When it comes to the Trump dynasty, there are plenty of bizarre and confusing stories one can put together. Take Donald Trump Jr., his eldest son, a feisty businessman whose previous union with Vanessa Trump was fraught with controversy. In addition, the Trump men have a long history of alleged womanizing, often accused of misogynistic behavior, extramarital affairs, and putting up a front while problems stayed behind closed doors.
Attacks on Trump Jr.’s private life are nothing new, and his marriage to Vanessa, which lasted almost 13 years, was no exception. But by following in his father’s footsteps, he was able to evade criticism for his extravagant spending, wanderlust, and divisive tweets as he and his ex-wife went on to have five children together.
As she concentrated on raising their numerous children, Vanessa appeared to play the part of the obedient housewife, supporting her ex-husband through every scandalous news cycle. But once their relationship soured, Vanessa supposedly moved on to the next best thing, her Secret Service detail (more on that later), and eventually filed for divorce.
Let’s take a journey down memory lane because the Trump family tree’s many marriages, divorces, and subsequent marriages have fascinated the public for years. Take a look at all the oddities in Donald Trump Jr. and Vanessa Trump’s marriage that were overlooked until the separation.
The first meeting between Donald Trump Jr. and his ex-wife, Vanessa Trump, wasn’t the smoothest. She was a model, and he was a businessman entitled to a huge fortune. However, if it weren’t for Donald Trump’s awkward facilitation, the couple might not have run out into the Mar-a-Lago sunset together.
Vanessa described how her future father-in-law helped her meet her future spouse in an interview with The New York Times. According to her, it wasn’t quite love at first sight during the first meeting. “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.
Donald Trump Jr. had 5 children with his wife Vanessa (left) then cheated on her with the woman on the right.
They settled an uncontested divorce in 2017 and now Vanessa is dating Tiger Woods.
Don Jr. is still with Kimberly Guilfoyle.Worst fumble of all time?? pic.twitter.com/P5a5xPmyb5
— The Hashslinging Slasher (@HashslingingThe) March 24, 2025
Before the program began, the two had a brief, awkward interaction, after which Trump attempted to reintroduce them 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.”
You wouldn’t expect an expectant mother to be taken to the Playboy Mansion. Nothing in the Trump family, however, is ever quite as it seems. In a resurfaced 2007 interview with Donald Trump Jr. on “The Adam Carolla Show,” the billionaire expressed his irritation at having his then-pregnant wife join him for his revelry at the former playground owned by Hugh Hefner.
“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.”
Why Did Vanessa Trump Divorce Donald Trump Jr.? Their Split
Read more click here: https://t.co/hspElMgmKh pic.twitter.com/UWNWkpePdo— I am watching u 🙂 (@netiblogpro) March 24, 2025
Donald Trump Jr.’s wandering eye has been the talk of the town, and he has even been known to publicly flirt with models on X, the former Twitter. In 2011, a month after Vanessa Trump gave birth to their third child, Tristan, model Melissa Stetten said the mogul sent her private messages and dubious Twitter threads.
In March of 2018, shortly before some startling claims of extramarital activities throughout their relationship came to light, Vanessa Trump filed for divorce from Donald Trump Jr. Shortly after, it reports surfaced that Aubrey O’Day, who met the “Apprentice” star on the set in 2011, had a year-long romance with him.
In 2012, images of Donald Trump Jr. posing with a severed elephant tail went viral online, enraging animal advocates. PETA expressed outrage after seeing pictures of the businessman and his brother, Eric Trump, on an African safari. The organization criticized the pair for engaging in large game shooting.
