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How Tiger Woods’ ex Rachel Uchitel ‘turned down’ Donald Trump, and why she has failed to get rid of the ‘mistress’ label even after the new Tiger HBO docuseries aired

Rachel Uchitel, best known for her relationship with famous US golfer Tiger Woods, hoped to reveal more about herself and her story in HBO’s new docuseries, Tiger. Photos: Bloomberg/HBO

This wasn’t how Rachel Uchitel wanted it to go. After a decade, she’d decided at last to talk about her affair with Tiger Woods so the public might characterise her as something other than a mistress. Maybe they’d stop writing “homewrecker” in the comments of her Instagram photos. Or at least understand that she’s a human who’s made mistakes and “deserves a break”.

Rachel Uchitel in a still from the official trailer of HBO’s Tiger. Photo: HBO

But days before she broke her silence in the HBO docuseries Tiger, the UK media published photos of her kissing a married lawyer. In a series of breathless headlines, the tabloid said the “infamous mistress” had met the man on the website Seeking Arrangement – where young, alluring “sugar babies” connect with older, wealthy “sugar daddies” – after which he proceeded to leave his wife and kids for her.

The reason I chose to do the documentary is because I wanted to tell my story in one place, at one time, and be like, ‘Listen, this is what happened. I’m not an awful person’
Rachel Uchitel
A promotional poster for HBO’s Tiger. Photo: HBO

Uchitel denied the account, insisting the lawyer had been separated from his wife for months before they’d met. Still, she feared the writing was on the wall. He was the third married man she’d been romantically linked to in 10 years. She dated Bones star David Boreanaz in 2009, after he told her he’d been living in his family’s guest house for nine months; it was only when his wife went into labour that Uchitel says she learned they were not separated.

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And then there was Woods. Uchitel met the golf star while working as a VIP concierge for a slew of popular nightclubs, where her job was to make sure wealthy clients were surrounded by top-shelf alcohol and attractive guests. But as she recounts in Tiger, Woods was more interested in her than the women she’d helped select to party with him. Their tryst was only one of several Woods would be exposed for having had while married to Swedish model Elin Nordegren. But it was also the first to hit the press, and after the National Enquirer broke the story, Woods and Nordegren got into such a big fight that he drove off in his SUV and crashed it.

 

“The reason I chose to do the documentary is because I wanted to tell my story in one place, at one time, and be, like: ‘Listen: This is what happened. I’m not an awful person,’” says Uchitel, now 45, video chatting from the New York City flat where she lives with her eight-year-old daughter, Wyatt Lily. “The media was really awful to me. They blamed me for something that happened between two people. One guy got to be a hero, while the whole world made a mockery of me.”

She was hopeful that the series “would attract a level of empathy,” but so far, she says that hasn’t been the case. Online, the comments she’s received are largely negative: “‘Oh, we don’t want to hear from Rachel again!’ or ‘You’re ugly. You’re so old. We don’t even know who you are. Disappear.’”

Maybe it’d be different if the series had come out closer to the beginning of the #MeToo movement, she says. Or if the latest gossip stories about her last relationship hadn’t coincided with the HBO premiere.
Tiger Woods at the Masters golf tournament on November 15, 2020, in Georgia in the US. Photo: Atlanta Journal-Constitution via AP

But Uchitel has always found happiness to be hard-won. When she crossed paths with Woods in 2009, she had only just landed back on her feet after years of tumult.

At 13, she was sent to Cedu High School, a Running Springs, California residential treatment centre for troubled youths. As detailed in the UCP Audio podcast The Lost Kids, the school, which closed in 2005, allegedly employed abusive practices in the name of “tough love”. Uchitel was traumatised by the experience. “They made me dig a grave with a spoon and then lay in it,” she recalls.

While Uchitel was at Cedu, her father died from a cocaine overdose. She was 15.

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Still, she managed to complete the programme and move to New Hampshire, where she studied psychology at the state university. After graduation, she landed a job at Bloomberg News, where she started on the assignment desk and worked her way up to segment producer.

It was there, during her 5am to 2pm shift, that she watched a plane hit the World Trade Center on September 11, 2001. Her fiancé, investment banker Andy O’Grady, had an office in one of the towers. In the ensuing chaos, she made fliers with his face on them in the hope that he might still be alive. A photograph of her pained face clutching one of the handouts was published on the cover of the New York Post, becoming one of the images that defined the tragedy.

Rachel Uchitel makes an emotional plea as she searches for her fiancé Andy O'Grady outside Bellevue Hospital in Manhattan on September 13, 2001. Photo: AP Photo/CP

After O’Grady’s death, Uchitel found that continuing to work in the news industry was too triggering. So she decided to start over, embarking on a road trip to Las Vegas where she found work.

