CARLO GAMBINO was the boss of New York’s Gambino crime family from 1959 to 1976. For nearly two decades, he was also the head of the Commission, the governing body of the American mafia, making him one of the most powerful mobsters of all time.

This mugshot came from a 1937 arrest for tax evasion, a crime for which he was sentenced to 22 months. Remarkably, this was his only time served during an organized crime career of over 50 years. Gambino died of natural causes in 1976 at age 74.