Sport: Baseball
Team(s): New York Mets (1986); New York Yankees (1996, 2000)
Champion: World Series (1986, 1996, 2000)
Offense(s): Violation of drug use probation
Sentence: One year. Served seven months.

Dwight Gooden is a hero wherever he goes in New York. From winning a chip in '86 for the Mets or getting two with the Yanks in '96 and 2000, Gooden knew how to win on the field. But all good things gotta come to an end at some point. After dodging lengthy sentences for a DWI, driving with a suspended license and a misdemeanor battery charge, he was arrested once again in March 2006 after he appeared to be on cocaine while meeting with his probation.

Still, after all that, Gooden was going to be handed a long probation, but he himself opted for prison in the hopes that jail time could help him with his addiction. In 2010, four years after getting released from prison, Gooden was again in trouble with the law. This time, he was charged with a DWI with a child passenger and leaving the scene of an accident. But surprise, surprise, Doc was only given five years probation for child endangerment.