JOE COLOMBO served as boss of New York’s Colombo crime family from 1964 to 1971. Colombo, who prevailed in a violent early 60s power struggle known as the Colombo War, has the distinction of being the first ever New York crime family boss who was born in America.

Joe is shown here from his 1966 arrest for contempt of court at age 43, for which he served 30 days in jail for refusing to answer a grand jury’s questions. It would be his only stint behind bars. Though sentenced to two and a half years for perjury in 1971, Colombo was assassinated before he could serve his time. He was 54.