First of all it's a little bit of an unequal comparison to compare the Chicago Outfit to the NY mob. Chicago is one organization whereas as N Y is made up of 5 families. However, with that said Chicago was still just as if not more powerful than NY. When Frank Sinatra's son was kidnaped and he paid the ransom and he thought the kidnappers double crossed him he was about to call Sam Giancana for help not anyone from the NY mob. It was the Chicago Outfit that pulled of the assistant ion of President Kennedy. There are many many more examples from history that show the far reaching power of the Chicago Outfit. Even though they are smaller and operate in a smaller city than the NY mob there power is about equal if not more than the 5 NY families