3. Bernie Kosar
Bernie Kosar played for the Cleveland Browns as their quarterback from 1985 to 1993. He then had two brief stints with the Cowboys and the Dolphins before he retired in 1996. After his retirement he pursued a range of different business ventures that never panned out in the long run.
In 2009 he filed for bankruptcy and had $18.9 million dollars in debt, some of his properties were foreclosed or seized by the government, and he owed the state of Ohio over $173,000 in taxes.
