Vanessa Trump: 12 Facts About Donald Trump Jr.'s Ex-Wife

Donald Trump isn't exactly shy about putting his family members in the spotlight. His sons, Donald Trump Jr. and Eric Trump, were major campaign mouthpieces every time he ran for president. Depending on who you ask, there are some signs that Ivanka Trump and Jared Kushner's marriage is destined for divorce, but that didn't stop the president from giving his daughter and son-in-law crucial White House roles during his first administration. Turn on Fox News at a certain time of day, and you're likely to see Eric's wife, Lara Trump, hosting her own show on the network. You may even be aware of Tiffany Trump, the president's other daughter, who has taken a bit of a back seat compared to her more famous family members.

Who, then, is Vanessa Trump? Despite the fact that she still uses the last name professionally, including on her Instagram, Vanessa isn't actually a Trump anymore; she divorced Donald Jr. several years ago. Nevertheless, she's continued to hang around the Trump family, even attending the president's second inauguration in 2025. Furthermore, she and Donald Jr. share several kids, which probably necessitates some closeness. If you're looking to learn more about anyone connected to the most controversial presidential administration in recent American history, read on to find out about Vanessa's time on the New York social scene, her headline-grabbing courtship with Don Jr., and even the rumors surrounding her divorce.

When Vanessa Trump first made headlines, she was known as Vanessa Haydon. She grew up the daughter of a socialite in New York City; her mother Bonnie Kay ran Kay Models, an agency. After Trump graduated from high school, she became a model herself, and it wasn't long before she was being written up in the society pages.

In fact, one of Trump's first brushes with fame came in the pages of New York Magazine. In the seminal 1998 article "Leo, Prince of the City" — the piece that broke the news of DiCaprio's infamous "P**** Posse" – writer Nancy Jo Sales reported on rumors that Leonardo DiCaprio, fresh off the success of "Titanic," had been seen cuddling up with a relatively unknown Manhattanite. "Leonardo DiCaprio has fallen hard for a stunning young model -– and pals say this time it's love. The superstar is so smitten with blonde beauty Vanessa Haydon that he's now a one-woman man," she quoted Star magazine as having written at the time. 

DiCaprio's publicist, however, told Sales that they were never romantically linked. What's more, Sales spoke to sources who claimed that Trump ginned up all the publicity herself. "Vanessa played the media really well," one former friend said. Another added, "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****." Noting that she'd dated a member of the Latin Kings gang for years, another classmate added, "She was an ill thug."

Thanks in part to her rumored association with Leonardo DiCaprio, Vanessa Trump became an integral part of the Manhattan party scene at the turn of the 21st century. By the time 2002 rolled around, Trump and her sister Veronika Haydon decided to go from clubgoers to club owners. At only 25 — they were born less than a year apart — the sisters opened a club called Sessa, named after Haydon's daughter's nickname for her aunt. (Vanessa, Sessa, you get the idea).

In an interview with Women's Wear Daily, Trump hyped up the club's decor, which was described as Polynesian. "It all puts you in Bali. I've never been there, but I'd like to go," she said. The sisters told the outlet that they wanted their club to be quieter than some of the places they used to frequent in their younger days. "I didn't know that there were drugs around," Haydon claimed. "I just thought [the club] was a place where people acted weird."

Unfortunately, it seems that the sisters' dreams for Sessa weren't long for this world. The New York Times reported in early 2004 that the club had voluntarily shuttered its doors, citing numerous local complaints and police investigations during its little more than a year in operation. "People were actually stumbling into the street, blood-covered, after being stabbed," one local told the paper. "This was a rough crew." So much for opening a quiet neighborhood spot.

Vanessa Trump was introduced to the man who would become her husband at a fashion show back in 2003. She told The New York Times that Donald Trump — senior, that is — actually initiated their first interaction. "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,'" Vanessa recalled him saying.

During the fashion show's intermission, the host of "The Apprentice" spotted Vanessa again ... and seemed to forget that they'd just all spoken to each other. "Donald comes back up to me again [and says], 'I don't think you've met my son Donald Trump Jr.,'" she remembered. Vanessa told him, "Yeah, we just met, five minutes ago." Then they all went their separate ways.

It wasn't until weeks later that Donald Jr. and Vanessa reconnected after running into each other at a mutual friend's party. It took an hour of conversation before they realized that they'd just met each other recently. Vanessa recalled telling Donald Jr. that she recognized him as "the one with the r******* dad!" The rest, as they say, is history.

