4. Curt Schilling – Green Monster Games Mess
Curt Schilling was one of the most accomplished pitchers in modern baseball history. A 6-time All-Star, 3-time World Series champion, and one-time World Series MVP, Schilling etched himself forever in baseball lore when he led the Boston Red Sox to a championship in 2004 while pitching on an injured ankle. His performance that year is so famous that the “bloody sock” from his injured leg sold for $92,163 at auction.
Schilling was a certified bad-ass on the baseball diamond. When it comes to business ventures, a bad-ass Mr. Schilling is not. Curt made over $100 million during his 19-year MLB career. In 2006, he used $50 million to found Green Monster Games, a video game company that went belly up in 2012 when Schilling defaulted on a $75 million loan from the state of Rhode Island. Schilling was forced to sell off most of his possessions and now works as a baseball analyst at ESPN, where he is currently serving an indefinite suspension for a general display of ignorance and intolerance on social media.
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