Rumors About Vanessa Trump We Just Can't Ignore

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The Trump family has been the subject of their fair share of rumors, speculation, and scandals over the years, ranging from some major controversies in their homestead state of Florida to some bitter and long-running family feuds. Vanessa Trump, the ex-wife of Donald Trump Jr., has not managed to come out unscathed, even after she and the president's eldest son called it quits on their 13-year marriage back in March 2018. In fact, Vanessa herself has been at the center of quite a few salacious rumors that simply cannot be forgotten or ignored.

One of the most scandalous claims surrounds the timeline of Vanessa's split from Don Jr. Vanessa filed for an uncontested divorce on March 15, 2018 and the pair finalized their divorce by the end of the year. In June 2018, Don Jr. went public with his new romance with Kimberly Guilfoyle, raising questions regarding what role, if any, that relationship may have played in his divorce — not to mention his alleged affair with singer Aubrey O'Day. However, speculation regarding Vanessa's potential infidelity surfaced in 2021, with allegations that she'd had a fling with a former Secret Service agent.

In journalist Carol Leonnig's book "Zero Fail: The Rise and Fall of the Secret Service," published in May 2021, Leonnig claimed "Secret Service agents reported that Vanessa Trump had begun dating one of the agents who had been assigned to her family." It's unclear when the supposed dalliance was initiated, although Don Jr. reportedly requested to end his family's Secret Service protection in September 2017, against the agency's advice. However, Leonnig wrote that the Secret Service agent in question faced no consequences because the romance became known after the agency was no longer working for the family. However, questions regarding Vanessa's clandestine romance still swirl.

While Vanessa Trump — born Vanessa Haydon — has certainly undergone a stunning transformation over the years, she grew up enjoying a luxurious childhood in the Upper East Side of Manhattan. However, Vanessa rebelled against her high-society upbringing in her teens. When she was 15, she allegedly began dating Valentin Rivera, a teenage member of the Latin Kings gang. Valentin spoke with Page Six in May 2018 and claimed that, during their whirlwind romance in the '90s, Vanessa drove him around to drop off weed and even wanted to stick by his side when he was sent to a maximum security youth prison.

During a brief incarceration at Rikers Island, Vanessa allegedly visited him and lamented his situation. "She was heartbroken that I was being taken away," Valentin told the publication. "She only came to visit me twice because her mother forbid her from coming to visit me." Eventually, Valentin said they broke up permanently in 1998 because she had reportedly sparked a romance with Leonardo DiCaprio. Vanessa's reps declined to confirm or deny Valentin's stories.

Even her tabloid-fodder fling with the "Titanic" star was the subject of speculation, though. A report in New York Magazine at the time suggested that Vanessa started the rumor herself by talking to gossip columnists at a film premiere where she'd gotten cozy with Leo. A source who had been close to Vanessa told the outlet, "Vanessa played the media really well." The source did, however, seem to confirm her rumored romance with Valentin, claiming, "Now she's all dolled up and ladylike and s***, but she used to be this hard-rock in leather and baggy jeans. She was a total gangster b****."