Licavoli's parents wanted him to become a Catholic priest, so he enrolled in Christian Brothers College High School in St. Louis to study for the priesthood.
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.
Convicted in 1934, Licavoli was sentenced to life imprisonment at Ohio Penitentiary, despite attempts by Cleveland mobster Alfred Polizzi to secure him parole.
In 1969, Ohio Governor James A. Rhodes commuted Licavoli's sentence from first to second degree murder, making him eligible for parole.