The Real Rachel Uchitel

Is the most famous of Tiger’s other women looking for money, love, a rich husband, or all three? The Daily Beast’s Jacob Bernstein goes inside Rachel’s Rolodex, childhood, and nightclub history.

The opening of the Griffin nightclub at the end of April was quite a scene. Sting and Kate Hudson mingled with socialites like Lauren Santo Domingo and Lola Schnabel at the latest club to invade New York’s meatpacking district. The partying went late into the night and received ample press coverage in gossip columns like Page Six and on Web sites like Guest of a Guest, where it subsequently was referred to as the “party of the week.”

Also at the opening was Rachel Uchitel, a 34-year-old VIP hostess on the bottle service scene, a world in which guys with lots of money to burn pay ample amounts of money for a nice table at a nightclub, complete with ample booze and copious pretty young things. That night, like almost every other night she was on the job, Uchitel was running around the venue, getting high rollers in without a problem, escorting them around, and making sure their every need was attended to. She wasn’t the main wrangler working the party, but people who saw her that night, and many others, say she was hardworking, certainly not a mess, nothing truly conspicuous.

“She rubbed people the wrong way, but nightclubs are filled with dysfunctional people who might have been lawyers or doctors or done really great things if they had the attention span or the follow-through to do it.”

None of them would have predicted that she would emerge months later at the center of the most baroque sex scandal in modern sports history, the mystery woman who reportedly spoke both to Tiger Woods and his understandably angry wife shortly before some sort of knock down, drag out fight that ended with him crashing his car into a fire hydrant and a tree, with the back window smashed in by his wife with a golf club.

So who is the other woman—or to be more accurate, the most famous of the other women?

Gerald Posner: Inside Tiger’s Double Life Abby Ellin: Can a New Cub Save Tiger’s Marriage? Though some say Uchitel’s Rolodex was filled with the kind of people who keep business popping at the joints she worked—Marquee, Pink Elephant, Tao, Avenue—her main contacts weren’t stars or prominent captains of industry, at least not the bulk of them. “She’s good at her job,” says one promoter who has worked with Uchitel. “I don’t think she has the biggest power-players on speed dial, but she has rich non-Page Sixers who spend big money. In her job, you wrangle people, make sure they have a great time when they’re at the club, provide them with connections in Los Angeles and Vegas when they’re there. It’s an extended client services job.”

Full coverage of the Tiger Woods scandal But at some point this year in Uchitel’s capacity as a VIP hostess, she did meet Woods, and the road since then has been paved with gold. After The National Enquirer closed in on proof that connected Uchitel to the golfing legend, his alleged paramour hired power-lawyer Gloria Allred, gave interviews denying being a homewrecker, scheduled a press conference (presumably to announce being a homewrecker), canceled said press appearance (presumably in pursuit of a payout that The Daily Beast’s Gerald Posner estimates to be in the ballpark of $5 million), and then popped up in Palm Beach this weekend just miles away from the golfer and his wife, Elin Nordegren, who may or may not be divorcing her husband. (This weekend, Nordegren was spotted nearby pumping gas without her wedding ring on.)

Until 2001, Uchitel was a young TV producer working in relative anonymity at Bloomberg Television, engaged to James “Andy” O’Grady, a 32-year-old managing director at Sandler O’Neill. Though she came from money and had attended private schools in Manhattan, Uchitel’s early life was not without turmoil. Her parents were divorced and her father—an entrepreneur who brought cable TV to Alaska and who was by and large out of touch—developed a cocaine addiction that he died from in 1990. O’Grady’s firm had offices in the south tower of the World Trade Center, and he was killed on Sept. 11, 2001.

The following January, an article ran in The New York Times, noting that Uchitel, like many women engaged to financial services professionals killed in the attacks, was battling O’Grady’s parents over money that was left behind. “He left the money to my daughter, she needs it, and she’s my first priority,” O’Grady’s mother told the paper. “If Rachel was in real need, and he supported her, things would be different. She’s very young, I think she’s going to marry someone with a lot of money. She’s just starting her career, and she’s going to be fine.”

Rachel’s response? “Money doesn’t necessarily compensate,” she said, “but in this society that’s what we use to compensate. What else is there unless they’re going to give me some knight in shining armor?”

A few years later, Uchitel appears to have fallen in love again. At the very least, she got married, to a guy who’d been interviewing at Cantor Fitzgerald the morning of Sept. 11 and exited the World Trade Center minutes before the first plane struck.

