I remember, when I first watched On the Head of a Pin, when Alastair described Dean as a righteous man and Castiel confirmed it, I disagreed. I did not think Dean was righteous. I don't remember quite why I thought that - perhaps I was influenced by reading other fan's journals, people who were so upset by Dean's increased use of misogynist slurs that some of them said that didn't feel sorry for him going to hell because of it. Which, okay. I am no fan of misogynist slurs and completely down with being upset by them. And at the end of the day, people feel what they feel. But let's put that in the context of being tortured in hell until you become a demon.
Nonetheless, I did not think Dean was a righteous man. And I still don't. I'm not sure that's a title anyone deserves.
There's also the bizarreness of the idea that John was the first “righteous man” in Hell, since we’ve seen many people make demon deals for all kinds of reasons. In fact, sometime before S10 aired (wherein that dude makes a deal to kill his wife) someone pointed out that we’d never seen someone make a demon deal for something evil.
Some people have fanwanked the "righteous man" into meaning that it was because John and Dean were vessels for Michael or whatever. Regardless of whether this fanwank is accurate, regardless of whether the writers intended it that way, S4 Dean didn’t even know he was a Michael vessel.
And Dean believes he is a righteous man.
Cas tells him, “The righteous man who begins it is the only one who can finish it. You have to stop it.” And Dean says he can’t.
“I can't do it, Cas. It's too big. Alastair was right. I'm not all here. I'm not—I'm not strong enough. Well, I guess I'm not the man either of our dads wanted me to be. Find someone else. It's not me.”
But for all his self-loathing, he doesn’t deny that he’s righteous.
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