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Dave Portnoy calls out Tiger Woods’ Vanessa Trump relationship request

Dave Portnoy isn’t a fan of how Tiger Woods hard-launched his relationship with Vanessa Trump.

The Barstool Sports founder trolled Woods for asking for privacy when he announced their relationship Sunday on his social media, as Vanessa is the former daughter-in-law of President Donald Trump.

“Tiger asking for privacy for dating Don Jr ex wife is an all time ridiculous request,” Portnoy wrote in response to Woods’ X post that included photos of the couple.

Vanessa was married to Donald Trump Jr. from 2005-18, and they have five children together.

Trump Jr. is dating socialite Bettina Anderson after they were first seen holding hands together last August.

He was engaged to former Fox News anchor Kimberly Guilfoyle and their split became public last November.

Dave Portnoy at Game 4 of the 2024 NBA Finals between the Dallas Mavericks and the Boston Celtics at American Airlines Center on June 14, 2024 in Dallas, Texas. Getty Images
Donald Trump Jr. and Bettina Anderson attend amfAR Palm Beach Gala on March 15, 2025 in Palm Beach, Florida. Getty Images for amfAR

“Love is in the air and life is better with you by my side!” Woods wrote. “We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts.”

Vanessa re-shared it to her Instagram Story.

“So happy for you both ! 🥰🥰,” her former sister-in-law, Ivanka Trump, wrote in the comments of Woods’ post.

Tiger Woods hard-launched his and Vanessa Trump’s relationship on social media on March 23, 2025. Instagram/Tiger Woods
Tiger Woods hard-launched his and Vanessa Trump’s relationship on social media on March 23, 2025. Instagram/Tiger Woods

The 15-time major champion is friends with President Trump and they enjoyed a round of golf at Trump International Golf Club in Palm Beach earlier this month.

Woods and Vanessa had been the subjects of romance buzz for some time before he confirmed Sunday they are dating.

The golf legend was seen with Vanessa and her 17-year-old daughter, Kai Trump — who committed to the University of Miami golf team last summer — at various events this past month, including the Genesis Invitational at Torrey Pines Golf Course in La Jolla, Calif. on Feb. 16.

Gold legend Tiger Woods speaks alongside U.S. President Donald Trump during a reception honoring Black History Month in the East Room of the White House on February 20, 2025 in Washington, DC.
AFP via Getty Images

The mother-daughter duo supported Woods at a TGL event in Florida, as seen in a video posted to Kai’s Instagram.

Woods’ children, daughter Sam, 17, and son Charlie, 16, are enrolled at The Benjamin School in Palm Beach, along with Kai. Tuition at the private institution for grades 9-12 runs at 38,595.

The Post confirmed Woods and Vanessa are quietly dating and taking things slow after their friendship blossomed into “something more.”

Kai Trump (L), Tiger Woods and Vanessa Trump (R) arrive to the course during the final round of The Genesis Invitational 2025 at Torrey Pines Golf Course on February 16, 2025 in La Jolla, California.
Getty Images

Woods and his ex-wife, Swedish model Elin Nordegren, were married for six years before their divorce in 2010.

It followed Woods’ infidelity scandal that played out in the public eye and nearly destroyed his career.

Earlier this month, Woods announced he underwent surgery after rupturing his left Achilles tendon while training at home.

Woods said he was back at home in Jupiter, Fla., and plans to “focus on my recovery and rehab.”

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