Estimated Career Earnings: $50,000,000
How They Lost It All: The crafty left-handed quarterback is known for his confidence and quick feet, but his most impressive talent might be in his ability to make money disappear. During his tenure in Jacksonville, Brunell founded the ironically named Champion, LLC—a company that invested heavily in Michigan real estate and a fast food chain called “Whataburger.” Since “No, but it probably sucks” would work as an answer to either “Have your ever been to Michigan?” or “Ever tried a Whataburger?” Brunell predictably lost millions and is facing another $25M in lawsuits. The Jets back-up has played 19 seasons in the league and, at 41-years-old, will likely have to play another two decades to get back into the black. Watch your backs Sanch-ebow, No. 8 is gunning for that starter money.