Poker News / Short-Stacked Shamus / 27 November 2009 / Leave a Comment

With a screen name borrowed from a character in J.R.R. Tolkein's The Lord of the Rings, it only took the player known as "Isildur1" a few short weeks to become the star of his own mythological saga.

Arriving relatively unannounced among the highest stakes games on Full Tilt Poker, Isildur1 was soon seen challenging the game's biggest names in heads-up pot-limit Omaha and no-limit hold'em, including Phil Ivey, Patrik Antonius, Tom "durrrr" Dwan, Ilari "Ziigmund" Sahamies, Cole South, Brian Townsend, and David Benyamine. Amid ongoing speculation regarding Isildur1's identity, the story took an historic turn last weekend when he and Patrik Antonius played out a single hand of $500/$1,000 pot-limit Omaha that resulted in the largest ever pot in online poker history.

Following a series of preflop raises, the pair got all of Isildur1's chips in the middle on the flop with Antonius holding a five-high straight and Isildur1 holding a wrap draw to a better straight. Isildur1's card didn't come, and in a flash $1,356,946.50 slid across the virtual felt to Antonius. That hand broke the record for the largest online pot ever by nearly half a million dollars, a record set by Isildur1 and Antonius in another PLO hand just five days before.

Just one day later, Isildur1 would be the recipient of the second-ever million-dollar online pot, winning $1.127 million in another $500/$1,000 PLO hand versus Phil Ivey. Indeed, in the space of just a couple of weeks, Isildur1 has been involved in over twenty $500,000-plus pots against Antonius, Ivey, Dwan, Sahamies, South, and Townsend.

Such figures are understandably difficult for the rest of us mere mortals to fathom. In The Biggest Game in Town, Al Alvarez noted how "the casualness and imperturbability with which that elite handles huge sums of money is beyond ordinary understanding. It is a question not just of a different level of skill but of a different ordering of reality."

As railbirds await the next dramatic episode in Isildur1's already epic journey, his story calls to mind other "men of action" -- figures throughout poker history with big bankrolls and egos to match, bound by a desire to compete in the biggest games around.

Nick "the Greek" Dandalos

Probably the most legendary of such figures was Nick "the Greek" Dandalos. In 1946, Benny Binion took over the El Dorado casino on Fremont Street. Binion rechristened the casino Binion's Horseshoe, and soon thereafter began advertising the Horseshoe as the place where gamblers could find the world's highest limits. Dandalos, a highly successful banker and real estate investor, soon arrived in Vegas -- some say in 1949, others 1951 -- announcing that he was looking for "the biggest game this world can offer." It didn't take long for him to be sent Binion's way.

Binion phoned his friend Johnny Moss, luring him from his games in Texas to come challenge the Crete-born high roller. What ensued was a match lasting several months, with the players sometimes playing for four or five days without interruption. The game was primarily five-card stud, and the stakes were enormous. Most accounts describe a single $500,000 pot, won by Dandalos after having fortunately picked up a jack on the last deal to pair his down card. Other players were allowed to buy into the game (at a $10,000 minimum), but they never stuck around for long.

As happens with the online railbirds watching Isildur1's adventures, the Dandalos-Moss match attracted spectators as well. Eventually Binion moved the match to the front of the casino to lure in Fremont Street traffic, and reportedly crowds of 200-300 would gather to watch the men play. Finally, with Moss reportedly ahead by $2 million or more, Dandalos decided he'd had enough action. "Mr. Moss, I have to let you go," he said, signaling the end of their unprecedented battle. Dandalos died in 1966.

Jimmy Chagra

Jamiel "Jimmy" Chagra was a high-volume drug trafficker who like Dandalos had a penchant for gambling at the highest possible stakes. By the 1970s, he'd relocated from El Paso, Texas to Las Vegas, where he'd routinely gamble hundreds of thousands of dollars at the craps tables or on the golf course. He also found opponents at the poker tables who were eager to take shots at his seemingly bottomless bankroll, including Johnny Moss, Jack Straus, Chip Reese, Puggy Pearson, "Amarillo Slim" Preston, and Doyle Brunson.

As Brunson writes in his new autobiography The Godfather of Poker (which I'll be reviewing next week), Chagra "was reputed to be the highest of the high rollers, what we call a 'whale' in Vegas. In those terms, Chagra was Moby Dick. He didn't play for hundreds or sometimes thousands of dollars.... Chagra played for hundreds of thousands of dollars. He might even lose millions in a single night."

Most reports of Chagra's poker exploits include accounts of games with more than $2 million on the table, with Chagra consistently coming out on the losing end of such encounters. Indeed, Brunson and his colleagues were more than happy to relieve Chagra of his money. "We liked the way he recklessly tossed his cash around, like it was Monopoly money" writes Brunson. "The U.S. government wasn't getting its share. But we were."

