Cost: $130,000,000 in legal fees and potential earnings
At the height of his career, Michael Vick bank rolled a dog fighting empire and quickly exposed the flaws in pitbull killing as a business model. Legal fees and a two-year prison sentence crippled Vick financially, forcing the former Falcons quarterback into Chapter 11. During his bankruptcy hearing, it's reported that Vick's horrible spending isn't limited to his K-9 slaughterhouse. He allegedly spends $8M in 23 months, which is like blowing $25 thousand a day, everyday for two straight years.