1. Michael Vick
Vick’s downfall was one of the most dramatic in sporting history. The former Atlanta Hawks’ superstar changed the quarterback position. However, being brilliant on the field doesn’t necessarily translate to being a great person. After a federal investigation uncovered his dog-fighting ring, Vick served almost two years in prison. Obviously, being in jail doesn’t help you raise the numbers in your bank balance.
Meanwhile, Vick lost all of his major endorsements and had to pay massive legal fees. Furthermore, he had all the mortgages, scandalous purchases, and family support that you come to expect from NFL players. He lost over $130 million before he got out of prison. After leaving jail, he found redemption with a $100 million deal with the Eagles. He cleared most of his debts but was no longer the mega-rich star of old.