On one of those steel-skied Manhattan winter mornings, when it seems like the city is encased by a slow-moving ironclad, I was sitting in the back seat of a Mercedes-Benz, eating a hot dog with two new friends. Exactly 44 $100 bills lay folded up in my wallet. I’d just met these two friends, both of whom had seen me pocket the cash, but I wasn’t much nervous. If they robbed me, I would see them again soon enough. As it happened, both were nice kids from Westchester County. I knew nothing about Westchester County except for the stigma that kids from Westchester act tougher than they are. My friends acknowledged the stigma and spent half an hour arguing over which was the more important debut, Eminem’s The Slim Shady EP or Biggie Smalls’s Ready to Die. I really listened, made a case for Nas’s Illmatic, and felt happy for the first time in months. After we finished the hot dogs, the kids drove me 20 blocks uptown and dropped me off in front of my apartment. I thanked them, walked up to my studio, and fell asleep.

During my last semester in graduate school, I made a lot of unexpected friends. I’d meet them in the card room above the OTB on 72nd and Broadway, or I’d meet them over Recession Specials at the Gray’s across the street, or I’d meet them in the poker pit at the Tropicana, or I’d sit next to them on the 5 a.m. bus from Atlantic City, trying not to think about what it meant that these were the only sunrises we saw anymore—the washed-out sun peeking out over the white, industrial cylinders of north New Jersey. My friends and I never really talked about anything. Mostly, we muttered about the bad beats we’d taken, each new friend a companion in losing. Sometimes, they would talk about the tits on some female dealer and we’d all smile in recognition. Once, an old Saudi man who sat to my left in a 5-5 No Limit Hold ’em Game at the New York Players Club told me that he missed the openness of the Middle East. When I started to laugh, he said he was talking about the flatness of the earth and the architecture, not the people. Occasionally I admitted to being a graduate student. Although I must have met more than 50 of these friends, I only remember telling one of them about my dream of becoming a novelist. He was a Filipino kid about my age from Queens, and when I made my confession in the back seat of a cab driving to a game he knew about in Chelsea, he only said, “What’s the book going to be about? Hold ’em, Stud, or Omaha?”

II

Jennifer Harman, the world’s best female poker player and a two-time kidney transplant recipient, has credited her success in gambling to her incredible pain tolerance.

Pain in poker comes in many forms. There is the loss you feel about living off of the dregs of a societal illness. There is the gambler’s moment of clarity when you realize you have become just like the old, sad men that you ridiculed in your younger, luckier days. There is the tedium of sitting at a filthy felt table for hours, sometimes days, feigning a studied intensity. There is the anxiety over explaining to a loved one exactly how you lost $30,000 in the course of a weekend. There is searing unease that comes from watching that same loved one twist uncomfortably whenever you give them a gift bought with the spoils of gambling. But none of poker’s daily pains are deadly or instructive, really. What’s more, all of guilt’s iterations can be cleansed by one monster score. Hit a set of 6s on a J-6-2 rainbow flop against the Donkey at the table, the one who is wearing a fake Versace rayon shirt whose outrageous patterning is the only thing taking attention away from his Dolce & Gabbana sunglasses and the poor, doting, usually underage girlfriend who sits behind his right shoulder, awash in the illusion that her boyfriend is Paul Newman from The Hustler—well, win $5,000 off a guy like that and you stop worrying about ethics and your misspent youth.

The fog of losing, which feels like a seething, dirty steam in the veins, seeps into everything.

The real pain of poker, the only chronic, threatening pain, comes from the daily loss of livelihood—how a player views himself in the face of losing. Pain tolerance, then, is not measured in how well the player can take a bad beat or how long he can sit at a table without questioning what the fuck has happened. Rather, it is how the player handles an inevitable losing streak and the extent to which he will allow losing to affect his idea of himself. After a month straight of losses, a player can become convinced that losing is his role. Going broke becomes his thing to do, his inevitable outcome. The fog of losing, which feels like a seething, dirty steam in the veins, seeps into everything.

