Estimated Career Earnings: $130,000,000
How They Lost It All: Proving the inherent flaws in dog-fighting as a business model, Vick lost an estimated $130M in actual and potential earnings while spending two years in prison. But even without the legal and personal recoil from creating a pitbull slaughterhouse, the Eagles quarterback was a financial cluster fuck. He blew millions by supporting an entourage of over 30 people. He bought his brother a new luxury car every year for his birthday (because anyone that spends more than twelve months pushing a Jag is a sucker). And he dumped millions into  car-rental company, Canadian real estate, and in several business ventures with an animal dealer who basically used Vick's investment as a personal slush fund.

During his bankruptcy hearing, it was reported that Vick had spent almost $18M in twenty three months. To put that into perspective, that's like spending $25K a day, everyday for two straight years. The four-time Pro Bowler recently inked a six-year, $100M deal with Philadelphia and an undisclosed endorsement contract with Nike. Provided the Eagles quarterback doesn't go back to spending money like a Saudi oil prince, he'll likely be back in the black by 2015 as a sort-of happy ending to a not-so-feel-good story.