Tiger Woods’ unexpected romance with Don Jr.’s ex-wife has already sparked a media firestorm—but it’s President Trump’s next move that’s raising the real eyebrows. Just days after the relationship went public, Trump made a gesture so subtle, yet so symbolic, that insiders are still debating its meaning. Was it disapproval? Strategy? A silent power play? The timing couldn’t be stranger—and it’s turning a headline romance into a full-blown family saga. For many, **the real story is just begi…
Tiger Woods has sensationally started dating Donald Trump Jr.’s ex-wife, DailyMail.com can exclusively reveal.
Woods, 49, and Vanessa Trump, 47, who both live in Florida, have been together since Thanksgiving and are quickly becoming golf’s new power couple.
Four sources confirmed to DailyMail.com that the pair are an item.
They live 20 minutes apart in the wealthy southern Florida enclave of Palm Beach and were spotted together at a golf tournament last month.
Vanessa’s eldest daughter Kai, 17, and Woods’ children Charlie, 16, and Sam, 17, all attend the $38,595-a-year The Benjamin School.
Other members of the Trump family, including all five of Vanessa and Don Jr.’s children, are aware they are an item, one source said.
A source said: ‘Tiger and Vanessa have been seeing each other since just before Thanksgiving.
‘She comes to his place on Jupiter Island. They’re not living together. She comes over maybe a few nights a week.
‘They just love hanging out, having dinner and schmoozing together. They’re sticking close to home, have decided not to make it a thing and go out in public. Not just yet anyway.’
Vanessa filed for an uncontested divorce from Don Jr. on March 15, 2018 in New York.
Since they officially split she has not had a high-profile relationship.
Don Jr. has remained a close adviser to his father and helped take over much of the business.
Kai Trump and Charlie Woods are both aspiring golfers with sights set on turning professional.
Golf star Tiger Woods, 49, has been dating Donald Trump Jr.’s ex-wife Vanessa Trump, 47, since Thanksgiving. They are pictured arriving at a golf tournament on February 16
The two families appear to have become increasingly close.
Last month, at the PGA Tour’s Genesis Invitational at Torrey Pines in California, they were pictured arriving together.
Kai, who committed to playing golf at the University of Miami next year, wore an outfit from Woods’ clothing line.
In February, Vanessa took Kai to watch a round of the TGL, the golf league created by Woods and Rory McIlroy.
Meanwhile, President Trump met up with Woods for a round of golf last month.
Eldest Trump grandchild Kai (center) arrived at The Genesis Invitational at the Torrey Pines Golf Course on February 16, 2025 alongside Tiger Wood (right) and her mother Vanessa (left)
Tiger’s kids Sam (center) and Charlie (left) attend school with Kai Trump at The Benjamin School. Sam Alexis Woods, 17, plays soccer and Charlie Axel Woods, 16, also golfs
Don Jr. ended his engagement with Kimberly Guilfoyle publicly after it was revealed in September he was dating Palm Beach socialite Bettina Anderson. Pictured: Bettina and Don attend President Donald Trump’s joint address to Congress on March 4, 2025 at the Capitol
Donald Trump Jr. shows off MAGA outfit and new girlfriend
But Woods’ golf career suffered a major setback on Monday when it was revealed he had ruptured his Achilles tendon.
The 15-time major winner was preparing for his latest comeback at home in Florida when he felt a ‘sharp pain’ in his left heel.
He underwent surgery on Tuesday and is expected to make a full recovery, but is ruled out of the Masters next month.
President Donald listens as Tiger Woods speaks during reception for Black History Month in the East Room of the White House
After his divorce from Vanessa, Don Jr. had a long-term relationship and engagement with former Fox News host Kimberly Guilfoyle, who is now President Trump’s Ambassador to Greece.
But in September, DailyMail.com exclusively published images of Don Jr. in southern Florida with West Palm Beach socialite Bettina Anderson.
By December, Don and Guilfoyle’s relationship was over and he began publicly dating Anderson after his father’s 2024 election win.
Sources say that Don Jr. and Anderson are aware that his ex-wife is now dating Woods.
Don Jr. and Vanessa Kay Pergolizzi married in 1998 and had five children together before they divorced at the end of 2018. Pictured: Vanessa and Don arrive at the Angel Ball at the Marriott Marquis in New York City on October 29, 2007
Don Jr., Bettina and Vanessa all attended the 2025 inauguration of President Donald Trump in Washington, D.C. along with the couple’s five children (all pictured except eldest Kai)
Vanessa chats with Hulk Hogan at the Republican National Convention in Milwaukee in July
Woods appeared alongside President Trump at the White House on February 20 during a reception honoring Black History Month
While no longer together, Vanessa and Don Jr. are often in the same room due to their five shared children or because of events for President Trump.
After news broke that Don Jr. was seeing Anderson romantically, tensions are said to have emerged between the socialite and her boyfriend’s ex-wife.
Anderson and Vanessa were once friends before she began dating her ex-husband.
According to those in southern Florida circles, Anderson no longer feels there is as much ill-will now that Vanessa is dating Tiger.
News
FOX NEWS MELTDOWN: Jesse Watters Clashes With Jessica Tarlov in Shocking Live Segment—His Sudden Call for Her Removal Ignites Chaos On Air, and Viewers Can’t Stop Talking About What Happened Next
Inside the TV Clash That Shook Fox News: Jesse Watters Calls for Jessica Tarlov’s Removal After Explosive On-Air Showdown…
Karoline Leavitt vs. The View: The On-Air Comment That Lit Up Fox News—and Left Whoopi Goldberg Reeling and the Hosts Speechless
Karoline Leavitt vs. The View: The On-Air Comment That Lit Up Fox News—and Left Whoopi Goldberg Reeling For a…
The real reason Karoline Leavitt quit her past career where she worked ‘on the dark side’, the most unexpected thing confirmed
“I Was on the Dark Side.” — Karoline Leavitt Finally Reveals the Unexpected Truth Behind the Career She Quietly Walked…
LIVE TV EXPLOSION: Nicolle Wallace LOSES CONTROL After Karoline Leavitt’s Blunt Retort—Audience in SHOCK as MSNBC Host ERUPTS in On-Air Rant! The Unexpected Response That Triggered Chaos and Sent Viewers Into a Frenzy—Is This the Most Unhinged Moment Yet?
LIVE TV EXPLOSION: Nicolle Wallace LOSES CONTROL After Karoline Leavitt’s Blunt Retort—Audience in SHOCK as MSNBC Host ERUPTS in On-Air…
“WHO’S THE PUPPET NOW?”: Karoline Leavitt FLIPS the Script on Jon Stewart in Viral Smackdown That’s Shaking Up U.S. Media
“WHO’S THE PUPPET NOW?”: Karoline Leavitt FLIPS the Script on Jon Stewart in Viral Smackdown That’s Shaking Up U.S. Media…
“I Almost Walked Away.” — Dylan Dreyer’s Tearful Revelation Live on TODAY Leaves Viewers and Co-Hosts in Disbelief
“I Almost Walked Away.” — Dylan Dreyer’s Tearful Revelation Live on TODAY Leaves Viewers and Co-Hosts in Disbelief For…
End of content
No more pages to load