10. Lawrence Taylor
Source: Iconosquare
The famous New York Giants linebacker, Lawrence Taylor, also known as “L.T.”, had his fair share of the high life and the title of one of the greatest linebackers in NFL history, until his shining light went out in 1998 when he filed for bankruptcy. After Taylor retired from football in 1993, he wasn’t focused much on his future expenses and continued to spend money without having a source of more income. With illegal substances, impressing the ladies, statutory sexual charges and tax evasion, the end of the long journey was bankruptcy.