Cigar Aficionado

In poker it's the riffling of chips. In backgammon it's the rumbling of dice. Either way, when that very distinct sound reverberates from multiple sources simultaneously, you can assume that something serious is transpiring. In both instances, it is the percussive sound of people playing a game that seems simple on the surface but is brain-bendingly complex at its highest level. Such is the case as I watch the action in Monte Carlo at the Fairmont Hotel.

The Mediterranean Sea, visible through the floor-to-ceiling windows at the Fairmont, is an illustration of affluence, punched up by yachts, private helicopters and cruise ships. Inside a nondescript ballroom at the hotel, which could be located anywhere from Newark to Naples, there's also plenty of affluence, but you'd never know it. People are dressed down, Champagne is not on offer and the energy is focused on rolling dice and moving checkers around a felt-topped board.

On some levels, this event, dubbed the World Backgammon Championship, feels like a throwback to the old days of poker, to a time when the World Series served as the centerpiece of an unambitious universe, populated by players focused on the game and unconscious of marketing opportunities. With a prize pool that is modest by Hold'em standards—1,000 euros to enter, first place pays a bit more than $100,000—these people play because they are passionate about backgammon.

While a handful of successful hustlers are in attendance—including one who's so press-averse that not being included in this story was a condition of his competing in Monte Carlo—most of the players are affluent guys who love the game but have built considerable wealth elsewhere. They're gentlemen gamblers, like Freddie Chamanara. Drawn to risk, Chamanara's suitably set up so that he can blow $100,000 on TV's "High Stakes Poker" and walk away with nothing more than a shrug of disappointment.

"Compared to poker, backgammon is very cruel; there is a lot of luck, there is no discipline required and the game can suddenly change," the Chicago-based Chamanara says, before settling into a match for $1,000 a point, where getting shellacked could constitute a six-figure loss. "I come out here for the action. I love the side action. But I also love Monte Carlo."

Indeed, for many this event is as much a social occasion as it is an opportunity to play a difficult game against a particularly competitive field. Much like the World Series of yore (which poker veteran Mickey Appleman once dubbed "a convention of gamblers"), the World Backgammon Championship is at least partially about renewing friendships, settling old scores and evening up on debts that had incurred during the year. And a nicer place to do this doesn't exist.

Situated along France's Mediterranean coastline (but officially in the independent principality of Monaco), Monte Carlo is home to Alain Ducasse's first restaurant, a three-star Michelin called Le Louis XV (order the foie gras and pigeon if you eat there, then finish up with a selection from the restaurant's cigar cave), stunning beachfronts and the world's most elegant hotel/casino: Hotel de Paris along with its adjacent Casino de Monte-Carlo, which both date back to the nineteenth century and, in a lot of ways, remain pretty much unchanged.

Fittingly, this particular backgammon tournament has been held here for 30 or so years, and the location nicely dovetails with the game's enduring image. It's long been the hobby of choice for jet-setters, European sophisticates, wealthy Americans and those who enjoy trafficking in that world. One participant here likes to talk about having taught Hugh Hefner to play backgammon aboard the Playboy pasha's private jet. Others have squared off against Arab potentates, Russian oil oligarchs and Hollywood icons. Because players follow the money, Gstaad, Cannes and Monte Carlo have long been stopping points for those who seek the steepest action.

When in Monte Carlo, the highest rollers all love Hotel de Paris with its old-world oak-accented suites and sophisticated party atmosphere that defines this locale in high season.

Despite those refinements, some people are drawn here purely by the game. They travel to Monte Carlo for opportunities that are financial rather than social. And, more often than not, they possess brains that eclipse their bankrolls. Case in point is a Belushi-proportioned genius named Matvey Natanzon. He is known as Falafel, and, by looking at him, it'd be easy to assume that he earned his moniker in the fry shops of downtown Tel Aviv. But in truth, Falafel, who was born in Russia and moved to Israel at age 4, spent his teenage years near Buffalo and received his nickname while playing backgammon for bucks in the parks of Lower Manhattan. On the road to game-playing enlightenment, he eked out a living and fortified himself on fried balls of ground chickpeas.

Along the way, Falafel became a professional gambler and evolved into a man who is regarded as the greatest backgammon player in the world. His success has afforded him a life that revolves around tournaments every couple months along with cash games when the stakes are high enough and the opponents appear trustworthy (backgammon is rife with cheating and welshing). Falafel recounts a recent trip in which he took on a wealthy businessman who ping-ponged from Vegas to Hawaii. Halfway through their series of matches, Falafel found himself six figures in the red. Then he turned things around and ultimately pulled down a cool 50 grand. "All I need to do," he says, "is play the right person a few times a year and I'm in good shape."

Falafel's high-flying career started inauspiciously. In 1991, after graduating from the University of Buffalo, with a degree in accounting that he figured he'd never use, he ended up in New York City. He had vague ambitions, arriving in town with the intention of playing chess.

