Memoir: I went from ultra-Orthodox yeshiva boy to millionaire poker champion

 The ancient rabbis had a saying about gamblers. “What crime do dice-players commit?” they asked in the Mishnah. “They do not occupy themselves with the welfare of the world.” It was part of my education at the Orthodox Jewish theological school I attended near Chicago, where I spent 14 hours every day poring over the sacred texts. Every so often, I’d encounter yet another screed against gambling: that it was akin to robbery, that it was a form of usury, and that people who made it their profession were disqualified as witnesses at trial.

My father was a rabbi whose career took him to congregations around the world. I was born in Toronto, and when I was a kid, we jumped from South Africa to Australia to the States. Our family was Orthodox; I kept kosher, observed Shabbat, and wore traditional garments like a yarmulke and tzitzit. After graduating high school, I studied for a year at an advanced yeshiva near Jerusalem, where I immersed myself in the Torah and Talmud. My family expected me to enter a career in religion or medicine or finance—something stable and conventional.

I ended up at New York University, with a double major in finance and business management. Wall Street was 10 blocks away, and I hoped to get a job there. Then I met Andrew, my second-year roommate and a brash online poker buff who specialized in no-limit hold ’em. Watching Andrew play, I began to think like a real player. Gambling might be wrong, I told myself, but poker was different. It was a game of skill. Ever the conservative, I started out betting pennies. I probably made only $300 over the entire semester.

When I graduated in 2004, poker was still a hobby. Instead of Wall Street, I ended up in customer service at a software company. I was bored, underpaid and discouraged. One of the highlights of my life was a weekly hold ’em game with my friends back at NYU. The stakes were low—we had a $40 buy-in—but I was getting good. After a few months, the guys around the table started talking about Bodog, a new online poker site full of green players. I decided to give it a try, depositing $150. That first weekend, I made $15,000—half my yearly salary.

I quit my job 10 days later, planning to devote myself to poker full time. The hard part was telling my family. I was less worried about their reaction as Jews than their reaction as parents. They wanted me to be secure and settled. As a poker player, I’d be betting everything I earned, never sure if I’d have enough to pay my rent. I finally worked up the courage to tell them about my plan—and to my surprise, they were supportive. It wasn’t what they wanted, but they agreed that I should try it for six months. If I lost more than I made, I promised to get another desk job.

Reconciling my profession with my faith was a little harder. I spent hours debating the subject with scholars and friends. The ancient rabbis admonished the greed of betting high stakes, the laziness of playing instead of working, the flippancy of devoting your livelihood to luck. I argued that poker is less a game than a profession. That it was just like buying stocks or real estate: a precise calculus of smarts, aggression and risk.

For those first six months, I played exclusively online, quickly rising to the top of the Bodog leaderboards. Eventually, the site owners got in touch and asked me to represent them at the World Series of Poker in Las Vegas—my first tournament. The website offered to pay all my expenses, including the $10,000 buy-in; whatever I won was mine to keep. I figured I had nothing to lose, but the tournament was a disaster. I was eliminated within three hours. When I went home, I was humiliated. I logged into Bodog, hoping to earn some money and rebuild my confidence, but my nerves were shot and my brain was cloudy—and I kept playing the wrong hands. After three days, I was $30,000 in the hole. From then on, I vowed to play smarter. I stayed conservative, slowly recovering what I’d lost by keeping the stakes small and incremental. Within a few years, I was clearing hundreds of thousands of dollars annually.

In 10 years, I’ve played 8,000 tournaments and won seven World Series of Poker Circuit rings. I’m ranked the 17th best poker player in the world and have grossed more than $5 million in winnings. I keep a humble one-bedroom apartment in North York, but I spend most of my time on the road, travelling to tournaments in Las Vegas, Atlantic City and St. Louis. When I’m not at home, I’m living out of my suitcase, crashing in hotels and on friends’ couches. All my income is fair game for poker: it’s my bankroll and my net worth rolled into one. I consider myself an Orthodox Jew—I still wear a yarmulke around the table—but I’ve relaxed my beliefs.

For me, poker is about the strategy as much as the money. I can quickly gauge how experienced players are based on how aggressively they handle the chips. For example, young players will often play a higher percentage of hands—and on average, the quality of their hands isn’t going to be as good. I can work with that. It’s a game of math, discipline and stamina. There’s no rush like it.

Ari Engel is a professional poker player who lives (mostly) in Toronto.

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