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.
In 1925, Buccieri was apprehended for the first time on charges of concealing weapons. During Prohibition's bootleg battles, it is said that Buccieri participated in at least ten gangland killings. In the 1960s, after Giancana ascended to the daily "boss" role within the Outfit, Buccieri acted as a top enforcer and personal hitman.