Meet Vanessa Trump: Donald Jr.’s Ex-Wife Is Dating Tiger Woods

Her mother, Bonnie Kay Haydon, ran the modeling agency Kay Models, and her stepfather, Charles Haydon, worked as a lawyer.

Vanessa attended The Dwight School, a private preparatory school in Manhattan, where she was a tennis star, The New York Times reported. She then studied psychology at Marymount College in Manhattan.

Schoolmates and fellow members of the Manhattan scene described her as a “hard-rock in leather and baggy jeans” and “total gangster” in a 1998 New York Magazine story.

While at school, she became involved with Valentin Rivera, a gang member who later served 16 months in prison for assault, as reported by Page Six. They went to her senior prom together, per Page Six.

She was voted Most Likely to Wind Up on Ricki Lake in her high school yearbook.

Haydon started modeling in the 1990s before signing with modeling agency Wilhelmina. She later worked with Next Model Management.

She also had a small role in the 2003 film “Something’s Gotta Give.”

New York Magazine reported the model “was seen nuzzling” DiCaprio at a premiere party for James Toback’s “Two Girls and a Guy” in May 1998.

From 1998 to 2001, she dated the Saudi prince Khalid bin Bandar bin Sultan Al Saud, the son of then-Saudi Arabia’s ambassador to the US, Bandar bin Sultan Al Saud, People reported.

Vanessa was introduced to Donald Trump Jr. by his father in 2003. The real-estate magnate introduced the couple twice in the span of five minutes, Vanessa recalled for The New York Times.

Six weeks later, they were introduced again by a mutual friend at a birthday party.

“We talked for an hour,” she told the Times. Eventually they realized they’d met weeks earlier.

Born 11 months apart, the model sisters grew up on Manhattan’s club scene, and the siblings became club owners themselves with the opening of Sessa, Women’s Wear Daily reported in January 2003.

The Polynesian-themed club aimed to be a place where people could “hang out without having to shout over the music,” WWD wrote.

In January 2004, the club was forced to close, The New York Times reported.

In November 2004, Trump Jr. proposed to the model with a complimentary $100,000 ring from a New Jersey jeweler in exchange for popping the question in front of the jeweler’s mall storefront with paparazzi present.

The couple married a year later on November 12, 2005, at Trump’s Palm Beach resort, Mar-a-Lago.

The couple had five children together: Kai, Donald John III, Tristan, Spencer, and Chloe.

Their eldest daughter, Kai Trump, 17, is an avid golfer and, in 2024, committed to playing for the University of Miami. She spoke at the Republican National Convention in 2024 and appeared at her grandfather’s inauguration in January 2025 alongside other family members.

From 2010 to 2013, the model released a line of handbags called La Poshett, although she eventually settled into the stay-at-home mom lifestyle, homeschooling her children over the COVID-19 pandemic.

After 12 years of marriage, Vanessa filed for a no-contest divorce in 2018.

The couple separated nine months before filing for a divorce, and Trump Jr. began dating Kimberly Guilfoyle, then a Fox News anchor, in 2018.

Donald Jr. and Vanessa have maintained an amicable relationship, spending time together at Mar-a-Lago and various official events.

Tiger Woods made a notable return to the White House on May, marking his first visit since publicly revealing his relationship with Vanessa Trump.

The 15-time major golf champion, now 49, was photographed with Indiana Senator Jim Banks, who shared an image of their meeting on X.

Woods’ visit comes just two months after going Instagram official with Vanessa Trump.

While the reason for the visit in May remains unclear, President Trump did confirm that he met with Woods, according to Golf Monthly.

Both Wood’s and Vanessa’s respective children are competitive junior golfers.