Donald Trump Jr. and his wife have filed for divorce — here’s an inside look at the relationship between the first son and the ex-model who used to date Leonardo DiCaprio

Donald Trump Jr. and his wife, Vanessa Trump

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Donald Trump Jr. and his wife, Vanessa Trump
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Brian Snyder/Reuters

  • Donald Trump Jr. and his wife, Vanessa Trump, filed for divorce on Thursday.
  • The businessman (and first son) and the former model have been married since 2005.
  • Since President Trump’s election, Donald Jr. has faced several high-profile scandals, while Vanessa has kept a lower profile.

Donald Trump Jr. and his wife, Vanessa Trump, have filed for divorce.

Vanessa Trump filed for uncontested divorce on Thursday, Page Six reported. That means the president’s daughter-in-law is not expecting a legal struggle over the couple’s assets or the custody of their five children.

The news comes after a scare in which Vanessa opened an envelope addressed to Donald Jr. that contained a mysterious white powder, which was later determined not to be hazardous. The duo has been married since 2005 and have five children together.

Here’s a look back at the couple’s relationship over the years.


Vanessa and Donald Jr. met in 2003, when President Trump introduced the pair at a fashion show — twice.

Vanessa told The New York Times in 2006 that Donald Trump had introduced her to his son at a fashion show twice within five minutes. The pair did not hit it off during the awkward interactions.

Six weeks later, they met again at a mutual friend’s party. They didn’t recognize each other until after an hour-long conversation.

“Then suddenly, something clicked: Wait, you were at that fashion show. Wait, you’re ‘the one with the retarded dad!’ Vanessa blurted out,” The Times reported.


Vanessa, formerly Vanessa Haydon, was working as a model at the time. Donald Jr. wasn’t her first famous beau — she made headlines after being spotted with Leonardo DiCaprio at a movie premier in 1997.

“In her yearbook, Haydon was voted Most Likely to Wind Up on Ricki Lake,” New York Magazine reported in 1998.

“Instead, she made it into ‘Page Six,’ which reported in May that her handlers were charging Sydney newspapers $15,000 for advance publicity stills while Haydon was Down Under shooting the cover of Australian Harper’s Bazaar,” New York Magazine continued. “‘Vanessa Haydon got game,’ says another former schoolmate.”

Source: The New York Times, New York Magazine


Don Jr., meanwhile, had at that point been working at the Trump Organization for a few years.

Donald Jr. graduated from the Wharton School of the University of Pennsylvania in 2000. He spent a few years as a ski bum in Aspen, Colorado before returning to New York City.


The pair married in 2005 at the Mar-a-Lago Resort.

“Donald Trump Sr. had taken his son to task on “Larry King Live” for accepting a free engagement ring from a jeweler at a mall in New Jersey in exchange for publicly announcing his engagement there,” The New York Times reported. “‘You have a name that is hot as a pistol, you have to be very careful with things like this,’ the elder Trump told King.”


The couple welcomed their first daughter, Kai Madison, in May 2007.

Source: People


The couple now has five children. The youngest, Chloe, was born in 2014.


For the first decade of their relationship, the couple’s comings-and-goings were covered primarily by gossip columns and tabloids.


Vanessa was a common presence on the charity circuit. While Don Jr. spent his early 20s hiding from the spotlight, the pair began to make headlines together more frequently after they married.

Source: The New York Times


However, as Donald Trump began campaigning in the 2016 presidential election, Don Jr. got involved as well.


Don Jr. aggressively advocated for his father and attacked critics on social media.

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A meme Donald Trump Jr. tweeted.
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Donald Trump Jr.

In September 2016, Donald Jr. posted an image comparing supposed terrorists hidden among refugees to poisoned Skittles in a candy bowl. The meme was critiqued by many as both offensive and factually inaccurate.


He was also willing to bring his children in on the pro-Trump campaign to support their grandfather.

Over Halloween 2017, Donald Jr. drew criticism after using a photo of his daughter, Chloe, to mock socialism.


Donald Jr. aggressively posts on social media, flooding his Twitter and Instagram with pro-Trump memes and pictures of his children alike.

A little #throwbackthursday pic of my favorite adorable deplorable. #throwback #tbt

A post shared by Donald Trump Jr. (@donaldjtrumpjr) on


Vanessa, meanwhile, has stayed out of the spotlight for the last few years — both on social media and in the realm of politics.


While Vanessa has a Twitter account, she rarely tweets, in comparison to Donald Jr.’s frequent posts.


Both Don Jr.’s brother Eric and his wife, Lara, have remained politically engaged since the campaign. In comparison, Vanessa has kept a lower profile.


The couple has made headlines over the last few months — for the wrong reasons.


Trump has been under investigation for his role in potential Russian meddling in the election, after The New York Times reported in July 2017 that he met with a Russian lawyer who had told him she had damaging information about Hillary Clinton.

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Twitter/Donald Trump Jr.; Harrison Jacobs/Business Insider

Trump has denied any collusion.

Source: Business Insider


In February, Vanessa was hospitalized as a precaution after she opened a letter addressed to Donald Jr. that contained a white powder.

Source: Business Insider


Later in February, Donald Jr. said that his father’s presidency was hurting his business in India, due to self-imposed restrictions.


Sources told The New York Post that Donald Jr.’s obsession with politics and frequent travels were contributing to issues in the relationship.

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Donald Trump Jr. campaigning in Pennsylvania earlier this week
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Andrew Rush/Pittsburgh Post-Gazette/Twitter

One source said: “Vanessa is by nature is 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 containing the white powder.”