I would think that Chris Flipping in a flashback scenario the rest off the series is a definite possibilty. JT spoke with Tony at the Bing and was BSing him about where the Persona of Sally Boy in the Movie came from the movie Born Yesterday, which he then rented. When Tony asked him about his eye and he said he hit it on the cabinet, Tony shrugged like he knew JT was bullshitting him. Also when he watched the Movie he was all broken up because he knew Sally Boy was not based on the character from "Born Yesterday" and that Chris probably intimated JT into telling Tony-which was truly the case.
The Chris wearing the Cleaver hat thing....Tony would not necc. need to know that FBI likes mic' ing up caps...the audience would know because they saw Dick Masserone wearing the hat/mic when trying to get Tony on tape. I think DC might want us to consider that Chrissy turned RAT or that this will be a part of the storyline in the FINAL 'sodes. We'll SEE!
"You Can't Kill me twice Sally Boy, I'm already fuckin' dead remember"