There's always been a strong connection between the Westside and the Outfit. Milwaukee Phil was originally from Yonkers, which is just north of the Bronx and kinda like an honorary "sixth borough."
The Outfit/Genovese connection goes waaay back, Masseria/Capone, Luciano/Ricca, Giancana/Costello, Giancana/Catena etc. I dont know much about the New York mob and its origins, but if the Genovese fam originated from the Morello organization than the Chicago connection starts from there with Rosario Dispenza, but im not sure
