Cigar Aficionado

DOYLE BRUNSON Iron Man

Doyle Brunson has played longer and at a higher level than anyone else in the game of poker. Over the last few years, despite competing in fewer and fewer tournaments, the 10-time World Series bracelet winner has still managed to take down in excess of $200,000 per annum. These tournament profits may pale alongside the winnings of today's tournament pros, but at 75, Brunson is generally more focused on playing in the Big Game—the high-stakes competition in Bobby's Room at the Bellagio in Vegas—than angling for prize money in the richest tourneys. In fact, according to Eli Elezra, another Big Game regular, it's usually Brunson who gets the action going these days.

Several years ago, when Chip Reese was still alive, Elezra re that Brunson's skills had slipped a bit. "Chip used to call me and tell me to make sure that Doyle is coming," says Elezra. "He is the old man, and his game had dipped down from where it was during its prime. We enjoyed good games, with Doyle misplaying hands." The last five years, though, have been different. Brunson's game has rebounded markedly. "The guy's a big winner, he picks his spots, he bluffs, he shows bluffs, he reads people," gushes Elezra. "I'll take Doyle against any of the Internet players. When he was in town, going up against Tom Dwan and the other kids, I begged Doyle to give me a piece of his action. He sold me 25 percent and I was so happy."

TOM DWAN Master Multitasker

After a short stint in college, 23-year-old Tom Dwan was making so much money at online poker that he lost his desire to continue studying. Dwan, known by the moniker "durrrr," quit school and torched the online poker world, emerging as a consistent winner in the highest stakes games, playing multiple tables as well as anyone and quickly turning into the kind of opponent that few people want to square off against. To encourage action, he issued what has become known as the Durrrr Challenge: he will play anybody except fellow online specialist Phil Galfond (for reasons that have more to do with friendship than a lack of courage) at four tables of no-limit Hold'em or pot-limit Omaha, for blinds of $200/$400 or higher. If, after 50,000 hands, the opponent is ahead, he wins a sweetener of $1.5 million. If durrrr is ahead, he gets $500,000. The 3-to-1 overlay has attracted Patrik Antonius (who was in the process of playing as this issue went to press). Interest has also been expressed by Phil Ivey and fellow high-stakes pro David Benyamine.

The challenge is indicative of Dwan's belief in himself. Over the last year or two, the poker world has taken notice. Phil Hellmuth is a case in point. After patronizing Dwan in the wake of his loss to the young player at 2008's National Heads-Up Championship (view it online at youtube.com/watch?v=zY3b27vZwYk), Hellmuth has gone from doubter to booster. "I never thought he was a bad player, but I thought he didn't understand the game," says Hellmuth, who revised his opinion after 30 or so hours of play against Dwan during 2008 and into '09. "I've come to see that he has absolutely no fear and a deep understanding. Not many people can play as fast as he does and still win money. The only way I can play against durrrr is to represent a hand, put maximum heat on him and hope he's playing a bottom pair. He knows how to exert pressure on people, he's good at reading his opponents and he may turn out to be one of the game's greatest."

PHIL GALFOND Mr. Methodical

That Galfond would adopt an intentionally goofy name, specifically "OMGClayAiken," for playing online says a lot about his desire to slip under the radar. As players become increasingly cognizant of their public images and overly eager to cash in on them, Galfond remains a low-key guy. Save for his involvement with the online instructional site Bluefirepoker.com, he doesn't want to be recognized and isn't looking to capitalize on the bigger business that surrounds poker. He's perfectly happy to sit in his lower Manhattan penthouse and extract money from the best online poker players in the world. Over the last year, as confirmed by cigaraficionado.lotteryjackpot.net, Galfond has won more than $5 million on Full Tilt Poker alone.

According to Andrew Robl, a successful online player in his own right and a longtime friend of Galfond's, a big contributing factor to Galfond's consistently winning ways is his ability to intellectualize what he does. A lot of successful players say that they do things on feel or intuition or base their plays on experiences that have been mysteriously absorbed. "Phil, though, can always say why he plays a certain situation the way he does," says Robl. "Phil is very good at narrowing down the hands that people have and making them react in certain ways. For example, most people don't like to check-call out of position because they don't gain any information on the hand that their opponent might be holding. Phil is confident that he will be able to figure it out and then take advantage on a later street. More than other players at his level, Phil goes through a conscious thought process. He's probably influenced my poker game more than anyone else."

