On Sunday, March 23, the world of celebrity gossip was set abuzz when golf legend Tiger Woods confirmed his relationship with Vanessa Trump, the ex-wife of Donald Trump Jr., via a heartfelt social media post. The announcement, accompanied by cozy photos of the pair, marked the public debut of a romance that had been quietly blossoming for months. But who is Vanessa, the woman who has captured the attention of one of the most famous athletes in the world? From her early days as a model to her high-profile marriage and divorce from a member of America’s most polarizing political family, Vanessa’s life story is one of intrigue, resilience and reinvention.
Early life and background
Born Vanessa Kay Pergolizzi on December 18, 1977, in New York City, Vanessa grew up in a well-connected family on Manhattan’s Upper East Side. Her father, Charles Haydon, was a prominent lawyer whose clients included icons like Marilyn Monroe, while her mother, Bonnie Haydon, ran Kay Models, a modeling agency that gave Vanessa an early entrée into the world of fashion and glamour. Raised alongside her sister Veronika, Vanessa attended the prestigious Dwight School, where she reportedly earned yearbook superlatives for her bold personality, including one suggesting she was most likely to appear on a talk show like Ricki Lake. Vanessa’s teenage years were marked by a rebellious streak. She briefly dated Valentin Rivera, a purported member of the Latin Kings street gang, hinting at an early penchant for unconventional relationships.
Modeling career and early romances
In her late teens and early 20s, Vanessa carved out a career as a model, working in New York’s competitive fashion scene. Her striking blonde looks and poised demeanor made her a natural fit for the runway and print ads. During this period, she was briefly linked to actor Leonardo DiCaprio in 1998, a rumored romance that placed her in the orbit of Hollywood’s elite. Following that, she reportedly dated a Saudi prince from 1998 to 2001, a relationship that ended amid controversy when the prince’s father left the U.S. after revelations of indirect ties to the 9/11 hijackers.
Beyond modeling, Vanessa showed an entrepreneurial spirit. In 2003, she and her sister Veronika opened Sessa, a Polynesian-themed nightclub in Manhattan aimed at offering a laid-back alternative to the city’s louder venues. Though the club shuttered within a year, it underscored her willingness to take risks and step into the public eye on her own terms.
Marriage to Donald Trump Jr.
Vanessa’s life took a dramatic turn in 2003 when she met Donald Trump Jr., the eldest son of real estate mogul and future U.S. President Donald Trump. The introduction came courtesy of Donald Trump himself, who reportedly played matchmaker at a fashion event—twice in one night, forgetting he’d already done so. A few weeks later, the pair reconnected at a birthday party through a mutual friend, sparking a conversation that lasted an hour and laid the foundation for their relationship.
The couple became engaged in 2004, with Donald Jr. proposing with a ring purchased from a New Jersey mall jeweler in exchange for publicity—an early sign of the Trump family’s flair for blending business with personal milestones. They married on November 12, 2005, at Donald Trump’s Mar-a-Lago estate in Palm Beach, Florida, in a lavish ceremony that cemented Vanessa’s entry into one of America’s most scrutinized families.
Over the next 12 years, Vanessa and Donald Jr. welcomed five children, namely Kai Madison (born 2007), Donald John III (born 2009), Tristan Milos (born 2011), Spencer Frederick (born 2012), and Chloe Sophia (born 2014). During their marriage, Vanessa largely stepped away from the spotlight, focusing on raising their children and supporting her husband as he took on a prominent role in the Trump Organization. She also launched a handbag line, La Poshett, from 2010 to 2013, though it eventually faded as she prioritized family life.
Divorce and life after Trump
By 2018, cracks in the marriage had become evident. Rumors of Donald Jr.’s infidelity—echoing the scandals that plagued Tiger Woods’ own past—swirled in the tabloids, alongside reports of financial strain. Vanessa filed for an uncontested divorce in March 2018, signaling an amicable split. The couple finalized their separation later that year, agreeing to co-parent their children while maintaining a cordial relationship. Since then, they’ve been spotted together at family events, including the 2024 Republican National Convention and Donald Trump’s January 2025 inauguration, reflecting their commitment to unity for their kids.
Post-divorce, Vanessa relocated to South Florida, settling in Jupiter, just 20 minutes from Tiger Woods’ estate on Jupiter Island. She embraced a quieter life, homeschooling her children during the COVID-19 pandemic and supporting their extracurricular pursuits—most notably her eldest daughter Kai’s burgeoning golf career. Kai, now 17, has emerged as a top junior golfer, committing to play for the University of Miami in 2026 and amassing a significant social media following.
Romance with Tiger Woods
Vanessa’s connection to Tiger Woods appears to have grown organically through their shared ties to golf and their children’s overlapping worlds. Both Kai and Woods’ children—Sam Alexis, 17, and Charlie Axel, 16, from his marriage to Elin Nordegren—attend The Benjamin School in Palm Beach, a private institution known for its rigorous academics and parental involvement. Their paths likely crossed at school events and golf tournaments, fostering a friendship that, according to sources, “blossomed into something more.”
Reports suggest the romance began around Thanksgiving 2024, with Vanessa becoming a frequent visitor to Woods’ $80 million Jupiter Island home “‘a few nights a week.’” The couple kept their relationship under wraps until March 13, 2025, when PEOPLE confirmed they’d been dating for several months, a story first broken by the Daily Mail. On March 23, Woods made it official with an Instagram post featuring two photos—one of them standing side by side, another lounging in a hammock—captioned, “Love is in the air and life is better with you by my side! We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts.”
Their bond seems rooted in shared values: a passion for golf, devotion to their children, and a preference for discretion despite their high-profile pasts. Vanessa accompanied Kai to Woods’ Genesis Invitational in February 2025, where they were photographed together, and she’s been spotted at TGL matches, the tech-infused golf league Woods co-founded with Rory McIlroy. Meanwhile, Woods has maintained a friendly rapport with Vanessa’s former father-in-law, playing golf with President Trump and receiving the Presidential Medal of Freedom from him in 2019.
Public perception and what’s next
Vanessa’s relationship with Woods has elicited mixed reactions. Some see it as a natural pairing—two Florida-based parents with golf-prodigy kids and a taste for low-key luxury. Others find it an unexpected twist, given Woods’ history of romantic tumult (his 2010 divorce from Nordegren amid a cheating scandal) and Vanessa’s ties to the polarizing Trump dynasty. Donald Jr., now dating Palm Beach socialite Bettina Anderson after splitting from Kimberly Guilfoyle, has reportedly taken it in stride, with a source telling PEOPLE he’s “cool” with the match.
At 47, Vanessa remains an enigma: a former model who traded runway lights for family life, only to re-emerge as the partner of a sports icon. She’s described as “discreet and smart,” a mother-first figure who’s comfortable with fame but not eager for its glare. As she and Woods, 49, navigate this new chapter—amid his recovery from a ruptured Achilles tendon and her focus on Kai’s college golf journey—they seem intent on keeping things “very casual,” as one insider put it, while leaving room for what the future might hold.