The Tragic Truth About Donald Trump Jr.'s Ex-Wife Vanessa

It's not easy being a Trump wife, overshadowed by your bombastic hubby and relegated to the sidelines. Poor Vanessa Trump (née Haydon) will be forever known as Donald Trump Jr.'s former other half; however, she has an interesting backstory all of her own.

Vanessa's family made millions in the pasta sauce biz, earning her the nickname of "Marinara Sauce Princess." Per Page Six, Vanessa's father sold the company in 2017, resulting in a $415 million windfall for the Haydons. Still, according to Star (via New York magazine), even before the corporate payday, the former Wilhelmina model was well-versed in the high-flying, glam lifestyle, despite friends claiming Vanessa was "a total gangster b****" and "an ill thug," both of which undoubtedly stood her in good stead for her future marriage.

Vanessa had a storied love life before marrying Donald Jr. She was even a member of Leonardo DiCaprio's "P**** Posse" for a hot minute. But it was all bets off when she and Donald Jr. locked eyes across a crowded room in 2003. "I'm at this fashion show," she told the New York Times. "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.'" Despite Vanessa insulting her future father-in-law, the couple married in 2005. And the rest is history. It's not been all love hearts and roses for Vanessa, though. She's had her fair share of adversity over the years.

Vanessa Trump earned her "ill thug" rep. As a teen, she embarked on a five-year romance with the Latin Kings' Valentin Rivera, and Vanessa was totally 'bout that action. "She wore big hoop earrings, hair slicked back. She thought she was a gangster. She had a gangster boyfriend, and she acted like a gangster herself," a friend told GQ. "She was somebody who went out of her way to intimidate people by having a scary boyfriend that could hurt people."

Rivera claimed Vanessa carried out drug drop-offs and drove around with illegal firearms in her stepdad's car, while he made sure everybody knew not to mess with his girl. "If anybody disrespected her in any way, I would physically put my hands on them," Rivera told Page Six. "Any type of disrespect — call out her name, mess with her, anything."

Vanessa was totally heartbroken when Rivera caught eighteen months on assault charges. He was held on Rikers Island while waiting for a transfer upstate, and Vanessa regularly visited along with his mom. "The first time [she came to visit], she was upset — she cried a little bit — but after a while, we get used to things," he said. Vanessa was waiting for Rivera when he was released, and they talked about getting married and having kids. However, he called things off in 1998 after learning Vanessa cheated with Leonardo DiCaprio. Rivera said Vanessa had wanted five children, a dream she later achieved with Donald Trump Jr. 

Vanessa Trump's career dreams were cast aside after she met Donald Trump Jr. in 2003. Before that fateful night, she was a successful model and aspiring actor. Vanessa was signed to the Manhattan agency Wilhelmina Models, and she was on her way to Hollywood fame after appearing in the Jack Nicholson flick, "Something's Gotta Give," per IMDB.

Vanity Fair reported Vanessa hob-knobbed with the rich and beautiful throughout the late '90s and early aughties. She was caught on camera at all the hottest events, rubbing shoulders with Kim Kardashian's bestie Jonathan Cheban, among others. A 1998 New York Magazine profile of Leonardo DiCaprio claimed Vanessa engineered a story about them being crazy in love so she could garner press. "Vanessa played the media really well," a longtime friend said. "Now she's all dolled up and ladylike and s***, but she used to be this hard-rock in leather and baggy jeans."

However, after saying "I do" to Donald Jr., Vanessa went from being a spotlight-seeking socialite and career girl to a stay-at-home soccer mom of five, firmly in the shadow of her hubby. Salon notes that Vanessa was relegated to the background while Donald Jr.'s star rose as his dad, Donald Trump, fought for the POTUS top. Still, her former publicist was holding out hope for Vanessa post-divorce. "I think she could still have a nice career," Christine Schott told the New York Times, adding, "She is in a position to do something great." Sadly, it was never to be.

In the 1980s, the De Beers Group introduced modern society's famous engagement ring rule. They declared that hopeful grooms should spend three months' salary on a sparkler to prove their true love and loyalty, per Brillianteers. However, Donald Trump Jr. threw caution to the wind. He went bigly on budget savings, short on true love and loyalty when he proposed to Vanessa Trump, resulting in a sharp slap across the face for his future wife.

According to The New York Post, "the cheapest gazillionaire" struck up a shady deal with jewelers Bailey, Banks & Biddle. He scored 100 grand of free bling in exchange for turning his proposal to Vanessa Trump into a paparazzi photo op. The new fiancee was forced to mug for the cameras in a set of cringe-worthy pics. She smiled alongside Donald Jr. in front of a sign for the jewelers at the Short Hills Mall in New Jersey, with her ring finger extended for maximum publicity effect.