The union lasted just four months.

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Around that time, Uchitel moved out to Las Vegas and connected with Jason Strauss, the owner of Marquee, a West Chelsea playpen for badly behaved celebrities and the people who follow their every move. Puff Daddy, Britney Spears, and Jay-Z all made appearances. They got the joint publicity and the publicity led to long lines dominated by rich businessmen (and trust fund kids) with black AmEx cards. By the time Strauss became involved with Uchitel (and gave her a job, first at his club Tao in Vegas, then in New York at Marquee), the club wasn’t truly exclusive, though it was certainly expensive.

The same description could be used to describe Uchitel. As far as her looks went, Uchitel was no runway model, but she was sexy in the slightly overprocessed way that her job demanded, with a taste for Christian Louboutin heels and a body that was, at least of late, widely believed to be surgically enhanced. When Uchitel’s relationship with Strauss busted up, she dusted herself off and moved on to other late-night locales, where she earned a reputation for being savvy and hardworking, albeit with sharp elbows and a bit too much drama.

“She was all business,” says Steve Lewis, a former nightclub impresario who now writes a column for about the industry. “She rubbed people the wrong way, but nightclubs are filled with dysfunctional people who might have been lawyers or doctors or done really great things if they had the attention span or the follow-through to do it. She gets taken to be a bitch but I found her professional.”

Among the other places she worked are Pink Elephant, Dune, Stanton Social, and then Griffin, and sources in the club industry say she left more than one of them on less than great terms.

No matter; her job was her BlackBerry, and that was transportable. Primarily, she was a concierge, a consiglière who made sure VIPs were being taken care of over the course of the night. “It’s a job where you deal with celebrities and the big bottle spenders,” says one acquaintance of Uchitel’s, a publicist with ties to the nightlife world. “It sounds more glamorous than it actually is, but it does pay fairly well.”

While Uchitel’s Rolodex may not have been composed primarily of top-tier celebrities, she did meet her fair share of athletes—among them Derek Jeter and Alex Rodriguez, both of whom she’s been linked to, albeit tenuously. (Months before her alleged affair with Woods, Star magazine linked her to married Bones star David Boreanaz.)

In June or July, by Uchitel’s own account, Woods popped into Griffin. “As usual in my job,” she told the New York Post, just before the decision to have the press conference and then not have the press conference, “I got a call from a promoter that he’s coming in. I went outside and brought him and his entire group in, walked them upstairs…I may have asked him if he needed anything.”

She told the paper it ended there, though it’s now fairly clear that she later traveled to Australia at the same time as Woods, stayed in the same hotel with him, and likely had the trip paid for by one of Woods’ companies.

It certainly looked and sounded like an affair—particularly after all the other women came out of the woodwork.

But then last week, the Gawker Media owned Web site ran a tantalizing piece suggesting the reason for her alleged payout was not that she was a mistress (at least not primarily), but rather a supplier of women. It was a delicious theory—something had to explain why Woods was allegedly willing to write her, and not all the others, a big check.

But subsequent reporting from both the National Enquirer (which initially broke the story of Woods’ affair with Uchitel) and The Daily Beast indicate she was more mistress than madam. “I don’t think she was doing anything illegal,” says the nightclub source. Adds the publicist with ties to the nightlife world: “She’s not a person I’d want to hang out with, but she’s not low end or really sleazy. I think she’s basically a girl looking for a rich husband.” Says a third source: “If she introduced him to women, I doubt it went much further than that [i.e. bringing them over to his table to make an introduction].”

Perhaps more likely is the theory that Uchitel could provide damaging details about what happened the night of the accident, having reportedly spoken to both Woods and the golf star’s wife just before his vehicular mishap.

Gloria Allred, Uchitel’s attorney, declined to comment when reached by The Daily Beast.

Uchitel spent last weekend holed up in Palm Beach, where she’s reportedly staying with her mother. Despite the fact that Woods has been tied to over a dozen other women with illustrious careers in escorting, pornography, and pancake houses, some continue to argue that Uchitel is the one he really wants—the mistress he likes best. “It looks like Elin’s going to stick around, at least for now,” Fox News quoted a source as saying. “But Tiger still loves Rachel and wants to be with her either way.”

How nice.

Jacob Bernstein is a senior reporter at The Daily Beast. Previously, he was a features writer at WWD and W Magazine. He has also written for New York magazine, Paper, and The Huffington Post.