Rachel Uchitel was sitting at a table in her Upper East Side apartment not long ago, alternately stoic and tearful, surrounded by hundreds of pages of legal documents. For more than a decade these have been familiar company: the wallpaper of a room she can’t seem to leave.
In 2009, days after the dramatic revelation of her affair with the golfer Tiger Woods, then married, Ms. Uchitel signed a nondisclosure agreement more than 30 pages long, prohibiting her from talking about Mr. Woods with anyone. She was represented by the famed Hollywood lawyer Gloria Allred.
In return for her silence, under pressure to protect a powerful man’s reputation and brand, she got $5 million and a promise of $1 million annually for three years to follow. “His lawyers are saying, ‘We want all your text messages and here’s the price,’” she recalled, “and you’re like ‘screw you’ and you move into deal-maker mode and all of a sudden, it’s the rest of your life.”
Now, at 46, Ms. Uchitel — tired of not being able to defend herself against continued insinuations from tabloids and gossip websites — is ready to blow it all up.
“I’ve had it with N.D.A.s,” she said.
In 2019 she agreed to be interviewed about her relationship with Mr. Woods for an HBO documentary, “Tiger.” “I wanted for once to be the one to narrate my story,” she said. She then filed successfully for bankruptcy, having spent the approximately $2 million she said she netted from the agreement. One of Mr. Woods’s lawyers, Michael Holtz, is challenging her protection from creditors — so he can bring a claim against her for millions of dollars on his client’s behalf for violating it, he told her.
Mr. Holtz did not respond to a detailed email seeking comment, nor did Mr. Woods’s agent, Mark Steinberg.
Ms. Uchitel said she can only find work related to her tarnished reputation, such as a spokeswoman gig for Seeking Arrangement, the online “sugar dating” service, which she is now suing for nonpayment of $60,000 and damages. According to her complaint, the company, which made headlines amid a Justice Department investigation of Representative Matt Gaetz of Florida, said it would continue to pay her only if she signed a contract with a restrictive N.D.A., on top of a boilerplateconfidentiality agreement she had already signed. (Seeking Arrangement denies any wrongdoing and is suing her too.)
Ms. Uchitel has come to believe that such documents are part of “a culture of extreme bullying.” She has been watching a public softening toward figures like Monica Lewinsky, Britney Spears and Meghan Markle and wondering if she can find similar empathy. Or at least some consideration that her name got pulped by a machine run by well-paid lawyers.
In response to a detailed email seeking comment, Ms. Allred sent a statement that read in part: “We are proud of the representation that we provided to Ms. Uchitel.”
But her former client thinks her case was mishandled, and these days she feels very much alone.
Earlier this summer, she burst into tears watching a preview of “The Me You Can’t See,” a documentary produced by Prince Harry and Oprah Winfrey about mental health. “Who is going to speak up for those of us who don’t have Oprah, or a prince to rescue us?” Ms. Uchitel said.
Glamour and Loss
Ms. Uchitel was perhaps predetermined for life in the gossip pages. In the 1960s and ’70s her paternal grandfather, Maurice Uchitel, owned celebrity hangouts including El Morocco. She was born in Anchorage to Bob and Susan Uchitel, who had made a small fortune in the state’s cable industry.
But her parents divorced, sending her to CEDU in Running Springs, Calif., a boarding school with ties to the Synanon cult. (It closed in 2005.) Bob Uchitel died of a cocaine overdose in 1990, when Rachel was 15.
She graduated from the University of New Hampshire and was working as a news producer at Bloomberg Television when her fiancé, James Andrew O’Grady, was killed in the terrorist attack on the south tower of the World Trade Center on Sept. 11. A picture of Ms. Uchitel holding his photo was published in newspapers around the world.
Ms. Uchitel began therapy for post-traumatic stress disorder, and in 2004 she married a high school friend, Steven Ehrenkranz. The marriage lasted about a year, after which she hopped into a car with her dogs and drove west to Las Vegas.
There she reconnected with an old friend, Jason Strauss, who was opening an outpost of Tao, a popular New York club, and hired her as the director of V.I.P. operations. Ms. Uchitel displayed an immediate zest for the job: taking the high-wattage contacts accumulating in her phone to New York, Miami, Los Angeles, the Hamptons; connecting clubs with the elite clientele who oxygenate nightlife.
“To me, the word ‘hostess’ does not describe what she did,” said Ron Berkowitz, the president of Berk Communications, who represented the Tao Group at the time. “She was the liaison between the club and big money. People trusted her and people called her to get into these clubs. She was the queen of it. She was the best. She had the Rolodex, she knew how to negotiate. And she also was very sweet. But then she got caught up in something that was not good for her business.”
