Don Jr. Isn't Vanessa Trump's Only Controversial Ex

Vanessa Trump left her ex-husband, Donald Trump Jr., in March 2018 after twelve years of marriage. While the circumstances vary depending on the media outlet, some have attributed the split to Donald's affair with Danity Kane singer Aubrey O'Day. Others allege Don Jr. was a cheapskate. No matter the actual reason for the split, the entrepreneur isn't the only controversial man in Vanessa's life.

As a teenager, she reportedly began dating Latin Kings gang member Valentin Rivera when they were both 15 years old and living in New York City. The two met at a school carnival in the fifth grade, and years later, reconnected at a house party, which kicked off their relationship. According to Rivera, who spoke with Page Six in May 2018, he and Vanessa dated for roughly a year until he went to jail for assault. However, that didn't stop the privileged daughter of Kay Models agency boss Bonnie Haydon and attorney Charlies Haydon from visiting him while incarcerated. After his release, Valentin claimed his wealthy girlfriend became somewhat involved in his street life dealings, even engaging in illegal activity, though Vanessa has never confirmed nor denied his story.

Vanessa Trump may have been a young, aspiring model in her teens, but she was seemingly living a double life with her gang member boyfriend. While a student at the Dwight School, Page Six reports that Vanessa allegedly used her stepfather Charlies Haydon's vehicle to transport an illegal weapon and marijuana with her boyfriend, Valentin Rivera. He also claimed Vanessa would drop him off at gang meetings.

Years before Rivera came forward, an insider who attended high school with Vanessa first brought their relationship to light. In a brief chat with New York Magazine, they explained, "She was an ill thug. She went out with this Latin King for like three years." This romance even allegedly led to physical altercations. Rivera told Page Six that Vanessa would get into fights with girls due to her jealousy. It seems that as Vanessa climbed the ranks in her modeling career, she wanted to leave the street life behind, setting her sights on a Hollywood A-lister.

Vanessa Trump supposedly began dating actor Leonardo DiCaprio in 1998, and abruptly ended her relationship with Valentin Rivera. Multiple publications reported on the blossoming romance. Page Six wrote in May of that year that Vanessa and the "Titanic" star were spotted holding hands and kissing during a SoHo party. Star Magazine (via New York Magazine) reported that DiCaprio was smitten with the future Mrs. Trump. It's unclear how long the fling lasted, but DiCaprio's publicist at the time, Cindy Guagenti, denied that the two were dating.

DiCaprio has never revealed the true nature of his association with Vanessa and given his guarded personal life, it's unlikely he ever will. After Vanessa married Donald Trump Jr. in 2005, she shied away from revisiting her dating history. Vanessa Trump now maintains a low profile since her divorce from Don Jr. was finalized in February 2019. The current status of her love life is unknown.