Estimated Career Earnings: $18,000,000
How They Lost It All: “Rocket” ran into unparalleled bad luck, but he was also a horrendous investor. The Notre Dame legend poured hundreds of thousands of dollars into a “rock n' roll” themed restaurant and, to this day, claims he has no idea what became of it. Having conquered the hospitality industry, Ismail took on entertainment, sinking millions into faith-based inspirational movies and a record label that boasted the not-quite-ready-for-MySpace King J and The Dynamic Twins.

The Notre Dame legend went on to fund a cosmetic procedure that pumped oxygen into the skin because, you know, blasting air into your face will make you look younger? When that failed, he started phone card dispensing machine, only to have cellular networks render the concept obsolete. And with a couple nickels left, he opened up a souvenir store in New Orleans that was destroyed by Hurricane Katrina less than two months after its opening. Is it too late for a comeback? Rocket has an idea for glow in the dark picture frames. It's going to be huge!