Curt Schilling: Lost $50 Million On A Video Game Venture
Schilling is on this list because after his retirement, he decided to invest in a gaming company called Green Monster Games, which he later renamed to 38 Studios. In February 2012, the company released its first game, Kingdom of Amalur: Reckoning, but had to close down within three months, owing to financial troubles. Schilling lost $50 million to the sinking company because he had put everything in his name.