14. Bernie Kosar – $29 Million

After setting a record for “Most Consecutive Passes Without Interception,” Bernie Kosar could have stayed in the league for at least five more seasons. But he sustained an off-the-field leg injury and decided to leave on a high note. Unlike most of his colleagues, the all-star quarterback didn’t touch his NFL earnings before retirement. Unfortunately, his career-ending injury was just the start of Bernie’s bad-luck streak.

wikipedia.org

After a brutal divorce, Kosar invested into his financial adviser’s business, which turned out to be a pyramid scam. He declines filing for bankruptcy until he pays back a few personal loans – particularly, the $500,000 he borrowed from the Cleveland Browns.