on Instagram and Twitter.

Editor's Note: This article was originally posted in May 2018 and was updated with the latest information.