Playing for Keeps

At the virtual gambling tables that support the strange world of online poker, the insiders have names for their prey. “Fishes,” they are called in the chat forums that accompany online games. And “donkeys.” Also, “suckers,” “muppets,” and “idiots.” By all accounts, “Darkhawk-2000” qualifies as none of these. But that didn’t keep him from losing $8,000 in a single sitting one fateful night in the summer of 2007.

In retrospect, he says, he probably should have known that it was time to quit once his bankroll had dwindled to $500. But at the time, playing it out seemed like a fine idea: lose it all or win everything back. The lights flashing from his computer screen, the adrenaline, and the late hour made the whole enterprise seem like a video game—with dollars as the points system. How simple it seemed. And yet, how perilous: his entire bank account gone in the time it takes most people to get a good night’s sleep.

Two years later, Darkhawk—a November degree candidate at Harvard—has gained back his losses and then some. In one year, he has bulked up his resources from $1,000 to $80,000. At one point, the number towered at $110,000. Most days, Darkhawk plays online poker from one to nine p.m. and often finds himself active on as many as 16 virtual “tables” at once. The life has its perks. He was due to party with Charles Barkley last year, winning two tickets to a bash hosted by the retired athlete as part of a grand-prize package in an online tournament. The loot also included airfare to Palm Springs and two tickets to watch a celebrity golf tournament. (He didn’t go, he says, only because his friends weren’t free to accompany him.) To Darkhawk, $8,000 dollars doesn’t seem like a lot of money anymore. “It’s all relative, I guess,” Darkhawk says.

“It’s definitely been a rollercoaster ride. You live and learn. There are mistakes I’ve made, but I’m okay with it,” he says. “I’m pretty proud of what I do.” But Darkhawk, who still lives at home, can’t really say the same for his parents. They’ve been nagging him to find a “real” job, and perhaps they have a point: “Let’s say you want to marry a girl. ‘What’s your job?’ ‘I’m a professional gambler.’ Like, c’mon.” Darkhawk requested his online moniker be used instead of his real name for this piece, expressing concern that his gambling activity could have ramifications for his impending graduation. He says that if he does find a good enough job, he’ll probably play poker on a more recreational level—but for the moment, the game is proving to be too lucrative to push into the realm of second options.

So what changed between that summer night of freewheeling gambling and his current success as an online player? When Darkhawk tries to explain the emotions he experienced when he saw $8,000 slip away, he struggles for words. The feeling was similar to what he imagines drugs must be like, he says finally. Something distilled, adrenaline-heavy, “scary,” even. He had messed with the wrong person, the wrong situation, the wrong set of “sharks.” For a moment in time, Darkhawk-2000 was a fish. The experience was a turning point, he says. The only way to redeem himself, he realized in the days after the fiasco, was to give the game the respect that it demanded.

You see, after that harrowing experience, Darkhawk didn’t quit the game. He vowed to play smarter. And he seems to have kept his promise.

THE MYTH OF GAMBLING

For hundreds of years, the most powerful voices in American society branded gambling a wicked sport—spittle in the face of the Protestant work ethic. Puritans drafted the first gambling regulations in the New World with self-satisfied relish. “If asked to name the greatest agencies of evil in the land,” declared one Methodist preacher from New Orleans in the late 19th century, “we would not have declared the giant evil until we had named the Louisiana State Lottery.” Preachers, the moral compasses of their day, took to the pulpit to rail against an activity in which whole pots of money hung on the whims of fortune. The hands of gamblers were unforgivably smooth, untouched by hard labor.

“When your gut tells you that it’s something to be stigmatized, it comes from somewhere—historically, it comes from gambling’s perceived threat on the moral order of the day,” says Bo J. Bernhard ’95, associate professor of sociology at the University of Las Vegas and director of gambling research. “You were supposed to gradually save up your money and put it away for a rainy day, but gambling comes along and promises something for nothing. You don’t have to save a penny a day. You don’t have to save all your life. You can win all of that tonight.”

It’s a guarantee that forms the very cornerstone of Las Vegas, an empire of gilded beauty. It’s a promise that has woven dramatic fantasies out of twinges of desire, and mind-numbing addictions out of vague curiosity. Do not doubt the mythological power of the instant win. The mere concept has been enough to provoke amateur card players into dreaming of the potentials and the possibilities, the becomings and the will-bes. No thinking, all intuition. No work, all play. This is the beauty of luck.

