Anthony likes to talk about how the bills felt in his hand when he first hit the big time playing online poker.

He was a sophomore at the time, with only a year’s worth of experience playing on the internet, but he didn’t get excited when the teller at the Bank of America on Elm Street handed him a thin white envelope packed full of cash. He waited until he was in the parking lot before opening it for inspection. There were 60 bills inside, all of them hundreds. The stack wasn’t excessively large, but it had a pleasant heft to it when he weighed it in his hand. It was the biggest sum Anthony had ever handled — and more than most Yalies have ever laid their hands on.

Anthony, who asked not to be identified by his real name, is part of a small community of students at Yale who have more than a casual interest in the game of online poker. Most are regular students who attend classes, keep up their grades and have serious plans for the future. They include varsity athletes, future CIA agents and aspiring lawyers who have little more in common than a shared affinity for risk, a love of fast profit and a competitive streak that compels them to continue playing when others would cut their losses.

When they started playing a few years ago, online gambling was still gathering steam as a global phenomenon. Now it is a $12 billion industry with hundreds of websites, millions of customers and a library’s worth of specialty literature. Had it not been for a law passed in October that banned most forms of online gambling in the United States, the spectacular growth spurt might have continued unabated.

The law made it illegal for Americans, who account for half of the industry’s total income, to cash out on their winnings in the United States. As a result, major poker sites saw their stock prices plummet, and some stopped serving American customers altogether. For the most part, poker players at Yale believe the law is unjustified and unenforceable. But a minority has taken the ban as a cue to put an end to their online gambling careers.

Eric Sandberg-Zakian ES ’07 was working as a summer intern for his state senator in the House of Representatives when he saw the bill being discussed on closed-circuit television in his office. He reacted strongly to the news. What he had viewed as a benign pastime was going to be condemned as an illegal activity; if he continued to play, he would be considered a criminal. Adding insult to injury, his favorite website had announced that it would no longer serve anyone with an American bank account. He decided to get out of the game.

“It was time for me to start applying to law school. I cashed all my money out and started working again,” he explains. But law school was only a part of his decision; Eric would not continue to gamble if it meant that he would be at odds with his community. “Really the decision came down to the fact that a lot of people disapproved of what I was doing, even though I thought it was legal,” he says. “I didn’t want to be doing something questionable in my community’s eyes.”

Eric had been playing for a just over a year when he decided to quit. By that time, he had become an accomplished player — turning a profit of $60-80 for every hour he sat down to play. Compared to the more serious gamblers at Yale, Eric’s habit was relatively benign — 10 hours per week with frequent breaks. Even so, it occupied a large part of his life, at times intruding on his schoolwork when classes were in session. It was hard to resist logging onto when the alternative was researching a history paper, he says.

“It’s very addictive. You can sit down to play for half an hour and end up playing indefinitely,” he explains. Still, Eric managed to keep his habit within reasonable bounds by weaning himself off poker for weeks at a time. The fact that he “played for fun — not for the money,” made it easy to take time off, he says. Quitting was just another step in the same direction.

In many ways, Eric was an exception. He was a skilled player who made himself a fair amount of money (he estimates his winnings at $4,000), but the game always took a back seat to his main priorities of getting good grades and applying to law school. And whereas others may use their winnings for spending money, Eric chose to put his toward paying law school tuition fees. Looking back, he doesn’t regret his decision to quit. “I don’t feel tempted to start up again,” he says.

Anthony is a different type of poker player — a gambler at heart who sees the world as one big poker game.

He is drawn to the psychological battles of online poker, the challenge of guessing what other players are thinking, predicting their betting patterns and exploiting their weaknesses. When he logs onto his favorite website,, he uses the screen-name Jenny3333, because the average player is male and tends to underestimate female opponents. One day, he told me, he hopes to put his shrewd instinct for human nature to use as a CIA agent.

When I caught up with him for an interview, he was reclining with a smoke in his off campus apartment — a place that looks no different from other pads, except, perhaps, for the expensive electronics that stand out like trophies in the afternoon gloom. Earlier this year, Anthony bought an X-box, flat screen television and stereo equipment after his roommates watched him win $2,000 dollars in their living room and goaded him into buying the equipment.

The topic of conversation is Anthony’s big winning streak at the end of sophomore year. With unconcealed pride, he tells the story of how, days before finals period at the end of spring semester, he retreated into a buddy’s room for an entire week and turned $120 into $11,500.

