 In 1985, at age 29, DiLeonardo married Antoinette "Toni" Marie Fappiano, a cousin of Gambino underboss Frank DeCicco.DiLeonardo had one son with Fappiano, Michael DiLeonardo, Jr. After twelve years of marriage, DiLeonardo started an affair with Madeline Fischetti.He kept Madeline in a rented apartment in Bay Ridge, Brooklyn while maintaining a home with his wife and son on Staten Island.