Backgammon Hustler
Michael Konik, 1999
Cigar Aficionado, Jan/Feb 1999

In the jet-set world of little ivory disks, impeccable manners are essential when separating a fool and his money.

He does not have a permanent address. But Simon Jones isn’t hard to find.

The presidential suite of the world’s better hotels. The finest restaurants in Paris, London and New York. The first-class cabins of transatlantic jets. These are his usual domains.

Whether in a dark Moscow nightclub or on a technicolor Balinese beach or upon the pulsing streets of Rio de Janeiro during Carnevale, you can pick Simon out of the crowd. He’s the one with the beautiful woman draped on one arm and a little black briefcase in the other. The woman is, he’ll admit, a frivolous accessory, one of the delightful spoils of being rich and generous. The briefcase, though, is another thing altogether. That briefcase is his life.

It contains a couple dozen polished ivory disks — “checkers,” Simon calls them — two leather cups, four dice and a cube with various exponents of the number 2 on each side.

Simon is the world’s finest backgammon hustler. Aside from the knowledge he stores in his head, his briefcase contains everything he needs to subsidize a life that seems torn from the pages of an Ian Fleming adventure. Simon Jones (his name and some identifying details have been changed) is in many ways a cipher, a phantom who occupies an all-cash shadow world that shields him from the scrutiny of inquisitive tax collectors and customs officials. But he is by no means obscure. Among the jet set, the preposterously wealthy

businessmen and royalty for whom no craving for luxury is unindulged, he is a regular fixture, as common a sight as a Bentley parked in the circular driveway of a European mansion. Simon is One Of Them. And this, it seems, is the secret of his gambling success.

In To Catch a Thief, dashing and debonair Cary Grant plays a dashing and debonair burglar, a charming con man who mixes easily with his unwitting victims. Some years ago, I interviewed a man named Albie Baker, the international jewel thief whose story inspired the 1955 Hitchcock classic. The thief insisted his lock-picking and safe-cracking skills were only average — “There were hundreds of guys who could do what I did,” he told me — but his “people skills” were unsurpassed. Dukes and duchesses welcomed him into their social circles; politicians and city planners revealed their most secret confidences. All the while, Baker was relieving them of their precious metals. “Nobody suspected me, of course,” the thief explained. “You don’t suspect a member of your country club of burglary.”

Simon’s strategy is nearly identical. He has slept in the royal palaces of several Middle Eastern nations; he counts among his acquaintances the young (and reckless) scions of one of the world’s largest distilleries and a major Italian bank; hall of fame athletes and Academy Award winners know his face. And most of them have sat across the backgammon board from him and happily watched Simon relieve them of their excess cash.

“All of these people, they like to be entertained,” Simon remarks, in the hushed, clipped tones of a well-bred British schoolboy. “I’m an absolute treasure to them. And, I suppose, they to me.”

Simon is handsome in an unthreatening kind of way; he doesn’t smolder, he comforts. His manners are impeccable. And though he is careful not to make a spectacle of himself, he is often considered the life of the party, a well-bred Dionysus who happens to be quite splendid at an ancient board game.

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.

“I pick my spots well. I’m not a gunslinger. I don’t need to beat the best. I’d rather play the guy who can’t see, hear or think. I want to beat the donkey,” he says, chuckling.

“There are gentlemen — well, Mr. McGrill, for instance — that I consider geniuses, great theoreticians who don’t care about money. If you offered them one billion dollars in exchange for 10 points off their IQ, they probably wouldn’t do it.” He glances around his penthouse suite overlooking New York’s Central Park, and laughs. “Me? I’ll take the money.”

Simon has just finished playing a weeklong match against a Pakistani fellow, a banker, whom Simon met at The Traveler’s Club in Paris. The Pakistani fellow beat Simon out of $250,000. Simon is not unhappy.

“I’ll eventually take this guy for a couple million,” he says dispassionately.