Take Chris Moneymaker. He may have had the name, but nobody—much less professional players—knew who he was a little less than a decade ago. Through a $39 buy-in satellite tournament online, the then-27-year-old accountant from Tennessee won a seat in the main event of the 2003 World Series of Poker, where he won the first prize of $2.5 million. The crowning of a regular Joe as World Champion had seismic effects: interest in poker spiked—a trend that has been dubbed the “Moneymaker Effect”—and hobbyists emerged from the woodwork as they realized that it was possible for the layman to overthrow the professional. The Davids rose up against the Goliaths. After all, they had luck on their side—and luck is the great leveler.

It’s an uncomfortable truth: in any one game, the worst player can beat the best player in the world. “That’s certainly one thing that makes poker sexy to the average guy,” says Matt Hawrilenko, a 27-year-old professional poker player who graduated from Princeton in 2004, where he worked in the dining halls for financial aid. “In any given day, you can beat the best. Or, certainly, in any given day, you can compete with the best. The average guy is never going to be in the NFL, but he can sit down and play with the best poker players.”

This luck-factor can detract from poker’s meritocratic sensibilities. But the fact remains that there are bad players. And then there are professionals whose faces make repeated appearances at the final table of World Series events. It’s dangerous, many professionals say, for people to play poker with the idea that luck will constantly provide an edge. More than three-quarters of all poker players are losing players (“There are a lot of people playing,” Darkhawk says. “A lot are bad”). In 2007, gambling industries—including card rooms, commercial casinos, and lotteries—grossed revenues of $92.3 billion. In other words, the streets of Vegas are paved with our losses.

William Jankowiak, anthropology professor at UNLV and former visiting professor at Harvard, is convinced of several things: most gamblers are liars, they usually remember their wins instead of their losses, and they don’t actually make much profit. In other words, compulsive gamblers have somehow convinced themselves that they are winning at an inherently losing game. “If you did all the calculations, you shouldn’t gamble. If you were really rationally put together, you wouldn’t gamble,” Jankowiak says. “There’s no way you can win over time.”

“It just doesn’t make sense to me on some level to be playing a game where you could be losing money,” adds Peter B. Gray, assistant professor in anthropology at UNLV. “On some level, I think I’m too rational.”

But while this may be true of compulsive gamblers, most professional players would argue that rationality constitutes the very foundation of their approach towards poker. Luck’s good side can push you towards a win, but professionals know that it’s not enough over the long run. They know that they need something more—and when they have it, they’re able to tame the game. That’s when luck is no longer in control. They are.

MAN OF SCIENCE, MAN OF MATH

Sitting in Dunster House on a recent evening, “Ian” is fidgety, shaking his legs and darting his fingers after a pen on a nearby desk before picking it up to twirl it into a plastic blur. He looks like a nervous student—not the stony-limbed picture of calm so familiar from televised poker tournaments. And yet Ian, who works with a student group at Harvard and requested that his real name not be used for this piece, is very much a poker player—a professional online, who says he has not gone to bed until nine this morning after a marathon game.

It’s quickly apparent that Ian brings a cerebral bent to his work. He actively seeks and hoards information, isolating and then coddling a nugget of curiosity until it blossoms into a sprawling research project. A few years ago, Ian decided he needed to understand economics, so he bought a batch of textbooks off of Amazon and EBay to work through. Most days, he says, he puts in an hour or so on Wikipedia. On a recent October afternoon, “William III of England” is open on his computer—just to look into some English history, he says. The accumulation of knowledge is like the gathering of currency: it works to your favor to have more. In Ian’s mind, college is wasted on most students because they don’t realize just how good they have it. He’s considered going back to grad school, but why should he commit seven years of his life to one academic discipline?

Ian, who graduated from a public university in the late ’90s, taught high school students for a few years, but soon realized he had no patience for kids who thought they were smarter and more hard-working than they actually were, and the “helicopter parents” who agreed. They should have all tried Math 55, Ian insists, referring to the legendary Harvard course catering to first-year math geniuses. During these frustrating years teaching, Ian played poker on the side.

