Dermontti Dawson
Dawson was an incredibly talented offensive linesman who was inducted into the NFL Hall of Fame. And on the other hand, Dawson filed for bankruptcy in 2010 after he claimed he was $69 million dollars in debt. Staggering.
Jamal Lewis
Jamal Lewis was a star running back for the Baltimore Ravens back in the early 2000s. However in 2007, Lewis declared bankruptcy due to the fact that he was $10 million dollars in debt. Shortly after, news broke that he sold his Super Bowl ring just to make ends meet.