5. Mark Brunell

Mark Brunell has a career as stellar as they come. His was a three-time Pro Bowler. He has played with Jacksonville Jaguars, Washington Redskins, New Orleans Saints and New York Jets. He earned more than $50 million during his stardom. He was in businesses as late as 2009. Yet in 2011, he filed for bankruptcy.

PHOTO: Spokeo

Brunell made plenty of bad investments and then some more bad investments. He financed nine businesses, five of which failed immediately. Failed businesses include a Whataburger franchise and a real estate company called Champion LLC. These two failures alone cost him $ 20 million. Michael Huyghue, Commissioner of the United Football League says Brunell’s financial troubles are due to his being a nice guy, apparently he is too nice to say no.

PHOTO: Wikipedia