“That was when I realized that, as a hobby or a part-time job, I was making far more per hour gambling than I was teaching,” Ian says, in his own version of a stock statement among professional gamblers. Disgruntled, under-appreciated—and then bewildered, struck by the clarity of the situation like Saul encountering the Lord: it’s a trajectory many working gamblers describe when they recount their transition from what some may call a “normal” life to a more alternative one. After five years teaching, Ian switched to online poker as his primary means of making money.

“My mom regularly lies about my occupation,” Ian says. “She says I’m still a teacher.”

In fact, Ian makes about as much as he did when he was teaching—around $50,000 a year. But there’s certainly a great deal less stress than before. The self-professed “night owl” likes that he can stay up until five a.m. and sleep in until noon. Ian suffers from mild carpal-tunnel syndrome, but that doesn’t stop him from playing five or six days a week, occasionally eight hours in a day. He usually has no more than 10 tables open (He has a friend with ADHD who juggles 24).

“The innumeracy of Americans really makes this possible,” Ian says about his poker profession. The “over-inflated self-esteem” of the country, combined with the seeming “disdain for math,” has made the environment opportune for learned players like himself, Ian says. More than 75 percent of players are losers, and, according to Ian, less than 10 percent of players play mathematically—in essence, fundamental mistakes that can be eliminated with simple instruction pervade the amateur scene. “Most people don’t read books, as far as I can tell,” he muses. If Ian were to give a relatively intelligent beginner a book to read over the weekend and hold a couple one-on-one sessions, he says, the student would be a winning player at the lowest limits, guaranteed.

“I’m not a very good poker player, given the people I know. But the thing is, at the hobbyist level, people make such hideous mistakes because they’ll do something like, ‘I feel lucky,’ or they think they have a read on someone when they really don’t,” Ian says. “They’re going to see someone like Phil Ivey [commonly known as the Tiger Woods of Poker] do certain things, not realizing that there might be 50 hands before, leading up to what he’s doing. But they just see this one hand and go,’I can do that.’ And they can’t.”

As the saying goes, the next best thing to gambling and winning, is gambling and losing—and that bodes well for professionals. Forget skill and luck—all you have to make sure is that you’re better than the next guy, and the multitudes that have flocked to online poker in recent years have ensured that there is a consistent crop of bad players. One of Ian’s friends said he liked gambling because he is “surrounded by inept people, yet none of them are his boss, and if they do something dumb, it makes him money as opposed to a mess for him to clean up.”

During the times he is not actively playing poker, Ian examines statistical records of his hands online to gauge which hands are leaking money and where he’s going wrong. He keeps tabs on other players for play tendencies to qualify his future decisions with that information. For all the conceptions of poker as a sport of luck, most professionals emphasize the importance of decision-making in the game. “Do I fold, do I raise, or do I call? Whoever makes better decisions wins over the long run,” Darkhawk says. “You’re always executing decisions, and you’re trying to make profitable decisions every time.”

“I always try to be very critical and keep the lookout…‘Okay, I lost money—did I put myself in a bad situation, or did I just lose money?’ ‘Okay, I won money—did I put myself in a good situation, or did I just get lucky?’ These are questions I ask myself everyday,” says Hawrilenko, one of the world’s best heads-up limit hold’em players. “People don’t do a very good job of being honest or applying any sort of intellectual rigor to try to figure out if I’m doing good or bad—and that’s a big leak in a lot of gambling.”

Hawrilenko, who now lives in Back Bay, describes his overarching perspective on poker as a “game tree.” Every time he or one of his poker friends chooses an action—whether to raise, fold, or call—he’s taking a different branch of the tree, which is composed of all the possible moves and all the possible ends. As you move up the tree, it narrows down to what is called your distribution, or the hands you can possibly hold. Professionals, Hawrilenko says, try to maximize the value of their distributions and balance the best possible hands with both good and bad hands. But even those with the heaviest intellectual machinery and the most rational approach can still be vulnerable.

In other words, don’t try real gambling if you’re not ready to possibly do it wrong and suffer the consequences. “For the majority of Americans, I’d say the best advice would be play for play money,” Ian says.