In no time at all, however, Falafel recognized that more lucrative opportunities centered around backgammon. He watched for a while and had enough hubris to assume that he'd be good enough to clean out the regulars who gravitated to Washington Square Park and Liberty Park, both in Lower Manhattan, and both serving as the sites for loose cash games back in the 1990s. "I thought I was the best and started playing," he says. "Immediately, though, I discovered otherwise. I lost all of my chess winnings."

Nevertheless, Falafel was bitten by the backgammon bug. He became obsessed with the game and fell in with a group of young players—including Phil Laak, Gus Hansen and Abe Mosseri—who'd all go on to gain recognition in the poker world. Possessing the focus and determination to spend many hours watching and absorbing, Falafel dedicated himself to learning the game through osmosis; he took in the moves and strategies of backgammon's best players in order to model a style of his own.

He frequented gambling clubs around Manhattan and asked so many questions that a particularly skilled amateur told Falafel that he'd start charging him for answers. Much to the amusement of others on the scene, Falafel coughed up $2 or $3 per question. "They laughed," he remembers, "but what I learned proved to be worth a lot more than what I paid for it."

One lesson, which cost him nothing, came courtesy of Gus Hansen. Hansen was playing a Wall Street executive for $1,000 per point. "I paid attention to Gus and noticed him doing something unusual," recalls Falafel. "Before making his play, in his head, he'd work out possible rolls and possible moves that the other guy could make. Gus was talking out loud and running through the numbers in order to come up with the optimal strategy each time. I had never seen that before." Falafel adopted the approach and saw his game improve considerably.

After becoming self-sufficient through backgammon, Falafel fulfilled a promise he had made to himself and moved back to Israel. He took up poker (he is now a part owner of a Tel Aviv poker club and plays there three nights a week) but also amped up his obsession with backgammon. Working with an astounding computer program called Snowie, he memorized every mathematically correct move and tightened up his game to the point where it is now close to perfect (in every situation, there is always one play that is most correct). As a competitor in Monte Carlo quips, "When you see somebody playing perfect backgammon online [a number of sites host money matches], you know it's got to be Snowie or Falafel."

When I tell a globe-trotting friend of mine that I am going to Monte Carlo to report this story, he responds with a rare expression of envy. "You're going to the Yankee Stadium of gaming," he tells me.

Upon arriving, I think I know what he means. Without a doubt, Monte Carlo is one of the greatest places in the world to gamble. Gamble high enough and you'll be comped for meals that no casino in Las Vegas can hold a candle to. Joël Robuchon, who is the talk of Vegas thanks to his pair of eponymous restaurants at the MGM Grand, has been here for years with a two-star Michelin that is part of the landscape. Ducasse's Le Louis XV is a foodies' destination, a place where you can have the kind of simple, elegant and perfectly prepared meal that stays with you for the rest of your life. Even Café de Paris, which is meant to be a casual spot for a quick bite, is pretty fab. And, as another friend points out to me, when it comes to people-watching at an outdoor table, the place is second to none.

It is nice to see pretty girls, but for me the casino is the thing, and Casino de Monte-Carlo is the one that defines this place (there are three others, all run by the same entity, but none are nearly as compelling). It's where the big action goes down and where everything started, back in 1863. That was when Monte Carlo initiated gambling for the same reason that Atlantic City and Las Vegas would: to bring in revenue while elevating its status.

Looking to make a big splash, the reigning forces here enlisted architect Charles Garnier (who was responsible for the very splendid Paris Opera House) and he came up with the era's equivalent of the Bellagio. Blowing away anything you might encounter in modern-day Vegas, Casino de Monte-Carlo has glass chandeliers, rococo ceilings and overhead frescoes so striking that they're almost as alluring as the games themselves. Without resorting to hyperbole, this casino really does feel like a palace.

In short order, the posh gambling den turned into a high society hotbed, drawing deep-pocketed customers from the wealthy precincts of Italy and France. Its reputation spread to the hoi polloi in 1892 when a notorious gambler by the name of Charles Wells won all the chips at a roulette table—apparently he found biases in the wheel—and inspired a popular song about the windfall. Smartly, the casino defined his feat as "breaking the bank" and played it up: after the last plastic orb went into Wells's pockets, a black cloth was dramatically placed over the table and it was pronounced dead.

These days, with biases harder to come by, a major draw for big players is Casino de Monte-Carlo's private gaming rooms, which are as elegant and ornate as the rest of the place. In grand style, they offer gambling's ultimate amenities: discretion and indulgence. If you are willing to play for 1,000 to 20,000 euros per hand at, say, blackjack, you essentially get a private party in a very fancy room. "You can do whatever you want in there," explains Jean-Marc Noaro, general manager of gaming for Casino de Monte-Carlo. "There was one guy who lost a lot of money. He climbed up on the table and began stomping around on the felt. What can you say about that? You can say nothing."

