Did Vanessa Trump Actually Date Leonardo DiCaprio Back in the Day? Here’s the Truth

Donald Trump Jr. ’s ex-wife, Vanessa Trump, has had quite the fame voyage. The former Wilhelmina model is rumored to have dated Hollywood star Leonardo DiCaprio at the peak of his Titanic stardom. Vanessa’s name popped up in a resurfaced New York Magazine profile from 1998 that deep-dived into the actor’s romantic history. But many critics pointed out that these rumors were a young Vanessa’s vain attempt at stardom.

As per the aforementioned report, DiCaprio’s infamous ‘posse’ of single young actors and models briefly involved Vanessa, in the story that hailed him as “Prince of the City.” The same year, another article by Star Magazine broke the news of an alleged affair between the two. It was reported that Vanessa was captured getting cozy with DiCaprio at an after-party of a movie premiere; apparently, DiCaprio had ‘fallen hard’ over the ‘stunning young model.’ “Pals say this time it’s love. The superstar is so smitten with blonde beauty Vanessa Haydon that he’s now a one-woman man,” the article stated at the time, per The Mercury News .

However, the actor’s publicist, Cindy Guagenti straight up denied any romantic involvement between him and Vanessa, 46. “He never dated her,” she confirmed. The New York Times and New York Magazine reported that Vanessa spread the rumors with the help of a private publicist. She reportedly wanted to be known as the star’s best woman in light of his fruiting success. As per the same NYT article, a classmate also said, “Vanessa played the media really well.”

It is also worth noting that Vanessa, now a mother of five children, was somewhat wild in her youth. She was a ‘gangster’ in prep school, as some of her classmates, from the Tony Dwight School in the Upper West Side, described in a New York Magazine report. Born in Manhattan, it is evident Vanessa was fond of the glitz and glamor and hired herself a publicist in her late teens and early 20s to shove her name into the spotlight. Eventually, she stumbled into modeling and dramatically changed her appearance and behavior. An insider recalled Vanessa, who once allegedly dated a Latin kingpin, getting ‘dolled up and all ladylike’ after becoming a model but added that she “used to be this hard-rock in leather and baggy jeans. She was a total gangster bitch.”

Vanessa seemed to have finally got her big break by sparking a real romance with Don Jr., the former U.S. President’s eldest child. The ex-couple met at a 2003 fashion show where patriarch Donald introduced her to Don Jr., twice, per the New York Times. However, he was not highly impressed; rather he seemed ‘annoyed’ when her publicist, Christine Schott, introduced herself at their grand 2005 wedding in the Mar-a-Lago, Palm Beach. Schott recalled, “The president said, ‘Vanessa has a publicist?’” The couple divorced in February 2019.