44. Steve Durbano
Criminal History: Drug smuggling, theft, pimping
Time Behind Bars: Seven years
Known as a fighter on the ice, Durbano once led the league with 370 penalty minutes during the '73 NHL season. Unfortunately for mouthy club goers, his aggression was not limited to hockey games. Durbano was routinely arrested in bar brawls and was charged in 1983 for trying to smuggle a half million dollars worth of cocaine into Canada. In an effort to show off his versatility as a criminal, the disgraced hockey star was arrested in the late '90s for running a prostitution ring. Durbano reportedly met with an undercover police officer and discussed price point for "services" and was hauled to jail after donning her with a code name.