Mark Cuban

Owner of pro basketball's Dallas Mavericks making a play for one of baseball's most storied franchises; said to be one of the final 3 bidders for the Chicago Cubs. Tribune Co. Chief Sam Zell put the lovable losers (who are making a serious run at the World Series) and their famed home, Wrigley Field, up for sale April 2007. Cuban also dabbling in extreme sports; created mixed martial arts league HDNet Fights to compete with Frank and Lorenzo Fertitta's lucrative Ultimate Fighting Championship. Former bartender sold Internet video outfit Broadcast.com to Yahoo for $5.7 billion in stock 1999; hedged stock before tech bubble burst. Reinvested in entertainment; owns stakes in HDNet, 2929 Entertainment, Lion's Gate.