When the Red Sox finally won the World Series after years of near misses and hard-luck stories, it was pitcher Curt Schilling who dragged them to victory. Being a huge sports star brings in stacks of money in both salary and endorsements, and Schilling's time in the spotlight brought him millions. He then made the wise decision to try to set himself up for later life with a series of investments. It was just his bad luck that none of them worked.
Schilling was a keen video game player, and decided that he'd open a video game studio of his own to make games for other people. He poured $50m into it - almost his entire life savings - and then took on a further $75m of debt to keep it going. The business didn't work out. By the time he had to accept defeat and close it, it owed more than $120m to creditors. To add insult to injury, Rhode Island then asked him to pay $2.5m in taxes!