Ms. Uchitel and Mr. Woods met in 2008 through a mutual friend, Derek Jeter, and began their relationship a year later. “I knew him to be cheating on his wife from the first time I met him, well before we got together,” she said. But Ms. Uchitel believed she had special status. Mr. Woods would fly her around the world to tournaments and events, and, she said, told her he would invest in a restaurant she dreamed of opening.
As tabloids began looking into rumors of Mr. Woods’s infidelities, Ms. Uchitel was in frequent communication with his handlers, even helping with crisis management. But the representatives stopped returning her calls after their star client’s car collision with a fire hydrant near his home in Windermere, Fla., following a dispute on Thanksgiving night with Elin Nordegren, then his wife.
As paparazzi swarmed outside Ms. Uchitel’s apartment in Chelsea, she realized she needed a lawyer of her own. She contacted three she had seen on “Nancy Grace,” a favorite show, including Ms. Allred, who called her the next morning and told her to get on a plane to Los Angeles.
Ms. Uchitel didn’t want to sell her story. She had been denying to reporters that she was involved with Mr. Woods and wanted them to leave her alone.
Then other women began coming forward to tell of sexual relationships with Mr. Woods. “By now,” Ms. Uchitel recalled, “I was pissed. And I was tired of lying for him as he and his lawyer and agent left me out to dry.”
She was being called a tramp, a mistress, a home wrecker and a “hooker “(as Joy Behar put it on “The View, later apologizing). “This is someone who everyone wants to be a hero,” Ms. Uchitel said of Mr. Woods, “and anyone who crosses that narrative will be shamed.”
Ms. Uchitel decided to arrange a news conference, one of Ms. Allred’s favored tactics. Within minutes after it was announced, one of Ms. Allred’s partners heard from Mr. Woods’s representatives. They offered her $200,000 to cancel, and to seize her phone and emails, Ms. Uchitel said.
Mr. Woods then called, instructing her to “get what you can.” It was their last conversation.
“Tell them $10 million,” Ms. Uchitel told her lawyers.
Both sides worked through the night. (Ms. Allred’s firm, Allred, Maroko & Goldberg wanted a 40 percent cut of Ms. Uchitel’s payout; she talked them down to 20 percent.) Sometime after 3 a.m., Ms. Uchitel was handed papers to sign.
“I’m not an idiot, I’m not a hooker, I’m not a prostitute,” she said. “I was and am a very smart girl and that’s why I negotiated $8 million, because I knew it was going to affect my life.”
But $8 million was not what she got. For one, there were taxes and Ms. Allred’s fees to pay — about $1 million for five days’ work — netting Ms. Uchitel about $2 million of the original $5 million, she said. Then, when it came for the first additional $1 million payment, Mr. Woods’s team balked.
‘The Scarlet Letter’
Substantially longer than most N.D.A.s, the document prohibited Ms. Uchitel from discussing “directly or indirectly, verbally or otherwise” Mr. Woods’s “lifestyle, proclivities, customs, private conduct, fitness, habits, sexual matters, familial matters,” among other topics, with anyone, “including but not limited to, family members, relatives, acquaintances, friends, associates, co-workers, journalists.” It also forbade her to say she had signed an N.D.A.
Days later, Ms. Uchitel also signed a retainer granting the lawyers 10 to 20 percent of any paid media appearances they helped to negotiate. This contributed to Ms. Uchitel believing that she could abide by the N.D.A. while doing narrowly focused interviews. The press was calling her names and she felt it important to respond.
“I was a person before him, and I am a person after him,” Ms. Uchitel said of Mr. Woods. “I wanted to answer, ‘Who is Rachel Uchitel?’”
Playboy offered her $250,000 to pose; Ms. Uchitel said no after hearing she would have to sit on a live tiger. She also said no to Michael Cohen, dispatched by Donald Trump to discuss appearing on “The Celebrity Apprentice.”
OK magazine promised not to ask her about Mr. Woods, which seemed OK. And they paid her $250,000. (The OK reporter did not ask her about Mr. Woods, but the magazine ran her photograph on the cover, calling her “Tiger Woods’ Rachel Uchitel.”)
Then came Dr. Drew Pinsky, of “Celebrity Rehab,” who told her he thought she had a compulsion for male attention, brought on by the losses of her father and her fiancé, and promised not to mention Mr. Woods if she’d come on the show, for $400,000. “I was mourning a relationship,” Ms. Uchitel said, and Dr. Pinsky “got me.”
But after the production began, when Ms. Allred first learned about it, she predicted there would be trouble, and she was right. Mr. Woods’s lawyers called Ms. Uchitel into arbitration, a confidential process through which parties can resolve disputes out of court. They wanted their $5 million back. And forget about that additional $3 million.
