5. Dermontti Dawson
Dermontti Dawson enjoyed a successful football career with the Pittsburgh Steelers, where he served as their center for 12 long years. He was even elected into the Pro Football Hall of Fame back in 2012. However his life outside of football was very difficult.
All of his financial issues came from his failed real estate business. After spending a few years as a developer, he filed for Chapter 7 bankruptcy in 2010 where he had $69 million in liabilities and debts, but only just $1.5 million in assets.
