Donald Trump Jr.'s Road to Divorce: Inside the Breakdown of His Marriage to Vanessa Trump

Don Jr. and Vanessa, who did an admirable job staying out of the political fray, have been married for 12 years and have five children together
By Natalie Finn Mar 16, 2018 12:55 AM
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In the end, this simply might not have been what Vanessa Trump signed up for.

After a decade of enjoying a relatively stable position amid the New York glitterati followed by almost three years of Twilight Zone-level attention paid to her husband's family, she has filed for divorce from Donald Trump Jr. 

"After 12 years of marriage, we have decided to go our separate ways," they said in a joint statement Thursday. "We will always have tremendous respect for each other and our families. We have five beautiful children together and they remain our top priority. We ask for your privacy during this time."

As any celebrity couple knows, being in the spotlight comes with a price. All that attention, photographers trying to document every date night and, inevitably, rumors that you're either having babies or breaking up can take their toll. It's hard to deal with and most couples—even the ones who knew what they were getting into—bend at some point. And plenty of them break. Especially if one of them wakes up one morning and doesn't recognize her surroundings.

For years on TV, Don Jr. seemed agreeable enough, even fairly charming, as one of his dad's advisors on The Apprentice and Celebrity Apprentice. It was only after Donald Trump ran for president that his namesake's pricklier side emerged, Don Jr. turning into the guy who'd wade even further into the Twitter fire than his father, much to the mingled amusement and ire of his critics and the delight of his fans.

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But despite Don Jr.'s increasingly aggressive nature as a public advocate for his father, there was always the fact that he was also a longtime family man who took his kids skiing and to get ice cream, and posted cute photos on Instagram.

Speaking of which, while just Wednesday he shared a photo of daughter Chloe sleeping in her striped-and-Spider-Man pajamas, Vanessa Trump's last appearance on her husband's account was Feb. 19, when he posted a shot of the whole family celebrating son Don III's 9th birthday by the ocean in—where else?—Palm Beach, Fla.

On Feb. 2, Vanessa was missing from the Trump siblings-and-spouses picture they took before President Trump's first State of the Union address in Washington, D.C., an indication she had remained at home in New York.

Manuel Balce Ceneta/AP/REX/Shutterstock

Vanessa's most recent public appearance with Don Jr. and their children was at the annual White House Christmas Tree Lighting Ceremony in November.

Manuel Balce Ceneta/AP/REX/Shutterstock

The couple had just celebrated their 12th wedding anniversary on Nov. 12 but sources told Page Six, which was first to report the divorce news, that they have been living separate lives for some time.

"Don and Vanessa are focused on their family, they are trying to do this quietly and privately, and when they have something to say on the record, they will do so," added one source. "This has nothing to do with politics, this is a personal matter between two people."

Judging by some of Vanessa's retweets, she seemed to be on board with the family politically, though her original tweets stick largely to family matters.

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Vanessa knew she had married a workaholic, but in the beginning Don Jr. was toiling behind the scenes, working 14-hour days for his father. Even after his foray into reality TV, Don Jr. was never as well-known as sister Ivanka Trump, let alone Donald Sr., and for years Vanessa was able to enjoy the perks of Trump life at a safe remove from the headlines that tended to swirl around her famous father-in-law.

Her husband's biggest scandal pre-Trump presidency occurred when photographs of him and brother Eric Trump, taken during a 2010 hunting trip in Africa, made the rounds in 2012. In one, Don Jr. posed with a knife and a severed elephant's tail. "I'm not going to run and hide because the PETA crazies don't like me," he tweeted in response to the uproar, which prompted Camping World to drop out as a sponsor of Celebrity Apprentice.

Less heatedly, the Trump brothers told E! News in a statement, "We are both avid outdoorsmen and were brought up hunting and fishing with our Grandfather who taught us that nothing should ever be taken for granted or wasted. We have the utmost respect for nature and have always hunted in accordance with local laws and regulations. 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."

The former Vanessa Haydon grew up on the Upper East Side of New York, the daughter of a lawyer and the head of a modeling agency. She played tennis at an elite prep school and had been modeling since she was a child, like her future sister-in-law Ivanka, before studying psychology at Marymount College. 

