Donald Trump Jr. and wife Vanessa to divorce: A look back at their marriage (updated)

Suzy Byrne
Editor, Yahoo Entertainment

Vanessa Trump has officially filed for divorce from Donald Trump Jr.

After five children, the Donald’s presidency, and even death threats, they certainly had a drama-packed 12 years of marriage.

Donald Trump Jr. and Vanessa Trump, on the set of Celebrity Apprentice in 2014, are divorcing. (Photo: Bobby Bank/GC Images)

Vanessa’s move follows a report in the New York Post’s Page Six on Wednesday indicating the two were “headed to divorce.” Even though they had “not legally separated” yet, friends told the newspaper the two were already in the dreaded state of “living separate lives.” Donald Jr., an aspiring politico himself, has been, along with brother Eric Trump, running the Trump Organization and doing extensive traveling, including trips to feed his hunting passion. “Vanessa is a devoted mother, but she is increasingly lonely and alone in the house with the children,” the newspaper reported. And their problems aren’t new. They “had hoped to stay together during the president’s time in office, but it is getting harder to resolve their issues. He’s never there.”

Furthermore Donald Jr.’s friends told the tabloid that he had “changed recently,” citing some of his tweets, including one attacking a teen survivor of the Marjory Stoneman Douglas High School shooting. Vanessa obviously had a very scary experience recently when she opened a letter, addressed to her husband at their home, that contained a threat as well as a mysterious white substance. She went to the hospital as a precaution.

The last year-plus of their lives has been truly a wild ride for the couple, both 40, but it really has never been dull from their first meeting — where they were introduced by the Donald — until now. Take a look …

2003: Donald Trump and his newly sober son Donald Jr. — who at that point was working off a reputation for drinking, womanizing, and frat boy antics — are at a fashion show. The future president, at the time engaged to Melania Knauss, spots the beautiful Vanessa Haydon — a native New Yorker, who modeled since childhood and was signed to Wilhelmina Models, and introduces himself and his son to her, Vanessa later recalled the meeting in a New York Times story, describing it as an awkward encounter. But it didn’t end there. At intermission for the same show, the Donald again approached Vanessa. “‘I don’t think you’ve met my son Donald Trump Jr.,'” Vanessa, who had been linked to Leonardo DiCaprio, remembered him saying. She replied, “Yeah, we just met, five minutes ago.”

Six weeks later, Donald Jr., who by then works for his dad at the Trump Organization (they mended their earlier rift in which Donald Jr. didn’t speak to the Donald for a year after his divorce from Ivana Trump), and Vanessa are introduced a third time, at a birthday party for a mutual friend. “We talked for an hour,” she told the New York Times, saying they initially didn’t recognize each other. Then something clicked: Wait, you’re “the one with the retarded dad!” Vanessa said. And love was born.

2004: Donald Jr. is called an “heirhead” and “the cheapest gazillionaire” after he accepts a free $100,000 engagement ring that he used to propose to Vanessa. But what is labeled “one the cheesiest wedding proposals on record” only got better. He invites reporters to the Short Hills Mall in New Jersey, where he proposes with his free ring in front of the press in the Bailey Banks & Biddle jewelry store.

Vanessa Haydon and Donald Trump Jr. during the “Bailey Banks and Biddle Fine Jewelers Provides Diamond Engagement Ring for Donald Trump Jr.’s Fiancée Vanessa Haydon” event at Short Hills Mall in Short Hills, N.J., in 2004. (Photo: Mychal Watts/WireImage)

Donald Jr.’s dad later makes fun of his son for the incident on Larry King Live. I guess he’s trying to learn from me … but I didn’t like it,”  the elder Trump says. “I said, ‘You have a name that is hot as a pistol, you have to be very careful with things like this.’”

November 2005: Despite the embarrassing engagement, Donald Jr. and Vanessa tie the knot at — you guessed it — Mar-a-Lago, the family’s club in Florida. His father had just married Melania there months earlier. There were 370 guests, including Dynasty’s Joan Collins, model Sophie Dahl, and reality-TV star Brittny Gastineau. It is also a big deal because it was a reunion between the Donald and Ivana, who had a crazy bitter divorce. Vanessa tells Extra that she told her groom that he wasn’t permitted to carry his Blackberry with during the wedding. They honeymoon in Fiji and Mexico.

