Not many poker players have as much bragging rights as does Doyle Brunson. He’s one of the most seasoned veterans at the felt, has won two WSOP Main Events and 10 bracelets, is a member of the Poker Hall of Fame and has penned several books on his favorite topic. He even has a hand named after him—Doyle’s Hand, a 10-2.

Despite over 50 years at the tables, he doesn’t always make the right call, and one word cost him $230 million. It was a decision that he said still gives him nightmares to this day.

About 14 years ago, Brunson took advantage of his status to launch Doylesroom.com, certain to be a popular site for online poker. It was the height of the boom, and he had everything going for him.  “Texas Dolly” signed several big names to help pitch the site, including Steve Gross, Chris Moorman and Amit Makhija.

In 2006, the site was performing well and Brunson was a happy camper. It wasn’t long before Brunson was presented with an offer to sell the site, of which he held 50% control. Expecting bigger things, though, Brunson said no.  And that is how you lose $230 million. In April of 2006 the Unlawful Internet Gambling Enforcement Act (UIGEA) was enacted and the site’s value dropped to almost nothing from one day to the next. Despite managing to stay alive for a little longer, the damage was done and the site eventually was sold to America’s Cardroom.