Strange Things About Donald Trump Jr. And Vanessa Trump's Marriage Nobody Noticed Until It Ended

There is no shortage of outlandish and bewildering puzzle pieces to place together regarding the Trump dynasty. Take Donald Trump's eldest son for example, Donald Trump Jr., a sharp-tongued businessman whose former marriage to Vanessa Trump raised plenty of question marks. Not to mention the fact that the men in the Trump family have a long-standing reputation for being womanizers, often accused of misogynistic behavior, extra-marital affairs, and putting on a front while trouble brews behind closed doors. 

Trump Jr. is no stranger to his personal affairs being attacked, and he and Vanessa's nearly 13-year marriage was no different. Taking a page from his father's book, however, he managed to breeze past the blows about his cheap spending habits, wandering eye, and controversial tweets while he and his then-wife went on to have five children together. Vanessa seemingly played the role of the dutiful homemaker, sticking by her former husband through every salacious news cycle while she focused on raising their many children. Their relationship eventually crumbled, however, and Vanessa ultimately filed for divorce, allegedly moving on to the next best thing — her Secret Service detail (more on that later). 

The twists and turns of the many marriages, divorces, and subsequent marriages within the Trump family tree have captivated the public for years, and it's only right we take a trip down memory lane. Here's a look at all the strange things about Donald Trump Jr. and Vanessa Trump's marriage that nobody noticed until it ended.

Donald Trump Jr. and his former wife, Vanessa Trump, didn't have the most seamless first encounter. She was a model, he was a businessman entitled to an enormous fortune, and in the words of Avril Lavigne, could it be any more obvious? Still, the pair might not have run off into the Mar-O-Lago sunset together had it not been for Donald Trump's awkward facilitating.

In an interview with the The New York Times, Vanessa recalled meeting her future husband with the help of her future father-in-law. The exchange, as described by her, wasn't exactly love at first sight. "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.,'" she explained. The two struck up a short, uncomfortable conversation before the show started, only to have Trump try to reintroduce the two again a second time. "Donald comes back up to me again, 'I don't think you've met my son Donald Trump Jr.,'" she explained, admitting she told the future president: "Yeah, we just met, five minutes ago."

After the fashion show, Trump Jr. and Vanessa ran into each other again weeks later while out with mutual friends. The pair talked for an hour, not remembering their awkward first meeting until it later dawned on them and became something to bond over. Still, Trump Jr. wasn't thrilled about his father playing matchmaker. "It wasn't really my M.O. to have my father try to pick up girls for me," he admitted.

It didn't take long for Donald Trump Jr. to pop the question to Vanessa Trump. It might've helped that he allegedly got his engagement ring free due to a promotion deal from the jewelry dealer Bailey, Banks & Biddle. 

Trump Jr., known for his reputation as a notorious cheapskate, got down on one knee in a New Jersey mall of all places, asking Vanessa for her hand in November, 2004. Television crews and photographers were the only ones allowed in Short Hills Mall to witness the excitement (or lack thereof) of their less-than-romantic engagement, according to the New York Post. The bride-to-be was all smiles, however, showing off her 4-carat emerald-cut diamond sparkler worth $100,00. 

A representative for the jewelry dealer declined to comment on their agreement with Trump. Jr., but an insider told the publication, "It's probably the same kind of deal his father has with Graff," referring to the deal involved with the former president's engagement ring to Melania Trump. "Graff has a lucrative product-placement slot on 'The Apprentice.'" Trump Sr. was quick to comment on his son's proposal in an interview with "Larry King Live," (per E! News) scolding the freebie engagement ring decision. "You have a name that is hot as a pistol, you have to be very careful with things like that," Trump Sr. reportedly said to his son at the time.

The road to walking down the aisle at Mar-O-Lago with Donald Trump Jr. included Vanessa Trump's need to get rid of the skeletons in her designer closet. More specifically, allegations that she was involved with a convicted gangster back in the day. 

In an interview with GQ, the former model's childhood friend claimed that Vanessa dated Valentin Rivera, a convicted criminal who was allegedly part of the Latin Kings, one of the largest and most notorious Hispanic street gangs. Rivera also confirmed the rumors to Page Six, sharing dozens of letters Vanessa sent him during their five-year relationship, which began when she was 15 and continued into his 16-year prison sentence. "My 18th birthday, you'll be back in my arms, my prom, and I want to get pregnant and have a baby with you after January," Vanessa reportedly wrote in one letter, dated 1993. The former socialite reportedly even visited Rivera at Rikers Island during their time together, while he was serving time for assault.

According to the publication, Donald Trump Sr. allegedly found out about Vanessa's romance with the gang member and arranged for a meeting to discuss the controversy. Vanessa reportedly confronted those demons in a conversation with her future father-in-law before she wed his son, assuring him that their dynasty wouldn't be marred by any lingering gang ties.

