Amarena was born in New York City in 1920. In 1946, he moved to Tampa and became an associate of the Tampa Mob. In 1951, he was arrested for illegal gambling in a bar he owned in Alabama. He was arrested for the same charge in another bar he owned in Louisiana four years later. Amarena also reportedly owned a restaurant in Cuba located across the street from the Havana Hilton hotel, to which he also reportedly provided security. His restaurant in Cuba was frequented by Santo Trafficante, Jr. and Fidel Castro. In 1959, Amarena sponsored the wedding and reception of Trafficante's daughter. He reportedly operated as a gambling club manager for the Trafficante crime family and was also an associate of Meyer Lansky and Frank Diecidue. During his time associated with the Trafficante family, Amar