The games finally ended in 1979 when Chagra was arrested on drug trafficking charges. On the day his case was to go to trial, John Woods, the presiding judge, was shot and killed, a crime to which Chagra was later connected. Although he'd never be charged with the murder, Chagra was found guilty of the drug charges and went to prison where he'd spend the next 24 years. He died in 2008.

Major Riddle

The aptly-named Major Riddle was indeed a paradoxical figure -- a highly successful entrepreneur who seemingly made all of the right decisions in terms of his business life, but whose fondness for gambling led to consistently bad decisions at the poker tables. After making a fortune with a trucking company in the midwest, Riddle moved to Las Vegas in the 1950s where he bought the Dunes Hotel, turning it into a money maker.

Like Chagra, however, Riddle soon became known as a significant contributor to the highest stakes poker games. Riddle's favored game was stud, and during one stretch he reportedly lost thirty days in a row. In Des Wilson's Ghosts at the Table, Wilson reports how Billy Baxter, the seven-time WSOP bracelet winner, picked up a tell on Riddle. "If he had a bad hand, he'd toss his chips in -- just kinda flip them," explains Baxter. "If he found himself with a good hand, he would place his bet on the table. And if he drew a face card, he would look at it and look at it."

Besides giving off tells, Riddle's understanding of hand values was apparently quite sketchy, too. In one famous hand of hold'em against Johnny Moss, Riddle reportedly called an all-in river bet with the board showing K-K-9-9-J. Moss showed pocket nines for quads, while Riddle turned over pocket deuces -- he couldn't beat the board! Riddle eventually would lose millions -- some estimates place the figure around $40 million -- before he died in 1980.

Archie Karas

Not everyone coming to Las Vegas to seek the biggest poker games around were consistent losers. A great exception was Archie Karas. Born in Greece in 1950, Karas came to the United States as a young man and eventually made his way to the Nevada desert where he quickly became known as a formidable razz player. He also became known as a lover of high-stakes action, and after having amassed a large bankroll began challenging the games top players.

It was 1993 when Karas began a three-month sequence commonly referred to as "The Run." In a display that anticipates the take-all-comers approach of Isildur1, Karas successively challenged Chip Reese, Stu Ungar, Doyle Brunson, and Johnny Chan, playing a variety of games and ultimately coming out ahead by approximately $10 million. Reese later reported that during "The Run" he suffered his single-worst session of poker, losing over $2 million to Karas in a night of $8,000/$16,000 limit hold'em.

Karas would eventually build a roll of approximately $30 million, but just as remarkably would lose it all at the craps tables, securing his place as the central character in one of the most incredible gambling stories ever told. Karas remains part of the Vegas scene, and regularly competes at the WSOP. This past summer Karas final tabled the $10,000 World Championship 2-7 Lowball event, finishing fifth.

Andy Beal

One last figure whom Isildur1's story readily recalls is the Texas-based banker and real estate maven, Andy Beal, the man who similarly took on poker's elite in some of the highest-stakes poker games ever played.

A longtime blackjack player, Beal became interested in limit hold'em in 2001, and before long became involved in a three-handed game of $2,000/$4,000 stakes with Ted Forrest and Chip Reese. Beal returned in the spring of 2002 and rejoined the pros, inviting them to increase the stakes to $10,000/$20,000, then $25,000/$50,000, and eventually all of the way up to $100,000/$200,000.

As a means to compete with the well-funded banker, a group of pros formed "The Corporation" and with a shared bankroll took turns competing with Beal. In addition to Forrest and Reese, the group would eventually include Jennifer Harman, Howard Lederer, Chau Giang, Hamid Dastmalchi, Barry Greenstein, Phil Ivey, Gus Hansen, David Grey, and Todd and Doyle Brunson.

The matches continued over the next couple of years, with staggering swings regularly transpiring. Indeed, heavy betting on single hands could produce pots in excess of $2 million. While Beal held the upper hand for a while, and indeed enjoyed a single-session victory of $11.7 million in May 2004, a huge downswing in which Beal lost $15 million in two days encouraged the banker to end the matches, declaring he was finished with poker. However, Beal would return for more action in 2006, ultimately losing another $8 million -- mostly to Phil Ivey -- before heading back to Dallas once again.

As Doyle Brunson explained to Al Alvarez in The Biggest Game in Town, "'In order to play high-stakes poker, you need to have a total disregard for money.... It is just an instrument, and the only time you notice it is when you run out.'" We'll see how long Isildur1's run lasts -- and whether he can avoid the fate of most of these other "men of action" and leave the table before the money runs out.

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