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

The Presidential Suites of the world’s better hotels. The finest restaurants in Paris, London, and New York. The first-class cabins of trans-Atlantic airplanes. 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 Carnaval, you can pick Simon out of the crowd. He’s the one with the beautiful woman holding one hand 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. And aside from the knowledge he stores in his head, his briefcase contains everything he needs to subsidize a life that seems shorn 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 luxury goes wanting, 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 Cary Grant movie. 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, the thief 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 all of them have sat across the backgammon board from Simon and happily watched him 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 school-boy. “I’m an absolute treasure to them. And, I suppose, they to me.”

Simon is handsome in a non-threatening kind of way; he doesn’t smolder, he comforts. His manners are impeccable. And though he’s 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”), 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 discovered his talent for backgammon, a game that’s ridiculously easy to learn, but ridiculously difficult to know.

“I played for fun, with a roommate, and I paid his rent every month with my losses,” Simon remembers. “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. 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 ten 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 and steadfast abstinence, Simon would have found himself beaten down by the cruel torments of reality, only to persevere the indignities of gambling-borne poverty and emerge several years later as a champion.

That’s not what happened. Simon was a success.

He didn’t become rich overnight, and his skills were not immediately commensurate with his tastes for fine wine and finer women. But at every level of competition he flourished. Simon began playing for the equivalent of $10 a point. Then $25, then $50, then $100. His rise came gradually—and, in his estimation, undramatically—his growing skills producing a growing bankroll. 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 re-double [challenge your opponent to double the stakes] when you’ve got a demonstrable edge, you’re playing too high. 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.

He does not, however, view his occupation with wonderment. The romantic ideal that most amateurs harbor 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 sanguine 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: himself.

His rise continued unabated, culminating with victories at the World Cup tournament and the annual World Championship tournament in Monte Carlo, the only player ever to win both. (He still attends most of the major tournaments, primarily to develop new clients.) Today, Simon is widely regarded by cognoscente as one of the top three backgammon players in the world. But, he insists, it’s 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 super-human 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, certain authors, for instance—that I consider geniuses, great theoreticians who don’t care about money. If you offered them one billion dollars in exchange for ten points off their I.Q., they probably wouldn’t do it.”

He glances around his penthouse suite overlooking Central Park, and laughs. “Me? I’ll take the money.”

Simon has just finished playing a week-long match against a Pakistani fellow, a banker, whom he 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, like a pool shark who acts as if he’s never seen a cue ball. 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, where higher stakes usually mean more talented players, high-stakes in backgammon don’t necessarily produce better players. In fact, most professionals will tell you the big games are lousy with bad players. And for some reason, they say, Simon attracts them like a flower does a bee.

“The ten 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,” the pro says, “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.” Still, many allegedly “professional” gamblers, a number of whom are seriously deficient in self-esteem and are more concerned with inflating their egos 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. If you’re constantly chucking spears at people, you can’t whine if sometimes you get one in your back.”

Not long ago, Simon was particularly flush. He’d spent the previous month in Monaco, playing a Kuwaiti sheik who knew he couldn’t win. On the other hand, he 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 spends about $20,000 a day on hookers alone; the money he lost to Simon was, likewise, cheap entertainment.

With nearly $400,000 of the sheik’s petro-dollars to the good, Simon traveled to Sweden for a tournament. There, one of the tournament directors challenged him to a match for cash. Knowing the guy 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 money collected by the tournament to pay for the hall and awards dinner. Which is why Simon was mortified when the tournament official, down nearly $10,000 and belatedly realizing he had no hope of recovering, 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 Stockholm. So, instead, I offered to let him borrow 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 tournament executive begrudgingly agreed—and has been paying Simon in small installments (an amount considerably less than 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.”