Team(s): Dallas Cowboys
Champion: Super Bowl XXVII (1993), Super Bowl XXVIII (1994), Super Bowl XXX (1996)
Offense(s): Drug trafficking
Sentence: Two and a half years
As an offensive lineman, Nate Newton was in charge of keeping defensive lineman off of the fragile Troy Aikman. More often than not, he succeeded, which led to multiple Super Bowl titles to Newton's name. Following his playing career, Newton was stopped and arrested on two separate occasions after being found with 213 pounds and 175 pounds of marijuana, respectively. After serving his two and a half year sentence, Newton has dedicated his life to speaking with children involved in athletics in the hopes of preventing them from going down the same path he did.