Scandalous Rumors About Vanessa Trump We Can't Ignore

Vanessa Trump's name made headlines once again on March 13, 2025, when her reported romance with Tiger Woods leaked out. Sources told the Daily Mail that Trump and Woods had "been seeing each other since just before Thanksgiving" and that while they were not living together, Vanessa was visiting Woods at his home on Jupiter Island "maybe a few nights a week." Merely 10 days later, however, Woods put all the gossip to bed once and for all with a splashy reveal that got everyone talking. "Love is in the air and life is better with you by my side!" the professional golfer penned in a bombshell Instagram post confirming the dating rumor alongside two photos of the loved-up couple. "We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts," he added. 

Alas, Vanessa also knows a thing or two about navigating rumors. Over the years, she's found herself smack dab in the center of some pretty scandalous gossip, mostly centering around her tumultuous love life pre-Donald Trump Jr. Let's get into it, shall we?

In 1998, long before she became Vanessa Trump in 2005, the New York City socialite and model was romantically linked to A-list actor Leonardo DiCaprio. According to New York Magazine, Trump and DiCaprio were spotted canoodling at a premiere party in New York City. Star Magazine later reported that DiCaprio had "fallen hard for a stunning young model — and 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."

It should be noted, however, that DiCaprio's publicist at the time vehemently denied that the pair ever dated. Someone who claimed to have been an acquaintance of Trump's since they were teenagers told New York Magazine it was actually Trump herself who was behind the DiCaprio dating rumors. "Vanessa played the media really well," the insider said.

It's rumored that Vanessa Trump used to have a thing for bad boys, even falling hard for one who had to serve time behind bars. "She was an ill thug," a former classmate of Trump's told New York Magazine in 1998. "She went out with this Latin King for like three years."

Former Latin Kings gang member Valentin Rivera told Page Six that he and Trump first met when they were both maybe in the fifth grade at P.S. 158 in New York City. However, it wasn't until they were 15 that they sparked a romance while attending the same house party. According to Rivera, their courtship became difficult when he was sentenced to prison on assault charges. "The first time [she came to visit], she was upset — she cried a little bit. ... She only came to visit me twice because her mother forbid her from coming to visit me," he claimed. Rivera also furnished Page Six with letters he claims Trump wrote to him while he was in prison. "I miss you a lot, especially since it's my birthday coming up. And I wish you were here to celebrate with me. But you'll be out [of prison] for my 18th birthday," she penned in one letter. In another, Trump told him all about her big plans for her 18th year of life. "You'll be back in my arms, my prom, and I want to get pregnant and have a baby with you after January."

As for Trump, when pressed for comment, her camp told the gossip column, "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." The world may never know.

Did Vanessa Trump enjoy a secret dalliance with a former Secret Service member? In May 2021, author Carol Leonnig published "Zero Fail: The Rise and Fall of the Secret Service." In the confines of the book, she claimed to have inside knowledge that Trump carried on an affair with one of the Secret Service members formerly assigned to her. 

To make matters worse, in February 2024, the Daily Mail published photos of Trump driving around Florida with an unnamed former Secret Service agent in her passenger seat. Meanwhile, her son, Tristan — one of the five children she shares with Don Jr. — was sitting in the backseat. While it's unclear whether or not this was the same Secret Service member Leonnig wrote about in her Secret Service tell-all book, it definitely kicked the rumor mill into high gear.

Gang members and actors and Saudi princes, oh my! In May 2018, a source told Page Six that fresh off the heels of her romances with a Latin Kings member and Leonardo DiCaprio, Vanessa Trump found love in Saudi Prince Khalid bin Bandar bin Sultan Al Saud. "They dated from 1998 to 2001 and lived together. He ditched her on 9/11; days after, he flew back to Saudi Arabia. They were planning to marry [at the time]. They were inseparable," the source claimed. A rep for Trump, however, denied that the relationship was ever that serious. "They dated in her early 20s. They never lived together and were not planning to get married."

Perhaps what makes Trump's rumored romance with the Saudi prince so scandalous is the prince's family's possible ties to alleged al-Qaeda terrorists. In 2016, a declassified 2002 congressional report revealed that upon the capture of alleged al-Qaeda terrorist Abu Zubaydah, the FBI uncovered a phone book in his possession that contained the phone number of a bodyguard who served at the Saudi embassy where the prince's father, Prince Bandar bin Sultan, served as the Saudi ambassador to the United States, as well as a phone number for a company that managed the ambassador's property in Aspen, Colorado. While the information wasn't enough to directly link the Saudi ambassador to the 9/11 attacks, former Senator Bob Graham said it was "one of the most stunning parts of the investigation," per CNN.