Born in Ybor City, Tampa, Florida to Sicilian parents, Ragano attended Stetson Law School and clerked for the Florida Supreme Court before admission to the Florida Bar in 1952 and beginning his trial practice in Tampa, Florida. In 1954 he was recruited by another attorney to represent several defendants arrested in Tampa for involvement in Santo Trafficante, Jr.'s illegal bolita operations. He immediately befriended Trafficante, who thereafter admitted him into the inner circles of Florida's organized crime scene.