4 Scandals That Will Always Haunt Vanessa Trump

Donald Trump Jr.'s ex-wife, Vanessa Trump, is one of the more elusive members of the Trump family. She's barely active on social media, rarely speaks out in public, and seems perfectly content to live her life outside the spotlight. In other words, she's nothing like the Trump family we know. But here's the thing: attention-hogging or not, Vanessa has always been surrounded by drama. Former high school classmates even told New York Magazine she was voted "Most Likely to Wind Up on Ricki Lake," the messy, personal drama talk show. 

Vanessa tried to ditch her bad-girl rep in her 20s and rebrand herself as a New York model, but controversy was never far off, and not everyone was convinced. "Vanessa played the media really well," a former friend told the publication. "Now she's all dolled up and ladylike and s**t, but she used to be this hard-rock in leather and baggy jeans." Eventually, Vanessa's transformation and Hollywood party life led her to the Trump world, where the scrutiny was harsher, louder, and impossible to evade. 

Vanessa Trump might never escape the scandal that followed after The New York Times ran a piece on her and Don Jr. shortly after their wedding. The article didn't just take a swipe at Donald Trump as a dad, it also detailed the awkward story of how Vanessa first met Don Jr. and revealed her rather surprising thoughts about her father-in-law. It all started with Donald Sr. playing matchmaker: "Hi, I'm Donald Trump," he said to Vanessa at a fashion show. " I wanted to introduce you to my son, Donald Trump Jr."

There were polite smiles, a bit of small talk, and they went their separate ways. But minutes later, Trump Sr. circled back with the exact same introduction. "I don't think you've met my son, Donald Trump Jr." Awkward? Absolutely. But somehow, it got worse. A month and a half later, Vanessa was at another party when she was introduced to a vaguely familiar man. They got talking and hit it off, but just then, it clicked! "Wait, you're the one with the ret***ed dad!" Naturally, Vanessa has never bothered to clear things up publicly.

Awkward first meeting aside, Don Jr. and Vanessa Trump got engaged a year later and tied the knot in 2005. Their marriage lasted 13 years before Vanessa filed for divorce in 2018. While she and Don Jr. fought it out in court, Page Six dropped an exclusive bombshell: A former Latin Kings gang member and felon, Valentin Rivera, claimed he was Vanessa's first love and spilled the deets about their messy relationship. Rivera claimed that she loved the gang life and even helped him deliver marijuana. Considering that another friend had described Vanessa as an "ill thug" back in 1998 to New York Magazine, it suddenly felt like the puzzle pieces were falling into place. 

"She liked the street life at the time. She liked that type of environment — being around gang members and stuff," Rivera told Page Six.  Even after he went to prison for assault and became further entrenched in the Latin Kings, Vanessa was there, waiting with open arms when he got home. Rivera shared pictures of them on dates and told Page Six that they only broke up because Vanessa cheated on him with Leonardo DiCaprio. When the headlines hit, a spokesperson for Vanessa hit back, accusing Rivera of "sensationalizing" decades-old stories. She, however, didn't deny Rivera's claims.

Like typical Trump family divorces, Don Jr.'s and Vanessa Trump's 2018 separation included a messy infidelity scandal that reportedly happened years ago. The story was that Don Jr. had an affair with Aubrey O'Day, a contestant on "The Apprentice" back in 2011. And thanks to the increased interest in the Trumps' lives, everyone wanted to hear O'Day's side of the story.

However, not only did she confirm the affair, she also spilled embarrassing information about Vanessa and Don Jr. In one appearance on the Mea Culpa Podcast, she revealed that Vanessa found out about their affair by snooping through Don Jr.'s phone and called her to warn her off. She even shared personal conversations that had tabloids clicking their heels with glee. "When she would talk to me, she would always talk about, 'You're young, you can find somebody else. I can't. You can do this. I can't.' And I would be like, 'Vanessa ... you haven't once said you love him. I love him,'" O'Day recalled. 

Even after the divorce, a 2021 book by award-winning author Carol Leonnig had Vanessa Trump's name back on the headlines. Leonnig previously won the Pulitzer prize for her report on the Secret Service and then wrote a book titled "Zero Fail: The Rise and Fall of the Secret Service." This book included a particularly juicy tidbit about Vanessa. According to Leonnig, Vanessa allegedly, "started dating one of the agents assigned to her and Donald Trump Jr.'s family."

The agent's identity was never revealed, but the whispers never truly died, and some insiders believe Vanessa Trump's Secret Service romance continued after she left the White House. Three years later, the rumors started up again when the Daily Mail published photos of Vanessa driving with her son in the back seat and a familiar face riding in front with Vanessa. The man was none other than a former Secret Service agent who had protected her family at the White House. But with Vanessa behind the wheel and her 'bodyguard' riding shotgun, it didn't exactly scream official business.