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All in

With an Ivy League education and a proud identity as a gay woman, top-ranked card player Vanessa Selbst is changing the face of professional poker

Author Steve Friess Photography Erin Patrice O’Brien

poker

Her cards were lousy: a five and a two, both spades. Not a hand that typically would embolden a player, especially not one in the final hands of a World Series of Poker event for the first time. But the first chance she got, Vanessa Selbst raised to $66,000, enough to prompt a few others to fold. Across the table, though, an opponent sat with that deadliest of poker hands, a pair of aces. Selbst couldn’t know that at the time, but she might have suspected he had a strong hand when he raised her $210,000. The typical move, with a measly five and a two, would be to fold. “All right, I’m all in,” the then-21-year-old replied, with a look that poker announcers would routinely refer to as “stone-faced” in the coming years, tidily shoving her neat stacks of chips—nearly $400,000—toward the center of the felt.

——

This was 2006, her first time at a “final table,” meaning she was one of nine finalists from a field of more than 1,900 players. The ultimate prize: $800,000. “Vanessa on the verge of self-destruction,” an announcer would shriek as he narrated the ESPN replay of the scene a few months later. “What was she thinking?” Selbst stood up from the table as the two hands were revealed, the crowd gasping and laughing as they saw the aces. “I got nothing!” Selbst said, a big, sheepish grin on her face. “Bad read.”

At that point, she still could have won the hand. In Texas Hold ’Em, the player’s hand is combined with the five “community” cards dealt on the table to combine for each player’s best five-card poker hand, and another three spades could have given her a flush. But then the dealer laid down the first three community cards, known as the flop, which included an ace and no spades. It was over. Selbst stepped away with a seventh-place finish and a payday of $101,000—and a reputation as a reckless aggressor.

Had she not gone on in the years to come to win three WSOP events, vault to No. 1 for a few weeks this past June in the Global Poker Index ranking (the first and only woman ever to do so) and amass a career of tournament victories that have won her more than $10 million, Selbst’s first wild moment in the spotlight would likely have been forgotten along with so many other absurd plays by overambitious newcomers outrunning their luck.

Instead, that hand is now revered as early evidence of a master poker player in the making. Phil Hellmuth, the veteran pro who has won the most WSOP tournaments in history, recalls hearing back then about the woman with the “really, really spiked-hair look who was allegedly from some Ivy League school” and who tried to bluff big with a five and a two. “People started talking about her and about how crazy she was,” says Hellmuth, adding this bit of likely revisionism, “and how good she was.”

Selbst herself now looks upon that move as a rite of passage. Just as the greatest baseball sluggers also top the strikeout lists, she sees honor in going big—win, lose or draw. “There’s a really fine line between being aggressive and being reckless,” the now 30-year-old Selbst tells me, “but if you’ve never busted out of a tournament on a huge bluff, if you never come and tell me stories of some ridiculous bluff you made that got called, you’re not bluffing enough.”

The WSOP season is comprised of 65 different events. The most famous of them, and the one most covered by ESPN, is the Main Event, the climax of which takes place every November in Las Vegas. Of the more than 6,500 players drawn to the July first stage of the No Limit Texas Hold ’Em championship, which costs $10,000 to enter, men outnumber women by at least 20 to 1. A more damning stat: In a 45-year history featuring hundreds of thousands of players, only one woman, back in 1995, has made it to the final table of the Main Event.

Selbst didn’t make it to this year’s final table, which takes place this month. Most well-known pros typically don’t fare well in Main Events, in part because they draw a lot of unknown players looking to make a name for themselves, often by making unpredictable, illogical and aggressive moves against their famous opponents. This year, the “last woman standing,” as poker bloggers actually refer each year to the female who survives the longest, busted out in 77th place.

Nevertheless, Selbst remains the most successful and perhaps most recognizable female face in the game today. As such, WSOP brass and the poker media know that Selbst has tremendous potential to alter the perception that the game is unfriendly to, or unpopular among, women. Thus, following a run of tournament successes in the first half of 2014 that earned her more than $2 million—and that historic No. 1 ranking—she graced the covers of some of the game’s most popular glossy magazines, including Global Poker Index, which declared her “Poker’s Leading Lady.”

“She’s terrific because she breaks down barriers and proves to people that the game of poker is for everyone,” WSOP spokesman Seth Palansky says. “Despite the belief that it’s a male-dominated sport, she’s proven she can dominate this game. Everyone who can get two cards or four cards or whatever variance of poker you’re playing, the cards and your smarts decide your success in the game.”
Of the successful women in professional poker other than Selbst, the only two with any significant profile are Annie Duke, who finished second to the late Joan Rivers on the 2009 edition of Donald Trump’s reality TV show “Celebrity Apprentice,” and Oscar-nominated actress Jennifer Tilly, who won WSOP’s Ladies Event and $158,000 in 2005. Ever since, Tilly has been “more of a poker player than an actress,” Selbst says.

