Sport: Hockey
Team(s): Edmonton Oilers and New York Rangers
Champion: 1987, 1988, 1990, 1994 Stanley Cup 
Offense: Vehicular homicide and driving under the influence
Sentence: One year

Prior to the 1984-85 NHL season, Craig MacTavish was arrested in Massachusetts after the former center struck Kim Radley with his car. Four days later, Kim died and MacTavish was convicted of vehicular homicide. He ended up pleading guilty and served a one year sentence for the crime. 

After he did his time in jail, MacTavish was released by the Boston Bruins. Later, he signed with the Edmonton Oilers and helped lead them to three Stanley Cup championships. And he wasn't done winning just yet. After a brief hiatus from hoisting the trophy, MacTavish was traded to the 1994 champions, the New York Rangers.