She met Don Jr., executive vice president for development and acquisitions for the Trump Organization, at a fashion show in 2003 when the real estate scion's father spotted her and made it a point to facilitate an introduction. A little later that night, Vanessa recalled to the New York Times in 2006, "Donald comes back up to me again, [saying] 'I don't think you've met my son Donald Trump Jr.'" To which she said she replied, "Yeah, we just met, five minutes ago."

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Six weeks later they saw each other again at a birthday party at a restaurant when a mutual friend introduced them.

The third time proved a charm. "We talked for an hour," Vanessa told the Times. She also claimed that, upon realizing she'd met Don Jr. before, she blurted out that he was "the one with the retarded dad!"

But she loved the son. All went accordingly, minus one snafu in 2004 when the elder Trump chided Don Jr. on Larry King Live for accepting a complimentary engagement ring from a New Jersey jeweler in exchange for publicly proposing at the store in the Short Hills Mall. Father reminded son, "You have a name that is hot as a pistol, you have to be very careful with things like that."

Michelle McMinn Photography/Getty Images

They got married on Nov. 12, 2005, at Trump's Mar-a-Lago estate in front of roughly 370 guests—less than 11 months after Donald and third wife Melania Trump also tied the knot there.

The groom's aunt Judge Maryanne Trump Barry officiated the wedding of Trump's eldest child. Vanessa played a role in designing her own dress, which was made by Reem Acra. Among the bold-faced names at the party were Joan Collins, Sophie Dahl and Brittny Gastineau, as well as the groom's immediate family, including mother Ivana Trump.

Michelle McMinn Photography/Getty Images

The newlyweds honeymooned in Fiji and Mexico and, a year later, in November 2006, Vanessa and Don Jr. revealed to friends at an intimate cocktail party at their Upper West Side condo overlooking the Hudson River that they were expecting their first child together.

Daughter Kai Madison Trump—the first of Donald Trump's now nine grandchild—was born May 12, 2007. Vanessa's water broke while the couple was hosting a charity event for Operation Smile and they still stayed another hour to mingle with their guests.

"The baby is really beautiful," Trump told People at the time. "I've never seen such hair on a baby in my entire life. Just an absolutely beautiful baby, and healthy and happy, so I'm thrilled."

Still marveling over the arrival, he said Kai was free to call him "anything but grandpa."

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Meanwhile, Don Jr. had decided to make more of the name he had inherited, having been less inclined to seek the spotlight after being old enough to read the papers during his parents' messy divorce in the 1990s. But ultimately, "I realized that there's an end goal, that I can use some of this," he told the New York Times in 2006, shortly before making his Apprentice debut. "It would be like having an advantage and not taking advantage of it. That's called stupid."

He had previously gone off the beaten path for a time, tending bar in Aspen after graduating from college and, according to the NY Times, spending 11 hours in jail for public drunkenness in 2001. But later that year he went to work for the Trump Organization, to be followed down the road by his younger siblings Ivanka and Eric Trump.

"Don is just a down-to-earth person," a friend, Dee Dee Sides, also told the Times in 2006. "I think the thought just never crossed his mind that he was going to have to be more visible because of the nature of the family company." Eric called Don Jr. his "best friend, a mentor," adding, "In a way, he raised me. My father, I love and I appreciate, but he always worked 24 hours a day."

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For Don Jr. and Vanessa, life became a seemingly happy blur of family, business and black-tie events. As a model, actress and active philanthropist who was ever-poised in front of the camera, Vanessa was the perfect partner to help raise Don Jr.'s profile in a good way. 

They announced in August 2008 that they were expecting their second child, and Donald Trump III was born Feb. 18, 2009. Son Tristan Milos Trump arrived on Oct. 2, 2011; son Spencer Frederick Trump, his middle name a nod to his late great-grandfather and great-uncle, was born Oct. 21, 2012; and daughter Chloe Sophia Trump, who's becoming quite the skier according to Dad's Instagram, rounded out the family on June 16, 2014.

