14. Bernie Kosar

Bernie Kosar had earnings of more than $19million. He is one of the most heartbreaking entries on the list. He was a squanderer, he didn’t waste his money on drugs and gambling. On the contrary he is a very nice guy – too nice in fact. He was “taken for a ride” by people he loved and trusted; such as his owner father, ex-wife, friends and financial advisers. He filed for bankruptcy in 2009.

PHOTO: Wikimedia

Falling real estate market, divorce settlements, bad advice and the inability to say “NO” to friends and family all contributed to his downfall. Kosar’s debt fell between $10million and $50million and his assets were worth $1million and $10million.