In 2004, Donald Trump Jr. proposed to Vanessa Trump. She told him to do it again just to make sure, so two months later, they held an event at the Short Hills Mall in New Jersey. Donald Jr. got down on bended knee in front of assembled paparazzi, and he presented her with a $100,000 engagement ring. However, he reportedly didn't have to spend a dime on it: The whole thing was a sponsorship opportunity, a photo op for a jeweler called Bailey Banks & Biddle. New York media had a field day with the story; Page Six, for example, labeled Don Jr. an "heirhead" and suggested he was a "cheapskate" for popping the question with a free ring.

Regardless, the whopper of a ring featured a 4-carat emerald-cut diamond with 56 other diamonds. Still, it seems that Donald Trump Sr. was less than impressed with the way his son approached the proposal. The future president went on "Larry King Live" to address the engagement, telling the host about the dressing-down he gave his firstborn. "I said, you have a big obligation, you have a name that's hot as a pistol, you have to be very careful with things like this," he recalled, claiming that he doesn't recommend big events when he makes deals, which would come as a surprise to anyone who's followed his presidency. "I don't do a big stunt over it," Donald Sr. insisted.

Still, he wished the couple well. "She's a great girl ... I think they're going to have a terrific marriage," the reality host said. "I mean, off to an interesting start with this publicity, but that's all right."

A year after their headline-grabbing (second) proposal, Vanessa Trump married Donald Trump Jr. in a November 2005 ceremony at Mar-a-Lago, Donald Trump Sr.'s Florida estate. The wedding was officiated by Maryanne Trump Barry, a judge who also happens to be Donald Trump Sr.'s eldest sister.

Understandably, the wedding featured a fair amount of press among the guests. Vanessa's publicist, Christine Schott, later told The New York Times that she helped reporters tell the difference between Bonnie Haydon, Vanessa's mother, and Ivana Trump, Donald Jr.'s mom. "They both were tall with big blond buns," she explained. Schott also noted that when she met Donald Sr., he apparently wasn't very warm or welcoming. "The president said, 'Vanessa has a publicist?' He was annoyed," she said.

Still, Schott said Vanessa had a lovely wedding. "Vanessa was very loving, she was very much in love with Donnie, she was excited to become a Trump," Schott recalled. "She told me at the wedding that she wanted five children. She was very specific about that. Not three, not four, but five." Soon enough, that dream would become a reality.

Even though she used to be a model, there are some Vanessa Trump style moments that seriously missed the mark. In the early 2010s, she took designing into her own hands. Alongside her mother, Bonnie Haydon, her sister Veronika Haydon-Gabriel, and a longtime friend named Shawn Modell, Trump launched a line of handbags called La Poshett. "Developed by four friends who aspired to give women the opulence they desire through creative handbags, La Poshett is an ever-expanding line that provides for its customers a blend of class, elegance and modern allure," the company's website read.

The handbag's launch was an event for Autism Speaks, a charity that raises awareness of autism and provides resources to families. A portion of proceeds went to the organization. Trump told NBC News that she'd designed six blue python bags for the event, meant to reflect the primary color of Autism Speaks. "Instead of just people making money and putting it in to buy a new car or a new apartment, I thought: 'You know what, I actually want to design bags and give a percentage of my profit to a charity,'" she said.

The company shuttered a few years later without really taking off. At its peak, the website's press section boasted only six celebs who had been spotted with La Poshett handbags; the list included Melania Trump, Ivanka Trump, and Ivana Trump.

Vanessa Trump told her publicist at her wedding that she wanted to have five children with Donald Trump Jr. someday, and that is indeed what wound up happening. Their oldest daughter is a golfer named Kai Trump, who may already be more mature than her dad. She spoke at the Republican National Convention in 2024, and she had nothing but glowing things to say about her grandfather, telling the crowd (via People), "He always encourages me to push myself, to be the most successful person I can be. Obviously, he sets the bar pretty high, but who knows, maybe one day I'll catch him."

After Kai, Vanessa and Don Jr. welcomed Donald Trump III. Next came Tristan Trump, followed shortly thereafter by Spencer Trump. Finally, Vanessa and Don Jr. had Chloe Trump. While Don Jr. frequently posts on social media about taking his sons hunting, it seems that Vanessa is quite close with their daughters. Like her older sister, Chloe seems to love golf, and Vanessa is all too happy to tag along when the girls practice their swings. In 2024, she shared a video on Instagram of Chloe and Kai hitting the links, and she captioned it, "My two golf super stars."

In 2015, Vanessa Trump's life changed in a major way when her father-in-law, Donald Trump Sr., announced his candidacy for president. Suddenly she wasn't just a socialite, not just an erstwhile handbag maven; instead, she was a campaign surrogate, put out in front of the media to support a man's policies that she may not have actually agreed with. The New York Times noted that her mother, Bonnie Haydon, had a public Facebook page at the time, and she shared a handful of memes that seemed to support Democratic policies, including but not limited to posts about reproductive rights.

