New York Giants MVP, sack leader, Hall of Famer, 2-time Superbowl champ
Estimated lifetime earnings: $50 million
After retiring from his superstar NFL career, Lawrence Taylor enjoyed his celebrity to the fullest. Known for cavorting with women, openly using cocaine and drinking late into the night, the former defensive end spiraled downwards after he left the league. Police jailed him three times for possession. The IRS caught him for filing a false tax return. Rumors claimed he was involved in a drug and gun ring. He finally declared bankruptcy in 1998. One year later, the Pro Football Hall of Fame rewarded him for cleaning up his act by inducting him.