Tragic Details About Vanessa Trump's Personal Life

If you have to rack your brain to try and figure out whether you know who Vanessa Trump (née Haydon) is, you're probably not alone. She's mostly kept out of the spotlight since she became a member of the controversial and political Trump family in 2005. Trump was married to Donald Trump Jr. until 2018, and the couple had five kids together. Vanessa wasn't completely new to the aspect of being part of a high-profile family given the fact that her late stepfather, Charles Haydon, was a pretty famous lawyer back in the day, representing the likes of Marilyn Monroe. Her mother, Bonnie Haydon, also headed Kay Models. It's not clear who her biological father is or if she ever knew him.

Vanessa grew up on Manhattan's Upper East Side with her sister, Veronika Haydon. Basically, her early life appears to have come straight out of a "Gossip Girl" episode, but as we all know, the characters in the show often had very tragic lives behind closed doors. The same could be said for Vanessa. Her life hasn't been smooth sailing all the way, and her introduction to the Trump family wasn't the best one either — upon meeting up with Donald Jr. after their first meeting, she couldn't remember who he was the second time they were introduced to each other. Then, she had a light bulb moment and blurted, "[You're] the one with the r*tarded dad!" Oof! Perhaps that was the first indication that things were about to go sideways.

Vanessa's high school sweetheart got imprisoned for assault

Vanessa Trump's first love was Valentin Rivera. To Trump, Rivera was her soulmate, and she wanted to start a family with him when she was as young as 18. The two connected in elementary school and fell madly in love. Rivera, however, had a pretty checkered reputation and was part of a street gang. Trump knew this but didn't mind, in fact, a friend of hers told GQ that she enjoyed having a gangster boyfriend and even tried to embrace the lifestyle. "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," the friend divulged, adding, "She was somebody who went out of her way to intimidate people by having a scary boyfriend that could hurt people."

Thanks to his dubious activities, Rivera soon found himself in prison for assault. During this time, Trump wrote love letters to him, which Page Six got a hold of in 2018. In the letters, Trump professed her love numerous times, despite hearing whispers that Rivera joined the Latin Kings gang. Rivera broke up with Trump after hearing about her alleged relationship with Leonardo DiCaprio. By this time, he'd been imprisoned several more times.

Donald Trump allegedly had his future daughter-in-law investigated ahead of her wedding and confronted her about Rivera, but she denied that she was ever involved with him. Page Six managed to dig up old photos of the couple, however.

Donald Trump Jr. allegedly staged his engagement to Vanessa for the paparazzi

It might be safe to say that few people who truly love someone cares what their engagement ring cost, but it's another matter entirely when your hubby-to-be proposes with a free ring that he managed to acquire solely because he promised the jeweler he'd stage a photo op for the paparazzi. That is what Donald Trump Jr. apparently did when he proposed to Vanessa Trump.

The future Mrs. Trump might've received a $100,000 ring when Donald Jr. went down on one knee, but it was allegedly all a farce because sources told the New York Post that Donald Jr. made a deal with the jeweler, Bailey, Banks & Biddle, to give him the ring free of charge in exchange for some advertising. When he asked his girlfriend's hand in marriage, the paps and some television crews were on standby to capture the moment. The New York Post dubbed Donald Jr. "the cheapest gazillionaire," and called his proposal a "taste-deprived ceremony." Even Donald Jr.'s father, Donald Trump Sr., thought it was a cheap move (which is saying a lot).

While making an appearance on "Larry King Live," Trump called out his son for the blunder. "You have a name that is hot as a pistol, you have to be very careful with things like this," he said. We're kind of surprised Vanessa said yes after finding out about the whole setup.

Sources claim Vanessa had a very unhappy marriage

If anonymous sources are to be believed, Vanessa Trump's marriage wasn't nearly as glamorous as her engagement ring. Apparently, Donald Trump Jr. giving his wife-to-be a free engagement ring was an indication of how the rest of their marriage was about to go, with sources claiming that one of the main reasons Trump decided to divorce Donald Jr. is that, despite being a rich man, he was allegedly never very generous when it came to her.

"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," one source claiming to be a friend of Vanessa's told Page Six. More friends revealed that Donald Jr. treated Vanessa like "a second-class citizen." "Don Jr. was never generous with money. Vanessa has had to rely on her mother for financial help for her personal needs," a source divulged. Another tipster told Page Six that Vanessa was also having a hard time because her husband was barely ever home. "Don Jr. has been busy traveling, which has contributed to their problems. Vanessa is a devoted mother, but she is increasingly lonely and alone in the house with the children," the source claimed. Vanessa's spokesperson, however, dismissed all these claims, calling them "absolutely false and utterly ridiculous." As for who to believe, well, we'll let you decide.

Sources also claim that Vanessa had relationship problems before she married Donald Jr.

Apparently, Vanessa Trump and Donald Trump Jr. were having relationship problems even before the two tied the knot in 2005. Whether or not this had something to do with how Donald Jr. decided to pop the big question is unclear, but sources claim trouble was plenty before the couple's nuptials, so much so that some of Trump's friends told her to break off the engagement.

"They were having problems before they even got married," a source told Page Six, adding that Vanessa was allegedly ready to finally give up on her marriage right before Donald Trump Sr. won the 2016 presidential election. "No one thought he'd win. He won and she decided to stay until his term is over," the tipster claimed. As we all know, Trump filed for divorce in 2018, two years before Donald Sr.'s term came to an end, and sources claim she did so because "she just couldn't stand it anymore."

