Curt Schilling
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As a pitcher, Curt Schilling amassed a jealousy-inducing career. He’s won World Series Championships, MVP awards, and was a six-time All Star. Off the mound, it’s a different story. The combative, outspoken conservative wound up founding a video game company, accepting a $75 million loan. They defaulted, and Schilling, who put the majority of his personal fortune in the company, lost everything.