Cigar Aficionado

The Poker Ace

For Greg Raymer, winning the world series of poker took knowledge, skill and a little luck

On a Saturday afternoon at a back table in Foxwoods Casino's sprawling poker room, Greg "Fossilman" Raymer steps up and sets down his blue nylon gym bag. He reaches inside the bag, past the fossils, "Tower of Terror" sunglasses and aspirin, and fishes out a wad of hundred-dollar bills rubber-banded into a tight roll. He drops his money upon the green felt and it lands with a satisfying thud. Raymer then announces that he needs chips so that he can play in the $75/$150 game of Omaha (a variation of Texas Hold'em, in which you get four down cards and must use two of them along with three of five community cards).

"Get some chips for me," one guy quips as he mucks his cards. Another player asks Raymer if he's bought himself a new car yet. Someone else remarks that he's waiting to see Raymer on TV. A fourth player jumps up from the table and waylays Raymer to tell him that he has a great idea in need of a patent. Raymer, a patent attorney by trade, listens politely, then informs him, "I'm no longer in that business."

Who could blame him? The day he won the 2004 World Series of Poker in May, beating out 2,575 players and pulling down $5 million, Greg Raymer instantly ceased being a lawyer and became a professional world champion poker player. These days the burly, bald, big-faced Raymer, who turned 40 in June, is traveling the world, entering poker tournaments in Los Angeles, Las Vegas, Dublin and Paris, getting backed by online site and loving his new life.

But here in rural Connecticut, Raymer is not exactly treated like high-stakes royalty. Since he has been competing with some of these guys for five years, he feels as comfortable here as in any home game (Foxwoods is located only six miles from Raymer's house). He gets his chips, takes his seat and plays poker. After losing a bunch of hands and dropping $1,000 or so, Raymer packs up his remaining chips so that he can grab some lunch. Then he playfully announces, "I'm out. You guys are too good for me."

The line gets a couple grunts of acknowledgment as Raymer reaches for a pocket-sized loose-leaf notebook and carefully jots down some information: the amount lost, the date, the place where he played.

Greg Raymer may be a World Series of Poker millionaire, but he has not lost the careful, calculating ways that got him there. "Maybe I pay more attention than other people," he says, trying to determine what makes him better than the average medium- to high-stakes player. "I don't go on tilt too easily. I take short stack factors into account, recognizing that people can make desperation calls without even looking at their cards and be big favorites. It sounds obvious, but a lot of people ignore that one."

Raymer estimates that he has played in 500 tournaments—live and online—and 2004 marked his third year competing in the World Series. Two years ago he lost $30,000 at the Binion's Horseshoe classic. "After that I was so sick of this game," admits Raymer. "I never wanted to play again. Then a few days passed and I went to Foxwoods."

He laughs and adds, "I wanted to win my money back."

Despite the financial hit and an 80th-place finish out of 600-some-odd players in 2002, he made an important discovery: "I was up against the best players and felt that I could control them to some degree," he says, adding that he went out of the tournament after correctly calling a stone-cold bluff from Tam "Tony D" Duong. "I was a three-to-one favorite; he had 10-4 offsuit and made a straight. He got to the final table that year and I got knocked out of the event. But with that hand, and with every one leading up to it, I felt like I had been making good decisions. I knew that I would have to play in every World Series tournament from then on. Clearly I was capable."

Raymer was hardly born with a deck of cards in his hand. His mother, a homemaker, frowned upon gambling and, as Raymer says, "My dad hates losing money. I'm cheap, but he makes me look frivolous."

The elder Raymer marketed mainframe computers, and the family moved several times due to his job. Greg Raymer was born in Lansing, Michigan, attended middle school in Clearwater, Florida, and graduated from high school in Manchester, Missouri. While he was attending graduate school at the University of Minnesota, an aunt presented him with an unusual Christmas gift: The World's Greatest Blackjack Book, by Lance Humble and Carl Cooper. That title's veracity is up for debate, but it did teach Raymer the basics of card counting and led to him hitting the Indian casinos near his school where he won at blackjack. He had a small bankroll, which allowed him to spread only $5 to $25 per hand, but it provided him with a steady income of $7 per hour or so, and he was happy.

After graduating from the University of Minnesota law school in 1992, he worked as an attorney in Chicago, where he wandered from a blackjack table to the poker room. He was instantly hooked. "First I played poker for fun, then I decided to get into it," says Raymer, remembering that he went to a used bookstore where he unwittingly stumbled across David Sklansky's Theory of Poker, a tome many gamblers view as indispensable. "The book taught me what to think. It brings to light the concepts you need to consider when making decisions."

