The media spotlight is glaring bright on Vanessa Trump, the ex-wife of Donald Trump Jr. who has recently gone public about her relationship with the golf superstar Tiger Woods.
There was a time in the 1990s and early 2000s when the former New Yorker and mother of five could be found on the step and repeats at fashion shows. Born Vanessa Pergolizzi, she attended the Dwight School in Manhattan. Her late stepfather Charles Haydon was a lawyer, and her mother Bonnie ran a modeling agency Kay Models.
Before she met and married Donald Trump’s older son, Trump dabbled in modeling, and walked the runway at Charlie Brown’s show at Australia Fashion Week in 1998 — wearing an ultra-sheer white top. In her single days, Trump and her sister Veronika opened a downtown Bali-inspired club called “Sessa,” a name that was coined from her young niece’s mispronouncing her name. The former Wilhelmina model had a short-lived handbag brand called La Poshett.
Vanessa Trump at the Douglas Hannant spring 2006 fashion show during Olympus Fashion Week at Bryant Park on Sept. 15, 2005, in New York City.
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The 47-year-old married Donald Trump Jr. in 2005 and the couple divorced in 2018. They reportedly were first introduced at a fashion show. Their engagement in front of Bailey Banks & Biddle jewelry store in Short Hills, N.J., turned out to be a paid $100,000 photo-op. HIs current girlfriend Bettina Anderson also understands the power of style as an influencer, who also dabbled in modeling.
Donald Trump Jr. (center) and his children, along with former wife Vanessa Trump (far right), depart following the inauguration of U.S. President Donald Trump at the U.S. Capitol on Jan. 20 in Washington, D.C.
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Having met Vanessa’s mother Bonnie Haydon years ago through New York parties, fashion designer Dennis Basso described Vanessa Trump’s style as “sophisticated, tailored and has an elegant look.” He dressed her for the festivities during President Donald Trump’s first inauguration in 2017. Basso said, “She was always very low-key even when she was married to Don Jr., and now she’s even more low-key. She’s not looking to be in the headlines — at all.”
Kai Trump, Tiger Woods and Vanessa Trump arrive to the course during the final round of The Genesis Invitational 2025 at Torrey Pines Golf Course on Feb. 16 in La Jolla, Calif.
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The designer added, “She’s an excellent mother and she’s done an incredible job with her children. She’s also a very devoted daughter. Vanessa is a very nice woman.”
Daughter of Donald Trump Jr., Kai Trump speaks on stage on the third day of the Republican National Convention on July 17, 2024, in Milwaukee, Wis.
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Trump has been photographed on and off the links with her eldest daughter Kai, who has committed to playing golf for the University of Miami next year. As an incoming college freshman, the 17-year-old is also going to be getting into the NIL game. Last month she signed an NIL deal with TaylorMade, which includes Woods, Nelly Korda and Rory McIlroy among its endorsed pros. In December, she inked another one with Leaf Trading Cards.
Donald Trump Jr, with his now ex-wife Vanessa and children departs St. John’s Church on Inauguration Day on Jan. 20, 2017, in Washington, DC.
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As for whether the recent media blizzard about her mother’s relationship with the five-time winner of the Masters tournament, could increase interest in Kai Trump’s NIL deals, that remains a question mark. Hunter Kirsch, cofounder and chief executive officer of the Lionheart Sports Agency, who works with Kai Trump, declined to comment Monday.
“NIL” refers to “name, image and likeness” and it is a person’s right to control how their image is used including for commercial purposes. Sponsorship deals have become big money for leading college athletes and less recognizable ones too, after the National Collegiate Athletic Association and state laws returned NIL rights to college athletes in 2021.
With 1.6 million Instagram followers, 3 million more on TikTok, 918,600 followers on X and 1.1 million YouTube subscribers, the high schooler already has significant social media reach and can drive a golf ball by nearly 300 yards. As of last month, the club-swinging teenager has a NIL valuation of $1.2 million, according to On3 Sports Valuation, an index for the standard market NIL value for high school and college athletes.
When announcing her commitment to the University of Miami last year — and thanking her parents, Kai Trump did so wearing a “Miami” baseball cap, a white tank, Daisy Duke cut-offs and a black Louis Vuitton belt.
Michael LeRoy, Labor and Employment Relations alumni professor at the University of Illinois at Urbana-Champaign, said that Kai Trump’s “dual connection” to Woods and Donald Trump “is likely to boost her NIL marketability at Miami, where golf and the president are popular.”
He singled out the University of Texas’ star quarterback Arch Manning as a relevant comparison. With an estimated $6 million NIL valuation, “it’s hard to separate how much of his value is tied to his talent and how much is tied to his family name, with Peyton and Eli Manning [being his uncles.]” LeRoy said.
In addition, women college athletes tend to be more valuable social media influencers, according to LeRoy, who gave the examples of Miami basketball players Haley and Hanna Cavinder, who have large social media followings and lucrative NIL endorsement deals.
