Tiger Woods initially wanted to keep his romance with Vanessa Trump a secret — but had to change his plans after news of their budding relationship went public.
‘He knew it would be a huge story when it came out,’ says a member of his inner circle. ‘And he didn’t exactly love it. But obviously Tiger dating a Trump is always going to make headlines, which is exactly what he wanted to avoid.’
Woods, 49, and Trump, 47, took great pains to be keep the romance under wraps — avoiding public places and not talking about each other with their friends.
But as their relationship became more intimate, it became an open secret at the $38,595 Benjamin School in Palm Beach, where both Woods and Trump send their children.
As the rumors spread, tongues started wagging.
‘Benjamin is like a small community,’ says the insider, ‘and there’s nothing that rich people like to do more than gossip about each other. Frankly, I’m surprised that it was secret for so long.’
Earlier this month, DailyMail.com exclusively broke the news that the golf icon was dating Donald Trump Jr.’s ex-wife — and the pair decided that it was time to go public.
On March 23, Woods posted pictures with Vanessa on his Instagram and X accounts. One snap showed them posed in front of a vine-filled wall and another of them cuddling on a hammock.
Tiger Woods initially wanted to keep his romance with Vanessa Trump a secret — but had to change his plans and post on Instagram after news of their budding relationship went public
‘Love is in the air and life is better with you by my side! We look forward to our journey through life together,’ Woods wrote. ‘At this time we would appreciate privacy for all those close to our hearts.’
The posts were well-received, garnering hundreds of thousands of likes and comments.
One of the people to congratulate them was Vanessa’s former sister-in-law Ivanka Trump, who commented ‘So happy for you both’ followed by several heart emojis.
Vanessa Trump’s oldest daughter, Kai, also liked the post.
One of Woods’ former employees tells the Daily Mail that the golfer often doesn’t comment about personal issues until his back is against the wall.
‘He has never been one to really share things until he absolutely had to,’ says the employee, who worked for him for more than a decade. ‘But once things are found out, he doesn’t really have a choice.’
‘It’s either post a couple pictures on Instagram now, or let one of the other parents at the school take a picture at an event and post it. He knows it’s better coming from him.’
Woods and Vanessa live approximately 20 minutes apart in Palm Beach, Florida. They have been together since Thanksgiving, DailyMail.com confirmed with multiple sources.
Although they were spotted together at a golf tournament last month, they laid off the PDA in hopes that their relationship wouldn’t be found out.
‘They just quietly did their thing,’ says the Woods insider. ‘But Tiger isn’t one to get kissy or handsy in public anyway.’
The golf legend, who hasn’t been in a high-profile relationship for more than two years, has started dating Vanessa amid doubts over his professional future after a series of serious injuries.
Vanessa married the President’s oldest son in 2005 and had five children. They divorced 13 years later.
Woods, 49, and Trump, 47, took great pains to be keep the romance under wraps — avoiding public places and not talking about each other with their friends
Woods and Trump are pictured arriving at a golf tournament on February 16, before news of their relationship emerged
Sources tell DailyMail.com that Vanessa is unworried about his 2009 sex scandal in which he cheated on then-wife Elin Nordegren with a bevy of beauties.
After the infidelity was discovered, Woods and Nordegren got into a fight on the Friday after Thanksgiving. He fled the house, barefoot and wearing shorts, and promptly crashed his black Cadillac Escalade.
The crash sparked an international scandal that landed Woods in rehab for sex addiction and ultimately led to the couple’s divorce. Woods eventually had to own up to the infidelity in a somber press conference several months later.
‘That is exactly what I mean,’ says the former employee, who was working for Woods during the scandal. ‘He doesn’t talk about his personal life until he absolutely has to. At least this is a positive thing, just a new relationship.’
‘I know that Tiger didn’t want to share the news,’ the former staffer says, ‘But now that he has, there has to be some relief. Now he can just go and live his life.’
Vanessa filed for an uncontested divorce from Don Jr. on March 15, 2018 in New York.
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. 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. 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
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.
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.
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.