Tiger Woods and the Trump family have long shared a bond through golf. But now, speculation is growing about a new, more personal link—one that has reportedly caught Donald Trump’s attention.
Golf icon Tiger Woods appears to have the backing of President Donald Trump in his reported relationship with Vanessa Trump, the ex-wife of Donald Trump Jr.
Tiger Woods on “TODAY” on Wednesday, May 1, 2024 | Source: Getty Images
An insider revealed that Trump is aware of the rumored romance and fully approves. “Trump knows about him dating Vanessa and is said to approve,” the source stated.
Both Woods and Vanessa reside in Florida, and golf runs deep in the Trump family. Vanessa’s daughter, Kai Trump, is an accomplished young golfer. She competes in championships and often plays with her grandfather, adding another possible connection between Tiger and Vanessa.
Ivanka Trump, Tiger woods, Donald Trump and Eric Trump at the Trump Doral Golf Resort & Spa on March 10, 2013 in Doral, Florida | Source: Getty Images
An insider revealed that Trump and Tiger have maintained a close relationship for years, noting that the celebrated golfer received the Medal of Freedom from Trump in 2019.
Tiger has also expressed appreciation for Trump’s contributions to golf. “Tiger speaks privately about liking Trump and what he’s done to promote golf,” the source added.
The golf icon recently attended a Black History Month event at the White House, where he was seen wearing the Presidential Medal of Freedom he received from Trump. Additionally, sources claim Trump has extended an invitation for Tiger to join him and Kai for a round of golf at his Florida club.
Tiger and Vanessa began making headlines for their reportedly new romance this week. According to the Daily Mail on March 13, the 49-year-old golfer and Vanessa, 47, have been quietly dating since late last year.
A netizen’s comment on Tiger Woods and his reported new romance, posted on March 13, 2025 | Source: Facebook/peoplemag
Both live just 20 minutes apart in Palm Beach, Florida. Their children — Tiger’s, Charlie and Sam Woods, and Vanessa’s eldest daughter, Kai Trump — attend The Benjamin School, a private institution.
Last month, witnesses spotted them together at a golf tournament, fueling speculation. A source told Daily Mail, “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.”
The source added that they enjoy each other’s company, often sharing dinners and conversation. For now, they are keeping things private and have chosen to stay out of the public eye.
Vanessa Trump attends the 140th Easter Egg Roll on the White House South Lawn on April 2, 2018 | Source: Getty Images
Despite the attention surrounding their romance, Vanessa’s ex-husband isn’t bothered. A source close to the Trump family told People that Donald Jr. is “cool” with the pair dating. He and Vanessa were married for 12 years before divorcing in 2018.
Meanwhile, other Trump family members and the former couple’s five children reportedly know about Vanessa and Tiger’s relationship.
Vanessa, Kai, and Donald Trump Jr. in Milwaukee, Wisconsin, on July 17, 2024 | Source: Getty Images
The New York Post reported that Tiger and Vanessa’s relationship began as a friendship. “But it’s not too serious, it’s heading in that direction, though,” a source mentioned. While they are taking things slowly, a source believes it could become “something really serious and permanent.”
“They have a lot in common. They’ve both gotten used to public scrutiny. They both know how to keep their private life private. They’re both parents,” the source added.
Tiger Woods with his son, Charlie, and daughter, Sam, during the PNC Championship final round in Orlando, Florida, on December 17, 2023 | Source: Getty Images
What Tiger admires most about Vanessa is that she isn’t drawn to his popularity. “Fame doesn’t interest her; that’s what he likes best about her,” the source explained, adding that she would date him even if he weren’t famous.
Before reports of their romance resurfaced, Vanessa was seen in the background of a photo taken on February 16, at Torrey Pines Golf Course in La Jolla, California. The image showed Tiger alongside Kai, during the final round of The Genesis Invitational, further fueling speculation about their growing connection.
Kai Trump and Tiger Woods arrive at The Genesis Invitational 2025, with Vanessa Trump in the background | Source: Getty Images
Vanessa’s appearance at the event fueled dating rumors and sparked online discussions about her resemblance to Tiger’s past partners. One commented, “Looks like his ex,” while other users pointed out that he clearly has a type, “You can tell he has a type. All of his girlfriends look alike.”
One observer noted Tiger’s preference for blondes. Someone joked that she seemed older and not as blonde as his usual type.
Vanessa Trump in Washington, D.C., on April 17, 2017 | Source: Getty Images
While some focused on her appearance, others reacted to the relationship itself. Another person found the situation unexpected and mentioned it wasn’t on their bingo card. A skeptic predicted it wouldn’t last, comparing Tiger’s dating history to going through water.
Not everyone was critical, though. A supporter expressed happiness for the couple and wished them well. Another echoed the same sentiment, “Good for them. Wish them much happiness.”
Tiger’s reported romance with Vanessa surfaced after he revealed a recent health setback, adding to public interest in his personal life.
