It's 11 p.m. at Caesars Palace on the Vegas Strip. During any given night a smattering of sketchy characters can cause concern for casino security. Cheats, pickpockets, confidence men and prostitutes like to mix among the straight clientele. But what about the spacey-looking blonde, carrying a backpack and wearing a miniskirt, looking as if she's searching for the next party? She'd be easy to ignore, and that's precisely the point. Wending through the craps pit and past the Pai Gow tables, she makes her way to the high-limit blackjack area, sits down and immediately orders a Red Bull. She extracts a fistful of Daddy's hundreds out of her backpack, cashes in and begins to play.
Though she acts as if she's high on ecstasy and seems poised to make a break for the dance floor, she stays put and wins. Then she wins some more. By nine o'clock the next morning, this supposed club kid, who appears too out of it to find an elevator, has beaten the casino for more than $80,000. Her happiest moment comes when she doubles down with a soft 20—and wins. Nobody suspects that she's an expert card counter who realizes that, given the high number of aces and 10s in the deck, going down and dirty is the only sensible thing to do.
"People wondered what I was up to, but I had been there all night at that point, and it seemed like I was having a lot of fun," says Joanna Pandini, who's also played at being a divorcée, a wealthy real estate investor, a hooker, a girlfriend and a shrew—all in order to, legally, separate casinos from their cash. Pandini (a pseudonym) is a member of a card-counting team and emblematic of the new generation of female gamblers: they play with an edge and are every bit as competitive as their male counterparts. "That night at Caesars, I kept grinding my jaw, trying to bet my jewelry, letting the dealer think I was dumb."
Blonde-haired and pop-star pretty, the 30-year-old San Jose, California-based Pandini is anything but dumb. She works as a chiropractor during the day and earns six figures a year counting cards on the side—employing a strategy in which she makes her largest bets when the deck is advantageous to players. Though this is not even close to cheating, casinos hate any player with an advantage and aggressively ban those who count. She fell into the lucrative profession through a friend, who happened to be living with an accomplished counter. Pandini says that she loves nothing more than going out with her teammates and bringing down the house. It's a nice way to earn a tidy piece of pin money, but, as she acknowledges, it also exacts a toll on any woman who wants a family and a life outside of the casino world. "If I'm given a choice between Prince Charming and gambling, that's a tough one," she says. "Women are programmed to get married and have children. Turn the guy down and you wonder what will happen if you never meet someone again."
Though Pandini has been through her share of rough experiences—like the time hotel security dragged her and a few team members into a back room, screamed at them, threatened them and banned them from ever entering their casino again—she finds the excitement and money too great to pass up. Plus, like a lot of successful female gamblers, she seems drawn to succeeding at something that few other women would dare to try.
It's the same thing with Evelyn Ng, an up-and-coming poker player raised in Toronto but now living in Las Vegas. The statuesque Ng was introduced to gambling as a teenager, hustling pool in the clubs around her hometown. "When guys lost to me," remembers Ng, "they would say, 'You're pretty good for a girl.' I'd look at them and say, 'Well, you must be pretty bad for a girl, 'cause I just kicked your ass.'"
A ninth-grade dropout, Ng was introduced to poker soon after she turned 18 and found herself working as a dealer at one of Toronto's underground clubs. She hadn't spent a lot of time thinking about the game, but became intrigued when she noticed that the certain players always seemed to win. Once she realized it was more than luck, Ng wanted in. She read a couple of David Sklansky's books and promptly began to terrorize Toronto's low-stakes games. Upon hitting Las Vegas, in the mid-1990s, she understood how to parlay her gender into profits at the poker table. "A macho guy loses a couple of hands to a young girl, and he thinks he needs to go after her. Next thing you know, he starts making mistakes because he thinks he needs to win," says Ng, long-legged and pretty, chilling out between tournaments at the Bellagio. "Then there are the guys who soft-play me because they want to be nice. Or else they think I'm not capable of making moves."
Big mistake. Ng is every bit the cash grabber that any man at the table might be. This lesson was learned by young poker pro Leo Alvarez when they confronted each another during a major Texas Hold'em tournament. "Before the flop, I had two jacks and raised Leo," remembers Ng. "He reraised me a big amount, and I called him—thinking that I had the worst hand but wanting to see the flop. I didn't get my jack but an ace hit the board. I checked, and he bet a really big amount—like one-third of my stack—but I didn't think he would bet that amount with three aces, and he wouldn't have reraised me before the flop unless he had a big pair. So he had to have kings or queens, and I didn't think he believed I had the stones to bluff at that point. So I went all in. He turned up his cards, showed two kings and said, 'If you have two queens, you are the best player in the world.' I let him think I had aces, but it got back to him that I only had jacks, and he was very bothered by it. He talked to himself for the next few days."
That was great for Ng, but over time she'll lose the potential to capitalize on her gender. Players will come to realize that she'll bluff with the same ferocity and gutsiness as any man. Such is already the case with Mimi Tran, a Vietnamese émigré who can't afford not to beat the pants off of her opponents. She's supporting 25 family members—10 in California and 15 in Vietnam—with her poker winnings. At the table, she's super serious, focused on the game, totally dispensing with banter. In a heads-up contest that she won against one-on-one specialist David Oppenheim, the sunglasses-wearing, leather-jacketed Tran played like a machine, enduring enormous swings without emotion and chipping away at her opponent until she managed to corral the last of his chips.