Both Duke and Tilly, however, are women who often play up their femininity. Selbst—who is married and gay, wears no makeup and shows up to tournaments in her usual uniform of T-shirt and jeans—is a decidedly different flavor.  “Anytime there’s someone who looks like me who is getting attention, it’s a good sign,” says Selbst. “It’s cool that I can be on TV and represent lesbians—and not even lesbians but masculine-gendered women, which is something that you don’t really see a lot of depicted in the media. I don’t know what effect it’s having, but it’s got to be pretty positive.”

Selbst got an early taste of what it’s like to be different, and to insist that she be accepted on her merits, when she was denied a tryout for the boys’ varsity baseball team at her high school in Montclair, New Jersey. She fruitlessly harangued the coach and school officials, but that denial and the ridicule she suffered from her peers for trying would help “develop kind of a chip on my shoulder about it,” she says. “I definitely knew what I was getting myself into, and I just didn’t care, because I just loved playing baseball.”

Her entry into the poker world was less fraught, but still a surprising career choice for a nice Jewish girl with a law degree from Yale. She didn’t seriously consider it as a possible occupation until, as an undergraduate at the prestigious university in 2003, she learned that an unknown online player named Chris Moneymaker had won $2.5 million in the WSOP Main Event. Curious, she got herself an online account, started playing cash games and realized she was good. By the time she graduated, she had $150,000 in her poker account.

Selbst tried, briefly, to do things the “normal” post-Yale way, taking a job as a management consultant in the New York office of powerhouse firm McKinsey & Company. But the cards kept calling her back. “I was playing poker for one-third the amount of time and making three times as much money,” she recalls. “I was like, ‘Okay, I’ve got to give this a shot.’”

Even before Selbst began her brief stint at McKinsey, poker had provided her with an unexpected source of solace. She was at the beginning of a year in Spain on a Fulbright scholarship when her mother, Ronnie, died at 52 from a freak abdominal blockage. To cope, Selbst says, she delved deeper into the poker scene in Europe. By the time she returned to the U.S., and her mother’s best friend, Susan Green, took her to the bank to apply for a loan to buy an apartment, she was listing “professional poker player” as her job. “I remember giggling to myself that that’s how she thought of herself,” Green says. “Of course, it was not at all a silly thought.”

Even as Selbst built up her reputation and bankroll, she continued to think differently from her peers, who, by now, were her poker colleagues. In 2008, she reduced her poker playing in order to attend Yale Law School, where she hoped to obtain enough legal expertise to someday help her use her poker winnings for social good. But a year into getting her law degree, in 2010, Selbst again returned to poker in a big way: She notched a $750,000 prize at an event at Mohegan Sun casino in Connecticut and $1.8 million at another in Cannes, France.

Selbst was exceedingly generous to her classmates, flying a group to Cannes for that score, and traveling with her showed them how differently she viewed money. Seth Wayne, a classmate, was on one vacation with Selbst in Mexico when his new friend discovered that $12,000 had been stolen from her luggage. “For Vanessa, being ripped off $12,000 was probably enough to ruin her day—but not her week,” Wayne says. “It’s not that she had so much money that she was uncaring or arrogant in her treatment of it, but as a poker player she constantly dealt in large gains and losses. Having the chutzpah to tolerate large setbacks and the security that you will come out on top in the end has to be in the DNA of a successful poker player, and Vanessa certainly doesn’t lack chutzpah.”

I watched Selbst for a few hours at the Rio All-Suites Hotel and Casino in June as she toiled through the first afternoon of WSOP Event No. 35, a $5,000 buy-in No Limit Hold ’Em match that drew 550 players. In a sense, it was a day at the office for her: taking part in some of the smaller, less notable tournaments of the season in an effort to finish “in the cash” for her investors—who usually pay buy-ins for famous pros in expectation of a good return. It’s impossible for spectators of live action to know if Selbst pulled any crazy bluffs during those hours, because at no point was she called on a weak hand and forced to show her cards. A successful bluffer, of course, will force opponents out of the game before ever having to show his or her cards.

In this case, it didn’t matter. She’s Vanessa Selbst, so legions of the admiring and curious stand with me for hours watching her typically inscrutable, intense-to-the-point-of-fearsome gaze, focused most often at some spot on the table. There’s little to see, but folks like Holly McDaniel of Chicago are immovable. “She’s one of the greatest players there is,” McDaniel tells me, in the hushed tone typical of golf or tennis spectators. “What she’s doing is amazing.”