On March 11, 2025, Tiger announced on X that he ruptured his left Achilles tendon while training, requiring surgery in Florida. Dr. Charlton Stucken performed a minimally invasive procedure at the Hospital for Special Surgery in West Palm Beach, assuring that the operation was successful and that Tiger is expected to make a full recovery.
Tiger reassured fans that he is “back home now” and focused on “recovery and rehab,” thanking them for their support. His injury drew strong reactions from analysts and former players on X.
Former professional golfer and current analyst Arron Oberholser reacted, “Unreal. How much more can an athlete endure. Just brutal.” Golf journalist Dan Rapaport added, “Ruptured achilles is a nightmare. I’m sad.”
Tiger Woods watches before the TGL match at SoFi Center on January 7, 2025 | Source: Getty Images
Another ex-golfer, Nick Leach, shared his thoughts, “As much as I love Tiger and how he’s impacted the way I view golf. It’s time to call it a career.”
ESPN’s football analyst Booger McFarland commented, “It’s not our place to tell him what to do however I hope enough is enough Body has been thru a lot. Enjoy your kids. We will cherish all 82 of the wins and in a lot of eyes He is the greatest to ever touch a club [sic].”
Tiger Woods arrives for a TGL match at SoFi Center in Palm Beach Gardens, Florida, on January 27, 2025 | Source: Getty Images
Tiger’s latest injury follows his microdecompression surgery in September 2024 to relieve nerve impingement in his lower back. The procedure was performed by Dr. Sheeraz Qureshi at the Hospital for Special Surgery.
At the time, Tiger shared on X, “The surgery went smoothly, and I’m hopeful this will help alleviate the back spasms and pain I was experiencing throughout most of the 2024 season.” He was eager to start rehab and return to his normal activities, especially golf.
Despite his perseverance, Tiger’s physical struggles were evident even before his two surgeries. In July 2024, he reflected on his performance in an interview with The Guardian.
“I loved it, I’ve always loved playing major championships. I just wish I was sharper physically,” he admitted. “Obviously it tests you mentally, physically and emotionally, and I just wasn’t as sharp as I needed to be. I was hoping to find it somehow, but I just never did.”
His struggles weren’t just physical — he was also coping with personal loss. Just a month before his left Achilles tendon injury, he withdrew from a tournament at Torrey Pines following the passing of his mother, Kultida Woods.
Tiger Woods at the driving range during the final round of The Genesis Invitational 2025 in La Jolla, California, on February 16, 2025 | Source: Getty Images
“I planned to tee it up this week, but I’m just not ready. I did my best to prepare, knowing it’s what my Mom would have wanted, but I’m still processing her loss,” Tiger said in a statement on February 10.
He thanked everyone for their support and kindness since his mother’s passing. Tiger announced on X that Kultida had passed away on February 4.
Tiger Woods hugs his mother, Kultida, after speaking at TPC Sawgrass on February 19, 2010 | Source: Getty Images
“My Mom was a force of nature all her own, her spirit was simply undeniable,” Tiger wrote. “She was my biggest fan, greatest supporter, without her none of my personal achievements would have been possible.”
Kultida, who is of Thai origin, was a constant presence throughout her son’s legendary career. Before she died, she attended and supported Tiger’s TMRW Golf League (TGL) debut.
Tiger’s mom’s strength and warmth left a lasting impact on those who knew her, including fellow golfers. Golfing legend Fred Couples paid tribute to Kultida on X, remembering her as a vibrant presence.
Kutilda’s influence extended beyond the sidelines, shaping even the smallest details of Tiger’s game — including a bold tradition that would come to define him: his red shirt on Sundays.
“My mom thought, that being born a Capricorn, that red was my power color,” Tiger once said. “And so, in some of the junior golf events in So Cal, I would wear red. And I won.” Wanting to test her belief, he deliberately switched to blue for other tournaments — only to be proven wrong.
Greg Norman and Tiger Woods at the 1995 Masters Tournament | Source: Getty Images
“I didn’t win,” Tiger admitted. “And so I then switched to red, and I had a lot more success wearing red.” Realizing the pattern, he eventually made a deal with his mother — he would reserve red for the final round of big events instead of wearing it every day.
Tiger Woods and his mom, Kutilda, during his 2005 Masters win after a playoff against Chris DiMarco on April 10, 2005 | Source: Getty Images
Kultida accepted the compromise. “She said, ‘Fine. Just wear it the last day,'” Tiger shared. From then on, his mom’s belief became a lasting tradition, one he carried into the biggest moments of his career.
As Tiger mourns this profound loss, he carries forward the lessons and strength his mother instilled in him — values that helped shape him into the champion the world knows today.
As Tiger honored his mother’s memory, he also reflected the deep love she shared with her grandchildren, Sam and Charlie, and expressed gratitude for the support he received during this difficult time.
