Giacalone was born on January 2, 1919, he was the brother of Vito Giacalone, known as "Billy Jack". Dan E. Moldea, author of 'The Hoffa Wars', detailed Giacalone's early career in the Detroit Mafia "running errands for bookmakers" before becoming an enforcer for crime boss Joseph Zerilli and was Zerilli's bodyguard and chauffeur for almost a decade before being promoted to capo with his own crew. He also allegedly attended the Apalachin conference with Zerilli and both narrowly escaped being arrested by police, although it has never been proved that Zerilli attended the meeting. He earned a reputation as a "tough guy and a natty dresser" with a stare of "cold intensity" according to Mike Wendland. In his early years, Giacalone sometimes worked as a bartender and in real estate while at the