Tom Dwan Opens Up: Cash Short Despite Big Winnings and Exotic Stories

Photo credit / Drew Amato

Tow Dwan is no longer the same high-stakes cash game player he once was, having become a suburban, occasional poker player despite the millions of dollars he once played for. In an exclusive interview with Michael Kaplan of Card Player, Dwan discussed how his life is going and admitted that he no longer has the appetite or the bankroll to play at the stakes he was once known for.

But, right now, I’d rather not play high stakes. Part of it is that I am cash short. Let’s just say that some people have been difficult with me. And part of it is that I can have a higher chance of losing in heavy situations than I did a few years ago

Cash Short Despite Millions in Winnings

That revelation may be a surprise to poker fans who remember the now 39-year-old Dwan as a cash game legend, playing in some of the largest cash game pots of all time. Fans may imagine Dwan and other high-rollers as living the lavish life with money to burn from their winnings.

But the high-roller admitted that the truth was different. The large swings in cash game poker now stress him out. He says that he used to be able to handle them, but not so much these days.

According to the Highroll Poker cash game tracker database, Dwan has over $4 million in career net winnings in cash games from 2007 to 2024 with a recent surge of $2.6 million from December 2022 to August 2023. He hit a peak of $4.8 in net winnings on Aug. 2nd, 2023.

But Dwan has also had his share of downturns. One of the most prominent was the “Durrrr Challenge” from over fifteen years ago. It began in 2009 when Dwan issued a challenge to anyone willing to play him online over 50,000 hands at $200/$400. If an opponent could turn a profit against him in that span, Dwan would pay them $1.5 million while the opponent would owe $500,000 if Dwan won the challenge.

Dan “Jungleman” Cates got the better of Dwan in the challenge, going up $1.2 million over 19,000 hands. Black Friday then put the challenge on hold, and it never regained momentum after that. A long, drawn-out affair followed in which Cates attempted to get the $1.5 million from Dwan for years. The pair finally quashed the beef in 2025, sitting down together for a video to talk it out.

Macau Escapades

Another interesting part of the interview was Dwan addressing the long-standing rumors of his time in Macau. There were popular tall tales in the poker world about Dwan’s time in Macau about how he owed the Triads millions or how he was playing in eight-figure pots on a regular basis with Chinese whales. Dwan denied some of these legends but did not entirely dismiss them.

I think I handled myself pretty well. I tried not to be an asshole, and I was the most famous poker player in China.

He talked about how rare it was for him to have a losing week in Macau. He said he was a good investment for backers while he was there.

Very few people who ever had a piece of me lost money. The chance I would lose in a week [while playing in Asia] was sub-30%. And if someone lost money having a piece of me, they could go whining about it to the game runner and I would let them have another piece.

The idea that he was down tens of millions to Triads was fiction, according to Dwan. But the legendary tales of eight-figure pots appear to have been accurate.

He told Kaplan that the record $3.1 million pot he played on Hustler Casino Live in 2023 vs Wesley Fei was peanuts compared to some of the pots he played in Macau, saying “I’ve played in lots of pots that were $10 million plus.”

But he declined to give a specific number for the largest pot he has ever played. After Kaplan guessed $20 million, Dwan responded:

If you gave a worse guess, maybe I would answer when the recorder is off. But you’re still an idiot.

Poker Writer

Jeffrey is an Expert Sports and Poker Writer with poker being his specific scope for the better part of five years. He has worked in various capacities at the biggest poker events in the world, WSOP, EPT, local tournaments and more. He has worked with PokerNews, Poker.Org, 888poker and the WSOP itself through the years. Jeff is also a fervent follower of many sports, professional, collegiate and international, with a particular interest in tennis. He received a Master's in Sports Management from the University of the Incarnate Word (UIW) and a Bachelors in the same field from Clemson University.