Caputo was 16 years old when he stepped on America’s shore in 1919. Like so many before him, a native of Palermo, Sicily, Caputo was looking for gold paved streets of America. He made his way to Chicago and was believed to have cultivated ties with the powerful mob family. In 1930 records indicate that Caputo was married to a Rosemary. His whereabouts during the 1930s are unknown. Law enforcement sources indicate that he was may have been officially "made" or became a member of the La Cosa Nostra syndicate of Milwaukee.