College of LAS « Illinois

Alumni Profile

A Winning Hand

As one of the world's best poker players, Barry Greenstein knows how to win. Now he is using that talent to help others.


Last January, Barry Greenstein stood expressionless beside a poker table in Tunica, Mississippi, as the dealer prepared to flip the card that would determine whether he would walk away with the $1.3 million jackpot. It was the final round of the World Poker Tour Open, and as is customary in tournament play, he and the other remaining player had stepped back from the table out of resignation to Lady Luck. Their gesture also was out of consideration to the audience and the cameras that would zoom in on the final card as it broadcast the game to some 5 million people—an indication of poker's skyrocketing popularity.

Four days earlier, 367 contestants had anted up $10,000 each in hopes of surviving until the final table. Like actor Ben Affleck, many players were forced to throw in their cards the first day. Remaining were these two polar opposites—the brash Randy Jensen and the deadpan Greenstein. Jensen, 33, is a relative upstart who is notorious for losing money as quickly as he wins it. Greenstein, 47, is a veteran of private, high-stakes poker games and considered "the best of the best," according to Mike Sexton, a commentator for the World Poker Tour.

The circus-like atmosphere of high-stakes tournaments makes Greenstein uncomfortable. For more than two decades, he has honed his skills in the private, cash-only games with limits of $4,000 to $8,000 or higher. Around these tables sit the rich and infamous, like Jerry Buss, owner of the Los Angeles Lakers, and Larry Flynt, publisher of Hustler magazine. "They are all smart people who can afford to lose," says Greenstein, by way of explaining how he insulates himself from players willing to risk their livelihoods.

But tournaments have cleaner reputations, which is why, three years ago, Greenstein decided to enter the fray. He had known since he was 12 years old that he had a gift for poker. By age 44, he wanted to do more with his talent than accumulate wealth. So he began playing for charity. And giving away millions.

Greenstein's destiny was literally written in the cards. His father, a grammar school principal and former army officer, taught him how to play poker when he was four. And, every day after school, it was canasta and gin rummy with his mother. By age seven, he was beating the kids in the neighborhood. By 11, he was winning against the juniors and seniors in the local high school—Bogan High School, in Chicago's Scottsdale neighborhood. In high school, when his friends were earning minimum wage at Burger King, he was pulling down $30 to $50 a night in pick-up games.

His teachers and parents saw only his gift with numbers. He got an A in calculus while skipping class in favor of the computer lab. He got a perfect score in math on his SAT test.

If his family had suspicions about how their son was earning his spending money, they were soon confirmed. At U of I, Greenstein skated through the computer science program in three years while winning enough to repay his father the cost of his education. By the time he was pursuing a PhD in math, Greenstein was flying all over the world playing high-stakes blackjack and five-card stud.


Greenstein's unusual lifestyle eventually attracted attention. A local FBI agent visited him after another U of I student complained that Greenstein was wiping him out at cards. Then there were the unexplained absences, when Greenstein would disappear for weeks. As recalls his thesis advisor and friend, Ken Stolarsky, "He was smart but he approached his work almost nonchalantly. It was as if he didn't really need us."

Which he didn't. After one such disappearance, Greenstein reappeared driving a Jaguar and wearing a designer suit. When confronted by Stolarsky about his elusive behavior, Greenstein let him in on his secret. Greenstein had been in London, playing in a "high-roller game with gentlemen from the Mideast." In three weeks he had won more money than Stolarsky would earn in two years.

Soon Greenstein was giving seminars to packed rooms and becoming the stuff of departmental legend. "I had so grossly underestimated him," recalls Stolarsky. "While he was earning a good income at poker he was pursuing knowledge for knowledge's sake. He was the most remarkable student I've had in my 30 years of teaching."

Greenstein didn't finish his dissertation (a fact that bothers him today). Instead, in 1986, he fell in love and married a woman from nearby Decatur, Illinois. He took a software programming job at a startup company called Symantec, in California's Silicon Valley, so that he would be respectable enough to adopt her three children. In 1991, when his wife was diagnosed with multiple sclerosis and his daughter with liver trouble, which eventually required a transplant, Greenstein re-evaluated his career choice. Realizing he could make more money playing poker than writing software, he quit.

It is not unusual for math whizzes to be good poker players. The game is based on probabilities. In a 52-card deck, there are 2,598,960 possible combinations of five-card hands. Some combinations are more likely to occur than others. For instance, in regular five-card draw poker, the odds of you drawing a straight flush are 64,973 to one. Your chances of drawing a three-of-a-kind are better: odds are 46 to one. The easiest combination is a pair. Because there are 1,098,240 pairs in the deck, the likelihood that you will draw one of these is 1.25 to one.

In Texas Hold'Em, the game preferred by Greenstein and all high-stakes players, the odds against any individual drawing a strong hand are greater, with few hands statistically worth playing. Your position at the table and the sequence of betting can so affect your chances of winning that even if you have the best starting hand, which is a pair of aces, you will win only 33 percent of the time.

Poker players devote hours to memorizing probability factors and learning the odds. Novices sometimes bring cheat sheets to games. For a natural mathematician like Greenstein, the ability to juggle these numbers is effortless, which is one reason that he emphasizes psychology over mathematics when he defines a successful poker player.

Luck can shine on any given day in poker, a possibility some people find intoxicating. What distinguishes a poker player from a gambler is restraint. Poker players wager only when the odds are in their favor. They measure their success over weeks, months, or even a year; not on the outcome of one game.

"Maintaining self control is the key to winning," says Greenstein, who has survived plenty of losing streaks. "There are times when I know I'm the worst player in the game that day. Sometimes it is best to go home and come again another day."

For much of his career, though, Greenstein was at the poker table 12 hours a day, six days a week. By 2003, he had all the money he needed. That's when he again re-evaluated his career and decided it was time to do something "productive" with his talent.

"Once, I thought I'd be a doctor to help people—my parents instilled in me the importance of helping others—now I'd found a way to do so. I decided I was going to play poker for charity," says Greenstein.

Crowned the Robin Hood of poker, in his first two years, he gave away more than two million dollars. He is well on his way to doubling that amount this year. His favorite charity is Children, Inc., which helps impoverished children. His former high school is a benefactor of his largesse. So is the Department of Mathematics.

"Giving away money is the most enjoyable thing in the world. The real heroes are those who have less than I yet are generous with what they have. My goal is to set an example, and to use the popularity of poker to inspire others to follow suit. Once they do, they will discover, as I have, what fun it is."

At the World Poker Tour Open at Tunica, when the dealer turned over the ace that assured Greenstein the win, he allowed himself a smile. Then he took the microphone. "I've got an unproductive profession. Giving the winnings away makes it productive. It is clearly the best thing I've ever done in my life."

By Holly Korab, July 2004