It is well known that the Chicago Oufit currently has a very strong operation where they make deals with biker gangs (most notably the Outlaws) in the Chicagoland area and midwest and then get kick backs from these partnerships. They have been doing this for years.
The Gangs do all the dirty work.
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As long as biker gangs are thriving which they are the Outfit will continue to be in business.
Also, I hate to be the one to burst your bubble, Rush. Because I know how much you love your Chitown. But the current Chicago Outfit, or what's left of it, has one foot on the banana peel (maybe even both feet.) They are an absolute wisp of their former selves, and, IMO, their days are numbered (and thats putting it kindly.)
They are NOT "a very strong operation" as you stated above. Nor are they even a semi-strong entity at this stage of the game --- notice that I didn't even bother to use the word "Family" --- because as I see it, they do not currently operate as a fully functioning LCN Family, as have all come to understand it.
And not withstanding what you may have read to the contrary, they are on their last legs! (just remember, that you heard it from me first)