The Secrets of Tiger Woods’ Many Sordid Affairs Revealed

Kevin Fallon
·9 min read
Mike Ehrmann/Getty
Mike Ehrmann/Getty

Do you ever get the feeling that everyone is talking behind your back? Imagine how Tiger Woods is going to feel after part two of the HBO documentary Tiger airs Sunday night.

The installment parses the all-time golf great’s extreme philandering and jaw-dropping infidelity—there’s a rumor that the New York Post ran more covers on the salacious details than on 9/11—the crumbling of his marriage, the shattering of his reputation, his humiliating DUI arrest, and his unraveling as injury and public shame torpedoed his career.

Then again, that’s also why Tiger, and its quick-moving three hours over the course of two weekends, is so good—and so refreshing.

It’s been a boom time for biographical documentaries of living legends, with Tiger joining the likes of Hillary Clinton’s Hillary, Taylor Swift’s Miss Americana, Michelle Obama’s Becoming, and the most direct comparison, Michael Jordan’s The Last Dance.

The glaring difference between those projects and Tiger is the subjects’ participation, going so far as to be a part of the conception and produce the documentaries in addition to being interviewed for them. They’re all fascinating, but even the most forgiving critics would scoff at the extent to which they’re all hagiographies, allowing a halo’s glow to lighten even the darkest times of their subjects’ lives.

It’s the trade-off in things like this: Obviously you want the person’s participation, but what is the cost to the storytelling?

And therein lies the juicy hook wrangling curious viewers to this dramatic recounting of the historic rise of one of the most significant athletes the U.S. has ever seen, and his turbulent fall amid tawdry scandal. It’s not afraid of getting into the dirt.

Tiger is missing the three most authoritative voices when it comes to telling the story of Tiger Woods: his late father, Earl, whose domineering pressure and intimate friendship shaped every bit of the man and athlete Woods would become; Elin Nordegren, Woods’ ex-wife whose life was torn apart when the affairs made global headlines; and Woods himself.

What it does have, however, is the VIP host who would recruit girls for Woods, Charles Barkley, and Michael Jordan at clubs; the Vegas madam alleging that he would sometimes request from her 10 women at a time; and the woman who, through no fault of her own, became the catalyst for the fall of Woods’ empire: Rachel Uchitel, the former New York club hostess who says that, 10 years later, “My name hasn’t lost the stigma at all. It’s always been ‘Rachel Uchitel, Tiger Woods’ Mistress.’”

Ex-girlfriends who were ghosted and childhood friends who were cut out of his life talk about the Tiger they knew, and their concern over who he became and his changing priorities. His former caddie, who had Woods as his best man at his wedding, speaks about being dropped to the curb after years of service and never contacted again. Everyone reacts with horror and pity to the upsetting footage of Woods’ fateful 2017 traffic stop and DUI arrest.

But Tiger is ultimately a story about triumph, because that’s what Tiger Woods’ greater story is.

Last weekend’s Part One chronicled not just the energy it took on young Tiger’s part, but also his father’s relentless—and sometimes overly aggressive—dedication to helping his son succeed as a Black person in elite golf, and Tiger’s transformation into a cultural phenomenon.

It talked about how he broke age and color barriers, how he rewrote the book on sports marketing, how brands would use racial discord for corporate activism, and the complicated position he was put in as a multi-racial athlete with the expectations of the world on his shoulders.

But Part Two tunnels its way to rock bottom in order to lend context to his incredible return to glory: In 2019, following four back surgeries and an avalanche of distracting personal controversy, Woods claimed his fifth Masters title, dubbed “the greatest comeback in sports history.”

The most addicting part of Tiger is its mischievous edge, an implicit contract with the audience that it’s going to “go there.”

For all the rightful talk about his accomplishments, it’s these elements that are likely going to garner the most attention. Former National Enquirer editor Neal Boulton is one of the installment’s pivotal narrators. He proclaims Woods as the ultimate cautionary tale: “Be careful of the image you create of yourself.”

The most sordid details surface, as is their wont, in Las Vegas.

