Moe Giancana was nobody's puppet, let's get that out of the way. Tony Accardo never pulled the strings for anyone, he was a lifetime consigliere, which is a high-ranking position as is, obviously. But a guy like Accardo couldn't sniff a guy like Moe's fuckin jockstrap, you can bet your ass on that.

Joey 'O'Brien' Aiuppa, 'Old Man O'Brien', or simply 'The Old Man' as he is universally referred to here, was the single wealthiest boss in Chicago Outfit history, and believe me: He was THE BOSS. He & Cerone bullied Accardo into switching to their side in the late 60's & got him to turn his cheek when they took out Moe.

I think Aiuppa going away didn't hurt the Outfit too much on the streets here, because he had already set up such a rock solid base on the Southside & in general. He had already implanted the LaPietra people in Bridgeport/Chinatown & Cicero had been locked down for years. He also cut down street-level bullshit to a bare minimum, and completely streamlined the Outfit's business endeavors. He set up the modern Chicago Outfit, it would simply not exist if it were not for Old Man O'Brien.

Old Man O'Brien was a shrewd man. He dressed & acted like a ho-dump small town fisherman, you would have never been able to point him out on the street as the boss of the Chicago Outfit. But he was, and boy was he rich, and ruthless. Joey O. never had any kids of his own (he caught something at one of Capone's brothels that prevented him from ever procreating) but he loved two gangsters like they were his own son: Louis 'Louie The Mooch' Eboli & Marco 'The Mover' D'Amico. He sponsored both of them when they were made into the Outfit during the late 70's.