He views himself as a walking casino, capable of absorbing losses, sometimes large losses, but playing all the time with an advantage. Even the most famous casinos on the Las Vegas Strip have a bad day, a bad week, maybe even a bad fiscal quarter. But in the long run they tend to get the money. So does Simon.

And like the casino that trumpets the number of jackpot winners who have periodically emptied out the casino’s slot machines, Simon doesn’t hide his losses. He advertises them. “If one of my clients beats me, I want them to enjoy themselves and spread the word. I want people to know how beatable I am. I want people to think I’m not as good as everyone says I am. If they didn’t think they had some chance of winning, why would anyone play me?”

In this regard, Simon is not a hustler in the traditional sense, in the pool-shark-who-acts-as-if-he’s-never-seen-a-cue-ball fashion. His deception is far subtler. He tells potential opponents, “I’m too good for you” — and they being highly successful titans of the globe, winners in the arenas of business and finance and power, are eager to prove him wrong.

Unlike poker, in which higher stakes usually mean better players, high stakes in backgammon don’t necessarily produce better players. Most professionals will tell you the big games are lousy with bad players. For some reason, they say, Simon attracts them like a flower does a bee. “The 10 best pigeons in the world are desperate to play with him,” one top professional complains. “Nobody else can get near them, and they’re falling all over themselves to play Simon. In my opinion, he’s not the greatest player. He’s very good, I think, but not great. But he makes more money than anyone in this business because he finds the games. Actually, that’s not true,” the pro says, reconsidering. “The games seem to find him.”

This assessment does not bruise Simon’s feelings. “I played a guy last year. He lost a hundred thousand to me in four days — and he was truly happy. He thanked me!”

Sometimes good players become surly when lesser players beat them. It happens all the time at the poker tables and almost as frequently over the backgammon boards. This, of course, only alienates the “pigeons.” Yet many allegedly “professional” gamblers, many of whom are seriously deficient in self-esteem and are more concerned with inflating their ego than their bankroll, seldom miss an opportunity to snivel or whine.

Not Simon. “If a guy is going to swim up a waterfall to beat me, I congratulate him, and I do it sincerely. I tip my hat to him. Gambling is like hunting. You can’t whine if you have a spear in your back.”

Not long ago, Simon was particularly flush. He had spent the previous month in Monaco, playing a Kuwaiti sheik who knew he couldn’t win but, on the other hand, didn’t mind losing $5,000 an hour to his newly discovered friend, as long as the laughs flowed as freely as the first-growth claret. This particular sheik typically spent about $20,000 a day on hookers; the money he lost to Simon was, likewise, cheap entertainment.

With nearly $400,000 of the sheik’s petro-dollars to the good, Simon returned to London, where the director of a brokerage firm challenged him to a match for uncommonly high stakes, $3,000 a point. Knowing the man had exactly zero chance of winning — “he couldn’t possibly get lucky enough” — Simon readily accepted, not knowing that his opponent’s playing stake was the product of an elaborate embezzlement scheme. Which is why Simon was mortified when the brokerage man, down nearly $300,000 and belatedly realizing that he had no hope of recovering the money, dashed for a nearby window ledge and threatened to jump.

“Of course, I immediately offered the man his money back,” Simon recalls. “Well, now he really wanted to jump — honor and such. It was a rather tense moment, this man being several stories above Hyde Park. So, instead, I offered to loan him the money. I assured him that he still owed me, that I wasn’t letting him out of his debt. That I expected every dime. But that we could consider it a loan.”

The brokerage executive begrudgingly agreed — and has been paying Simon $10,000 a month (approximately equivalent to Simon’s monthly hotel tab) ever since.

“Looking back on my choice of profession, I could have made more money as a stock trader,” Simon figures. “Much more than what I earn playing backgammon. But,” he says, sighing contentedly, “I’ve met a lot of interesting people this way.”

Michael Konik, Cigar Aficionado’s gambling columnist, is the author of The Man with the $100,000 Breasts and Other Gambling Stories.

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