When they had Punk/Cena in Boston last year, creative had to strip everything from Punk's face character that was emphasized in the first 9 months of his reign and proceed to trot out every legend they could to piss on what he did during that time frame, trying to say that it was irrelevant and that he had to prove himself by beating John Cena (when he's beaten Cena almost every time they've been in singles since the beginning of 2011). And he still didn't completely turn his hometown audience against Punk.
Automatic disqualification from consideration.
The answer is Bret and Flair in some order, followed by CM Punk. No one really resonated with their hometown not just in reaction, but in persona the way that they did. Did the Road Warriors even elicit the emotion from Chicago fans that CM Punk elicits nowadays?