The Playboy Mansion isn't the first place one would think to bring expecting mothers. But in the Trump family, nothing is ever quite like it seems. In a resurfaced 2007 interview featuring Donald Trump Jr. on "The Adam Carolla Show," nothing was off limits — including the businessman's frustration of having his then-pregnant wife tag along to his debauchery at Hugh Hefner's former playground. The Huffington Post published a transcript of the interview, which was saved by the Internet Archive, and it's every bit of cringeworthy as expected.

"Can you believe the hell I'm going through? I'm at the Playboy Mansion with a pregnant wife!" he shared during the show, four months before Vanessa gave birth. "It doesn't get worse than that, does it? Now, I love my wife, but that is rough. And I'm going to pay for these statements later on tonight. I'm gonna pay." 

Trump Jr. even spoke about the possibility of welcoming their firstborn, Kai, during a natural birth at the infamous Playboy Mansion grotto. "I don't know that I wanna do that," he admitted. "If it's a girl, I don't know that I want her birthed at the grotto. I don't know what's in those grottos."

Donald Trump Jr. has a history of having a wandering eye, even going so far as publicly flirting with models on X, formerly Twitter. Model Melissa Stetten claimed that the businessman exchanged questionable Twitter threads and private messages with her in 2011, just a month after Vanessa Trump gave birth to their third child, Tristan.

"Surprised his marriage didn't work out since he was sending me DMs a month after his wife gave birth," Stetten wrote on X in 2018, shortly after news broke that he and his then-wife were divorcing. Stetten shared a screenshot of a private DM from Trump Jr., where he responded to her original tweet about pulling a muscle while removing a tampon. "Well I'm getting s–t 4the bacon comment glad I opted not 2send the tweet asking 4pics from ur bathroom tweet last night;) people need2chil," his message to the model read. Trump Jr.'s spokesperson shared the entire conversation between him and Stetten with People at the time, saying that the interaction was a joke. 

Stetten wasn't so convinced, however. The model shared another screenshot between the two from 2011 in which Trump Jr. replied to a previous tweet of hers in which she mentioned him, writing that she planned to douse her body in bacon, one of his favorite scents. "Stop that!!! I am a happily married man ;)" he allegedly tweeted in response at the time. In another, he reportedly tweeted that Stetten was "toying" with his emotions.

Vanessa Trump filed for divorce from Donald Trump. Jr in March, 2018, just before some shocking allegations surfaced about extramarital affairs during their relationship. News broke shortly after that Aubrey O'Day claimed to have had a year-long affair with the "Apprentice" star after meeting him on the set of the show in 2011.

Us Weekly was the first to confirm the news through anonymous sources, with an insider claiming, "When it started, they were very serious all of a sudden." Their affair reportedly ended, however, when Vanessa discovered emails between the two. The spouses ultimately decided to stay together, later having two more kids before their marriage came to an end. 

In the aftermath of their divorce, the former Danity Kane singer began speaking out about the shocking details of her alleged relationship with Trump Jr. In an interview on the "Sofia With an F" podcast, O'Day claimed that at one point, Trump Jr. was ready to leave Vanessa for her sake. "[It] was, 'I'm leaving my wife and kids, and this is gonna be what I want, and I love you and you're my wife and everybody knows what it is,'" she said, referring to a message the businessman reportedly wrote her. "My response was always, 'I never cheated on anyone.'" 

The singer also said that Michael Cohen, Donald Trump Sr.'s former lawyer, helped bury news of the affair for years. Trump Jr. has never publicly commented on the alleged affair or his relationship with the reality star. 

Donald Trump Jr. had animal lovers up in arms in 2012 after photos of him posing with a severed elephant tail made the rounds online. Photos of the businessman's African safari alongside his brother, Eric Trump, led to an outcry from PETA, who blasted the men for taking part in big game hunting.

A now infamous photo of Trump Jr. features the father of five smiling while holding the tail of the elephant he killed, a move which he likened to charity. "We have the utmost respect for nature and have always hunted in accordance with local laws and regulations," the brothers wrote in a statement to E! News. "In addition, all meat was donated to local villagers who were incredibly grateful. We love traveling and being in the woods — at the end of the day, we are outdoorsmen at heart."

PETA, however, wasn't convinced about their choice of past-time. "If the young Trumps are looking for a thrill, perhaps they should consider skydiving, bungee jumping, or even following in their anti-hunting father's footsteps and taking down competing businesses—not wild animals," PETA shared in a shade-filled statement to E! News. 

Donald Trump Jr. made his views about socialism known on social media in 2017, albeit through questionable means. The businessman took to X to share a photo of his and Vanessa Trump's daughter, Chloe, on Halloween that year, vowing to "teach her about socialism."

