Poker Stories: Tom Dwan’s Ridiculous Prop Bet

Tom Dwan, also known by his online alias durrrr, is a poker legend for the new generation of poker players. Although he sharpened his knife on low stakes online cash games when he was just a teenager, he’s now a world-renowned crusher who plays the biggest, baddest games around, including ones for millions in Macau.

He’s also well known for being a bit crazy. One of the main reasons that he’s one of the most popular contestants on poker TV shows like Poker After Dark and High Stakes Poker is because of his loose-aggressive style. Not only does he put his opponents into tough spots, but he brings the entertainment value by ratcheting up the action.

This story, however, isn’t about money. It’s hardly even about poker. It’s about a crazy prop bet between two friends who just happen to be big-time poker players.

The Prop Bet

At the 2008 World Poker Tour Championship, Dwan made a hilarious prop bet with a friend that we can only assume he later came to regret. And no, he didn’t even lose a million bucks!

His friend bet him that he couldn’t arrive on time every day for the tournament. Dwan took him up on it. But the friend had the last laugh, as it wasn’t long before he slept in just a little too late and arrived well after the cards were in the air.

After that, Dwan had to pay up: for the rest of the tournament, he was forced to wear funny hats. He started off with the Chiquita Banana woman hat, before moving into a not-so-stylish bowling pin hat that could have had DUNCE written all over it.

Photo: PokerStrategy.com

The real kicker, though, was the final table. Dwan wore a huge pink flamingo hat that stretched up into the air. Imagine making a big bluff and trying to keep a straight face with a massive pink flamingo perched on your head.

From then on, Dwan realized that he should probably stick to betting dollar bills instead of humiliation.