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In the seven years since Donald Trump Jr. and Vanessa Trump ended their marriage, Don Jr.’s love life has never strayed far from the spotlight. For most of that time, he was engaged to former Fox News personality and current ambassador to Greece, Kimberly Guilfoyle, whom he only recently parted with in somewhat scandalous fashion. (In lieu of any breakup announcement, Jr. simply went out and about with a new woman, socialite Bettina Anderson, leaving Guilfoyle looking jilted and raising questions about how and why she scored that ambassadorship.) Meanwhile, no one heard much of anything about Vanessa—until Thursday, when it emerged that she is now dating Tiger Woods.
Yes, that Tiger Woods, who is having a busy week, having also just announced that he is recovering from surgery to repair a ruptured Achilles tendon, while, meanwhile, Barack and Michelle Obama are looking to make a biopic about him. Time for a third-act rewrite to add in Vanessa! The Daily Mail reported that the two have been dating since Thanksgiving. It’s unclear exactly how they met, but Vanessa, who is 47, has close ties to the golf world in the form of her and Don Jr.’s oldest daughter, 17-year-old Kai, who is an accomplished golfer. According to Page Six, Kai attends the same school as Woods’ two teenage children. Woods, 49, has also known President Donald Trump for years; just last month, the two played golf together and Woods was separately honored at a White House Black History Month event. (I guess DEI is OK if Trump can find a way to make it about golf.)
While it is tempting to think that Don Jr. might feel somewhat insecure to know that his ex has moved on with one of the most famous athletes in the world, the only thing we know about Don Jr.’s reaction to this news is that an “insider” told People that he is “cool” with it. He’s usually really level-headed, so that seems right. He and Vanessa were married for 12 years and share five children together; their marriage was plagued by rumors of infidelity and financial tensions. During their divorce, tabloids reported that Vanessa had been “emboldened” to file after inheriting a small fortune thanks to her father’s investment in Rao’s Specialty Foods, which brought her what People called at the time a “marinara-sauce windfall.” (As if we needed further confirmation that Don Jr. is sauceless.) The two have been mostly cordial since the split, with Vanessa attending President Donald Trump’s second inauguration earlier this year alongside Don Jr.’s new squeeze Anderson, who is reportedly a former friend of hers.
Though it’s been a while, you may recall that, in addition to being considered one of the greatest golfers of all time, Tiger Woods is also one of the most notorious cheaters of all time. The revelation of his affairs during his marriage to Swedish model Elin Nordegren, who is the mother of Woods’ two children, was huge news in 2009. His romantic life has calmed down somewhat since then—though there was also a spat with an ex-girlfriend over a nondisclosure agreement a couple years ago—but you can see how his history might give some women, er, pause before entering into a new relationship with him. Before Don Jr., by the way, Vanessa was linked to an accused member of the Latin Kings gang, a Saudi prince, and Leonardo DiCaprio. So maybe the concept of red flags is just lost on her.
Ultimately, what are we to make of this pairing? Can we count it as a win that it’s probably giving Don Jr. a conniption, or is it too depressing that another public figure has become further entrenched in Trumpworld? To be honest, it’s probably a little bit of both. A sick part of me, of course, is wondering how Trump himself feels about this news. It takes a lot for me to be at all interested in golf, so kudos to everyone involved for that.
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