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I'd say his strongest stretch was WM24-26 where he was beginning to develop his cold blooded Viper character, and then WM26 cementing his big face turn which continues to this day.
However, this directly lead to probably his worst stretch, WM27/28 where he pretty much got John Cena's sloppy seconds. Punk and Kane were both feuding with Cena before going to Orton. At least Kane's feud with Cena at least came to an "end". The year before, Punk pretty much just dropped his beef with Cena out of nowhere because Mania was coming up and they wanted him to fight Orton.
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