Cost: $2,000,000  

In a seemingly calculated effort to go broke, Terrell Owens dumps $2M into an Alabama entertainment complex that includes a Bingo hall. Nevermind that the NFL has a policy against its players investing in gambling, but the complex's devices are also illegal in the state of Alabama. Oops. The project collapses and Owens becomes another former athlete with a $1,500 credit limit.