Vanessa Trump, the ex-wife of Donald Trump Jr., keeps a low profile as far as Trump family members go. Unlike Donald Trump himself, she doesn’t make headlines for controversial comments. And you may not have heard much about Vanessa since she divorced Don Jr. in 2018.
But the 42-year-old mother of five has had a storied life and a downright shocking dating history. Here is the unknown truth of Vanessa Trump, from her wild teenage years to her controversial partners, to her troubled marriage and divorce, and what her future holds.
Vanessa Trump’s early years
Born Vanessa Haydon in 1977, you might think that marrying into the Trump family gave Vanessa newfound access to wealth and power. In reality, she was actually born with a silver spoon in her mouth.
Her family was wealthy, allowing Vanessa to spend her formative years in Manhattan’s Upper East Side, all while attending the expensive (and private) Dwight School.
Where did the money come from? Simple: her stepfather Charles Haydon was a celebrity attorney and her mother Bonnie Haydon was in charge of a high-profile modeling agency.
Vanessa’s parents were busy enough that she spent a lot of time with a nanny. However, the nanny didn’t exactly confine her to the house, and Vanessa often partied with models growing up.
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Vanessa Trump’s high school sweetheart was a gang member
You might be surprised to learn that Vanessa Trump was considered a “wild child” in high school.
How wild are we talking? She was voted Most Likely to Wind Up on Ricki Lake in her high school yearbook, according to New York Magazine.
When she was 15, Vanessa began a five-year relationship with Valentin Rivera, a member of the Latin Kings gang. Photos have been published of the two dancing at prom together. And Rivera claims Vanessa was torn up when he went to a maximum-security juvenile facility for assault, one year into their relationship.
“She was heartbroken that I was being taken away,” he told Page Six in 2018. He also claims that Vanessa visited him at Rikers Island until her mother put an end to it.
However, getting over Rivera may have been just what Vanessa needed to put those wild high school days behind her.
Vanessa Trump reportedly dated Leonardo DiCaprio
You might think that Vanessa’s relationship with Rivera ended because of his criminal convictions. Instead, he claims he broke up with her after discovering she was cheating on him with… Leonardo DiCaprio!
Page Six reported DiCaprio and Vanessa’s relationship on May 1, 1998, when Vanessa was 20. “The passionate pair have been inseparable over the past two weeks,” the publication wrote. “The couple could be seen holding hands, kissing and cuddling into the wee hours in a dimly lit corner” at a private party in SoHo.
However, DiCaprio’s camp was quick to deny a relationship. “He never dated her,” DiCaprio’s publicist told New York Magazine in 1998.
Regardless, Rivera believed the gossip and put an end to their relationship. In the years since, he has quit the Latin Kings gang and seems to harbor no ill will toward Vanessa. “I’m happy for her that she has five beautiful children and she’s doing well,” he told Page Six in 2018.
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Vanessa Trump almost married a Saudi prince
What’s better than marrying into the White House? The answer would be “marrying into a kingdom.”
And that’s what nearly happened with Vanessa. In 1998, she reportedly began dating Saudi prince Khalid bin Bandar bin Sultan Al Saud. The relationship lasted several years. Page Six even reported that they lived together and planned to marry.
But the relationship ended shortly after the 9/11 attacks. The prince’s father Bandar bin Sultan Al Saud was suspected of indirect ties to al Qaeda. Despite a lack of evidence of direct ties, the prince flew back to Saudi Arabia days after 9/11.
Vanessa Trump was a successful model
What is one trait shared by many female Trumps? Spending time as a model, of course!
All of Donald Trump’s wives have been models. His daughters Ivanka and Tiffany Trump have modeled as well.
As for Vanessa, modeling runs in the family: her mother ran a modeling agency. So, perhaps it’s no surprise Vanessa has modeled since childhood and was a fairly successful model in her 20s. She even appeared on a Harper’s Bazaar cover in Australia!
In retrospect, modeling was probably the best way for her to catch the attention of Donald Trump Jr.!
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How Vanessa met Donald Trump Jr.
Vanessa’s road to marrying Donald Trump Jr. was a rocky one. In fact, they met in 2003 three times before they clicked.
Vanessa told the story of how they met to The New York Times in 2006. “I’m at this fashion show. Donald Trump comes up to me with his son: ‘Hi, I’m Donald Trump. I wanted to introduce you to my son Donald Trump Jr.'”
They made small talk and parted ways, but not for long. “Donald comes back up to me again, ‘I don’t think you’ve met my son Donald Trump Jr.'”
“Yeah, we just met, five minutes ago,” Vanessa responded.
It wasn’t love at first sight, but two months later they ran into each other again and clicked.
In 2004, Don Jr. proposed, but the engagement made headlines for all the wrong reasons. While the $100,000 engagement ring was beautiful, the New York Post reported that he got it for free from Bailey, Banks & Biddle in exchange for proposing in front of their store.
Why Vanessa and Donald Trump Jr. got divorced
Vanessa and Don Jr. got married at Mar-a-Lago in 2005, the same place where Trump Sr. married Melania in 2004. The wedding ceremony took place by an extravagant pool, and Vanessa rocked a dress she had designed herself.
But unfortunately, this wasn’t going to be a happily ever after: in 2018, Vanessa filed for divorce. She had stuck through a rocky marriage for nearly 13 years. Reports surfaced that Don Jr. had an alleged affair with a Celebrity Apprentice contestant that Vanessa found out about in 2012.
But there were other problems with their marriage besides the alleged cheating. As Page Six reported in 2018, one source claimed, “He gives her very little help and has been keeping her on a tight budget. She doesn’t live a lavish life and can very rarely pick up a check at dinner.”
Another source said, “Don Jr. was never generous with money. Vanessa has had to rely on her mother for financial help for her personal needs.”
Still, Vanessa tried to tough it out. “The couple had hoped to stay together during the president’s time in office, but it is getting harder to resolve their issues. He’s never there,” a source told Page Six.
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Vanessa is focusing on her children
Nowadays, Vanessa seems all about keeping a low profile. She hasn’t made many public appearances or statements, mostly confining herself to social media. And much of her social media activity focuses around her children.
Vanessa and Donald Trump Jr. share five children together: eldest daughter Kai (born in 2007); sons Donald III (born in 2009), Tristan (born in 2011), and Spencer (born in 2012); and youngest daughter Chloe (born in 2014).
“I’m a mother of 5 amazing kids. My children are my life!” Vanessa’s Twitter profile says. It seems she is content focusing on “mommy mode” for the time being.
Vanessa made millions from pasta sauce
For some, it’s inconceivable to divorce one of the Trumps. How can someone walk away from that much wealth? As it turns out, Vanessa is wealthy all on her own!
When her stepfather passed away in 2005, he owned significant investments that he passed on to Vanessa and her mother. This included a 30% stake in Rao’s Specialty Foods, makers of Rao’s Homemade pasta sauce. Vanessa and her mother each made $62 million before taxes when the company was sold in 2017.
Reportedly, Don Jr. couldn’t get his hands on any of this money in the divorce because it was an inheritance. In other words, Vanessa doesn’t have to worry about money and can simply focus on her happiness and that of her children.