That is the pain of poker that must be endured and held at arm’s length: the existential pain that causes you to turn your vision of doom into a fate-bound story, as tragic and merciless as fiction.

III

Six months after that morning in the Mercedes-Benz, I was sitting in the driver’s seat of my Subaru Outback, in a massive parking lot in Commerce, Calif., a suburb of Los Angeles known for the blasts of dust that terrorize its inhabitants. Twelve thousand dollars lay wadded up in the glove compartment. I was trying to decide if I had what it took to drive home. To help delay a decision, I remember turning the radio to a Dodgers game. I don’t know how long I sat there listening to Vin Scully sing his nasally song of balls and strikes, which, even in the age of digital radio, still sounds as if it is being transmitted through a tin of victory cabbage. I remember thinking some nostalgic, self-pitying thoughts about my younger days. I forced myself to say out loud, “You are a degenerate gambler,” but doing so only made me giggle. I opened the glove box, pocketed the cash, and walked back through the sliding doors of the Commerce Casino, back to my table in the Crazy Asian 400 No-Limit Game and to the eight friends at my table who had kindly managed to save my seat.

Some time later, I drove home. All the money, of course, was gone. As I drove home through the network of highways that tie up a concrete bow just east of downtown Los Angeles, I felt no compulsion to slam the Outback into a guardrail. In fact, losing almost all the money I had in the world in six hours stirred up only a cold, scraped-out feeling of knowing—the calm that freezes out your brain when you watch someone younger make the same mistakes you made at their age. Staring out at the empty skyscrapers, I tried to figure out what might be the right reaction to losing $12,000. At the 7-Eleven on Venice and Sepulveda, I bought a bottle of NyQuil, drank half of it in the parking lot and drove the rest of the way home in a warm, creeping fog.

If Hellmuth is the Reggie Jackson of poker—a disciplined perfectionist who decided to turn himself into a brash, obnoxious television personality—Mike “The Mouth” Matusow is the game’s Mike Tyson

The next day, after teaching three sections of world history, I drove to the bank and emptied my bank account. When I arrived in Commerce, most of my friends were still sitting at the table. I waited till a seat opened up, handed $400 to the man in charge of bringing me my chips, and smiled at everyone. Mexican Jeff, perhaps the best-groomed 350-pound man I’ve ever met, smiled and tossed me a $5 chip. To prime the pump, he said. Big Mike, another 300-plus-pounder, chuckled, shook his head, and went back to watching his portable DVD player. A few months before, Big Mike let me watch half a season of Star Trek: Deep Space 9 with him at the table. Every time I got involved in a big hand, he politely turned down the volume in my earphones. Big Mike probably took more than $2,000 off me during the year we played together at the Commerce, but how could I think of him as anything but a friend?

When I stood up from the table at 3 a.m., I had amassed more than $6,000 in chips. Driving home this time, I felt no rush, no belief in balance restored. Why get excited? Nearly breaking even over two days was an expectation of a good player, not something to celebrate. The next morning, I called in sick, drove back to Commerce, and finished second in the daily re-buy tournament, pocketing $2,750. I bought my girlfriend a pair of sunglasses and felt good about it. What courage to return after such a bad beating! What pain tolerance! The bad day, I reasoned, had been nothing more than extreme bad luck. Everything was back in order now; the odds had returned to my side; they always would. Playing poker, after all, was nothing more than a ride on math’s pendulum. Put yourself on the right side of a 55 percent/45 percent split enough times and you’ll inherit the earth, right?

IV

Hollywood has gone to great lengths to dress up poker as a society of charming con men, international playboys, and wayward geniuses. The brainy guys who reduce poker to algorithms all went to school in Cambridge; the slicksters are always refugees who use gumption and craftiness to realize the American dream. The Texans are Texans, the Jews are Jews, and the cowboys wear steer-skull bolo ties. None of them, however, ever walks away a loser. And if they never lose and you are like them (immigrant, high school dropout, M.I.T. graduate, black, white, Jewish, or Asian) and if you possess the talent to sit at a card table and play a simple game, then it stands to reason that you, too, could be poker’s next millionaire.

