8. Bill Buckner
A former baseball player and a major leaguer, Bill Buckner, achieved lot of milestones in his career. He played first base and won a batting crown. However, a serious blunder in Game 6 of the Boston Red Sox, the World Series of 1986 brought him down. It was only a fielding error that cost him his legacy, even though he didn’t deserve it. When he retired, he chose to open his own car dealership in Idaho. Unfortunately, he was unsuccessful as a car dealer. Finally, in 2008, Bill Buckner filed for bankruptcy and ended up with bad credit scores due to his losses and difficulties.