Vanessa Trump: The Untold Truth

As the father of five children, President Donald Trump defied norms by including a revolving door of family members in his campaign and administration during his first term in office. However, daughter-in-law Vanessa Trump largely stayed out of the spotlight until her marriage to Donald Trump Jr. disintegrated very publicly in March 2018. 

Despite having five kids of their own, the former model and the president's first born apparently couldn't make things work. If the tabloids are to be believed, a hefty dose of scandal played a role in the union's collapse. Let's take a closer look at her ambitious past, road to the altar, and marinara sauce fortune. We'll also find out how she really feels about all those cheating rumors and her opinion on her ex's new love. This is the untold truth of Vanessa Trump.

Did Vanessa Trump have Hollywood dreams?

Before there was Vanessa Trump, there was New York socialite and model Vanessa Haydon. Think Paris Hilton, except instead of hotels, Vanessa's mother ran the Kay Models agency, according to Elite DailyHer mom's agency reportedly gave Vanessa her first taste of good, old-fashioned nepotism (a Trump family staple) when she started modeling as a child. 

According to Bustle, Vanessa landed a contract with Wilhelmina Models and attempted to launch an acting career. Unfortunately, her sole acting credit is a minor role in the 2003 romantic comedy Something's Gotta Give. A year later, she entered the Trump family orbit, but if she was looking for a career boost, she barked up the wrong tree. According to Bustle, Vanessa served once as a "celebrity judge" for the Miss U.S.A. pageant, and she made an appearance on The Apprentice. Just the regular one, not even Celebrity Apprentice. That's pretty much it.

From there, Vanessa faded into the background as Mrs. Donald Trump Jr., which had to be quite the adjustment considering the height of her modeling days saw her romantically linked to one of the biggest names in Hollywood...

Vanessa Trump allegedly dated Leonardo DiCaprio

Following the blockbuster success of Titanic, Leonardo DiCaprio was the biggest heartthrob on the planet in the late '90s. We're talking not even Justin Bieber has had this level of heat on him. Leo was huge. Which also means that he had his pick of young models and starlets, and according to New York Magazine, Vanessa Trump (née Haydon) was one of them, although there's some dispute about what really happened in the heady days of 1998, when Leo was king of the world and Vanessa was an up-and-comer on the catwalk.

While the two were reportedly spotted nuzzling at a premiere party, Leo's publicist denied they were dating, and sources accused Vanessa of planting stories with gossip columnists about Leo finally settling down with a "down to earth" girl. Apparently, Vanessa was anything but. "Vanessa played the media really well," an old friend told the mag. "Now she's all dolled up and ladylike and s***, but she used to be this hard-rock in leather and baggy jeans. She was a total gangster b****."

"She was an ill thug," said a former high school classmate. "She went out with this Latin King for like three years." (More on that in a minute.)

Vanessa Trump had harsh words about her future father-in-law

The story of how Vanessa Trump (née Haydon) met Donald Trump Jr. is one for the ages, provided your definition of an epic romance involves using a highly offensive word to describe your future father-in-law. In a 2006 interview with The New York Times, Vanessa recalled how she first met DTJ at a 2003 fashion show, thanks to an introduction from his famous dad. According to Vanessa, the three had a "brief, awkward conversation" and then parted ways, but the story didn't end there. "Donald comes back up to me again, 'I don't think you've met my son Donald Trump Jr.,'" Vanessa recalled, to which she responded, "Yeah, we just met, five minutes ago."

Six weeks later, Vanessa and Trump Jr. were supposedly introduced again at a birthday party for a mutual friend. For a moment, the two initially didn't remember each other, until it hit Vanessa. "Wait, you're the one with the retarded dad!" That dad would become the 45th president of the United States, and the woman who reportedly used the "R-word" became his daughter-in-law. Awkward.

Donald Trump Jr. cheaped out their wedding

After somehow landing a model who may have dated Leonardo DiCaprio, you'd probably want to pull out all of the stops when it comes to your wedding, right? Not Donald Trump Jr. The heir to his family's real estate throne was labeled a cheapskate by the New York Post when it came time to plunk down on an engagement ring. According to the tab, Junior proposed to Vanessa Haydon inside a jewelry store at a New Jersey mall while paparazzi and TV cameras conveniently captured the moment. In exchange for the publicity and future promotional appearances, Vanessa's $100,000 ring was reportedly on the house.

As for the wedding itself, Junior once again spared no expense for his bride (No, really, he didn't spend anything.) They held their 2005 wedding at Mar-a-Lago, his family's Florida golf club — the same joint where Trump Sr. married his third wife, Melania, just a few months earlier. 