HUCK SEED Heads-Up Tournament Champ

Veteran poker player Erik Seidel describes Huck Seed as "the Phil Ivey of his day." And he's right. Back in 1996, when Seed took $1 million by winning the World Series of Poker championship, he was already known around town as a top cash-game player and had built a sporty reputation by accepting all sorts of offbeat prop bets. Hobbled, however, by some bad habits and unfortunate breaks, Seed all but disappeared from the elite poker circuit for a number of years. Recently, though, he's surfaced and appears poised to reclaim his former glory. By recent tournament results alone, he's establishing himself as a top live heads-up Texas Hold'em practitioner, and his final tabling of the $50,000 buy-in H.O.R.S.E. event at the 2008 World Series of Poker is indicative of Seed's broad-based skills.

In 2005, when Phil Hellmuth won the National Heads-Up Championship, he acknowledged, "Huck had been my toughest opponent." Long a er of the lanky pro who left Cal Tech to pursue a career in poker, Hellmuth sounds impressed by Seed's recent winnings, which include finishing first in this year's National Heads-Up and last year's Canadian Open Poker Championship. "Huck is extremely tough at heads-up," says Hellmuth. "He focuses in on playing his opponent very well. He's continually changing gears and recognizing the importance of playing his cards based on where he thinks his opponent is at and what that person is capable of doing." According to Hellmuth, when Seed was at the final table at this year's Heads-Up, going against Vanessa Rousso, "he played so well that Vanessa may have had zero chance of winning."

ERIK SEIDEL Risk Manager

At a certain point, most people who no longer need to play poker for money or accolades lose interest in the game and wander away from it. Not Erik Seidel. As one of Full Tilt's original sponsored players, he's achieved serious riches. But the way he continues to go at it, you'd think that he needed to win in order to eat. Over the last three years, Seidel has averaged more than $1 million annually in tournament winnings; he has snared eight World Series bracelets during the course of his career and captured his first World Poker Tour championship in 2008. Prior to winning, Seidel characterized his lack of a WPT finish as "something missing from my résumé." No longer.

Howard Lederer first met Seidel in the 1980s, when both players were bouncing around New York City's gambling scene. Lederer is one of the people who took a flyer by backing Seidel in the 1988 WSOP (in his very first tournament, Seidel shocked everyone by finishing second to Johnny Chan) and has always had plenty of faith in Seidel's skills. "Erik is unique in that he is incredibly careful, almost conservative to a fault; but when he thinks he has the best of it, he will bet big," says Lederer. "He's willing to take calculated risks in pushing small edges. Few poker players have that combination, where they are cautious but also able to put serious money behind their convictions. For as long as I've known Erik, he's had this quality of jumping in with both feet, but only when the water temperature is exactly right."

PATRIK ANTONIUS Short-Handed Specialist

Born in Finland, Patrik Antonius came to America to attend Averett University, in Virginia, on a tennis scholarship. But, already an accom-plished online poker player, he dropped out of school after only one year and hopped a plane to Vegas. Considering his competitive nature and adeptness in the one-on-one game, it's not surprising that Antonius excels at heads-up poker. At the time of this writing, he is currently competing in the Durrrr Challenge. As of May 13, Antonius had played 13,556 hands and won $391,704. "When playing two-, three- or four-handed, Patrik is a tactician who knows how to put pressure on people and make them do things that they don't want to do," says poker stalwart Barry Greenstein.

Antonius is so skilled at playing short-handed that when he began competing in the Big Game (where success requires participants to excel in at least nine different forms of poker), he was able to overcome deficiencies simply by waiting for his number of opponents to shrink. Though Antonius has no qualms about playing live poker, he is strongest on the Internet, where he has multi-tabled his way to more than $6 million of profit over the last 12 months. "Patrik is the most dangerous guy," says Ilari "Ziigmund" Sahamies, a fellow Finn who frequently battles Antonius in the so-called nosebleed-stakes games online. "He manages to be solid but treacherous, playing so aggressively that you never know what he has. He bluffs at the right times and never does anything stupid. He's one of the few players that I don't like going up against."

DANIEL NEGREANU Card Reader

When it comes to tournaments, Daniel Negreanu's record is singular: without the benefit of a Main Event windfall, he's No. 2 in tournament winnings. As opposed to board leader Jamie Gold (the lion's share of his poker profits has come from a single, charmed World Series of Poker championship in 2006), Negreanu has been a consistent tournament finisher since 1998. Most stunning of all, Negreanu enjoyed a run during 2004 and 2005 that earned him poker's hat trick: he was named player of the year by the World Series of Poker, Card Player magazine and the World Poker Tour.