“It was the most stressful week of my life,” he recalls. After borrowing the seed money from a friend, he hunkered down and cut himself off from all distractions, determined to multiply his initial investment many times over. Playing up to six tables of Texas Hold ‘em cash games at once (the online poker equivalent of the prizefight) he gradually fattened his bankroll up to $1,000 by betting aggressively at the lower stakes tables. Once he’d made it that far, there was no looking back.

“I kept going to bigger and bigger tables to make more profit,” he said. “I saw it as 120 bucks. It was all profit.” Although it wasn’t his own money, Anthony was nervous about losing what he’d made up to that point by making a stupid mistake. He played poker in high school (“I would hang out with 23-24 year old guys and take all their money”) and had been gambling online for a year, but was out of his depths at the high stakes tables. He faltered briefly against the tougher competition, dropping from a high of $4000 down to $2000, but came back up again when he adjusted to the intensity of the game play.

By the end of his week-long bender, the number labeled “bankroll” in the corner of his screen read $11,500. Still, the dollar amount had no value in the world of online poker, he explained to me. It was an abstract quantity, valuable only insofar as it could be used as a tool to intimidate strangers around a virtual poker table. “Pressing a button and pushing off three hundred dollars is nothing — it’s just pressing a button,” he said. The real reward was the white envelope filled with cash that he received from the teller at the Bank of America. “It was beautiful, bro,” he says of the moment he received the wad of bills (he cashed out the other $4,500 at a later date). This was physical money that deserved to be treated with a modicum of respect; he took it home and stowed it in a lockbox under his bed, to be spent on something important down the line.

Anthony has since taken a break from playing poker, but says that he has no intention of quitting because of the ban on internet gambling. He says that when he first heard about the law, which goes into effect in 2007, it “blew [his] mind”. He was astounded by the way Republican senator Bill Frist had pushed his internet gambling ban through Congress by attaching it to a defense bill designed to boost security at the nation’s ports. More importantly, he felt the law violated his right to do as he pleased with his money.

“One of my fundamental beliefs,” he says, “is that there’s nothing more private than what I do with my money — than what I bet on.” Unlike Eric Sandberg-Zakian, who says that he understands that “not everyone can handle poker the way [he] can,” Anthony is a strong believer in personal — or parental — accountability when it comes to gambling. Parents, he says, should be responsible for making sure children don’t use their credit cards — not the government. Nevertheless, the two agree on the point that the U.S. ban, which has not been replicated in any other country (in fact, the United Kingdom has recently passed legislation to regulate and tax online gambling), is unfair in view of international trade agreements.

“We have an obligation to the World Trade Organization not to make [online gambling] illegal,” Eric says, adding that the ban aims to prevent foreign websites from cashing in on American dollars while protecting domestic gambling operations. He doesn’t believe legislators are being honest when they argue that online gambling poses a serious threat to the nation’s moral and social norms — horse races, lotteries and fantasy sports betting, he points out, are all exempt from the ban.

What exactly will happen once the law goes into action is unclear, but industry specialists predict that the world of online poker will be split into two groups: casual players who are put off by the potential legal repercussions of their hobby, gradually migrating to prize-based sites or quitting altogether; and hardcore gamblers who will stay on despite the ban. Offshore funds transfer services like, which are not restricted by the law, enable gamblers to deposit their winnings directly into an online bank account and access the funds from the United States. Players like Anthony and his friend Jean-Francois Boucher ‘08, another serious online poker player at Yale, placed themselves firmly in the second category when they came up with their own scheme to get around the new restrictions.

According to their plan, Anthony will transfer his winnings to an online account held by Jean-Francois, who is French-Canadian, and can still withdraw funds in the United States. He takes the cash out at an ATM, hands it over to Anthony and — “bingo, done deal.” Although he has yet to test his scheme, Anthony says that he is confident that it will work and feels relatively safe from prosecution by US authorities. (He also mentioned a business plan that would take advantage of a loophole in the law but declined to discuss it in detail because he doesn’t want his idea to be stolen.)

During our long conversation, there was only one question that Anthony didn’t answer with a burst of rapid-fire speech: Was his online gambling poker an addiction? “I’m addicted to all kinds of things,” he shrugs, gesturing at the lit cigarette in his hand. “But poker isn’t a problem for me.” Like Eric, he takes breaks for weeks at a time when he needs to focus on his school work (he claims to have never handed in a late paper). But Anthony’s passion for the game — and the way his eyes light up when he talks about a winning hand — makes it hard to believe that he will ever convince himself to give it up altogether.