"Its a girl!!!! @MrsVanessaTrump and I are very excited to be bringing home our little bundle of joy today. #FullHouse," Don Jr. tweeted.

A year later, on Chloe's first birthday, Donald Trump announced he was running for president and life would ever be the same again.

REUTERS/Lucy Nicholson

As a mother of five with her entire life in New York, Vanessa Trump understandably didn't play much of a role on the campaign trail. She joined the family for major events, such as Inauguration Day, keeping warm during the daytime ceremony in a burgundy coat and donning a metallic gown for the evening ball.

A few weeks later, on Feb. 10, 2017, she and her husband saw 50 Shades Darker on opening night, which we know because Don Jr. tweeted about being the only guy in the theater.

And then things just got...well...let's just say hectic. Don Jr., while he had already been traveling a lot for work, was now making headlines with trips to Uruguay, and the Dominican Republic, and Dubai, and Vancouver and, most recently, India. He was tweeting up a storm, making appearances on Fox News and otherwise heading up international business for the Trump Organization while simultaneously defending his father and lashing out at perceived opponents on a regular basis.

The stream of adorable family photos never ceased, but Don, while already a polarizing tweeter on a good day, caught extra heat (perhaps at home, too) when he posted a pic of Chloe and joked that he was going to take away half of her Halloween candy in order to teach her about socialism.

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Don Jr. also raised eyebrows in September when he declined further Secret Service protection, citing his wish for privacy. It wasn't clear whether he had opted out on behalf of his whole family or just for himself.

"I'm not a curated kind of guy," the younger Trump told The New York Times in March 2017. "I don't sit there and try to massage every possible word. I'm probably a little more like my father in that sense. You know, I say what I'm thinking. Most logical people will interpret it right. But if you are looking to create a story, you can probably come up with something. I learned about that the hard way, in terms of politics."

As for his father, "I haven't spoken to him. Maybe just to say hello. It feels trite. I feel ridiculous bothering him."

The photo that accompanied the article, of Don Jr. in a plaid shirt, jeans and hiking boots, sitting on a tree stump in the woods and looking broodingly into the distance, became an instant-classic meme.

His family went to Disney World in December, celebrating Vanessa's 40th birthday there on Dec. 18, and posed for a group photo in front of the Christmas tree at Mar-a-Lago, complete with a tiny MAGA hat ornament. Vanessa had previously shared pics of the decorations she and the kids were putting up at home in New York as well.

Don Jr. turned 40 on Dec. 31, sharing that he was enjoying the last night of his 30s with his kids at Mar-a-Lago (none of the Trumps seem to be into public displays of happy birthdays or anniversaries on social media). 

Last month, the family received a literally too-close-to-home scare when Vanessa opened an envelope addressed to her husband at their home in Manhattan and it contained a white powdery substance. She called 911 and after she started coughing and feeling dizzy and nauseous, she was taken to the hospital. The powder turned out to be harmless, but a Massachusetts man has since been charged with mailing threatening communications for allegedly sending multiple envelopes like that to public figures, including Don Jr. 

"Thank you so much for all the help today in NYC! I appreciate all the quick response to make sure that I was safe ! Thank you @FDNY @SecretService @NYPDnews @NYPDCT @NewYorkFBI," Vanessa tweeted on Feb. 12. Added Don Jr.: "A special thanks today to the great men & women of the @NYPDnews @FDNY @SecretService @NewYorkFBI and the Joint Terrorism Task Force for their decisive action and incredible words of support to my wife and family. Their professionalism under pressure made a rough day manageable."

And after the suspect was arrested March 1, Don Jr. tweeted. "My family and I are incredibly relieved to hear this news. No one should ever have to deal with this kind of sickening behavior. Truly amazing work from the @SecretService and other agencies involved. Thank you all for your dedication to law and order." 

Vanessa wrote, "Thank you so much to everyone that helped catch the person who sent the horrifying envelope that I opened up two weeks ago! A special thanks to @SecretService and all the dedicated state & federal agencies in Boston, NYC & around the US!"

And that was all she wrote.