Part of Negreanu's success comes from his ability to read opponents—an image that's been fostered on the TV show "High Stakes Poker" and is well illustrated in a World Series hand he played (see it at youtube.com/watch?v=zV829yG2Kcc). Erik Seidel points out that Negreanu uses his reputation to leverage advantages at the tournament tables, which sometimes results in free cards and frozen opponents. "Daniel takes people out of their comfort zones and makes them play hands that they shouldn't," says Seidel, adding that Negreanu is particularly adept at turning his public image as a nice guy into a big edge against amateurs. "He's a creative thinker who is clearly comfortable in all the games. Daniel had one unbelievable year, where he won $4 million, and he has consistently done well. He may very well be the best tournament player."

BARRY GREENSTEIN Poker Brain

Few people possess enough intelligence, versatility and social skills to succeed in both the business and poker worlds. Barry Greenstein has managed that feat. Between 1984 and 1991 Greenstein worked for the company that eventually became Symantec, helping to develop a wide range of software products. The whole time, though, Greenstein was making more money at the poker tables than the software firm was paying him. After turning to poker full-time, he took his first shots at the Big Game, where he was thought to be a fish and was welcomed with open arms. In short order, however, Greenstein established himself as a winner, at all the games, and later explained that he entered that highest realm of poker with no ego at all. He simply, and correctly, believed that he'd be able to make lots of money.

Eli Elezra points to Greenstein's mathematical understanding of poker and his ability to play the game with little emotion. "If Howard Lederer is the professor of poker, then Barry is the genius," says Elezra. "If we want to talk about certain hands, about percentages, about outs, about the optimal way to play, then we turn to Barry. He is so solid." But, Elezra adds, Greenstein is not as straightforward a player as that makes it sound. "He knows how to sense weakness and take advantage. Plus, his patience is unbelievable. I've played 18 to 20 straight hours with Barry and watched him maintain focus while nursing a small stack like nobody else in the game. If he loses, he shows just a tiny bit of disappointment, always keeping his composure and waiting for the next opportunity."

PHIL HELLMUTH Tournament King

Having inarguably earned his nickname, Poker Brat, Phil Hellmuth is an easy pro to dislike. He blatantly bullies weaker opponents, explodes at less seasoned players and rarely seems to take winning or losing with a whole lot of graciousness. That said, his skills at no-limit tournament Hold'em are pretty much unassailable. Hellmuth has won 11 WSOP bracelets, more than anyone else, and has established himself as the most recognizable personality in the game. It's allowed him to attract loads of sponsorship deals and speaking engagements.

Some in the poker world claim to be embarrassed by Hellmuth's notorious outbursts. Others, like Erik Seidel, view them as a tactic. "He intimidates people, he gets people afraid to play pots with him, and all his chatter makes it more difficult for them to think," says Seidel. "Sometimes they lose their minds a little bit." It's an approach that works well against the many amateurs that tournament pros inevitably find themselves up against. But what about the other experienced pros that Hellmuth has had to get past to earn his bracelets? "He has more trouble against the best players, though he obviously has to be able to beat them," says Seidel. "What he does is a bit of a mystery. But it works." A cornerstone of the Hellmuth approach is small-ball poker, which involves playing lots of hands and making many small raises. Despite this approach, says Seidel, "he paints a picture for people of always having good cards. Clearly, his tournament record is remarkable."

PHIL IVEY Best of the Best

Phil Ivey emerged on the poker scene in the 1990s as a video game fanatic who played increasingly escalating stakes in Atlantic City casinos. Then, at the start of the next decade, came a jaunt to Southern California, where he rented a room upstairs from the Commerce Casino's legendarily busy poker room. According to Jerry Stensrud, who runs the Commerce room, "Every morning Phil would start his day by playing $100/$200 poker. He got quite a reputation."

These days Ivey is hailed by top online players as the toughest to beat at nosebleed stakes of no-limit Texas Hold'em and pot-limit Omaha. Barry Greenstein, who knows Ivey as well as anybody and has played many hours against him in Bobby's Room, describes Ivey as "a bit of a chameleon" who can change his playing style and take opponents out of their comfort zones. "Phil seems to figure out what opponents will do and what will give them problems. He stays one step ahead of you more than anyone else does. As soon as you think you know he's going to call, he pulls the rug out from under you and does something else. I would rarely say that somebody is the best player. But Phil has been taking on all comers, at the highest stakes, and from what I see he wins the most. I don't know what other metric you can use."

Michael Kaplan is a Cigar Aficionado contributing editor.