In March 2004 at the age of 17, Dwan began playing online poker at Paradise Poker with $50 his father had given him for his 17th birthday. He believed the alias “durrrr” would put players on tilt if they’d lose to him. Dwan initially focused on $6 sit-and-go tournaments and ended up losing $35. With his last $15, he continued to focus on these sit-and-gos until he was able to turn a profit. After finding he could beat these games, he turned to cash games, where he built his bankroll starting at low stakes and slowly climbing his way up, eventually reaching the largest games found online. After beating multiplayer cash games, Dwan switched his focus to playing heads-up No-Limit hold ’em against other professionals, such as Frederick Halling at the $10/$20 stakes level. He challenged Prahlad Friedman at $25/$50 stakes but kept losing to him for several months, forcing him to drop to lower stakes before coming back again and again until he was able to beat Friedman.
According to HighStakesDB.com, a site that tracks high-stakes online poker action, Dwan earned $312,800 in 2007 on the Full Tilt online poker cardroom and $5.41 million in 2008, even though he has gone through several large swings throughout his career. Before the 2007 World Series of Poker, Dwan claimed to have lost, at the time, $2 million of his $3 million bankroll, over a span of four months. He was able to recover from this loss within a year. In January 2009, Dwan lost more than $3.5 million, which he managed to recover after six months. However, from late October to late December 2009, Dwan suffered his largest downswing, losing approximately $2 million to Phil Ivey and Ilari “Ziigmund” Sahamies, and $5 million to Viktor Blom
In mid November 2009, a player from Sweden using the online name “Isildur1” challenged Dwan to a series of heads-up No Limit Holdem cash games. Isildur1’s foray into online high stakes cash games began in late October, when he initially lost $1.1 million to Patrik Antonius, Brian Townsend, and other high stakes players. However, by the beginning of November, Isildur1 had recovered his losses and challenged Dwan to a heads-up marathon playing six tables at a time with over a million dollars in play. By the end of the week, Isildur1 had gone on the largest run in the history of online poker, winning approximately $5 million from Dwan, prompting Dwan to issue a live challenge to play Isildur1 at the Full Tilt Poker Durrrr Million Dollar Challenge.
At the end of 2009, HighStakesDB.com reported that Dwan had lost $4.35 million in 2009, putting his cumulative online poker winnings at Full Tilt since January 2007 at approximately $1.4 million. HighStakesDB.com also reported that after stepping down in limits following his massive loss to Isildur1, Dwan won $2.7 million in December 2009. According to the same site, Dwan had more than recouped his 2009 losses in the first few months of 2010; he was reported to have won $1.6 million in the first two weeks of April 2010 alone, and after a session in which he won $1.6 million off Sahamies in a little over 2 hours, was up $7.3 million for the year to date as of April 21. However, in an illustration of the swings of fortune often associated with high-stakes play, Dwan lost about $4 million in the next three weeks, leaving him up about $3.3 million for 2010.
In January 2009 Dwan issued a $1,000,000 challenge to play anyone online, “with the exception of Phil Galfond”, heads up for 500 hands 4-tabling $200/$400 or higher No-Limit Holdem or Pot-Limit Omaha. If his opponent is ahead after 500 hands, Dwan agreed to give them $1,500,000 more, while if Dwan is ahead, he will get $500,000.
Patrik Antonius and Daniel Cates are playing Dwan as part of the challenge, but no 50,000-hand challenge is yet complete.
Dwan was 19 when he cashed in his first live tournament, finishing 12th in the £3,000 no limit Texas hold ’em Main Event of the European Poker Tour’s second season held in London, earning £7,000 ($12,398). His next cash wasn’t until he was 21 years old at the World Poker Tour’s 2007 World Poker Finals, $9,700 No Limit Hold’em Championship Event, where he finished 4th, earning $324,244. In January 2008, Dwan finished second at the Aussie Millions A$3,000 Pot Limit Omaha with Rebuys event, winning A$103,200 ($90,716) and later finished in 62nd place in the A$10,000 No Limit Hold’em Main Event, good for A$25,000 ($21,976). Dwan finished second to James Michael Sowers at the 2008 WPT Borgata Winter Open in the preliminary $5,000 No Limit Hold’em event, earning $226,100.
Dwan cashed twice in the first year that he was eligible to play in a World Series of Poker (WSOP) event held in the United States. Dwan reached the final table in the $10,000 World Championship Mixed Event at the 2008 World Series of Poker finishing in 8th place, earning $54,144. He then nearly made another in a seven person final table, but finished again in 8th, this time in the $5,000 No-Limit 2-7 Draw with Rebuys event, earning $45,110.
Dwan participated in the 2008 NBC National Heads-Up Poker Championship, where in his first match he defeated Phil Hellmuth in the third hand. Dwan was eliminated in the next round by Mike Matusow. At the 2008 Five-Star World Poker Classic (the $25,500 WPT Championship), Dwan finished in ninth place, winning $184,670.
At the 2010 WSOP in the $1,500 No Limit Hold’em event, Dwan finished in second place for $381,885.
In 2011, Dwan cashed three times at the 2011 WSOP, including a 5th place finish in the $10,000 H.O.R.S.E. Championship for $134,480.
As of 2011, his total live tournament winnings exceed $2,100,000.
Live cash games
Dwan holds the record for the largest pot won in a recorded live game at over $1.1 million, which occurred during the fourth season of Full Tilt Poker’s Million Dollar Cash Game. This record broke the previous record of over $919,000 also won by Dwan in the fifth season of High Stakes Poker.
Full Tilt Poker Durrrr Million Dollar Challenge
Dwan’s Million Dollar Challenge was expanded to a 500 hand live heads up format in the Full Tilt Poker Durrrr Million Dollar Challenge. The event was held November 17 to 19, 2009, at Les Ambassadeurs Club in London and televised by Sky Sports.
The rules of the Challenge were that each player paid $250,000 for the privilege of playing, blinds were set at $500/$1,000 with each opponent having the choice of playing either Texas Hold’em or Pot Limit Omaha (PLO). Neither player could leave the match until at least 500 hands had been completed or one of them lost all of his buy-in and decided not to re-buy.
Dwan’s opponents were Marcello “luckexpress” Marigliano, Ilari “Ziigmund” Sahamies, and Sammy “Any Two” George respectively.
The first match between Dwan and Marigliano consisted mainly of Texas Hold’em, although the players did agree to play PLO near the end of the match. Dwan lost $22,500 which was highlighted by two bluffs by Marigliano.
In the second match between Dwan and Sahamies the players played only PLO. Although the match started surprisingly slow considering the history of online competition between Dwan and Sahamies, the match eventually became aggressive as expected. There were several large pots resulting in large swings in the players’ stacks. After 12 hours, the match concluded with Dwan winning $68,000.
The final round pitted Dwan against George in an exclusively Texas Hold’em match. During the match, the parties agreed to a 7-2 prop bet wherein if a player wins a pot with 7-2 then he earns an additional $10,000. This led to one of the most memorable bluffs in television poker when Dwan bet $479,500 on the river, all in, into a pot of only $162,000. Dwan was bluffing with 7-2 against George’s two pair (aces and sixes). George folded his two pair after much consideration even though Dwan, after making a 6x pre-flop raise, had said he had 7-2 and just wanted the blinds. George went on to lose $750,000.
Dwan made a final profit of $795,500 after winning 2 of the 3 matches.