“I was the director of operations for the No 1 nightclub in the world. I had a real, serious job. I was making close to a million dollars a year,” says Uchitel. “People think I was a waitress, but I don’t even know how to open a bottle of champagne.”

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But Uchitel didn’t meet Woods in Las Vegas. She met him in New York, where she’d moved back to help a few new clubs get off the ground. It was there that business and pleasure began to overlap; she no longer counted celebrities only as her clients, but sometimes as her boyfriends. She dated Derek Jeter and, on holidays to St. Tropez, she’d “get caught up and dabble”, hooking up with the likes of Ryan Seacrest and Stephen Dorff.

But Woods was different. After their first night together, she remembers in Tiger, she thought: “How am I ever gonna be with a mere mortal ever again?”

Golfer Tiger Woods shakes hands with former US president Donald Trump after being presented with the Presidential Medal of Freedom during a ceremony in the Rose Garden of the White House in Washington on May 6, 2019. Photo: AFP

But now that she’s completed her eight-hour sit-down with the Tiger directors, Uchitel will no longer discuss Woods. Though she alludes to a confidentiality settlement in the docuseries – she says Woods told her to “get as much as you can” – she won’t say if or how much he paid her. When asked if she signed a non-disclosure agreement that perhaps gave her the freedom to talk about the relationship after 10 years, she would say only: “I can’t get into that. But it’s interesting that you’re the first person who has brought that up.”

When it comes to her attraction to married men, though, Uchitel is surprisingly candid.

“Now, every time I date somebody, I’m going to be like, I need to see your documents,” she says, only half-kidding. “I need to know that you’re divorced. Because it’s embarrassing now. Obviously, going forward, I can’t even date anyone that’s separated. They have to be 100 per cent single.”

Rachel Uchitel spoke about her past relationship with Tiger Woods in HBO’s Tiger. Photo: HBO

She describes herself as a love addict, a label first given to her by Dr. Drew Pinsky when she went on VH1’s Celebrity Rehab in 2010. After the Woods tabloid storm, Uchitel was bombarded with reality television offers. The first came from Donald Trump, whom she says called her at 7am to offer her a spot on The Celebrity Apprentice. After a dinner meeting with Trump’s then-lawyer, Michael Cohen, she accepted, thinking the show would give her an opportunity to fix her image.

“I thought Donald would be nice to me,” she says. “I thought he’d think I was cunning and see I was smart. I don’t know. I thought it would be a good move for me.”

Professional golfer Tiger Woods stands with his girlfriend Erica Herman, his mother Kultida, his children Sam Alexis and Charlie Axel Woods, former US president Donald Trump and his wife Melania after the Presidential Medal of Freedom ceremony in 2019. Photo: AFP

But she was simultaneously being courted by VH1 executives, who were desperate to have her appear on the fourth season of Celebrity Rehab. Uchitel balked at the idea, but agreed to meet with Pinsky anyway. Over breakfast, she felt such a connection with him that she began bawling and checked into his Pasadena rehab that same night. The US$400,000 pay cheque – more than 10 times what Trump’s Apprentice was offering – didn’t hurt.

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Since the affair with Woods, Uchitel says she has struggled to find consistency in her life. In addition to her stint on reality TV, she earned a graduate certificate in forensic investigation. She got married, had a baby and got divorced. She opened a New York children’s clothing boutique named after her daughter, Wyatt Lily; it has since closed. She says she was one of five finalists considered for the open slot on the 12th season of The Real Housewives of New York City. (It went to Leah McSweeney.) Recently, she’s been working with a recovery centre called Transcend, trying to raise awareness about love addiction.

 

“I would love some opportunity [to come from Tiger], because I haven’t been able to get a real, normal, sustainable job for the last 10 years,” she says, noting she has been turned down for jobs at Bloomberg and MSNBC. “I would love to go work in a newsroom again. I would love to do something normal again. They’ve told me flat out that I’m too scandalous.”

 

And she gets it. By her own admission, she doesn’t “necessarily come off as the most empathetic or sweet”. She can have a “bad tone”, get a “little harsh”, a “little defensive”.

“So I think I get misunderstood a little bit, and people don’t like me,” she says. “I try my best, and sometimes I don’t do a good job. I’ve made some wrong turns. But that doesn’t define me. … I have a daughter. I love animals. I’m not this person who is trying to sleep with married men and be scandalous or whatever. I’m just doing my best to be happy and figure out my purpose in life. And I think people are really hard on me.”

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Tiger Woods

Before she got offers from reality TV shows like Donald Trump’s The Celebrity Apprentice and VH1’s Celebrity Rehab, she was a Bloomberg News assistant struggling with losing her fiancé to 9/11