He played in a $3/$6 Omaha game and learned the beauty of competing against soft players. "Sometimes, for six hours, I would be the only one to fold before the flop," says Raymer. "The hand selection in that game was terrible."

It turned Raymer into a winning small-stakes poker player.

He moved from the law firm in Chicago to one in Milwaukee. There he found a $10/$20 Texas Hold'em home game, where there was a $500 buy-in and as many as 13 people crammed around the card table. By the time he took his next job at a law firm in San Diego, Raymer was a decent poker player and quickly became a regular at the Oceanside Card Club, where he won $2,500 playing in a $2/$5 blind pot limit Hold'em game.

He got married soon after and learned the complications that come with being a good, honest husband who gambles with an upside. "I won the $2,500 on a Saturday," Raymer recalls. "Then I went back on Sunday and lost $500. It was the most I had ever won and the most I had ever lost. And when I came home to tell my wife [Cheryl] what had happened, she became furious. She told me that 'we can't afford to lose that kind of money.' I said, 'What about the $2,500 I won?' She said, 'You brought that home. It's our money now.' I heard about guys who never tell their wives the real numbers. They always say they win less. That way they have extra money to compensate for the losses."

Did Raymer ever employ that tactic? He hesitates for a beat, then diplomatically says, "It was tempting."

What Raymer did do to appease his concerned wife was agree to put a cap on any potential gambling debits. "She was afraid that I would become addicted to gambling and lose all our money," he says. "So I made an agreement: I would have a bankroll of $1,000. If it's gone, then I'm done playing poker."

Fortunately for Raymer, it was plenty of money, and he supplemented the grand by selling fossils to poker players. Raymer, who first got turned on to fossils by his wife, promoted the products by using a long black fossil to guard his cards when he turned up their corners to look. Now Raymer never plays without fossils in front of him and often wears a lovebead-style string of semiprecious gemstone chips around his neck.

In late 1998, yet another job beckoned, this one with the pharmaceutical company Pfizer, and the Raymers made a final relocation to Connecticut. They wanted to buy a house but had only 5 percent of the required down payment. They needed twice that. "We were trying to figure out what to do," says Raymer, "when I won $22,000 in a tournament. Suddenly we had down-payment money. That was when my wife's opinion about poker began to change."

By the time he moved to Connecticut, Raymer was a fully formed poker player. He regularly posted on the player bulletin boards, and (a poker-oriented bulletin board monitored by the book publisher of the same name), where people would seek advice on how various hands could have or should have been played. Raymer became a star contributor, posting opinions on strategies and settling feuds. Ever the good student, participating on the boards allowed him to exercise his poker mind and develop various moves that came in handy at the tables.

On-screen, Raymer evolved into a successful Internet player without picking up any of the bad habits that betray online specialists when they play in live games. Raymer, a veteran of both worlds, sees Internet players showing a level of impatience at live tables, telegraphing that they will fold or bet before the action comes to them—probably because nobody can read your tells in cyberspace. And, he adds, "During no-limit Hold'em tournaments, I see poorly calculated bet sizes from Internet players. They make a lot of mini-bets. That's probably because online you can click a button real quickly for a standard bet rather than adjusting a sliding scale or typing in a number for a larger bet."

It's easier to make the small bet, and slowly, right or wrong, that becomes the ingrained thing to do. Conversely, says Raymer, "They also go all-in way more than they should. They get used to doing it during the low buy-in tournaments online."

In 1999, Raymer entered the New England Poker Classic, a no-limit Texas Hold'em tournament, and managed to increase his chip stack 15 times within the first couple hours of play. "We got a lot of weak players back then," he says, sounding a little nostalgic. "While playing in that tournament, I happened to run into a guy I had met the previous winter at the World Poker Finals. He was a decent player but not a winning player. About half an hour into it, he came over and whispered in my ear: 'Can you believe these guys we're playing against. They make me look like Johnny Chan.' I thought it was funny because he made me look like Johnny Chan."

Raymer's not kidding. The action at Foxwoods was so suitably soft that he'd win six out of 45 weekly no-limit tournaments over the course of a year. With up to 150 players and a first prize of $10,000 to $15,000, the money began to add up. It wasn't Chan-size money, but it was plenty for a straight-laced family man like Raymer (he and his wife have one daughter, Sophie). Poker evolved into a financial keystone for the Raymer family. Besides supplementing their down payment with poker winnings, he used the extra money to pay for landscaping, for a vacation and for an upgrade on his wife's engagement ring.

