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Backgammon Hustler

In the Jet-Set World of Little Ivory Disks, Impeccable Manners are Essential When Separating a Fool and His Money
Michael Konik
From the Print Edition:
John Travolta, Jan/Feb 99

(continued from page 1)

The son of a career diplomat, Simon was born in Maryland, near Washington, D.C., but spent most of his youth in European boarding schools, reading James Bond novels instead of studying Latin. ("We should all be Bond," he is fond of saying.) After a nomadic year trekking through Nepal in search of something ("I can no longer recall exactly what," he says) Simon attended Cambridge, where he studied economics and psychology--disciplines that have prepared him well for his "career," if you can use such a common word to describe the life Simon has made for himself. He never took a degree. But it was at Cambridge that Simon developed his talent for backgammon, a game that is ridiculously easy to learn but ridiculously difficult to master.

"I played for fun, with a roommate, and I paid his rent every month with my losses," Simon recalls. "Somehow I found out that there were books written about the game. This struck me as something of a revelation, the fact that there might actually be a way to master the game beyond rolling a lot of good numbers. Without my friend knowing, I went to the library and read all the books on backgammon. [Paul] McGrill's book, and so forth. Shortly thereafter I was making more money in a day than most people make in a week of honest work."

In only a few months, after several profitable forays into private London clubs, Simon believed he could earn a living playing backgammon. "I knew I was the best player in Cambridge, and probably in the top 10 or so in London. And since I had always harbored these juvenile Bond fantasies, I thought it appropriate to do something utterly irresponsible and impulsive and attempt to live by my wits."

Were this a movie, a banal morality tale promoting the virtues of steady employment, Simon would have found himself beaten down by the cruel torments of reality, persevered despite the indignities of gambling-borne poverty and emerged several years later as a champion.

That's not what happened. Simon achieved success quickly.

He began playing for the equivalent of $10 a point. Then $25, then $50, then $100. His rise came gradually--and, in his estimation, undramatically--matching his growing bankroll with his growing skills. Now he's comfortable playing for $2,000 a point, some of the highest stakes in the world. Any higher and he feels himself starting to play conservatively, in violation of one of his essential rules: if you don't redouble (challenge your opponent to double the stakes) when you've got a demonstrable edge, you're playing too high for your bankroll. Given the chance to triple his net worth or go broke--for example, in a match against the Sultan of Brunei--Simon would take the chance.

Despite the fantastic stakes, he does not view his occupation with wonderment. The romantic ideal that most amateurs have of the successful professional gambler is, according to the world's greatest backgammon hustler, mistaken. "What I do is like selling insurance," he says. "You go to work every day. Some days are winners, some are losers. I try not to get too emotional about either result."

He has always been similarly dispassionate about his talent. He recognized it early, developed it fully and uses it to earn a living. But he does not stand in awe of it.

"Backgammon is an open information game," he explains. "There aren't any hidden cards. You can see when people, yourself included, make mistakes. If you're properly objective, you can assess your opponents' weaknesses. And more important, you can assess your own weaknesses." In the late 1970s, only a few years after reading his first book about backgammon, Simon could identify the best player in London. It was he.

His rise continued unabated, culminating with victory at the annual world championship tournament in Monte Carlo. (He still attends most of the major tournaments, primarily to develop new clients.) Today, Simon is widely regarded by cognoscenti as one of the top three backgammon players in the world. But, he insists, it is not pure playing talent that has made him the most successful backgammon player on earth. His math skills, he claims, are average, probably equal to an accomplished ninth-grader. His ability to analyze a table situation (a "proposition," in backgammon parlance) is less the function of technical prowess than keen intuition. And, he freely admits, he has neither superhuman resolve nor cojones the size of grapefruits.

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