YEAR: 1989
CRIME: Smuggling cocaine across U.S.-Canada border
SENTENCE / TIME SERVED: 3 months / 3 months
COMPLEX SAYS: At 24-years-old, Probert was caught with 14 grams of cocaine while crossing the Detroit-Windsor border. The Red Wings enforcer was suspended indefinitely by the league in 1989 but reinstated after completing his prison sentence. Soon after Probert would rejoin the Red Wings and treat NHL fans to 11 more seasons of epic fights such as this bout with Tie Domi. Dude was badass and moved more white than your favorite rapper ever dreamed of, before dying in 2010, a probable result of the numerous concussions he suffered as a player. R.I.P.