Estimate members: Between 50 and 90 made members First Boss: James "Big Jim" Colosimo Primary rackets: Gambling, extortion and loan sharking. Boss: The Chicago Outfit has always been very secretive about its bosses. The last decade several names popped up time after time: Joseph Lombardo, James Marcello, John DiFronzo. Of these three men only DiFronzo is living in freedom. The other two were found guilty in the Family Secrets trial. Whether DiFronzo is the new boss is open for discussion. According to an article in the Chicago Sun-Times 84 year old Alphonse Tornabene also is an important leader within the Outfit. He allegedly holds the rank of consigliere. Tornabene has been seen meeting with mobster Anthony Zizzo, who went missing in 2006.