Phill Ivey would be one of the first people to tell you that he's a degenerate gambler. I'll have to look for it, but I watched an interview where he talked about his days before he made it big. He would cash his McDonald's paycheck, go lose it playing poker, and then end up spending a few weeks sleeping on the streets.

Also, I remember one time a WSOP bracelet showed up on ebay. Apparently, its owner had made about $10 million in career earnings in poker, but he was so broke from betting on horses that he was selling his beloved bracelet for gambling money.