Not expecting to provide such an uninhibited display, I decide to give the famed Casino de Monte-Carlo a whirl and put some of my own hard-earned cash on the line. Unlike American casinos, you have to pay an admission fee to get in (10 euros) but, also unlike American casinos, you feel as if you are playing in a museum of gambling. A display of handcrafted vintage slot machines dominates a side of the room near the entrance. Century-old photos, propped inside a display case, capture the early days of the casino and, if you can look past a relaxed dress code, it is easy to time-trip back to Monte Carlo's Belle Epoque glory days.

As for the gaming itself, it feels distinctly different from that in the United States. Dealers and pit personnel are solemn, players remain emotionless even as they endure roller-coaster swings, and it's not unusual for a sommelier to decant bottles of vintage wine for customers in mid-gamble. Player cards—which track play and comps in the States—are nonexistent here, making the whole process feel a bit more gentlemanly.

The games have their unique quirks as well. Here the roulette wheel has one zero instead of two (an advantage for the players), tuxedoed croupiers run the games with an appealing bit of flare, and chemin de fer and punto banco (variations on baccarat) are both on offer. As for the blackjack, frankly, it is not very good, at least from the perspective of a player hoping to find an edge. Standard blackjack minimums are higher and maximums are lower than the Vegas norm, rules are similar to those in Atlantic City (no surrender, no re-splitting aces), and the dealer doesn't take his down card until everybody has played out his hand. Worst of all, if you are playing two spots and the table is full, a new player who wants to get in can steal your extra spot. And, take it from me, when things are running well, that is not very gentlemanly.

Despite all of that, the experience is enjoyable, the sense of history is palpable, and playing in Monte Carlo is something that every serious gambler should do at least once in his life, if only to experience what it feels like to be a mini—James Bond.

Like a lot of gambling ventures, my run at the blackjack table here starts off fairly well, as a Russian guy and I seem unable to lose. But when things get ugly, they really get ugly, and our downfall is punctuated by his beautiful blonde girlfriend sipping Bordeaux and continually, spookily murmuring, "Forget it. There is nothing here for you. Go away. Go. Before you lose it all."

After my bankroll takes a modest and very polite beating (don't worry, I get 'em back a day later), I leave the Russians, stash my remaining cash in the room safe next door at Hotel de Paris, and spend a few minutes admiring the Ferraris, Maybachs and Maseratis that get to seem weirdly commonplace in the manicured drive-ups here. Then, after filling my quota of gawking, I decide to hop a cab across town to Jimmy'z, a venerable time capsule of a 1970s disco. When I tell the taxi valet that I need a cab, he directs me toward a waiting Bentley.

"How much is this going to cost me?" I want to know.

"As you wish," the guy replies, stuffing me into the backseat.

I'm convinced that he has mistaken me for somebody else, but it still feels pretty damned racy to pull up to the club in such a fancy ride. Never mind that the people there are way too jaded to be impressed by a mere Bentley.

A couple mornings into the backgammon tournament, after I watch the starting field whittle itself down amid flurries of ever increasing side action, tournament organizer Patti Rubin steers me toward a gambler named David Nahmad. He is presented as a prime example of the game's old guard: a wealthy player to whom the action comes simply because he's got enough money and enough gamble to make it potentially worthwhile for certain players. His family, I've been told, is in the fine arts business and they have more or less cornered the market on Picassos. Nevertheless, he seems to be just as proud of having won the World Backgammon Championship in 1996, and his passion for the game is considerable.

A day later, over espressos at a beachfront restaurant near his apartment in Monte Carlo, he tells me that he views backgammon as being parallel to life itself. "The way you play, the way you attack, the way you defend yourself, it's a picture of life," says Nahmad, looking sporty in shorts and a golf shirt. "It gives you equilibrium."

Reportedly a multibillionaire, Nahmad is not into backgammon for the money; he likes the competition, which is why he prefers tournaments to cash games, and enjoys the reality that one high-risk play in a tournament can cost you the entire event. In a cash game, you can do all the gambling you want and reach into your pocket to right the wrong.

But even Nahmad, a man who could easily weather any backgammon loss, has his limits. He remembers playing once at the Monte Carlo Beach Club, gambling for $500 a point. The doubling cube was at 16 and he was concluding a set of games, preparing to roll dice with a likely outcome that would leave him ahead by 98 points or down by 48 points. "It was 50 percent either way, and a $75,000 swing," he recounts. "Plus, I was playing with a German who is always lucky against me. I don't know why, but he always seems to win. So I decided to settle—in a deal that was not in my favor—against somebody who uncannily beats me. Sometimes you get superstitious."

I can't help but wonder if Nahmad tossed the dice anyway, just to see what numbers would have hit. He shakes his head in the negative, squints into the morning sun and checks an incoming cell phone call. Rolling for fun, he explains, would not have been the same as rolling for real; he would have rolled the dice differently and the outcome would have been completely different. Then, before taking the call, he adds one other lesson that crosses over from backgammon to life: "Sometimes you have to hold back and not be so curious."

Michael Kaplan is a Cigar Aficionado contributing editor.