"I'm going to take half of Chloe's candy tonight & give it to some kid who sat at home. It's never to [sic] early to teach her about socialism," he tweeted, along with a photo of his daughter in a police costume looking solemn as she shows her collected candy. 

The controversial remark earned some heavy hits online, including Harry Potter author J.K. Rowling. "Fill her bucket with old candy left by her great-grandfather, then explain that she has more because she's smarter than all the other kids," Rowling wrote in reply. 

The strange parenting tactic earned mixed reviews, but Trump Jr. remained seemingly unphased given his reputation for tweeting outlandish remarks. Still, we can't help but hope that Chloe was able to reap the rewards of her Halloween bounty.

Donald Trump Jr. made a bold move in 2017 when he decided to relinquish his Secret Service protection. As reported by the Florida Times-Union, a source close to the businessman admitted that he has wanted to give up the 24-hour security detail for not only himself, but his wife and five children. 

Whether or not his decision to forego round-the-clock security pertained to his family remained unclear, however, as Secret Service representative Catherine Milhoan declined to comment on the terms of his family's protection agreement.

While insiders claim Trump Jr. made the decision in order to lead a more private life, it posed risks to those closest to him at the time. "In today's global risk environment, waiving this detail poses great danger to him and to his family," said Jonathan Wackrow, a former member of Barack Obama's security team. "What he is becoming potentially is a target of opportunity." 

Vanessa Trump was in for quite the scare in 2018 when she was rushed to the hospital after opening a suspicious package. 

In January of that year, the former model opened an envelope addressed to Donald Trump Jr. that was handed to her by her mother, Bonnie Haydon, only to find a white powdery substance inside. She was taken to the hospital out of precaution, alongside Bonnie and a Secret Service agent, after experiencing nausea, as per CNN. NYPD tested the substance, later confirming that the unknown substance was corn starch and did not contain any hazardous qualities. 

"Thankful that Vanessa & my children are safe and unharmed after the incredibly scary situation that occurred this morning," Trump Jr. tweeted amidst the debacle. "Truly disgusting that certain individuals choose to express their opposing views with such disturbing behavior."

If Vanessa Trump's free engagement ring was any indication, Donald Trump Jr. isn't exactly a big spender. The businessman has had a reputation for nickel and diming his way through life, even when it comes to his wife. 

According to Page Six, one of the reasons Vanessa filed for divorce from Trump Jr. was due to his cheap lifestyle. "He gives her very little help and has been keeping her on a tight budget," an insider revealed to the publication. "She doesn't live a lavish life and can very rarely pick up a check at dinner." 

Sources also claimed that the "Apprentice" star treated her "like a second-class citizen" and she was left to borrow money from her mother. The former model's spokesperson debunked those allegations, however, telling Page Six, "All of these claims are simply not true. Don and Vanessa have tremendous respect for each other and always have. The notion that she has had to rely on her family for assistance is absolutely false and utterly ridiculous." 

Insiders close to the couple tell a different story, however, alleging that the two lived "separate lives" for years. "Even before all this Trump presidency stuff started, they weren't good and their marriage was strained," one source told People.

Speculation surrounding Vanessa Trump and Donald Trump's split points to the former allegedly coming into a large fortune before she decided to file for divorce. Reports suggest that the mother of five may have finally been able to walk away from her former husband after receiving a large inheritance after her father's passing.

According to Page Six, Vanessa's father, Charles Haydon, had invested in several stocks and assets that turned a profit since he died in 2005. "I can't speculate as to how much they received, but it was life-changing," an insider told the publication. 

It was enough for Vanessa's mother, Bonnie Haydon, to pay $6.5 million in cash for a lavish penthouse in New York City, and it might have been the straw that broke the camel's back in terms of Vanessa's strained marriage. But it doesn't just boil down to money, as Trump's infidelity was constantly questioned throughout their relationship. "There have been numerous affairs," the source claimed. "This divorce has been in the works for a long time."

Vanessa Trump made shocking headlines in 2021 when reports surfaced that she had begun a romantic relationship with a Secret Service agent during Donald Trump's presidency. As per journalist Carol Leonnig's tell-all "Zero Fail," Vanessa and Trump Sr.'s daughter, Tiffany, allegedly canoodled with agents, getting "inappropriately — and perhaps dangerously — close" to them (via HuffPost). 

While Leonnig doesn't specify whether Vanessa began seeing the Secret Service agent before or after she filed for divorce, that hasn't stopped the tabloids from speculating she may have been having an affair. "[Vanessa] started dating one of the agents who had been assigned to her family," Leonnig revealed, adding that the agent was not punished because "neither he nor the agency were official guardians of Vanessa Trump at that point." 

While Vanessa's camp didn't comment on the controversy, Tiffany's representatives released a statement. "Tiffany's experience with the Secret Service was entirely professional," said her spokesperson to The Washington Post.