Cost: $50,000,000 

When your life's signature moment is pitching with a bloody ankle, you probably shouldn't try to build a video game empire. The Red Sox legend's 38 Studios (Get it? 38 like his baseball number) attempts to take on industry behemoths like Activision and EA, but flops worse than Atari Jaguar. Schilling dumped $50M in career earnings into the company and went broke trying to win the favor of Red Bull addicted teenagers. In May 2012, 38 Studios laid off all of its employees and ceased operations.