ON THE OTHER SIDE OF LUCK

According to Bernhard, the UNLV sociology professor, gambling constitutes any activity in which valuable items are wagered with no guarantee of the outcome. The description sounds a lot like poker—every hand has a good or bad outcome. It’s the mere possibility of the former, coupled with the ease with which it can happen, that draws legions to the game. But many experienced poker players chafe at the use of the term “gambling,” wincing as soon it’s mentioned and politely interrupting to clarify the distinction between gambling and card playing—well, at least their form of play.

“I don’t think poker is gambling,” Darkhawk says. “Everything I’m doing, I know and have calculated—not completely, exactly. But over the long run, I’m going to make money.” A skilled poker player will have reduced his risk until he is confident of the results of his game, according to Darkhawk. With all its connotations of irrational risk-taking and unpredictable outcomes, gambling is no longer an applicable term when the game of poker has a firm foundation in analytics and intellect. Yes, one can never determine the outcome with complete certainty, but the game is no longer a crapshoot. In fact, Darkhawk says, the odds will be in his favor over the long run.

Say a friend offers you a deal in which for every coin flip that ends in heads, he gives you $11, and for every tails, you give him $10 dollars. If you had $1,000 in your bankroll, you would be foolish not to take up the deal. The first 10 tosses might not generate any heads, leaving you $100 down—but in the larger scope of things, in a world attuned to the rules of probability, you will leave the game having gained a profit. But now, say the stakes are upped and instead of $11, your friend has to give you $110, and instead of $10, you have to give him $100. You could wipe out your entire coffer after 10 coin tosses. The idea is similar for smart poker-playing: the trick is to play at levels at which you have a negligible risk of going broke, but you’re still able to make a significant profit.

Hawrilenko doesn’t make as clear a distinction between gambling and professional poker playing, but he says that he has greatly diminished the risk factor associated with compulsive gambling. “A lot of times, when people think ‘gambling,’ they think ‘gambling your savings away,’ or playing with money you can’t afford to lose. My cousin asked me the other day, ‘So, can you sit down at the table and lose your house?’ It’s a legitimate question, but it’s taken a while to explain to my parents that if you do it properly, it’s a lot like managing your portfolios. Could you lose everything you own in the stock market? Sure you could. But you can balance your portfolio such that essentially, your risk of ruin is zero.”

Hawrilenko—who used to work in finance but now makes his living playing online poker—says that after he had played a large number of hands, he ran different kinds of win-rate analyses and determined that his chance of going bust was “pretty much zero,” which meant that he would win in the long run. And it’s safe to say that he has: at the 2009 World Series, Hawrilenko won more than a million dollars when he came in first place at an event. He took $100,688 at yet another one. But these are just incidental wins in a longer stream of acquisitions.

For his part, Darkhawk tries to diminish his chance of disaster with a simple rule: his bankroll should be at least 100 times the buy-in for a given game, to ensure that the game’s variance won’t leave him broke.

“In a lot of ways, it’s harder to be a professional gambler than to work on Wall Street because on Wall Street, you’re really screwing around with other people’s money,” Ian says. “To be blunt, a lot of them really don’t have enough of their own skin in the game.” Though some poker players might be capable of beating a bigger game, they don’t move into higher stakes because they know that their bankroll can’t withstand the variants, he says. One of the biggest mistakes a novice player can make is to be too bold, too early. “If you’re a gambler and you do something really, really dumb, and you wipe out the bankroll, you’ve just wiped out your means of making money.”

But losing—and a tolerance for losing—is also an essential aspect of successful play. Players at all skill levels will have both winning days and losing days. It’s the interpretation of these events that can make all the difference and constitute divergent perspectives on the game. As a general rule, wins on individual hands cannot be interpreted as indications of future success. Novices often fall into the trap of thinking that they are performing well when they make money on a particular hand. They focus on the intermittent rewards, rising and falling with each incremental shift in their fortunes. But for the professionals, it’s only the wide-lens view that matters. It’s the difference between magnifying a single dip or rise in the Dow Jones and seeing it from a few feet away as a simple hiccup in a concerted (and, for the expert poker player, orchestrated) upward trend. You’re not really a gambler until you’ve gone broke and made it back. “Losing is normal. You’re supposed to lose,” Darkhawk says. “Winning has to be detached from how well you’re playing.”

