"The Reckoning" : The Beginning of Winn's Descent to Villainy?
So, obviously, throughout the series Winn was various flavors of unpleasant. A simmering, unfortunate mixture of heady self-righteousness and scheming opportunism. However, there was always JUST enough there to keep her from out-and-out villainy (her attempts to take out Bareil in her first episode not-withstanding). "The Rapture" especially made a pretty solid go of fleshing her out (admitting to Kira she had been wrong about Sisko's status as Emissary, discussing her own persecution at the hands of the Cardassians for preaching the Bajoran faith, etc.).
IMO, though, "The Reckoning" is more or less the moment in the series that begins her descent into full-on villainy. And, honestly, it's hard not to feel a LITTLE bad for her (even if I still hate her). Think about the events of the episode from her perspective: as we find out later, she spends her whole life never once hearing from/being spoken to by the Prophets. Something which happens to literally EVERY other major character in the show (sometimes multiple times), including goddamn QUARK. And now, one of them straight-up appears on the station, brought there by the alien Emissary (Sisko) and possessing the body of someone who openly hates her (Kira). After a lifetime of devotion and doubt, of being convinced she must matter despite a lifetime of evidence to the contrary, she is finally in the presence of the thing she has made the fixation of her existence. She gets on her knees, offers herself to it, and begs it to talk to her. And the Prophet doesn't address her, acknowledge her role on Bajor, or even just say "Fuck off, I'm busy." It straight-up IGNORES her.
I gotta admit, as much as she is the fucking worst, it was hard not to feel kinda bad for her in the moment. All in all, I'm pretty sure THIS is the moment that begins her final fall. But, maybe I'm off. Anyone else have an idea when her final descent into villainy begins? Or was she always a villain, and this was just a well-deserved karmic kick to the face?