Vanessa's former publicist Christine Schott told The New York Times that her client had worried about her husband's involvement in the campaign, particularly taking issue with his controversial love of big-game hunting. "I know she wanted to keep it on the DL," Schott said. "She knew that was going to be a big issue, socially." Vanessa was correct; animal rights groups frequently take Donald Trump Jr. to task for his love of killing big animals and posing with their carcasses. For his part, Vanessa's husband has defended his hobby. "I have no shame about [the photos]. I HUNT & EAT game," Donald Jr. once wrote on X.

Sometime soon after Donald Trump Sr. took office, Vanessa Trump, who is of Danish descent, reportedly jetted off across the pond to visit some relatives in Denmark. The trip was kept relatively under wraps, but her uncle John Porting spoke with the Danish Broadcasting Corporation in 2017 about what happened when the family member of an American president made a quiet visit to their small island.

According to Porting, Vanessa was accompanied by multiple Secret Service agents. She also brought one of her children along on the trip, though Porting didn't say which one. While he did say that he was happy to spend time with his niece, Porting had no interest in talking to the news outlet about American politics or what his family thinks about her famous father-in-law. 

The meeting, it seems, was not simply a family visit. While in Denmark, Vanessa also had lunch with Prime Minister Lars Løkke Rasmussen, Crown Prince Christian, and Crown Princess Mary.

Being related to a controversial politician by blood or marriage can be dangerous business. In 2018, little more than a year into her father-in-law's first term in office, Vanessa Trump experienced a scary situation when she opened some mail that had been addressed to her husband, Donald Trump Jr. Curiously, the letter had been sent to the home of Vanessa's mother, Bonnie Haydon. When Vanessa opened it at her mother's residence, white powder fell out. According to Fox News, the letter read, "You are an awful, awful person. I am surprised that your father lets you speak on TV. You the family idiot. Eric looks smart." Subsequently, one or both women began coughing and feeling ill, so they were taken to the hospital.

Ultimately, authorities determined that the powder was cornstarch, so Vanessa and her mother were released from the hospital. Don Jr. took to X to report that everyone was okay, writing, "Thankful that Vanessa & my children are safe and unharmed after the incredibly scary situation that occurred this morning. Truly disgusting that certain individuals choose to express their opposing views with such disturbing behavior." A month later, Daniel Frisiello of Beverly, Massachusetts, was arrested, and authorities discovered that he'd also mailed white powder letters to controversial figures like Republican actor Antonio Sabato Jr. and Senator Debbie Stabenow.

In 2018, Vanessa Trump and Donald Trump Jr. divorced. Sources claimed to Page Six that Don Jr. was stingy throughout their marriage, and that Vanessa had to ask her own family for money. "He treats her like a second-class citizen," one alleged. Another added, "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." Vanessa's spokesperson, however, told the tabloid that this wasn't the case. "Don and Vanessa have tremendous respect for each other and always have," they said.

Still, there were signs that Vanessa and Don Jr.'s relationship was doomed from the beginning. One source claimed that Vanessa had been looking into divorce lawyers as far back as 2016, before Donald Trump Sr. was even elected. "No one thought he'd win," a source said. "He won and she decided to stay until his term is over. But she just couldn't stand it anymore." Vanessa's spokesperson denied this too, explaining, "Decisions that she and Don have made on their marriage have nothing to do with politics."

Whatever the cause, Vanessa and Don Jr.'s divorce seems to have gone off without a hitch. After filing for an "uncontested divorce," they announced to People, "We are incredibly lucky to have five amazing children and are committed to raising them together. Our kids and their happiness will always be our first priority."

After divorcing Donald Trump Jr., Vanessa Trump laid low for several years. She kept the Trump name, but aside from a few public appearances like attending Donald Trump Sr.'s second inauguration, Vanessa hasn't made headlines on her own. That all changed in early 2025, when Tiger Woods confirmed his relationship with Vanessa Trump. "Love is in the air and life is better with you by my side! We look forward to our journey through life together," the golfer wrote on Instagram. "At this time we would appreciate privacy for all those close to our hearts."

In July 2025, sources told Page Six that Vanessa's new romance was serious. "She's so happy! She's finally found happiness," one unnamed friend said. "She's found happiness for the first time in her life."

Donald Jr. moved on, too; he'd gotten engaged to, and then broken up with, former Fox News personality Kimberly Guilfoyle. There were painfully obvious signs Don Jr. and Guilfoyle's marriage would've been miserable, so perhaps that's all for the best.