Vanessa Trump: Model, Socialite, and Now Tiger Woods’ New Flame?

Vanessa Trump has lived a life straight out of a tabloid headline—from modeling runways to high-profile romances and a whirlwind marriage into the Trump dynasty.

Born Vanessa Kay Pergolizzi on December 18, 1977, she grew up on Manhattan’s Upper East Side, surrounded by wealth, privilege, and a touch of drama. With a mother who ran a modeling agency and a stepfather who was a high-powered lawyer, Vanessa’s life was destined for the spotlight.

In the ‘90s, she made a name for herself as a Wilhelmina model, even snagging a small role in Something’s Gotta Give. But it wasn’t just Hollywood she dabbled in—Vanessa co-owned a nightclub, ran a luxury handbag line, and even popped up on The Apprentice while married to Donald Trump Jr., whom she wed in a lavish Mar-a-Lago ceremony in 2005.

vanessa trump

Their marriage, which produced five children, ended in a headline-grabbing divorce in 2018—but not before some eyebrow-raising details surfaced, like Don Jr.’s staged proposal with a free $100,000 ring.

Vanessa’s love life has always been intriguing. She once dated a local street gangster, had a rumored fling with Leonardo DiCaprio, and was in a serious relationship with Saudi prince Khalid bin Bandar bin Sultan Al Saud before his dramatic exit from the U.S.

khalid bin bandar bin sultan al saud

Now, in 2025, she’s back in the gossip columns, reportedly dating golf legend Tiger Woods. While neither has confirmed the romance, their public sightings and shared Florida lifestyle have only fueled speculation.

Tiger Woods

From the glitzy NYC social scene to the golf greens of Florida, Vanessa Trump continues to keep people talking. Whether her rumored relationship with Woods is just a casual fling or something more serious, one thing is certain—she knows how to stay in the spotlight.