JOHN GOTTI served as boss of New York’s Gambino crime family from 1985 to 1992. Gotti earned the nickname “The Teflon Don” after beating three high-profile trials in the 1980s (thanks to jury tampering and witness intimidation).

This famous mug shot (smug shot?) is from his 1990 arrest for murder, conspiracy to murder, loansharking, illegal gambling, obstruction of justice, bribery, and tax evasion at age 50. All the charges would stick to Gotti this time, and he was sentenced to life in prison without parole, dying behind bars in 2002 at age 61.