Every family has that one person who somehow pulls everyone else into their orbit of chaos. In the Trump family, that person is Donald Trump himself. So, imagine willingly marrying into that. Vanessa Trump spent twelve years doing the foxtrot on a sinking ship — and somehow emerged without drowning.
Vanessa is Donald Trump’s former daughter-in-law. She married his eldest son, Donald Trump Jr., in 2005 and divorced him in 2018. That’s the straightforward part. What’s more complex is what that connection actually meant in practice. It meant holiday dinners where the conversation inevitably circled back to how great someone named Trump was doing. It meant watching your father-in-law transition from real estate developer to reality TV star to a convicted felon.
Before she became Vanessa Trump, she was Vanessa Haydon, a New York City socialite. Born in 1977, Vanessa grew up on Manhattan’s Upper East Side and attended the Dwight School. She had a brief modeling career in the early 2000s and even dabbled in acting. She actually comes from a fairly interesting background herself. Her mother, Bonnie Haydon, ran a modeling agency, and her late father, Charles Haydon, was a prominent attorney whose clients reportedly included Marilyn Monroe. So, she wasn’t exactly a stranger to the spotlight before she met the Trump clan.
Vanessa met Donald Jr. at a fashion show in 2003
The junior Trump introduced himself not once, but twice, apparently forgetting they’d already met. That should have been a red flag. Maybe even five. But somehow, Vanessa and Don Jr. hit it off, and within a year, they were engaged.
As the wife of the eldest Trump son, Vanessa held a particular position in this hierarchy. Don Jr. was being groomed as a potential heir to the Trump business empire, and by extension, Vanessa was expected to fit into this dynastic vision. Their five children — Kai, Donald III, Tristan, Spencer, and Chloe — represent a significant portion of the next generation of Trumps. However, unlike some political wives who actively campaign for their husband’s family, Vanessa largely stayed out of the 2016 presidential race. While Ivanka and her husband Jared Kushner became White House advisors and Melania reluctantly embraced her First Lady duties, Vanessa maintained a lower profile.
As Donald Sr.’s presidency polarized the nation, everyone associated with the Trump name found themselves caught in the crossfire. This became frighteningly literal for Vanessa in February 2018, when she opened a letter addressed to Donald Trump Jr. containing an unidentified white powder. Though the substance turned out to be harmless, the incident highlighted the very real security concerns that come with being related to Donald Trump. Vanessa reported feeling unwell, experiencing coughing and nausea, and subsequently called 911 for assistance. She and two others were hospitalized as a precaution, and the perpetrator, Daniel Frisiello, was eventually caught and sentenced to probation.
Here’s the interesting part: While Vanessa was pregnant with their third child, gossip started swirling that Don Jr. was having an affair with pop singer Aubrey O’Day. Yes, the same Aubrey O’Day who once starred on The Apprentice and later released a song that many believe is about their alleged relationship. Subtle. By 2018, Vanessa had apparently had enough and filed for divorce, citing irreconcilable differences. While Don Jr. continued to court controversy (and Kimberly Guilfoyle), Vanessa has largely stayed under the radar — though reports suggest she’s now dating golfer Tiger Woods.
Published: Mar 16, 2025 08:38 am