Vanessa Trump is a stay-at-home mom

Despite her early years as a fixture in the New York party scene, Vanessa Trump seamlessly transitioned into her new role as a stay-at-home mom to a brood of five! As Romper noted just after the 2016 election, Vanessa's Twitter was a shrine to her kids, even as she began retweeting endorsements for Trump policies. However, Vanessa also has an eye for philanthropy, and she was active in humanitarian efforts while growing her family. 

According to her now-deleted biography on the Eric Trump Foundation website (via Romper): "Vanessa is an avid humanitarian" who volunteered with Don Jr. "on an Operation Smile medical mission in Nicaragua in 2008, where they worked side-by-side with the medical volunteers to help the young patients and comfort their families and bring global awareness of children who suffer from cleft lips and cleft palates. As the mother of five young children, Vanessa is committed to helping Operation Smile transform the lives of children in developing countries." As for why Vanessa's bio was scrubbed from the page, Eric reportedly ceased fundraising efforts for his foundation when he and Donald Jr. were tasked with running the Trump family business after their father's presidential win. 

And that's when the trouble began...

Donald Trump Jr. claimed Vanessa Trump is into guns, bigly

As an avid trophy hunter, it's no surprise that Donald Trump Jr. is a vocal supporter of second amendment rights, and in an interview with SilencerCo, he claimed Vanessa Trump shares his fervor for firearms. "I'm on the road a lot. I have five children at home. I have a wife. You know, she's a tough woman," Junior said (via Heavy). "She puts up with me and she puts up with my kids and does a great job raising them. But she can't stop an aggressive bad guy who's out to get her. She needs that ... she has a concealed weapons permit. She practices with me and she enjoys it. It's a big part of our lifestyle. And we need to be able to defend ourselves."

It's worth noting that at the time of this writing, Vanessa's has not publicly waded into the nation's conversation about gun control, either for or against, or waxed poetic about what her husband called a "big part" of her life. After the deadly Las Vegas shooting in 2017, she did make a public statement offering sympathy to the victims, but her social media presence appears to avoid venturing into contentious political issues. That may be because she had a close encounter with the scary side of public service.

A terrifying letter put Vanessa Trump in the hospital

On Feb. 12, 2018, Vanessa Trump was hospitalized after she opened an envelope containing a suspicious white substance. The threatening letter was addressed to her husband, and the incident sent Donald Trump Jr. into a justified rage. "Thankful that Vanessa & my children are safe and unharmed after the incredibly scary situation that occurred this morning," he tweeted. "Truly disgusting that certain individuals choose to express their opposing views with such disturbing behavior."

Fortunately, authorities determined that the substance was only corn starch, according to NBC News, and a suspect was arrested in Boston. "Thank you so much to everyone that helped catch the person who sent the horrifying envelope that I opened up two weeks ago!" Vanessa tweeted. "A special thanks to @SecretService and all the dedicated state & federal agencies in Boston, NYC & around the US!" Though Vanessa's case was handled by a slew of law enforcement agencies, she reportedly struggled in its aftermath. A source told Page Six the mother of five was "worried for her kids."

Politics took a toll on Vanessa Trump's marriage

Not long after the white substance scare, Page Six ran an exclusive report that claimed Vanessa Trump's marriage to Donald Trump Jr. was on the rocks. According to sources, the couple always had issues, but things only grew worse as Don Jr. became wrapped up in his father's administration (and the accompanying scandals) along with running the family business. "Don Jr. has been busy traveling, which has contributed to their problems," an insider said. "Vanessa is a devoted mother, but she is increasingly lonely and alone in the house with the children."

Page Six also reported that friends grew increasingly concerned about the way Don Jr. had "changed." They cited his erratic tweet attacking the survivors of the Parkland, Fla. shooting and an awkward Halloween tweet that used his daughter to criticize socialism. On top of that, the envelope incident was allegedly an eye-opener for Vanessa. "Vanessa is by nature is a very low-key person," a source said, "and she is uncomfortable with the attention her family is getting now [that] the Trumps are on the world stage." Before the ink could dry on Page Six's bombshell report, Vanessa made her move.

Did an affair end Vanessa Trump's marriage?

Vanessa Trump's exact reasons for divorcing Donald Trump Jr. are up in the air, but tabloids have hinted at infidelity possibly contributing to the union's demise. In March 2015, retired model Melissa Stetten accused Trump Jr. of sending her private Twitter messages, and former Danity Kane singer Aubrey O'Day also alluded to some sort of scandal involving the president's oldest son. 

According to Page Six, O'Day and Don Jr. met on The Celebrity Apprentice, where he allegedly hunted her down even though he was married to Vanessa. American Idol star-turned-politician Clay Aiken, who also appeared on the Apprentice alongside O'Day, also hinted at shenanigans between O'Day and Trump Jr. Vanessa was reportedly pregnant at the time, and Don Jr. allegedly told the songstress that their marriage was ending. Rumor has it that it was Donald Trump Sr. who stepped in and told Junior to "knock it off."