A month later, in Brooklyn, I find a more approachable Selbst—but a woman who is still cautious about how much she reveals. A few times, she cuts off her wife, Miranda, who has far less experience with journalists, when she veers toward topics that Selbst doesn’t want on the record. They have a cozy home they share with their two Chihuahuas, Indie and Papi, far from the Vegas glitz, with just one piece of evidence of Selbst’s illustrious career on display in their living room: a silver trophy from Poker Stars, her sponsor, in honor of the day—January 14, 2013—she became the “highest earning female poker player of all time.” Only when asked does she show off one of the few indulgences bought with her winnings, a vintage Ms. Pac-Man arcade game in her office.

This, Selbst says, is where she prefers to not constantly think about being a famous poker figure. To Selbst, it seems, hitting No. 1 was like being the coyote who catches the roadrunner: Now what? She could keep playing at her current pace to regain her No. 1 rank (she fell to No. 2 after busting out of a couple of tournaments this past summer), or she could play less and focus on her philanthropic efforts, like Venture Justice, the “venture capital firm for social justice causes,” as Selbst calls it, which she founded last year. Its first goal, to be reached by the end of this year, is to fund a legal fellowship in police accountability. Selbst got the idea after a disturbing incident she endured while co-hosting a party at Yale for her fellow gay law students. She was thrown against a wall, placed in a choke hold and arrested for disorderly conduct and other charges after persistently asking police officers why they were breaking up the party. “I’m a wealthy white woman, and I can feel this bad this one time in my life, and there are people for whom that’s just their daily reality,” she says.

“I don’t need to make the most money,” Selbst says when asked how she plans to split her time between her poker career and Venture Justice. “I’m very happy with my life the way it is. I’m very comfortable. There’s just stuff that I want to do that has nothing to do with poker, and I don’t want to put that off.”

Thanks to social media and YouTube, Selbst’s wildest poker moments have become the stuff of legend. One such moment has resurfaced time and again. In 2011, for a televised tournament featuring well-known pros, she was going head to head with Antonio Esfandiari. Esfandiari, already a big star at the time, is now the world’s winningest poker player, with lifetime tournament earnings exceeding $28 million. In the eight-minute confrontation, Selbst drew a queen of spades and a nine of diamonds, a middling, uninteresting hand. Esfandiari drew a nine and a six, both hearts. Other players at the table folded before the flop, which added a six of spades and a four and 10 of diamonds to the mix. That gave Esfandiari a pair of sixes and Selbst a trio of diamonds—the best she could have hoped for with the remaining two common cards was a flush. Of course, neither player yet knew what the other had.

Selbst’s odds were lousy, but she bet $2,300 anyhow; Esfandiari called. The fourth card on the board was a three of diamonds, which improved Selbst’s prospects of a diamond flush but left her, thus far, with nothing. She checked, meaning she opted not to bet—a move that often signals a weak or uncertain hand. Esfandiari bet $5,200 and Selbst, to the surprise of the announcers narrating the hand, didn’t back down. Instead, she raised her opponent another $16,200. He called.

The final card, known as the “river,” was a two of spades. Esfandiari had her beat—but he didn’t know that, and Selbst’s blank face betrayed nothing. She bet $59,700 more, leaving Esfandiari baffled over whether she was bluffing or, perhaps, held a five, which would have given her a straight, a better hand than his sixes.

Esfandiari squirmed. He shot looks at Selbst, who didn’t look back, instead training her eyes straight ahead at the felt. He clearly agonized for a few long minutes, then flicked his winning hand away in surrender.

As Selbst pulled in the heaps of chips and organized them in front of herself, Esfandiari and others bantered about what she might have had. Selbst, meanwhile, remained tight-lipped, her expression grim, giving no sign that she’d pulled off a heist. Later, everyone would see on TV how she had played it. Several versions of the footage have racked up thousands of views on YouTube, and her performance serves in poker circles as a master class in the art of bluffing. Still, though, it makes one wonder if she wasn’t tempted to crack a smile.

“It’s just better to keep people guessing, especially after a big pot,” she says. “Keeps them off their game. If you always let them know when you bluffed, then when you don’t show that means they folded correctly, and that’s too good for their confidence. So it’s better to just never let anything on.”

Steve Friess, a journalist based in Ann Arbor, Michigan, has written for The New York Times and Newsweek. He spent 10 years living in Las Vegas and always bets on black.

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