Within this men’s club setting, there are two anti-heroes: Phil “The Poker Brat” Hellmuth and Mike “The Mouth” Matusow. Both are known for the braggadocio that accompanies their wins and the violent, profane outbursts that accompany their losses, but the similarities end when the cameras shut down. Hellmuth’s brattiness is a bid for airtime. In actuality, he is a control freak who meditates every morning and plays poker with a disciplined, almost mechanistic focus. On the rare occasion he loses a hand, it’s almost always a result of a bad play by an opposing player, to the point where you start to believe his claim that if poker did not involve luck, he would never lose.

If Hellmuth is the Reggie Jackson of poker—a disciplined perfectionist who, for whatever reason, decided to turn himself into a brash, obnoxious television personality—Mike “The Mouth” Matusow is the game’s Mike Tyson, a homely, overweight dropout best known for the wild swings of fortune that have derailed his life. In the professional community, Matusow is the wild card, the only admitted degenerate. He admits to losing hundreds of thousands of dollars in a matter of hours. Unlike Hellmuth, who never places himself in direct danger, Matusow seems to thrive on throwing his fate into destructive, impossible situations—the allure of watching him extricate himself from his self-set traps is only bested by the anticipation of his downfall.

All of us problem gamblers idolize Matusow. He is poker’s pain. His losses are so stunning, so magnificent, they demand their own narratives. Recounting a Matusow blow-up, you find yourself saying, “And then he…and then he…and then he…” He is the narrator of his own bildungsroman, a story where women are easy, money is copious, and disaster is inevitable.

V

When I won, I watched TV, mostly reality shows and televised poker tournaments. When I lost, I read modern novels with unreliable, angry young narrators. Céline and Rilke made me feel like I was in some club of colorful self-destruction. I stopped work on my novel because my narrator’s earnestness sickened me. I went broke three or four times—I don’t really remember. My friends at the casino stopped being my friends, but then I’d win again and stop feeling their pity for a while. I remember overhearing a player say about me, “He’s here a lot but he almost never wins anymore.” I did not know if he was telling the truth. On the advice of a better gambler, I decided to keep track of my wins and losses in a notebook. After two straight losing sessions, I ripped out the first few pages and used the remaining pages as an attendance log for my world history class.

Some time later, I was playing at the Wynn Casino in Las Vegas, where the breasts on the cocktail waitresses are made of Tupperware, the seats are plush, and all the well-groomed floor men make sure to remember your name. It was 4 a.m. and my girlfriend, an exceedingly level-headed girl who believed that time was the only panacea for waywardness, was asleep in our room upstairs. I was losing again, but not painfully. Everyone at my table was Korean or Vietnamese, and for an hour or so we had been telling jokes about all the damage we compulsive gamblers were doing to the reputation of the studious, industrious Asians of America. A nice Korean kid to my left said he felt bad for his mother who had given birth to two degenerate gamblers and only one doctor. Some haggard Vietnamese guy made a joke about handjobs, Asian prostitutes, and the Korean mothers. We all laughed. I felt as if all my friends had come back—here we were, exhausted and slightly hopeful. Between 4 a.m. and 9 a.m., I hit a streak of cards that crippled my new friends, and by the time the outbound hotel guests began spilling out of the elevators, I was up $6,000. Some of the Asians trickled away and were replaced by studious, focused college kids who had been told by some book to visit a casino in the early hours, to better take advantage of the degenerates who had been gambling all night. I cleaned them out. When my girlfriend came to check on me, a day trader from New York told her she was a lucky woman to be dating such a skilled player. To complete the illusion, I handed her two $100 chips and told her to go spend some time in the hotel’s spa. She looked at me queerly, but did as she was told, probably because she wanted me to feel glamorous, at least for one good minute.

In gambling narratives, the bottom is followed by the fantasy and the fantasy is followed by the bottom. The high is always the pain and the pain is always the high.

