Cashing Out

This is a game about money. Money is the ball, the field, and the referee.

First, you pay the antes. Without the antes, there would be nothing to play for. With nothing to play for, this wouldn’t be poker. You’re in the hand, now. The dealer cuts the deck crisply and straightens at the waist. Swiveling from the hips like a rotary sprinkler, he flicks one card after another off the top of the deck, each tracing its own shallow parabola before landing and sliding to a stop on the felt, just in front of its target.

This is a game about money. Money is the ball, the field, and the referee. In a hand of poker, each betting round follows the same pattern: information is revealed to you in the form of cards, public or private, faceup or facedown. From this information you evaluate the strength of your hand. Then you bet or do not bet, fold or do not fold. This repeats a number of times. The pot grows. In the end, either one player has convinced the rest that she has the best hand, and wins the pot uncontested; or she encounters a skeptic, who calls her bets and bring the hand to showdown. This is how it ends. Hands are opened. There is a winner. The winner takes the money.


To the casual player, winning or losing a poker game is a mysterious thing. To her, there is a certain ineffable energy that permeates the game and the act of playing. It is out of this thing which the results manifest. We perform our acts, and are given a judgment: we win or we lose. For many, this anointment is the draw of gambling.

To become a “serious” poker player is to divest the game of this mystery. The serious player sees the game as a series of decisions which can be more or less correct. The correctness of these decisions accumulates throughout a hand, or a night, or a life, at the end of which the player will have a quantifiable chance of gain or loss. Sometimes she will make these decisions well and lose, and sometimes she will make them poorly and win. She may complain, but she won’t ever be surprised.

I used to be a serious poker player. In the middle of the last decade, I was one of a large number of young men (and we were mostly young men) who developed a fascination with the game; less commonly, I was able to turn that fascination into a sort of success.

My earliest memory of poker, I think, is of playing with school friends for quarters on an overnight school trip. I invented the rules and made out quite handsomely. After that? I remember when I started playing with friends from my summer job, working at a provincial park near my hometown in Ontario, Canada.

The first time I played online was for play-money with my weird German cyber-friend Christoph, whom I met playing computer games in high school. Soon I was going online with play-money of my own and becoming interested in the game’s underpinnings, exploring Internet forums and discovering how much I didn’t know.

But this is how it really started: I won $25 playing a small game with friends. I was beginning to feel like one of the better players in this small group of people. I heard that somebody they knew had been playing online poker for real money—and winning. Apparently, it wasn’t hard. I was curious—wouldn’t you be?

Late summer, 2005: I was at my parents’ place, at the end of my first summer home from university. I sat in front of a computer with my credit card on the desk. Open in my browser was an online poker site. I had made a rule for myself: I would only play with money I had also won playing, in the $5 games I’d been playing with friends. I entered my credit card information. Was it hot out, or was I just sweating? I entered the $25 that represented my summer’s winnings. My mouse hovered. I swallowed once. I clicked Submit.

I don’t really want to talk about the “poker boom” at length, but just to provide a bit of backstory: in the early 2000s, poker experienced a massive upswelling of interest in the United States. The Internet and personal computers had finally matured to a level where mass-market, online gambling games were feasible. A lot of people suddenly wanted to play poker, and were now able to do so from the comfort of their living rooms, dens, and college dorms; this meant online poker games were flooded with new and inexperienced players. It only takes ten million people, depositing a hundred dollars each, for there to be a billion dollars floating around out there, and there were certainly many more than ten million people depositing more than a hundred dollars.

The night I played my first-ever hands of Internet poker, a very important thing happened: I did not go broke.


That first evening, I made $100. It felt easy, preordained. The game grabbed my interest. I started spending time in online forums dedicated to strategy and discussion, and I started learning how to review hand histories (poker hands can be recorded using a standard notation, as chess games can). I was newly confident. If I could make $100 in my first night, clearly as I got better I could only expect greater success.

Then I was reading some forum, as usual, when I came across a post by someone who seemed to know more than I did (everyone seemed to know more than I did). He was describing what he felt was a certain sort of common situation: that of the new online player who made $100 in their first night and decided that this was probably reasonable, that they could probably expect to make $100 every night. So they cashed out their winnings, not knowing that they had just been lucky, and when their luck broke they had no cushion to fall back on and quickly went bust.

After the first night, when I didn’t go broke, stumbling across this post at the time I did was probably the second major piece of fortune in my poker life.

The realization of my good luck made me cautious. Soon, I was back in college full-time, but it was not particularly challenging. I did not have a busy social life. I had time. I began to play poker in the evenings after dinner, for roughly two hours a night. I started to track my results and worked to improve my play. A journal entry from about three months into the school year states that my initial $25 had grown to $480. By the end of the school year, I had built my bankroll up to around $2100: a nice-seeming number which actually works out to a wage of less than $5 an hour.

My plan that summer had been to go back to my parents’ place and return to the job I had held the summer before: working as a maintenance supervisor at the nearby provincial park, driving a truck around to pick up and drop off the high-school students tasked with cleaning the garbage from campsites and beaches.

This didn’t really appeal to me all that much.

Sitting in class that year, I started to punctuate my notes with the foundations of another idea: evaluations of my living expenses, rough estimates of how cheaply I could support myself, calculations of how much money I might be able to make in various situations, and general speculations on whether or not it might be possible to support myself through the summer with poker money.

I figured I would need to make $1000 a month to get by—my rent was only around $300 a month, and I lived frugally. If the plan didn’t work out, I could always get a job or even just go back to my parents. But if I managed to get through the first month without going broke, I would probably have in that time become a much better player—which would put me in a position to do better in the subsequent months, and so on. Finally, there was the fact that if I was able to survive the summer playing cards, I would be in the position to supplement my income in the fall by continuing to play part-time.