Ms. Allred instead urged mediation, warning that an arbitrator could potentially force Ms. Uchitel to repay the money she had already received, in addition to damages. Mediation — also secret — would mean she was willing to compromise on a solution.
This didn’t sit well with Ms. Uchitel, who said she spoke to the press only to distinguish herself from some of Mr. Woods’s other lovers, like those in pornographic films, and she never mentioned him or their relationship. She didn’t think she should be giving up any money. “If I’m going to walk around with the scarlet letter, then they’re going to have to pay me $8 million, not five,” she told her lawyers.
But mediation, they said, was her best hope to hold onto the $5 million. To find a resolution with Mr. Woods, they urged her during a two-day hearing in April 2011 to give up the additional $3 million.
Then, another indignity: As Ms. Allred’s associates presented Ms. Uchitel with the signature pages of this new deal, they flagged a provision stating that Mr. Woods agreed to pay their firm $600,000: their cut of the $3 million Ms. Uchitel was giving up. This made no sense to Ms. Uchitel, their client; why would she owe them 20 percent of money she was being pressured by them to give up? But she still signed, worrying that getting another lawyer’s opinion would violate her N.D.A.
Her regret was immediate. “It has nothing to do with not getting the rest of the payout. It’s that I feel, ultimately, like I was bullied,” she wrote to her lawyers in an email. “I feel duped.”
Frustrated by what she saw as Ms. Allred’s firm’s mishandling of her case, Ms. Uchitel retained Michael Piuze, a Los Angeles lawyer who had won a $28 billion verdict from Philip Morris, the tobacco company. In 2014, on her behalf, he won an award of $600,000 from Allred, Maroko & Goldberg in an arbitration proceeding, proving breach of contract and breach of fiduciary duty related to the $600,000 payment from Mr. Woods to Ms. Allred’s firm.
During the proceedings, it emerged that Ms. Allred and her associates represented between five and 10 other women besides Ms. Uchitel in matters involving Mr. Woods. Ms. Allred’s firm was negotiating settlements so frequently with one of Mr. Woods’s lawyers, that the lawyers “developed a written protocol,” according to Mr. Piuze’s closing argument.
(Soon after the arbitrator issued his final decision, the parties agreed to vacate it — essentially a nullification — choosing instead to enter into a settlement agreement, with Ms. Allred’s firm still forking over the $600,000 to Ms. Uchitel, plus $56,000 in other fees.)
“At every turn, I was up against these big-shot lawyers, and I really felt vindicated,” Ms. Uchitel said. She treasures an email she received from Mr. Piuze when the whole business was over. “I was impressed by your smarts, street and otherwise,” he wrote. “You are young and talented. Not platitudes. Time to move on to the next chapter.”
He died last year. In matters related to the N.D.A., Ms. Uchitel is currently on her own.
‘Time to Take the Reins’
After her breakup with Mr. Woods, Ms. Uchitel tried to move on. She met Matt Hahn, a businessman, in late 2010 and they married in Las Vegas and had a daughter, Wyatt, in 2012.
Since they divorced in 2014, she has struggled to find romantic partners who will overlook her reputation as “Tiger Woods’s mistress.”
A few years ago, in an experience typical of others, Ms. Uchitel got her hair blown out for a proper date with a man she’d matched with on an app and went to the bar where they’d agreed to meet. Nearly two hours later, he emailed her after Googling: “I know who you are and I’m not going to be able to be seen with you.”
She also tried to find a lower-profile career, opening two high-end children’s clothing boutiques, one in New York City in 2013 and another in Scarsdale, N.Y., two years later. But her overhead was too great, she said, and she believes she lost customers when the mothers realized whom they were buying rhinestone sweatpants from. She closed the New York City store in 2017 and the Scarsdale one in 2019, in debt to both landlords.
With bills mounting, family estranged and a perpetual feeling of being denigrated by the press, “I felt the world closing in on me,” she said.
In early 2020, she checked herself into a residential mental health care facility. Upon arriving, she began panicking about the potential impact on her custody rights and worried that discussing her silence and shame might violate the N.D.A. After 10 days she left, even more depressed.
When the pandemic forced New York into shutdown and the governor announced a moratorium on evictions, Ms. Uchitel stopped paying rent, then moved out before her lease was up — drawing ire from her guarantor (a mother she knew from her daughter’s previous school) and her landlord.
Before the pandemic, she was approached by the producers of “Tiger” — not with money, but with an opportunity for credibility. “Ten years later, people were still talking about me as a player in a story I had never talked about,” Ms. Uchitel said. “I felt like it was time to take the reins.”
After all this time, she reasoned, she couldn’t harm his reputation or earnings. Mr. Woods is currently tied for 12th with Naomi Osaka on the Forbes list of highest paid athletes; the magazine reported that he earned $60 million from May 2020 to May 2021. In 2019, he reclaimed the title of Masters champion. (He had another car accident this spring and is recovering from injuries.)