Around two in the afternoon, a fantastic stripper sat down. A pair of heart-shaped sunglasses hung off her nose, the same kind Sue Lyon wore in Kubrick’s Lolita. I could see the reflection of her massive, conical breasts in the lenses. Her lips, thin and permanently pursed, had been shellacked pink. Her hair was brown, blonde, another shade of blonde, and black, all of it gathered into a ponytail that sat high on top of her petite skull. She looked, I thought, like a very sexual tropical plant. Someone said he recognized her from TV and she admitted that she had appeared on a couple of poker telecasts. We, at the table, all felt better about ourselves for playing with a bona fide TV pro. In a matter of 40 minutes, she wrested control from me and began stacking her chips into odd, asymmetrical shapes. When asked what she was going to do with all the money, she said, “Shopping addiction, babies. Fendi, Gucci, Prada, Chanel, baby. I gotta support it all somehow.” When a bewildered player pointed out that she probably had men lining up to buy her clothes, she said, “Yeah, but that’s only the half of it.” Her excess was charming. We enjoyed losing to her. By five that evening, she equaled my still-mammoth chip stack. She was from Florida and said she hated America for what it had let the Bush administration do to it. I liked her idea of accountability and we got to talking about the differences between Las Vegas and Florida, the types of cars we drove, which buffet on the strip had the most decadent pyramid of shrimp, blah, blah, blah. My girlfriend called me from the pool and told me she had finished her book and was now ready to leave. I told her I’d meet her in an hour.

Whenever I had a ton of money on the table, there was a word game I would play. I would think, “Who can get up from this table? Who can get up from this table?” After some mindless pause, I would say, “Not I, said the Kang.” The thought always made me smile, which, in retrospect, was crazy.

Some hours passed. The stripper kept winning and we ran out of things to discuss. I think the last thing she said to me was, “Tell your friend to always look for the drunk girls, you know, the ones who dance all sloppy and you know their eyes can’t focus when they look at you? Those girls will do anything for $20.” The word game went through my head a few hundred times. I watched the Red Sox win and tried to muster some enthusiasm for the team that had been my boyhood obsession, but if there’s a cost to gambling, it’s that it strips you of the ability to just sit and enjoy a game. After a few innings, my boredom became intolerable, and I walked to the sports book and spread $500 on the long-shot ponies.

Around eight, I walked back to the table and started up the old rhythm. On the third or fourth time around, I looked down at my hole cards and saw the king and ten of spades. The stripper had bet $50 into the pot and everyone else had folded. Up on the TV screen, I watched as one of my ponies trotted across the finish line in last place. No matter. I called the $50. The first three community cards brought the ten of clubs, the ten of hearts, and the six of clubs, giving me three tens. She was first to act and raised double the size of the pot. With her giant chip stack and aggressive style of play, I knew it wasn’t out of the realm of possibility that she would make a large raise with two suited cards—maybe the five and six of clubs or the jack and ten of clubs. Just an hour and a half before, I had seen her push someone all in with a similar draw. When he had disgustedly folded his pair of kings, she flipped over a four and six of clubs. At this point, there were only two possible hands that could beat mine—an ace and a ten, or two sixes. Being a loose, aggressive player, I knew if she had either of those hands, she would have disguised the strength of her hand by checking the flop. The only logical hand I could put her on was a flush draw.

