As a youth, Buccieri was born is Southern Italy and eventually immigrated to Chicago. When he arrived in Chicago, he was a member of the Chicago 42 Gang with future Outfit boss Sam Giancana. He was the brother of mobster Frank Buccieri. During the 1920s, the two men worked as gunmen for future Outfit boss Al Capone. In 1925, Buccieri was arrested for the first time on concealed weapons charge. During the bootleg wars of Prohibition, Buccieri was reportedly involved in at least 10 gangland slayings. In the 1960s, following Giancana's rise to the day-to-day "boss" position in the Outfit, Buccieri served as a top enforcer and personal hitman. He was also involved in labor racketeering bombing, arson and loan sharking.