Even after those splurges, poker was so consistently profitable that Raymer was able to maintain a bankroll of $50,000 or so, which was critical for him since he's the kind of gunslinger who requires lots of bullets. "When I play cash games, I usually play deep money, meaning I have well over 100 times the big blind," explains Raymer. "I want to make significant decisions all through the hands."

Often that will necessitate throwing around lots of chips. "I'm most skillful with a big stack, meaning that I'm not afraid of risking some of that stack when I think it's appropriate."

It is an approach that can be extremely volatile, and Raymer experienced the downside a couple years ago when his bankroll dipped to $15,000 or so. Looking back, he doesn't think he played bad so much as he ran bad. Cards stopped coming his way, and moves that should have paid off suddenly didn't. "I wanted to keep playing in a $150/$300 game at Foxwoods, which was surprisingly easy, but with a $15,000 bankroll I couldn't do it," says Raymer. "I needed to raise money."

He turned to the online bulletin boards and offered to sell shares of himself for $500 apiece. He received plenty of flames—why should I invest in you if you've become a losing player?—but had built up enough of a reputation in the online communities that people were willing to take a shot. Many of the investors were friends, but a number of outsiders stepped up as well. "One investor contacted me from Poland," says Raymer. "[But] my biggest investor was a poker player from the Bay Area. He bought 10 shares for $5,000."

Raymer originally raised a total of about $30,000 from investors, put in about $13,000 of his own money and received an extra 35 percent for the time and effort of playing. Travel expenses came off the top, and he ended up with 57 percent of all profits. The deals were structured in six-month periods and the World Series of Poker's final day marked the end of the fiscal year.

During the first six months, investors lost $12 per share. In the second six-month period the value of Raymer's stock went to $555, and in the third period it rose to $601. "After I won the World Series," says Raymer, "each share hit $36,300. My major investor got a check for $363,000, and I paid out a total of $2.1 million to shareholders."

Asked if he regrets having taken them on, Raymer answers without a moment of hesitation: "I'm happy. Without the backers I might not have been able to play in the Series."

When Greg Raymer arrived in Las Vegas for the 2004 World Series of Poker, he was coming in as a bit of a loser. Though he won his seat via a satellite tournament on, between late February and May he was $45,000 in the hole. Then he dropped an additional $15,000 during the days before the World Series—never mind that he got to Vegas early with the intention of winning money.

However, on the Saturday night before his first day of Series play, Raymer won $5,000 in a satellite tournament at the Horseshoe. "I decided there would be no more poker till the big game," he says. "I wanted to go into the World Series on a win. I'm not superstitious, but it helps to be in a positive frame of mind. Otherwise you might not be making your best decisions."

That did not seem to be Raymer's problem on Sunday, the first day of the Series. He pulled cards when he needed them—flopping a set of 8s, then going all-in against an opponent with two kings—and played loose enough to negotiate some fancy moves, like a reverse bluff against the talented Marcel Luske. "He was under the gun [first to act] and made a raise that was three or four times the big blind—relatively standard. Three or four people needed to act before me. I quickly decided that when it came to me, I would look at my cards and, if I had aces or kings, I would push all-in and grunt. I wanted to do it in a real macho, caveman style, so he'd think I was bluffing. I looked at my cards, I saw aces, and instantly said, 'All-in!' Figuring that I had a bad, no-pair hand, he called me with ace-king, and I picked up more than half of his stack."

Raymer spent the day knocking out players and vacuuming stakes and wound up among the tournament's top 15 chip leaders. On the second day he continued playing gangbusters poker and began the third day, Tuesday, with $297,000. Ironically, despite starting the day in sixth place, he came close to getting knocked out of the Series by Michael "Mike the Mouth" Matusow, a highly emotional professional who finished sixth in the 2001 World Series.

The two players had been mixing it up a bit, and when Matusow raised Raymer in the big blind, Raymer called with jack-ace of diamonds. After the flop came 10-9-3 with two diamonds, Raymer made an unconventional bet: he went all-in, hoping to catch a straight or a flush, realizing that if he made a medium-sized bet, Matusow (who had more chips) would be likely to put him all-in anyway. Raymer hoped that the large bet would induce Matusow to fold.

Matusow became theatrical, begging, "God, this one time, let the good guy win."

He insisted that Raymer had to be on a bluff. After minutes of internal and external debate, Matusow decided to call. "We showed our cards, he had 9-7 for two 9s and jumped up from his seat, thrilled," remembers Raymer. "I asked him why he was so happy, since I was a 60 percent favorite with so many outs. I caught a diamond on the turn, and he kept trying to convince people that I would have made the same call if I had hearts in my hand instead of diamonds. But that was his mistake. I wouldn't have."

