Licavoli quickly rose through the ranks of the criminal world and by the mid-1920s was one of the most powerful gangsters in Detroit. With
Prohibition as the law, Licavoli and his brother Peter Joseph had established themselves as a formidable force in the Detroit underworld. Well known for their brutal tactics in dealing with rivals, the brothers soon controlled a large-scale operation smuggling liquor from Canada across the
Detroit River to the United States. In 1927, Licavoli and his associate Frank Cammerata were convicted of carrying a concealed weapon in
Windsor, Ontario and served three years imprisonment in Canada. After Licavoli's release from Canadian prison in 1930, the family attempted to expand its liquor operations to
Toledo, Ohio. However, they were met with stiff resistance from local bootlegger Jack Kennedy. The two sides fought a violent gang war which would eventually end in Kennedy's death in July 1933. Licavoli's gang may have been involved in the death of "Gentleman Jimmy" Hayes, who operated casinos, in Ohio and Michigan. Licavoli was arrested for conspiracy to commit murder in the slayings of Kennedy and three others. Convicted in 1934, Licavoli was sentenced to life imprisonment at
Ohio Penitentiary, despite attempts by Cleveland mobster
Alfred Polizzi to secure him parole. ==Prison and death==