Tran is quick to point out, however, that poker was not always so profitable for her. In 1991, she was a broke player with no job (due to a back injury), piddling amounts of disability, two kids and bleak prospects. Then she happened to meet poker star/philanthropist Barry Greenstein (currently regarded as the game's top high-stakes practitioner) and things slowly turned around—to the point where she now plays in and beats the $500/$1,000 games in California and Las Vegas. The two of them made a deal: Tran taught Greenstein to speak Vietnamese; he taught her to play poker. "He showed me everything about the game—how to beat aggressive players, passive players, good players, bad players," Tran says, over a steak dinner following her defeat of Oppenheim. "Now I am thought of as an aggressive player. I don't play chicken. When I have good cards, I raise. People don't get the chance to stay in a hand for cheap. Most importantly, Barry taught me how to find games in which I will be a favorite."
Ironically, Tran's family members remain convinced that poker is gambling and that she is lucky. But Tran understands that the game is all about hard work and dedication. In light of her success, Tran remains indebted to Greenstein, who still serves as her poker sensei. "In 1991, Barry told me that his lessons are a million-dollar gift," Tran says. "Four years later"—after she made her first million—"I called him and thanked him for the gift. I originally wanted to win $100,000 and open a hair salon. But now that I've learned to beat the game, it would be stupid to stop. No job can pay me the way poker does."
Tran is not the only world-class woman with a male tutor to thank. Annie Duke learned about poker from her big brother Howard Lederer. His lessons not only preceded her becoming the most famous woman in poker—a point punctuated by the fact that NBC is shooting a pilot for a sitcom loosely based on her life (a divorced woman who's playing poker professionally while raising four children)—but they also provided the foundation for her to become an impressively winning player. In 2004, her best year yet, Duke cleared just shy of $2.5 million in tournament winnings. Her most stunning victory of the season took place in September at the World Series of Poker Tournament of Champions on ESPN, during which she cleared $2 million by outlasting a murderer's row of poker professionals: Doyle Brunson, Chip Reese, Phil Ivey, Greg Raymer and brother Howard among them. Ultimately, it came down to Duke and Phil Hellmuth, a notorious psych-out artist. "I like Phil, but everybody knows he's a baby who spends a lot of time berating other players," explains Duke, who was just a hair shy of earning a PhD in psycholinguistics before taking up poker. "I know him well enough that what he said didn't bother me. I agreed with him and replied, 'Yeah, Phil, I am terrible. I hope I get lucky.' It diffused things and tilted him a little bit. When he told me that I'm no good, it seemed like the obvious response."
In terms of how women handle themselves at the poker table, Duke believes that they have some advantages and some disadvantages. On the upside, female players tend to be more intuitive. On the downside, though, girls growing up have historically been discouraged from becoming mathematical and competitive—two big detriments for anyone who wants to make it in the poker world. Slowly, however, the gender biases are changing. Encouraged by players like Duke, increasing numbers of young women are getting into poker. "Even those who don't play tell me that I'm inspiring them. [My success] shows that women can do anything," explains Duke. "It's a cool thing to have results that are better than almost any man on the planet. I can now say, 'Don't call me one of the best women players in the world. Call me one of the best players in the world.'"
Women are matching up against men, and beating them, in locales beyond the casino. In Costa Rica, an American woman runs one of the more successful sports betting operations; in New York, a top backgammon player generates a healthy living by playing against men online; and in Dallas, a female pool shark pockets a steady income from hustling pool.
The pool shark, a rangy redhead by the name of Orietta Strickland, frequents the local billiards halls and bars where she supplements her straight gig (as a computer operator with MBNA) by hustling dinner money off of unsuspecting opponents. It may not sound like much compared with what the Annie Dukes of the world pull down, but the hours are short, the money adds up and the swings are virtually nonexistent.
Plus, she gets to beat the pants off of men. And, unlike Mimi Tran, who's in it for the Benjamins—anybody's Benjamins—Strickland finds it particularly pleasurable to humiliate males at 9-ball. "I remember being in a bar one night and a guy said that he could outshoot me with one arm," recounts Strickland. "I was quickly ahead by $20. Then he told me that he plays better two-handed. He played with both hands and I got my lead up to $300. He wanted to play double or nothing, and I told him that I would play one last game for $300. I won, took the money, and he started cursing me out. I got an escort to my car and went home with $600 for a few hours of work."
Tonight, Strickland is plying her trade at a pool hall called Clicks. It's a modern place with a DJ and a young clientele. She's shooting balls around the table, hoping for somebody to come over and challenge her. When a guy in his 20s snaps at the bait, she gets ahead by a couple games, then slows down and lets him win. He knows he's outmatched, but the stakes are low enough—$10 per game—that he doesn't seem to mind very much. Her style is friendly and easygoing. She compliments him on his good shots, blows the ones that don't mean very much to her, and is careful to maintain the illusion that he actually has a chance at beating her. Finally, though, after about two hours, she runs her lead to $100. That's when the guy pays off and goes to shake her hand. But Strickland's having none of it. She gives him a friendly hug while pocketing his dough.
Strickland figures that she's made a customer for life. And, no doubt, he's just discovered the upside of losing to a woman.
Michael Kaplan is Cigar Aficionado's gambling columnist.