The clash with Matusow typified the day that Raymer characterizes as "a real roller coaster."

Within 20 minutes of starting, his $297,000 in chips was down to $200,000. "I put a guy all-in in a spot where I thought I had the best of it and was wrong," Raymer says in explaining how his chip stack decreased by nearly one-third. "But 40 minutes after that I was up to $350,000. I was not making big hands that day and not getting them paid off. I did a lot of stealing and bluffing. It was up and down all day. I finished at $466,000, but that was blind luck because of when the day ended."

For each day of the World Series, Raymer fell into a comfortable routine: rising early in the morning, eating a lunch of beef teriyaki at the California Hotel (across from Binion's Horseshoe), filling a 48-ounce cup with Diet Coke and topping it off with Cherry Coke during every break. He ate a tuna sandwich and shrimp cocktail for dinner every night and wound down with two cans of caffeine-free Diet Coke.

By Wednesday he was settled in and showed his table superiority by garnering respect from very solid player Josh Arieh. Before the flop, Raymer made a $40,000 bet. Arieh called. After 8 of diamonds—10 of diamonds—queen of clubs came on the flop, a flurry of back-and-forth betting ensued before Raymer went all-in and forced Arieh to fold. It added a quick $500,000 or so to his quickly rising chip stack, which closed out the day at $1,807,000.

On Thursday morning, after going through his pre-tournament ritual, Raymer walked into the Horseshoe and discovered that he was the World Series chip leader. Others noticed as well. Suddenly people were asking this hulking guy with funky glasses and fossil for his autograph. While it was too soon to predict that he'd win the World Series, Raymer realized that another, more modest goal was within reach: "I figured that if I could win enough money from the tournament, I'd be able to quit my job and open a solo practice. With that in mind, even if I didn't finish first, it could have been fine."

He started the day with nearly $2 million and played solid poker throughout, taking advantage of his position and using his chip lead to dominate his tables. He pulled off a neat bluff against young John Murphy, who showed up late with bed-head, insisting his alarm clock failed to go off. "I raised him with 10-8, just to steal the blind," says Raymer. "He raised me back, and I pushed all-in with 10-8."

Raymer laughs and says, "I didn't think he was bluffing so much as I figured he had a decent hand but not a great one. He threw his hand away and I showed him my 10-8."

It felt good for Raymer, who had been bluffed out by Murphy earlier in the tournament when Murphy had 2-3 and a gut-shot straight. "He looked at my 10-8 and I told John, 'That's for the deuce-three.' He smiled and tapped the table."

After the dinner break, Raymer stepped up with two queens to knock out a player who seemed a bit reckless with the all-in moves (in this case he had only a king-queen).

But Raymer's really smart playing didn't come till the tournament was down to 10 players, nine of whom would make the final table. That was when Raymer noticed some of his opponents suddenly becoming risk-averse. "A lot of decisions in poker are very marginal," Raymer says. "When some other factor comes into play—like being on the bubble of making the final table and appearing on television—that often tips the decision to the safe one: folding. I sized up who was playing it safe and took advantage of that. In about two hours I went from $5 million to $8 million by pushing people around and stealing blinds and antes. I cared about being on TV, but not so much that I would let it affect my winning the tournament."

The final day of the World Series of Poker was strangely uneventful. Raymer came in the chip leader and went out the chip leader. Early on, he caught a third 10 to knock out Michael McClain, who squeaked into the final table with $885,000. After catching a straight on the river, Raymer did in a young Swede named Mattias Andersson.

Although his chip stack got shaved down a bit—he was bet out by Arieh and beaten on the river by Al Krux—Raymer never relinquished his lead. He came close after losing a large pot to fourth-place finisher Dan Harrington. Harrington made a $900,000 all-in bet after the flop. Raymer called with the top pair of jacks to Harrington's 9s. But this time it was Harrington's turn to get lucky on the river, and he wound up winning the hand with three 9s.

In the end, however, Raymer needed only 14 hands to knock out the last two players. Arieh bit the dust when two queens came on the flop, giving Raymer a set to Arieh's pair of 9s. Just six hands later, Raymer won the tournament with an unexpectedly superior hand: both he and David Williams had full houses after the flop, but Raymer's pair of pocket 8s beat Williams's pair of 4s. "During the instant after he called my all-in bet, I felt he had to have me beat," says Raymer. "Then he turned his hand over and I tried to figure out how he won."

A split second later, Raymer realized that Williams hadn't won. Raymer had the best of it. He raised his fists, raked in the piles of cash and made poker history.

Michael Kaplan is Cigar Aficionado's gambling columnist. He won the media tournament at the 2004 World Series of Poker.