Sport: Basketball
Team(s): Los Angeles Lakers
Champion: 2001 NBA Finals 
Offense(s): Possession of cocaine, battery, evading a police officer
Sentence: Seven months

In the twilight of his playing days, Isaiah Rider was able to get himself a ring as a member of the 2001 Lakers. And while pursuing a chip became something that lasted his entire career, so did his efforts to stay out of trouble off the court. For the most part, Isaiah was successful in dodging jail time, but that all changed in 2007 when he was given seven months in jail after pleading guilty to cocaine possession.