6. Mark Brunell
Source: Iconosquare
17-year career in the NFL does not secure an endless amount of money, even though $50 million is a great start. Like many athletes, Mark ventured into other financial solutions and he chose real estate. Needless to say, this journey didn’t last long because the housing market tanked and left Brunell with nothing. After defaulting on many loans, in 2010, Mark filed for bankruptcy.