Case in point: In Hawrilenko’s worst month, he stepped up to a bigger play and lost about a million dollars. “That hurt,” he recalls. But the month before, he had won $700,000. And the month following also proved fruitful. Hawrilenko never totally depleted his bankroll that year—a “great year,” in fact. A seasoned player, Hawrilenko had the funds, the temperament, and the knowledge to buffer the loss of even a million dollars. In the long run, he knew, it was just a bump in the road to the top.

It’s a determinist attitude with an interesting corollary. Novice players are known for chasing the rush of big swings, not understanding that professionals purposely buffer their losses with their bankrolls. They’ll swing $500 in a day to feel the adrenaline, lose the rush the week after, and bump it to $1000, looking to find the thrill again. For one Harvard undergrad who usually plays a couple hours of online poker a day, his approach to the game differs substantially from that of a professional. Upon the encouragement of his roommate, an experienced player, the individual began playing online his freshman fall and soon found the game “addicting.” The most he’s won in a sitting is $650—but in total, he’s $200 down the hole. “There are times when I get pretty into it. Whenever I get a bad beat, it’s pretty tough to take,” says the individual, who requested to remain anonymous for legal issues. “There’s some yelling that goes on.”

Taken to a more extreme level, it’s a pattern of behavior that calls to mind the drug-user analogy that Darkhawk made as he searched for a way to describe the night he lost it all, a mindset that he associates, pointedly, with “gambling” and not poker-playing. For the pros, the Hawrilenkos and Darkhawks of the world, riding a long smooth curve of expected value and carefully weighed percentages, the adrenaline rush is largely a thing of the past.

“I don’t sit down at the poker table, and I don’t really feel that rush,” Hawrilenko says. “I find that the more logical you are, the more you try to analyze every situation, and the more you can kind of see the big picture and the long view, the less it feels like gambling.” In fact, some days, Hawrilenko just doesn’t want to play—but he has to, he says, because it supports his very livelihood.

“It’s something which is very counter-intuitive to a lot of people,” Ian says. “I laugh when people are like, ‘It’s so risky!’ Do you have money in the stock market, or do you have money in a hedge fund? Here, at least I’m more or less betting on my assessment of myself rather than handing my money over to somebody else.”

THE FAST LIFE OF A GAMBLER

A reserved, introverted man who speaks softly with a slight lisp, Hawrilenko won a large tournament at the World Series in Vegas this past summer and was swiftly reminded just how unevenly his own lifestyle matches up with the stereotype of the poker champion. “People were asking me, ‘So how are you going to celebrate it? Are you going out to get booze and strippers?!’” Hawrilenko recalls. “Most of my housemates don’t really drink that much, and I don’t really drink and party that much in Vegas. We celebrated at 2 a.m. by going to the Tropical Smoothie Café.”

Hawrilenko says that there are plenty of low-key intellectual players like himself, but the flamboyant, self-described “high rollers” tend to get more camera time, fueling a media image of a scene of excess, debauchery, and ballooning egos. “My friends and I, we laugh at these guys. They have their bling and their backwards hat”—Hawrilenko makes the vigorous motion of pulling an invisible hat back—“and their sunglasses on”—he puts on a pair of shades. “These guys are so cocky that they can’t possibly be good. If you can’t consider the fact that other people have brains, too, how can you play at a high level? You can’t.”

But there’s something to be said about the lure of the game—not only in the monetary rewards that its most skilled players can reap over time, but also the sheer thrill of engaging in an environment often depicted as risqué and fast-paced, a break from the mundane nine-to-five job. As UNLV professor Peter Gray observes, many players derive their enjoyment from adopting a new persona for a limited time—the incognito nature of an online poker table, the stoicism needed at a live game, or the chance to escape for a weekend to an exotic island.

In the past, Darkhawk has tried to win the “Aruba Poker Classic” package, which includes airfare and a week-stay at a hotel, all advertised with the help of scantily clad females. “I was kinda close,” Darkhawk says. “I was getting really excited. It’s not like going to a poker tournament—it’s like a vacation.” He says the “Caribbean Poker Adventure” sounded pretty good, too. For many professionals, such luxuries are close realities proffered by the world of gambling.

And when you’ve played the game well enough so that it’s no longer playing you, it’s a hard offer to resist.