It wasn't exactly the special day that most wannabe brides dream of, but perhaps Donald Jr. wanted to prove his love was worth more than cold hard money. However, it's unlikely. Even his dad, Donald Trump, who's not renowned for his romantic side, disapproved of the cheap stunt. "I wasn't thrilled with what he did, to be honest with you," Donald told Larry King. "And he got a free ring for promoting the jewelry company. And who knows if the jewelry company is even any good."

Vanessa Trump's life took a terrifying turn in 2018 when a mystery white powder fell out of an envelope she had opened. Given the spate of anthrax attacks in 2001, which killed five people, authorities were on high alert and quick to respond. Vanessa was rushed to the New York-Presbyterian/Weill Cornell Medical Center after complaining of feeling nauseous, along with two others, including her mom. "The substance had arrived by mail and it was addressed to Donald Trump Jr.," New York Police Department spokesman Carlos Nieves announced in a statement (via Reuters).

"Thankful that Vanessa & my children are safe and unharmed after the incredibly scary situation that occurred this morning," Donald Jr. posted on X, formerly known as Twitter. "Truly disgusting that certain individuals choose to express their opposing views with such disturbing behavior."

Vanessa spoke out about the ordeal to Axios. She said she was petrified after being "targeted and terrorized by a coward with a vendetta." Vanessa admitted to suffering the "longest two weeks of my life" while she waited for the substance to be analyzed — it was ultimately found to be unharmful. "I spent the entire time thinking about the horrifying possibility that I would never see my 5 beautiful children again," Vanessa shared. She admitted that the "cowardly act" resulted in her being struck with terror every time she opened the mail. Per NBC News, Daniel Frisiello was found guilty of the offense and sentenced to five years' probation in 2019.

Vanessa Trump's friends begged her to end things with her tight-fisted fiance before it was too late, believing the couple was doomed. "They were having problems before they even got married," a source told Page Six. "People were telling her not to marry him before the wedding." The friends claimed Vanessa hated Donald Trump Jr.'s social media posts. Her former publicist singled out his love of gunning down animals as a major point of contention. "I know she wasn't thrilled that he hunted as he did," Christine Schott told the New York Times. "I know she wanted to keep it on the DL. She knew that was going to be a big issue, socially."

The misery continued for Vanessa after they said, "I do." A source told Page Six that Donald Jr. treated his wife like "a second-class citizen." Her fortune-hoarding hubby refused to hand over any cash, forcing Vanessa to beg her mom for money. "He gives her very little help and has been keeping her on a tight budget," the source claimed. "She doesn't live a lavish life and can very rarely pick up a check at dinner."

The source said Vanessa wanted to leave their marriage for a long time but felt forced to stay with Donald Jr. for appearances' sake. "She was interviewing divorce lawyers before [Trump's presidency]," they claimed. "No one thought he'd win. He won, and she decided to stay until his term was over. But she just couldn't stand it anymore."

Vanessa Trump faced heartbreak and betrayal thanks to Donald Trump Jr.'s wandering ways during their marriage. His first offense was sliding into model Melissa Stetten's DMs in October 2011, just weeks after Vanessa gave birth to their son Tristan Trump. When the couple announced their divorce in 2018, Stetten posted a screenshot of one of Donald Jr.'s gross messages on X, formerly known as Twitter. "Surprised his marriage didn't work out since he was sending me DMs a month after his wife gave birth. (I tweeted a joke about pulling a muscle and changing a tampon, and he replied, asking if I smelled bacon? Cool joke)," she wrote.

A year later, the lusty lothario was allegedly getting down and dirty with Danity Kane singer Aubrey O'Day. Sparks reportedly flew between them after meeting on the "Celebrity Apprentice" set in 2012. Vanessa apparently discovered Donald Jr. was cheating when his phone started pinging with sexts from O'Day while he was in the shower. "To Don Jr., [the affair] was very exciting," an insider told People. 

However, it wasn't Donald Jr.'s roving eye that spelled the end of their marriage. The New York Post claimed it was his tight-fistedness that ultimately hammered the final nail into the romance coffin. Meanwhile, Vanessa's school pals had made an eerie prediction about the doomed marriage years before it occurred. Vanessa's high school yearbook labeled her "the most likely to get a divorce" and "most likely to end up on 'Ricki Lake,'" per Harper's Bazaar.