1. Marty McSorley
With 3,381 career penalty minutes, McSorley had already established himself as one of the NHL's most brutal enforcers when his vicious hit on Donald Brashear became one of the most shocking moments in sports history. The attack resulted in an assault conviction and a one-year suspension (longest in league history); McSorley never returned to the league. Brashear suffered a Grade 3 concussion, but returned to play later that season. Marty should consider himself lucky that Donald wasn't more seriously hurt. He could've seen some serious jail time. Dirty!