10. Curt Schilling
The New Job: Bankrupt Videogame Maker / Commentator
As a pitcher for the Phillies, the Diamondbacks and the Red Sox, Curt Schilling enjoyed quite the playing career, with a couple of World Series rings to back up his greatness. Following the conclusion of his playing days, Curt formed a video game company called 38 Studios in the state of Rhode Island. The video game company was not to be though, and the resulting legal dispute between Curt and Rhode Island regarding tax breaks his company received has ruined his reputation with many New Englanders.