Jean-Francois, a varsity hockey player at Yale, has a poker habit that puts both Eric and Anthony in the shade. Last summer, he made $16,000 in a 24-hour span by winning 3 high stakes tournaments on Tournament guys are the endurance runners of the poker world, he explains; their game has little in common with the fast-paced, in-and-out action of the cash game. But tournaments take time to play — often upwards of 4 hours, and Jean-Francois plays in up to 8 of them at once on a dual-screen “poker setup” in his room.

He went from casual gambler to quasi-professional during his sophomore year at Yale, after a friend who’d won $9,000 in a tournament lent him the money to start playing high-stakes games. Since then, his hobby has become an all-consuming habit, occupying the lion’s share of his free time and leaving little room for classes and a social life. On most days, he wakes up to attend hockey practice in the morning, then goes home to sleep until the tournaments begin late at night, when participants from Europe and Asia are logging on.

His girlfriend, whom he taught how to play poker and is now a serious player herself, puts up with his poker schedule because she understands what it means to be down a few hundred dollars in a tournament. They used to go out to the movies together on Friday nights, but lately Jean-Francois has been canceling their dates. “Instead, I’ll end up playing all night by myself,” he admits.

Unlike other poker players at Yale, who insist that they are in control of their habit, Jean-Francois is open about the detrimental effects gambling has had on his life. “It’s more than negative,” he says about his all-day-every-day habit. “I haven’t been to classes all year. My parents aren’t happy about it.” Asked if he thinks online poker is an addiction, he responds with equivocation. Skilled poker players don’t suffer from a lack of willpower, he says; arrogance is what causes them to take excessive risks. “You think you’re better than the game,” he says. “That’s how it starts to go downhill.”

Recently, Jean-Francois took a loss during an early round of the online World Series of Poker that emptied his bankroll and got him thinking about his future as a poker player. “I lost everything,” he says. “Poker’s not sweet enough to lose everything.” He mentions wanting to quit in the near future but seems equally drawn to the prospect of playing professionally for a year or two after graduating from college — perhaps even moving to Las Vegas to try his luck at the World Series of Poker.

He wouldn’t be the first Yalie to go. Alex Jacob ’06, now a top-ranked professional poker player, placed 5th at a Texas Hold ‘em event of the World Series last July. Jacob became a living legend among poker fans at Yale when he won the US Poker Championship and took home $878,000 — making him the first Yalie to become a millionaire by playing poker. Others like Christopher Bartley and Alexander McBurney ‘06 turned their passion for poker into a business after graduating from Yale: they started the College Poker Association, an internet forum that allows poker players to compete for prizes but not gamble for money.

What sets a Yalie apart from the average online poker player? At first glance, nothing but the cost of his education — the world of online poker is an egalitarian space in which social status has no bearing. Many players sharp enough to make a living from poker don’t have college degrees; aside from their screen-names, the only difference between two poker players is the skill they bring to the table.

Eric Sandberg-Zakian said that the intellectual pride that defines many of his peers at Yale can be either a blessing or a curse when it comes to poker. “What makes you a better player is learning about [poker] by reading books — that’s how I got better,” he said. “Ivy-Leaguers would be more likely to pick up the books — but it’s also possible that they’re less likely since they assume they’re already smarter than everyone else.” Anthony credits a book called Supersystems by Doyle Bronson (“pretty much my favorite book ever”) with helping him to “understand the fundamentals of how bets are meaningful and how you can make money.” But Jean-Francois says he has never cracked a poker book in his life and hasn’t suffered for it.

Indeed, the kind of intelligence required at the poker table differs from the academic smarts that define many Yalies; a brain for mathematics and an ability to do fast mental calculations are far more valuable around the poker table than being well read. The ability to recognize patterns and predict the outcomes of a wide variety of situations can only be achieved through live experience. By and large, the typical life priorities of Yale students make them unlikely candidates for poker glory: the fact that most scrupulously divide their days between schoolwork, extracurricular activities and their social lives leaves little time for the kind of commitment it takes to hone their poker skills.

Still, poker players have at least one thing in common: a repository of poker wisdom, a set of rules by which to play and live. “Honestly, it’s a lifestyle,” Anthony says at the end of our interview together. But now the US government has officially disapproved of that lifestyle. Someday, when he interviews for the CIA, his poker face might come in handy.