Details About Donald Trump's Ties To Tiger Woods' Former Mistress

Rachel Uchitel has a history of being connected to famous men. She first became a media darling in 2009 when she was named as a mistress in Tiger Woods' alleged affairs. Even actor David Boreanaz admitted to having an affair with Uchitel while he was married. And it turns out Uchitel also had a different kind of run-in with another big name: none other than President Donald Trump.

In July 2010, TMZ reported that Trump invited Uchitel to appear as a contestant on the celebrity version of his show, "The Apprentice." TMZ also claimed she told the outlet at the time she would accept the invitation, but just a couple of days later, news broke that Uchitel was joining a different reality show. On July 19, 2010, VH1 announced in a press release that Uchitel would be on the fourth season of "Celebrity Rehab with Dr. Drew" (per PR Newswire). While it was first assumed that Uchitel would be addressing a drug addiction on the show, sources told Us Weekly that she was looking to remedy her personal relationship issues. "Rachel is addicted to love," the insider said. 

Famous golfer Woods was likely upset that his former mistress was nabbing so much screen time (and this was years before Woods sued Uchitel for violating an NDA by speaking about him publicly). But Trump was the one who had the harshest reaction to Uchitel joining "Celebrity Rehab." 

Following news of Rachel Uchitel joining "Celebrity Rehab with Dr. Drew," Donald Trump couldn't hold back his disapproval. According to The New York Post, Trump rescinded his invitation for Uchitel to appear on "Celebrity Apprentice." He claimed Uchitel was the first one interested in joining the upcoming season of his show but that he no longer had any desire in casting her now that she has committed to another series. 

He expressed a similar sentiment to TMZ, saying that choosing "Celebrity Apprentice" would've been a better choice for Uchitel in the long run: "It's a terrible decision. We have zero interest in her now. ... Look at what 'Celebrity Apprentice' did for Piers Morgan. He's getting Larry King's job. She made a bad mistake." Trump added, "'Celebrity Apprentice' is a huge show and 'Celebrity Rehab' is not. I have 10 people who want to be on the show for every slot that's available. I'm moving on."

Uchitel had a challenging time on the VH1 series and almost left the show prematurely after she walked out of one of her sessions. After the season concluded, Uchitel spoke highly of her experience on "Celebrity Rehab with Dr. Drew" and told CBS News she was continuing therapy as a result. 15 years later, Uchitel appears to be living a wildly lavish life and announced in March 2025 that she is engaged to Dan Donovan.