Donald Trump Jr. and Vanessa Trump cut a slice of wedding cake at their wedding reception at Mar-a-Lago in November 2005. (Photo: Michelle McMinn Photography/Getty Images)

November 2006: Two days after their first wedding anniversary, the pair invite a small group of friends and relatives to their two-bedroom condominium on the Upper West Side and announce they were expecting their first child. Donald Jr. starts stepping out into the spotlight,  including appearances on his dad’s baby, The Apprentice“When I started working, I realized that there’s an end goal, that I can use some of this,” he says of fame tied to to the Trump name. “It would be like having an advantage and not taking advantage of it. That’s called stupid.” Meanwhile, Vanessa also pursues the limelight, nabbing the cover of Hamptons Magazine and playing “Beauty” in the 2003 film Something’s Gotta Give. That is her only acting credit.

Vanessa Trump and Donald Trump Jr. attend the launch party for the holiday issue of Hamptons Magazine on Nov. 15, 2006. She was on the magazine’s cover. (Photo: Bryan Bedder/Getty Images)

May 2007: The first Trumpette is born:  Kai Madison Trump.

February 2009: Their son Donald Trump III makes his debut.

October 2011: Son Tristan Milos Trump joins the party.

Soon after the birth of their first child, Vanessa Trump and Donald Trump Jr. enjoy a night out at  Roberto Cavalli’s Halloween Party at Cipriani 42nd Street in New York City on Oct. 31, 2007. (Photo: Michael Loccisano/FilmMagic)

October 2012: Their son Spencer Frederick Trump is born.

Also that year, Donald Jr. — an outdoorsman since his Colorado days — finds himself at the center of a scandal after photos surface, from 2010, of him with his arms around an endangered dead leopard and posing with bloody elephant tail. At least one sponsor stops advertising on Celebrity Apprentice over the incident. Junior doesn’t back down from his love of hunting.

June 2014: Their daughter Chloe Sophia Trump arrives.


2016: As the Donald campaigns for president, Donald Jr. becomes  “a close political adviser to his father,” as described by the New York Times. He campaigns, gives speeches, and maybe makes shady dealings.

2017: After his father wins, he focuses on the family business with Eric while the Donald and Ivanka head to Washington.  However, he’s accused of shady dealings related the the campaign and is grilled by the S enate Judiciary Committee.


After that, Donald Jr. seems to take a step back — though not on social media. He continues to make controversial posts and hints that he may run for election himself. One related to his family, and referenced in the Page Six story about the possible divorce, was the photo of the couple’s daughter Chloe’s Halloween candy, which he captioned, “It’s never to [sic] early to teach her about socialism.”


He also briefly ends the Secret Service detail for their family, only to have it restored a few weeks later. According to Page Six, Vanessa, who is described as “low-key,” is “uncomfortable with the intense focus on the Trump family,” causing trouble at home.

2018: Donald Jr.  is reportedly never at home, according to Page Six. He “ has been traveling a lot. In February he was in India, and he has continued to take his hunting trips.” Vanessa “ is increasingly lonely and alone in the house with the children.”


Also during that month, she experiences a traumatic incident when she opens a letter addressed to Donald Jr., which was mailed to their Manhattan home, and it contains an explicit threat along with the white powder. Although it is later determined not to be hazardous, “it was terrifying for Vanessa,” who is  hospitalized as a precaution. She is “naturally worried for the safety of her children,” reports Page Six. Donald Jr. speaks out about the incident via Twitter, calling it an “ incredibly scary situation” and saying he is  “Thankful that Vanessa & my children are safe and unharmed.”

On March 14, Page Six runs with its bombshell story about the couple talking divorce. The pair did not address the chatter with the paper reporting, “ A spokesperson for Donald Jr., Vanessa and the Trump Organization has declined to comment, despite numerous requests to do so over two days.” 

Vanessa filed court papers for an uncontested divorce the following day, according to the Associated Press.

[Editor’s note: This post was originally published March 15, 2018 at 1:15 p.m. ET.]

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