It all sounded sort of reasonable. It was also all basically guesswork.

That April, I cashed out $300 and bought a used PC off craigslist. I set up an office in a spare room of my apartment and took a few days off. On the 3rd of May, I sat down for my first session of full-time play. I booked a $133.03 win in four hours. The next day I lost $59.36 in five and a half. It was up and down. May ended with a small winning streak, but more importantly it ended with my rent paid and my bankroll intact. In fact, I made $1488.04. This was enough to keep me alive and put me in a position to play the next month.

I didn’t go broke then, either. I made $2100 in June, $3800 in July. In August I made almost double that.

I felt like I’d found a cheat code for life.

Then, that fall, I had my first experience of a downswing. It felt like I was losing every hand I played. I tried moving down in stakes. I tried playing different games. I tried playing longer hours or shorter hours, but nothing really seemed to work. I won modestly in October, but in November I had my first losing month.

It’s hard to describe the experience of a serious losing streak. You get up every morning and do what you think is the very same thing you’ve been doing successfully for months, but instead of winning, you lose. You start to wonder if you’ve changed your play, which results in actual changes; you wonder if the games have gotten harder, or the other players better; you wonder if you’re playing scared because you’ve been losing, or if you’re playing too aggressively because you’re worried about playing scared. Your results seem to be completely unrelated to your work. I remember beginning to feel tremendous anxiety for the first time and believing that I would probably go broke, and that this experience had been a mistake and a failure. I was shaken.

I broke even that fall, and only started winning again in December. By the end of the year, however, I had still managed to make about $26,000. My first playing day of the new year, January 2, I made a little over a grand. A little jokey note in the margins of my spreadsheet says, “on track for 300k?”

By the end of February, I had already made more than in all of 2006. In May, I doubled that. In June, with my bankroll now at over fifty grand, I decided it was time to go to Vegas.


Filling out my US customs form on my flight, I checked the box indicating that I was “carrying currency or monetary instruments over $10,000 US or foreign equivalent.” When I told the American customs officer I had ten grand in hundreds in my carry-on and was going to Las Vegas, he nodded absently and waved me through.

I went there for the World Series of Poker, a tournament series that attracts the game’s top players (and a healthy number of amateurs and hangers-on) to the city each summer. This was 2007, and Vegas seemed unstoppable. I spent hours just wandering through the crowds and casinos like a kid at the zoo. It was a place unlike anything I could have imagined, and the sense of artifice—of a place that could have been built in a factory and dropped on the desert, piece by piece—was something I had no reference for until I visited Dubai, several years later.

While in Vegas, I played 12 hours of poker a day, ate bad food, and felt perfectly at home. Financially, the trip went poorly—until the very last day, when I made up my losses in two now-blurry hours. On my final hand of the trip, I made a royal flush in a big multi-way pot, erasing my losses and covering my hotel bill.


That summer, I moved up to $5/$10 antes, where you could easily win or lose $1000 in a hand; then I moved up to $10/$20. I kept winning. Eventually I was playing $25/$50.

Then in November, in 70 hours of play, I made $131,375.89—around $1,875 an hour—in some of the biggest games available at the time. I was still in college.

There are two ways to feel about wagering: excitement about the prospect of winning, or fear of losing. I have always firmly been in the second camp. Winning was nice, but losing was awful. Having a good day never made me feel as great as a bad day made me feel terrible. I knew losing was part of the game, and I tried to rationalize my attitudes, but I couldn’t help feeling badly when I lost. My poker results started to seriously impact my mood. Losing stretches would leave me despondent and disinterested in the world. The pressure of playing—and of playing for ever-increasing amounts of money—made me anxious, more easily upset. My heart hurt. I started to develop involuntary muscle spasms.

The first week of December, I lost seventy grand. I rested a few days before I started playing again, at lower stakes, but my heart wasn’t in it.

I took the rest of the month off. After Christmas, my then-girlfriend and I flew to New York for a week’s vacation. We played grown-up at a family friend’s apartment on the Upper East Side and spent more on single meals than I’d been spending on a month’s rent just a year earlier. Afterward, she flew home. I flew south to play poker.

When I look back at this part of my life, I see now that this is where it ended: in a thick-curtained and low-ceilinged hotel room overlooking the employee parking lot of the Gold Strike Casino Resort in Tunica, Mississippi, bordered by a stand of trees obscuring a small riverlet, the Mississippi River no more than a mile away. I wanted to go home. I was sick of my hotel room; I was sick of buffet food; I was sick of the hyper-oxygenated air. I’d spent most of the trip losing, again, and I was sick of that too. Mostly I was sick of poker.

As my interest waned, my play deteriorated. The poker boom was ending, anyway: the bad players were getting tired of losing and the good players were increasingly forced to compete against one another. When I had started, being merely okay was enough to guarantee a profit. Now, decent players who had been making hundreds of thousands of dollars for five or six years were slowly finding themselves outclassed by hungrier opponents. Those that were slow to recognize this shift and adjust their expectations went broke.

I just knew I wasn’t having fun anymore.

I kept playing, on and off, for the next few years, but I was never excited by the game again in the way I was when I had first started. When I had started playing, poker was something that fascinated me. It was something I truly enjoyed playing and enjoyed thinking about. Somewhere along the way, it had started to become something I, at best, tolerated. It ended up being something I dreaded. Eventually it made its way into the background of my life—almost a dream, another world, a funny story, this interesting thing I used to do.