#10 John Daly – Daly made 13 million in PGA Tour wins, but is now broke and could be homeless in a few years. The wild boy from Arkansas loved booze, women, and gambling. Recently he revealed he lost over 55 million in gambling. Daly’s credit rating is probably lower than his golf score on 18 holes. The bad boy is a recovering alcoholic and has spent numerous stints in alcohol rehab for treatment of his severe alcoholism. We still love John, whether he’s playing golf or selling car insurance to make ends meat.