Failla was raised in the Bensonhurst section of Brooklyn, a neighborhood dominated by New York's La Cosa Nostra families. Failla eventually relocated to a modest home in Staten Island. In 1951, Failla was convicted of bookmaking and illegal gambling charges and paid a $25 fine. During the 1950s, Failla became close to Carlo Gambino, underboss to Albert Anastasia, boss of the Gambino family. Failla later serving as Gambino's chauffeur/bodyguard. After the October 25th 1957 murder of Anastasia, new boss Carlo Gambino appointed Failla as his point man in the waste hauling industry.