Las Vegas became Woods’ escape from the pressure of being Tiger Woods. Tiffany Masters, who used to work as a host for his trips to Sin City with Jordan and Barkley, remembered, “In that entourage, Tiger was a bit of a geek. It wasn’t like he was mack daddy, like Casanova.” Woods would ask Jordan what he was supposed to say to the girls that Masters and the other hosts would choose to party with them, and Jordan told him, “Tell them you’re Tiger Woods.”

According to Masters, Woods’ sexual encounters didn’t slow down when he married Nordegren in 2004. Biographer Armen Keteyian said, “His ability to live a double life began in Vegas.”

Before Woods’ affair with Uchitel heated up the watercooler, he almost got caught with another woman. The National Enquirer got a tip about his torrid sexual relationship with Mindy Lawton, a hostess at the Perkins restaurant near his home with Nordegren. When they were together, he made a careless mistake, unaware that reporters from the Enquirer were tailing him.

One night they followed him to a church parking lot where he and Lawton had sex. The reporters took photos and even collected the used tampon that Lawton had discarded to keep as proof.

When the photos were too blurry to use, the tabloid bargained them as collateral: If Woods agreed to appear on the cover of Men’s Fitness magazine, which shared an owner with the Enquirer, they’d kill the Lawton affair story.

But it wouldn’t take long for Woods to get caught again.

Rachel Uchitel worked at the exclusive Griffin nightclub in New York, which was frequented by the likes of Drake, Rihanna, Beyoncé, and Jay Z. One night she was working and saw Woods sitting and sipping his drink alone. She made small talk with him, since it was her job to make sure VIPs were enjoying themselves. At the end of the night, he asked for her number. By the time his car reached the next block, he began texting her.

He offered to fly her to Orlando, where he would then meet her. “That was the first night I had sex with him,” Uchitel says. “I remember thinking with him, how am I ever going to be with a mere mortal ever again?” He would refer to his time with her as “plugging in,” his time to get recharged away from the madness of his professional life.

The Enquirer had been tracking him since the Lawton story. “Tiger Woods, like so many powerful, wealthy celebrities, felt that he could get away with anything, and unfortunately that wasn’t the case,” Boulton says.

Woods had invited Uchitel to join him at the Australian Masters. An Enquirer stringer trailed her arrival to his hotel room. No matter what his team did, they couldn’t kill the story.

When Woods got back to Florida, he warned Nordegren that the story was coming, but swore it was false. He put Uchitel on the phone with her for 30 minutes in an attempt to convince her. Days later, Uchitel and Woods texted each other, relieved. That night Uchitel got a call from Woods’ phone. She answered, “Hey babe, I thought you went to sleep.” It was Nordegren: “I knew it was you.”

The affair was the perfect opportunity for those who didn’t like Woods to bring him down. Other women came out of the woodwork. It seemed like one every day. People started to delight in his tabloid comeuppance. But the thing that took him down wasn’t sex. These weren’t one-night stands. He had relationships with the women. They all loved him. They were heartbroken.

What’s so well done about Tiger is that it recognizes that this chapter of his life is not just part of his story. It’s part of their stories.

You see the hordes of paparazzi hurling slurs at Uchitel as she walks down the street. You watch Nordegren hunted by them. The amount of people in his life who were cut off completely from him at this crisis moment is astounding. Uchitel says she only heard from him once, when he told her that she was being offered a confidentiality statement and she should ask for as much as she can: “I think, to him, that was the only way to love me at the time.”

The climax of all of this is the 2017 DUI tape. It’s excruciating to watch.

The dashboard camera footage from the police officers’ cruiser reveals that Woods didn’t even know where he was when he got pulled over. They administer a sobriety test, asking him to recite the alphabet backwards. He thinks they've asked him to sing the national anthem. He had five different prescription drugs in his system, and you watch as he sits in his holding cell, hands shackled behind his back, as they all kick in and an incoherent man behind the wheel becomes a pathetic, passed-out one in police custody.

This is all necessary information and crucial footage. It would be so insightful to hear what Woods, who has, for all of his fame, always been a public enigma and rarely candid or deep with the press, has to say about it all. But if he had been involved, the footage may not ever have been included.

It’s refreshing to be reminded that an icon’s painful history is a part of their legacy, and that ignoring that does a disservice not only to what they endured and who they are, but to what they accomplished. It’s a delicate, tricky shot to take, but Tiger sinks the putt.

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