Ms. Uchitel did the interview for “Tiger,” speaking about Mr. Woods publicly for the first time, she said, and then filed for Chapter 7 bankruptcy and was granted protection from creditors early this year.
After the documentary came out in January, she heard from Mr. Holtz, Ms. Uchitel’s main adversary in managing the N.D.A., who calls himself “Ray Donovan with a pen,” on his website.
“If you get a job, I’ll come after your wages. If you get married, I’ll go after your joint bank account. I will come after you for the rest of your life,” she said he told her. Soon she got notice of Mr. Holtz’s intention to continue to pursue damages against her, despite her bankruptcy protection.
In an email sent in April to Mr. Holtz and Mr. Woods, Ms. Uchitel proposed a $275,000 annual stipend from Team Tiger that would allow her to live within about 30 miles of her ex-husband (per her custody agreement) while forgoing the only work she says she can get, which requires her to interact with the press.
Otherwise she could, she wrote, “kill myself, not sure why you are trying to make someone do that? You are trying to make my life unlivable.” Or, “You can leave me alone completely, with a notice that you will, so I will back off too.”
Or, she wrote, “I can sing like a canary,” adding an expletive.
Mr. Holtz did not reply.
But he did show up at the virtual bankruptcy hearing in May, himself represented by Jerrold L. Bregman, known for his commentary on the bankruptcy of Gawker Media after its legal battle with Hulk Hogan. He argued that Mr. Holtz wasn’t notified of Ms. Uchitel’s bankruptcy filings in a timely fashion.
“This is Rachel Uchitel, representing myself,” Ms. Uchitel said, and tried to explain that she repeatedly told a lawyer who prepared her bankruptcy filing to add Mr. Holtz, as the representative of Mr. Woods and his company, to the papers and to notify him of her intent.
The judge cut her off and granted Mr. Holtz’s motion to move forward. “This is the same feeling I always have,” she said afterward. “It’s a bunch of lawyers and judges and men who don’t let me talk.”
In the past weeks, Ms. Uchitel requested twice that Mr. Bregman agree to delay the proceedings, explaining that she cannot “just pick someone out of the phone book” to go up against another “lawyer for a ‘party who cannot be named.” He said no.
A hearing is scheduled for Aug. 10. Late last week, Maureen Bass, a partner with the New York law firm Abrams Fensterman, agreed to represent Ms. Uchitel in the bankruptcy matter, pro bono.
‘Some Weird Greek Tragedy’
Earlier this year Ms. Uchitel asked Jeffrey Lichtman, the criminal defense lawyer whose clients have included Joáquin Guzmán, the drug trafficker known as “El Chapo,” for help. He agreed to call Mr. Holtz on her behalf.
“I felt badly for her,” Mr. Lichtman said. “She had a consensual relationship with Woods, no more her fault than his, but after it was over he was able to move on with his golf career, while she was stuck with the stigma of being the other woman.” But he understands Mr. Holtz’s position too. “If she didn’t want to sign the agreement, she wasn’t required to do so.”
One day this spring, Ms. Uchitel received an offer from an influencer company, telling her it could help her make between $5,000 and $30,000 a day on OnlyFans, a site where content creators often sell suggestive pictures of themselves.
“So I can work in a Starbucks,” she said, “and keep my dignity” or show her body, the one thing she fully owns, for much more. “People have called me these names for years. What’s the shame in stripping?” she said, adding, “I’ll literally be working and making money to pay back Tiger for the rest of my life. How’s that for some weird Greek tragedy?”
She declined the offer, but recently accepted $10,000 from a German production company to be interviewed as she visited the 9/11 memorial in Lower Manhattan, her first time at the museum. The producers asked her repeatedly to watch a video of her younger self, anguished at Bellevue Hospital, where she went to look for Mr. O’Grady.
“It’s hard to describe how I felt in my body,” doing so, Ms. Uchitel said. But she needed $10,000 to pay the lawyer who would help her sue Seeking Arrangement.
These are the cycles she finds herself in, making one fraught decision to deal with the one before it. “I feel there is a bomb ticking and it’s all coming to an end,” Ms. Uchitel said in her dining room, placing a plate of scrambled eggs for the dog, Mishka, at her feet.
As the summer has worn on, she has become increasingly worried about the institutional silencing of women, like the anonymous one covered in a recent BuzzFeed article about the proliferation of N.D.A.s handed out to those who engage in casual hookups with even B-list celebs.
Ms. Uchitel reads everything she can about the culture she is now an elder stateswoman of — the culture of celebrity, sex and the media.
“It’s actually terrifying when I think about it,” she said, her voice catching. “I know what they’re getting themselves into. But they don’t.”
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