A strong bet will usually force a precise, book-learned player to lay down his flush draw. But when the opponent has a lot of money and has shown a penchant for erratic, wild play, it’s advisable to bet an almost unreasonable amount of money. If she feels a rush and calls, then you are on the good side of the odds. If she folds, then you take down what’s already in the pot. So, when the stripper added her $100 bet into a $100 pot, I tossed five $100 chips into the center of the table. She frowned, thought for a good minute, and called. Fourth street brought a king of clubs—the perfect card. If my instincts were correct, the flush she had just made was crushed by my full house. To confirm my suspicion, she checked the bet, the exact move someone would do if they hit their flush and wanted to disguise the fact. I knew that if I bet now, she would put in a huge raise. I bet $800. She raised the bet to $2,000. I made a show of frowning and putzing around and methodically counted out my remaining $6,000. Then, with an affected flourish, I pushed the rest of my chips into the middle of the table. The stripper lowered her glasses to the tip of her nose and stared at me with sympathetic eyes. She muttered, “Baby, it’s a bad time to hit the second best full house…” and pushed the rest of her money into the middle. The table gasped in delight. She flipped over her two kings. My tens full of kings were beat by her kings full of tens. I have no idea what the last card was, just that it wasn’t the case ten, the only card in the deck that would’ve won me the hand. The fantastic stripper apologized and apologized again as she stacked up my $9,000. I couldn’t face her sincerity, so I got up from the table and wandered off to the sports book, where I dropped myself down on a club chair and wondered aloud what exactly had happened. I remember thinking about the narrator of my now-dead novel and I pictured him walking sick and earnest through the streets near Seattle’s Pike Street Market, one of the 10,000 places in America where neon is the saddest color.

It occurred to me that I was trying to have a literary moment. Something demanded that I learn something. I sat there for about an hour, watching all the horses of Texas and Washington race around on the plasma screens. At some point, I called a friend from the Commerce to tell him about the hand. He whistled and reminded me that in the movie Rounders, Matt Damon had gone broke in almost the exact same way. The thought made me feel better. I took my betting tickets out of my pockets and checked the results board. Only one of my long shots had come in, paying out $300. I thought, “Why bother?” and laughed a little. I ordered a drink. The ninth race at Emerald Downs was about to post. I looked down and saw that I had put down a $60 9/2/5 Box Exacta on the race. I remembered the ninth horse was named Randini. Randini, bless his heart, was going to post as a decent underdog. The no. 2 and the no. 5 horses were long shots. I had no idea what the payout might be.

We all know the end to this story. Randini ran out to a strong lead and never faded. At the final turn, the 2 and the 5 horses streaked past fading no. 4 to claim the place and show. The cashier didn’t even flinch as she counted out $14,000 and only offered up a polite nod when I handed over a $100 tip. My girlfriend wondered out loud, “How much more is enough?” I told her we were getting out of Vegas as soon as possible. Before we left, I bought her a $500 skirt at one of the Wynn’s boutique stores. It’s a gorgeous, delicate thing—cerulean blue, hand-stitched, and perfectly balanced, and one day she will finally feel comfortable enough to wear it around.

VI

The literature of addiction is vainglorious. The writer nudges you in the ribs, raises his eyebrows, and launches in on his idea of a seedy tale. But once the air has been expelled out the bag, the reader is not asked to recognize the mistakes the writer made, but to acknowledge his suffering.

For example, I could tell you that during a 36-hour period in July of 2006, I lost $18,000 in Las Vegas. Or I could tell you I once picked through every corner of my car, including the grating underneath the spare tire, for five dollars of spare change so that I could make the minimum bet at a blackjack table (a bet I lost). And my interest in divulging these details would not be to instruct or to edify, or even to elicit empathy from fellow addicts. My interest would be to rip open my suffering heart and show you its beautiful beating, and in this way, I might think of myself as having been more alive than you, my hopefully horrified reader, were at a similar age and time.

As a literary society, we have long since gotten over our modesties. The literature of addiction, once the exclusive territory of imbalanced, suicidal poets, has now come to dominate the market. We no longer recognize self-indulgence as self-indulgence. The term itself has fallen out of use, relegated mostly to protests from bitter Amazon.com reviewers and the curmudgeons of the weekly book reviews. Stylish women in New York write chatty columns about how much of their paycheck they spent on the latest “must have” designer handbag. The bestseller shelves are flooded with the memoirs of 30-year-old alcoholics. Sex addicts write 200-page books, complete with sex-cougar dust jacket photos.

