Bernie Kosar
As a quarterback, Bernie Kosar won a Super Bowl championship. After his career, however, he declared bankruptcy in 2009. He filed for Chapter 11, stating that he was nearly $20 million in debt. However, the court ordered it changed to a Chapter 7 filing, which might put Kosar’s NFL pension in jeopardy. Later, in 2010, Kosar lost more property due to unpaid back taxes.