13. Shawne Merriman
Former San Diego Chargers linebacker Merriman enjoyed three Pro Bowl seasons in his first three years in the NFL. After that, injuries took their toll long enough but he stuck around the league long enough to make millions. He also dated the reality TV and internet celebrity Tia Tequila. But it all fell apart for a variety of reasons. First of all, the mortgages on his properties began to pile up.
Then, to make things worse, legal fees entered the picture. The family of Kimberley Fattorni, a deceased Playboy employee, sued him for wrongful death. Long story short, they accused him of slipping a date-rate drug into her drink one night. But her body reacted badly to it and she tragically passed away. In the end, he declared bankruptcy because he couldn’t afford anything anymore.