Conspicuously absent from the deluge of divulgences, however, are the degenerate gambling stories. Books have been written about gambling, but the lion’s share are either strategy handbooks or glitzy tales of careerists. The best-selling books in the past few years about gambling have been Doyle Brunson’s Super System, an 800-page handbook on how to play successful, winning poker, and Ben Mezrich’s Bringing Down the House, the story of a shy kid from M.I.T. who gets recruited into the school’s famed underground blackjack team. Once initiated, the shy kid wins hundreds of thousands of dollars, gains confidence, sleeps with N.F.L. cheerleaders, and spends quality time with Patrick Ewing.

I cannot really pinpoint the time when the idea of a gambling problem became more than a funny joke.

Unlike drug narratives, which fixate on withdrawal and destruction, gambling narratives tend to glamorize the upswing—the writer/gambler will always tell you about his biggest score, how quickly he blew the money, and how fast he was back at the tables, but he will rarely tell about the scraped-out bottom. Massive losses are almost always followed up by a massive rallying—a man’s last five dollars turned miraculously into the $10,000 dollars he needs to pay for his fiancée’s wedding ring. Indeed, the only truthful gambling narratives are told by the family members and friends who witnessed the fallout: the bank account receipts, the early morning arrivals, the hanging stench of re-circulated cigarette smoke. Whereas drug literature comes from those who have bottomed out, there exists no bottom in gambling because every new hand brings fresh hope and possibility. Is it any wonder why most narratives written by gamblers read like boyhood fantasies—every casino a palace, every bellhop a best friend, every dealer an alchemist? Gambling narratives are projections of casinos’ fantasies—the tracers of lights that flash inside a gambler’s head as he watches the ball spin around the roulette wheel.

In gambling narratives, the bottom is followed by the fantasy and the fantasy is followed by the bottom. To put it better, the high is always the pain and the pain is always the high. There is never any difference.

VII

Sometimes I lost on purpose. In particular, I can remember sitting on a bench outside of the Hollywood Park, a casino and horse track in Inglewood, Calif. A procession of fillies paraded skittishly from the parking lot to the track’s receiving area, where a group of children had gathered to welcome them. The spectacle of pennants, kids, and color upset me. I felt older, somehow, and suddenly became aware of my karma. The fillies finished their little march. I walked back to my table of friends who were no longer friends. For the next five hours, I played recklessly and without any hope for winning. Of course, I won big that day, and the next day and the next day, before I went broke again.

There were other times, but there’s no need to list them here. Suffice to say, things got worse.

I cannot really pinpoint the time when the idea of a gambling problem became more than a funny joke. Maybe it was when I blew through a year of savings from my teaching job in the course of two weeks. Or maybe it was when I had to pay for a half-gallon of gas in quarters. Maybe it was that day at Hollywood Park, watching the brightly colored fillies march past. But during those last months when I lived in Los Angeles and thought about nothing but leaving, I know that the fantasy of poker, the millions of dollars one could win and the easy-living lifestyle, had long since burned itself out. Only in losing could I find a story that made sense.

The pain of poker is a simple disease. The symptoms are simple, the prognosis simpler. It’s true that I stopped gambling when I moved back to New York to continue work on my novel. Fifteen months later, when it became clear that the thrifty, sensibly coiffed girls of New York publishing were just not that into me, I haunted up my old casino friends. And while it’s embarrassingly obvious to me that my gambling problem steers into port only when I can see the bottom rising up, it’s also true, at least in some way, that playing cards has become my last ballast, the only narrative that involves any hope for absolution, however sadistic, crazy, or mathematically impossible. I keep playing because the narrative of losing is, in every important way, just as fantastic as the spectacle of winning. We problem gamblers have so much trouble identifying with other stories. After years in the casino, it’s obvious to me that most of us were born into the wrong century. Gambling allows us to narrate our own downfall—each new hand another turn of fortune or squalor. Once, in Las Vegas, I lost $9,000 in one poker hand to a fantastic stripper wearing the same heart-shaped sunglasses that Sue Lyon wore in Kubrick’s Lolita. I won it all back in the 83 seconds it took for a long shot named Randini to cross the finish line at Emerald Downs. What other story could I possibly tell?