Montresor is the Bad Ending of White Raven
So Montresor has a religious trauma. And from what little we know of the flashback to his death, the man was apparently a corrupt preacher.
What that tells me about his life made me crack my knuckles, because holy shit, this guy is an even better villain than I expected. And not for the reasons I thought at first.
Montresor's possible backstory
A fun fact: "unholy men" used to be called "sons of Belial". Same as Monty's Spectre type, so there's the initial connection, but with what we saw in chapter 87, this phrase from his mother resonates quite a bit:
Montresor was most likely a bastard (literally), and if he was raised in a religious community, that immediately made him and his mother outcasts. Possibly his mother hated him for "ruining her life". Whether this is true or not, the implication is that he grew up a victim of a system that decided he was sucked by the devil from birth.
In this light, Montresor's attitude towards the world is actually a logical consequence: he has decided that abuse is the only way to relate, and you can either be the victim or the victimizer. Of course, he is now the victimizer.
But he decided that because life taught him two lessons that were important enough to make him the person he is now.
"I know this game better than anybody"
We know from the clothes and hat in his flashback, and the cross around his neck, that Montresor was a preacher. And I would venture to say an excellent one: he has heard all his life that he is a demon, he knows better than anyone what terror hell produces in people, so he knows exactly what to say (or not say) to manipulate others through that fear.
Montresor, like Annabel, is someone who exploits his own traumas.
Annabel has been almost conditioned to behave like the perfect high-society lady, and that includes going to impressive extremes if it means getting something in return. She has engineered her way through life by identifying the currency of the people around her and knowing exactly what to give them so that they will, in her words "kissing her rings".
Loyalty gained through fear vs. loyalty gained through pretended sympathy.
Same goal.
If the world has made them that way, both Annabel and Montresor will use every last footnote of knowledge gained through trauma to get what they want.
But then there's something else they have in common: this deep knowledge of the rules of the game has also made them both know that the odds are too stacked against them to ever win. In the past, we've seen Annabel throw in the towel on her arranged marriage, but Montresor took a different path, much more along the lines of…
"So I'm not afraid to cheat."
Montresor decided that if people wanted a demon. He would give them one. The worst demon of all, because this one knows the rules: he knows how to play the game, he knows how to cheat and get away with it. We don't know the extent of his atrocities, but given what happened in the flashback and the fact that his idea of a sleepover is stuffing someone behind a wall to slowly suffocate, this guy must have a long rap sheet.
So long, in fact, that he was tied to the tracks of a train to be torn to shreds without even a trial.
Because if the rules are just there to screw you, then screw them: the only option left is to cheat.
Which is exactly what Lenore did when she burned down her house and pretended to be a man to go after Annabel. Lenore jeopardized everything Annabel said was important to her.
And she got away with it. At least until they were both killed (or, if those of us with our chips on Annabel's childhood friend, they may have both died without anyone knowing).
Now, in Nevermore, Lenore is still doing that, as we can see in her reluctance to kill or destroy Montresor: she refuses to play the game, refuses to follow the rules.
She will look for ways to cheat here, as she did before (something Annabel actually expects her to do). The woman is too stubborn to bend, and so far she seems to have the wind at her back (the question is, for how long?).
The bad ending
These elements make Montresor a complete exhibition of the ultimate consequences of taking Annabel and Lenore's attitudes to the extreme: a person who instrumentalizes her own traumas to unravel and try to inflict them on others, and who is not afraid to cheat for her own benefit if it means getting what she wants.
The only thing that separates Annabel and Lenore from Montresor is that they both still use these attitudes in the name of other people: Annabel for Lenore herself, and Lenore for the people she cares about. That both of them (still) seem to have their hearts in the right place.
But if Annabel continues to use her vast knowledge of this twisted game to work her way through people without caring, and Lenore still believes she's above all rules, here's Montresor to show them (and us) what's waiting for them at the end of the road.
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the "big picture" - whether that refers to some detached, calculated greater good; ruthless ambition and progress for the sake of progress; or even the dear listeners' cosmic indifference - as an antagonistic force in wolf 359 is so fascinating to me because of the way eiffel as a protagonist is set up to oppose it, just by nature of who he is. eiffel retains his humanity even under the most inhumane circumstances. his strength is in connection, and with that he's able to reach others who share his core values, but he's operating under a fundamentally different framework from the show's antagonists. he can never understand where they're coming from or be swayed by their points of view because, for better or worse, he can only see the world through a close personal lens.
it's an ideological conflict he has with all of them, but notably with hilbert: "you talk about helping people, but what about the real, live people around you? [...] that's your problem. you're so zoomed out." eiffel will never, ever see that "big picture" because he is so zoomed in. at his best, he puts things into perspective and grounds the people around him. at his worst, his perspective narrows so drastically inwards that he becomes blind to everyone and everything else. his failings are deeply, tragically human - they're personal, they're impulsive, they're self-destructive. they're selfish. no matter how much he might try to narrativize or escape from himself, he's still left with doug eiffel: "it's taken me this long to realize that running from everyone else means that you're alone with yourself." eiffel could never be convinced to harm others on purpose, but he has hurt people, and it's never been because he didn't care. the very fact that he cares so much, that he's incapable of reconciling the hurt he's caused with the things he values, is what keeps him from real growth for so long. where many of the other characters in wolf 359 will justify their cruelty in service of something they consider more important, eiffel is so caught up in vilifying himself and the fear that he's always going to harm the people he cares for without meaning to that he shuts himself off from the people who care about him and perpetuates his own self-fulfilling prophecy.
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