It's not entirely clear what kind of problems the couple was dealing with prior to their marriage. Vanessa's former publicist, Christine Schott, told the New York Times that an issue the couple dealt with early on was Donald Jr.'s love of big-game hunting. Vanessa did not approve of this and didn't like how this so-called hobby portrayed them in the eyes of the public.

Vanessa was hospitalized after opening shady mail meant for her husband

Aside from apparently dealing with marital problems, Vanessa Trump also got a big scare in 2018 when she opened a letter addressed to her husband, which, upon opening, she realized contained white powder and a threatening letter. The letter, according to ABC News, read, "You are an awful, awful person, I am surprised that your father lets you speak on TV. You make the family idiot, Eric, look smart. This is the reason why people hate you, so you are getting what you deserve." The last line is probably what alerted Ms. Trump to the possibility that the letter might not just be a hoax. She called 911, and after undergoing decontamination, she was sent to the hospital.

The letter did turn out to be an empty threat — authorities determined that the white powder was cornstarch — but Trump was reportedly left rattled by the incident, sources told Page Six. "Vanessa is by nature a very low-key person, and she is uncomfortable with the attention her family is getting now the Trumps are on the world stage. She is also worried for her kids, particularly after she received the threatening letter," one tipster claimed. Authorities managed to track down the culprit, who turned out to be 25-year-old Daniel Frisiello from Massachusetts. Michael Cohen, Donald Trump's former lawyer, condemned Frisiello's actions, "How disturbed must a person be to do what they did to a mother of five young children?" he told the New York Post.

Vanessa's husband reportedly cheated on her

It appears that Donald Trump Jr. has a wandering eye, which is very likely one of the reasons his marriage ended in shambles. In 2011, he was sending flirtatious texts to former model Melissa Stetten, who shared a screenshot of one such text from Donald Jr. on Twitter in 2018 after it was announced that Vanessa Trump filed for divorce. "Surprised his marriage didn't work out since he was sending me DMs a month after his wife gave birth," Stetten captioned the screenshot.

It appears Ms. Trump was blissfully unaware of her husband's online activities, but the illusion was shattered in 2012 when she reportedly found out about an affair he was having with singer Aubrey O'Day. O'Day was a contestant on "Celebrity Apprentice," which used to be hosted by Donald Trump Sr. According to Page Six, Donald Sr. had his son work as an advisor during this time, and this is how he first met O'Day. "[Donald Jr.] pursued [Aubrey]. It was him who chased her," a source told the outlet, adding, "He told her that his marriage was already in the process of dissolving." Meanwhile, Trump only found out about the affair when she saw flirtatious text messages from O'Day on her husband's phone one day while he was taking a shower, a source told People. She confronted Donald Jr. and he reportedly ended the affair. "To Don Jr. [the affair] was very exciting," an insider told the outlet.

Vanessa apparently had a messy divorce

When news first broke of Vanessa Trump and Donald Trump Jr.'s divorce in March 2018, it appeared that the couple's split might not turn into a classic soap opera. Page Six first reported the news, explaining that Ms. Trump had filed for an uncontested divorce, which indicated that there would be no ugly court fights regarding custody of the couple's children or assets. They announced their split to the world via Page Six in a joint statement, and it appeared that the two would divorce quietly, but a few months later, sources told InTouch that things weren't proceeding as originally planned.

Vanessa came into some money shortly after filing for divorce, thanks to an investment her late stepfather made. This appeared to ruffle Donald Jr.'s feathers, who brought the matter up in court proceedings and ordered his ex to disclose her new net worth. Sources claimed that Vanessa wasn't about to give Donald Jr. what he wanted. "Between fighting over money, Vanessa not wanting to be publicly embarrassed anymore than she already has, and Don Jr.'s ego, it'll get bad," one source predicted.

What exactly played out during the divorce isn't public knowledge. Norman Heller, Donald Jr.'s lawyer who handled the case, initially thought that all would be finalized in a matter of weeks, but Page Six reported that the couple's divorce was finalized by the end of 2018. Apparently, things didn't go as smoothly as Vanessa had hoped.

Vanessa's original career didn't exactly pan out

When Vanessa Trump first met Donald Trump Jr., she was an aspiring actress and model. She landed a very small role in the 2003 flick "Something's Gotta Give," but she didn't take on any more acting roles after marrying Donald Jr. Prior to tying the knot, she also made an appearance on "The Apprentice." Vanessa got into modeling at a young age, thanks to her mother running the Kay Models agency. She was also later signed with Wilhelmina Models, and it seemed as if Trump was well on her way to building a career in both the entertainment and modeling industries. Unfortunately, it appears her marriage to Donald Jr. cut this short, and she opted to become a stay-at-home mom and devote all her time to her five children instead.

During her marriage to Donald Jr., Vanessa launched some business ventures, one of which was her designer handbag line La Poshett. The line was short-lived, however, and the bags were only sold between 2010 and 2013. She was also seen at her husband's side during Donald Trump's presidential campaign. Vanessa's former publicist, Christine Schott, told the New York Times in 2018 that she thought Trump had a chance at creating a new career for herself now that she's divorced. "I think she could still have a nice career," Schott told the outlet, adding, "She could be a mommy blogger and she could take on a cause. She is in a position to do something great."