11. Lawrence Taylor
Lawrence Taylor is a legend according to many followers of the game. He is a true NFL Hall of Famer as a defensive player. At the top of his game, he was at times unbeatable on the field. He gathered $50million in earnings and yet he has declared bankruptcy. Taylor has been arrested for drugs possession and filing a false tax return.
It is believed that he messed up his wealth and status by diving into drugs. His cocaine addiction cost him dearly. He also developed a partying lifestyle. Since then, he has worked as commentator and as a small time actor. He has appeared in movies like Any Given Sunday and When in Rome.