DiLeonardo grew up in Bensonhurst, Brooklyn, a neighborhood with long history of organized crime. In March 1998, after 43 years in Bensonhurst, DiLeonardo moved to Eltingville, Staten Island where he lived until June 2002. One of his brothers was Colombo crime family mobster Robert DiLeonardo, who was killed in a gangland execution on July 16, 1981. DiLeonardo's other brother is James (Giovanni)DiLeonardi, who is not involved in organized crime. His parents were second generation immigrants, with his father's parents coming from Bisacquino, Sicily. His mother was a seamstress and his father was a professional gambler who frequented the horse tracks. His mother died in 2003 of natural causes. DiLeonardo's grandfather, Vincenzo DiLeonardo was a soldier in the Brooklyn gang run by Salvatore D