4. Lawrence Taylor
Many regard Taylor as the greatest defensive player in NFL history, but he definitely wasn’t the most fiscally responsible. If you had a choice between leaving your wallet on the sidewalk and giving it to Taylor to look after, the former would definitely be much safer. A two-time Super Bowl winner with the New York Giants, this linebacker was a force. But his everyday life was very controversial.
Taylor partied hard and went through cocaine like it was sugar. He even claimed that he spent $1,000 per day on drugs alone. That’s not counting his penchant for alcohol or prostitutes. Meanwhile, his company All-Pro Products went bust, while he also served house arrest for tax avoidance. Overall, Taylor’s spending habits and bad investments meant that he lost almost everything.