8. Lawrence Phillips

Team(s): St. Louis Rams, Miami Dolphins, San Francisco 49ers
Years: 1996 - 1999
This guy got more chances than Lindsay Lohan—and went to jail just as much. When you rely on talent alone, you're not working hard or doing extra work after practice. A young NFL player not working hard has plenty of time on his hands to get in trouble with the law like Phillips did.