O'Day initially claimed she would not speak publicly about the subject, but that didn't last long. In 2013, she released a song titled "DTJ" that's about having an affair with a married man who has the initials DTJ. Subtle. By 2019, she was apparently ready to let the cat fully out of the bag, revealing on MTV's Ex On The Beach (via iHollywoodTV) that Trump Jr. was her "soulmate."  

Vanessa Trump a marinara sauce heiress

Donald Trump Jr. isn't the only heir in the Trump household. Vanessa Trump happens to be heiress to a marinara sauce fortune, which begs the question: Do they serve her sauce at Trump Grill or do they exclusively serve taco bowls?

According to Page Six, Vanessa's family made its fortune when her late father, Charles Haydon, invested as much as $1 million in Rao's Specialty Foods. Haydon was pals with Frank Pellegrino Sr., who owned the famed Italian eatery Rao's, and Ron Straci, a lawyer who co-founded Rao's Specialty Foods in 1992 to sell the restaurant's marinara sauce. Haydon reportedly owned about 30 percent of the company, which yielded a lot of cheddar when the business was sold for $415 million in 2017.

As a result of the massive payout, Vanessa's mom reportedly purchased a Fifth Avenue penthouse (what else does someone do with that much cash?) No word on if she plans to scoop up some property at Trump Tower, but we're hearing that's a pretty good bargain at the moment. According to May 2019 Bloomberg report, Trump Tower is one of the most undesirable luxury buildings in NYC, and tenants are selling at a loss.

Was Vanessa Trump's first love a gangster?

Vanessa Trump wasn't always the poised and proper wife of a politician. According to Page Six, her prom date and first love was a member of the infamous Latin Kings street gang. Vanessa reportedly met Valentin Rivera in grade school, but they didn't cross paths again until a house party when the pair was around 15 years old. At the time, Rivera had returned from juvie and Vanessa was in a $47,000-a-year Upper West Side prep school. Things were allegedly serious enough between the couple that she visited him on Rikers Island when he was convicted of assault (much to the dismay of her parents).

Rivera ended up joining the Latin Kings after he was transferred from Rikers to a maximum security youth facility in Upstate New York. He told Page Six that by the time he got out of prison, his relationship with Vanessa was so serious they discussed getting married and having kids. She even reportedly drove him around to gang meetings and took him to "deliver weed with his illegal gun stashed in the trunk of her convertible."

"She talked with an urban, gangster accent," a supposed friend told GQ. "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." It's certainly worth noting that Vanessa denies all this. Anyway, the rumored romance allegedly ended when she maybe hooked up with actor Leonardo DiCaprio circa 1998.

Vanessa Trump supports Donald Trump Jr.'s new flame

Amidst his divorce from Vanessa Trump, Donald Trump Jr. started dating Fox News personality Kimberly Guilfoyle. Perhaps Sean Hannity set them up when he was helping Trump Sr. make important decisions about the country, which is something he does, according to USA Today. Anyway, Vanity Fair reports that Don Jr. thinks Guilfoyle is a "cool girl" who "fishes, shoots guns" and "also wears makeup and the fashions." 

As it turns out, Vanessa seems cool with her too. She even defended the Fox News star after an article suggested the network should fire Guilfoyle over her relationship with Don Jr. (because, you know, conflicts of interest). "The lengths people will go to attack a woman simply because she's dating Don," Vanessa tweeted. "We've been separated for over nine months and respect each other's decisions and privacy. We'll focus on raising our great kids. Would be nice if the press did the same rather than obsess over our private lives!"

It seems if there's one thing Vanessa isn't, it's petty. Way to take the high road.

Vanessa Trump pulled the trigger on the divorce

On March 15, 2018, TMZ broke the news that Vanessa Trump filed for divorce from Donald Trump Jr. She didn't contest custody or spousal support, which may indicate that she signed a prenuptial agreement. As for Junior's reaction, well, he didn't seem too broken up about the whole thing. In fact, a source told TMZ that Don Jr. was "relieved." 

However, Page Six noted that the fallout from the divorce couldn't be worse. Vanessa reportedly filed papers on the same day that Special Counsel Robert Mueller's investigation into the president's alleged collusion with Russia subpoenaed the entire Trump Foundation — which includes Don Jr. Making matters even more complicated, Vanessa hired a criminal attorney for the divorce, which is a "curious choice," according to a family law expert. According to Page Six, the pair finalized its divorce in late 2018 and reportedly signed a confidentiality agreement to keep the terms of the settlement private.