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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Just watched TOS's episode Journey to Babel and there was a moment that had me giggling.
Around 5 minutes in, when Jim is giving Sarek a tour and Spock is not-so-inconspicuously sulking in the foreground with Amanda, Sarek says 'My wife, attend.' which we can presume is a Vulcan thing, probably a nice and polite way of reminding others who your mate is without all of the pre-Surak stabby-ness.
And then not even ten seconds later, when Spock turns to leave, Jim turns to him and says 'Mr. Spock, a moment if you please?'
And I can't help but see the little parallel. Its like Kirk felt the need to also show the room who his boyfriend is but copying Sarek, who Kirk only learned two minutes ago was Spock's dad, would have been a bit too cheeky. First meeting with the in-laws and all that.
Plus Jim calls Spock over to explain the Enterprise's computers which Sarek does not need to know about. Almost as if Jim had to come up with a reason on the spot to explain away why he just called Spock over like Sarek did with Amanda.
Double plus, Sarek and Amanda are Vulcan kissing the entire agonising trip Spock takes to walk over to Jim. Like, not a light brush of the fingers, those babies are firmly pressed and not budging. And they don't stop until Sarek has insulted Spock and sent him away. Its more a makeout session than a kiss.
So, anyway, Jim calls Spock over both because he's maybe a little intimidated by Sarek and wants his best friend/boyfriend to support him and also because, no matter the species, men behave similarly when it comes to certain things like mates and Jim was not about to be shown up on his own ship.
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(Tfw you're the most reliable person in the roster and you're only like 12)
Httyd 2 is where the Hooligans start to think Elder may be too carefree and naive to be chief, Snotlout is too gradious to do the job right, and find that they truly appreciate the wise, diplomatic nature of Younger. Maybe we should make the little guy chief instead 💁
Bonus:
#1 most irresponsible older brother 😂
(Speech bubble text beneath readmore:)
Hiccup the Younger: If I had a gold piece for every time Gobber told me to usurp my brother for the throne of Berk I'd have three gold pieces and at this point I'm starting to think he's being serious
Little Fishlegs: Well, why not? It's a very honorable position– and you'd be great at it!
Younger: Sure, but that's Hiccup's job. It's not like I WANT it. Besides, Snotlout's the runner-up heir, not me, so I'd have to challenge him, too. I'm in Last Place, Fishlegs. Maybe it's better that way.
Little Fish: You sell yourself too short. Most of the tribe would be happy to see you on the throne instead of Snotlout. Heck, they're prefer you to Mr. Elder! All the adults say Mr. Elder is too immature. Gobber even says they're going to approach Stoick personally about lifting your rank.
Younger: Very funny.
(Silence)
Younger: WAIT— ARE YOU SERIOUS?!
...
Astrid: Shirking your heirly duties, as usual.
Astrid: You know, maybe Gobber's right, and Minicup should usurp you and take over the tribe.
Astrid: NO— YOU'RE NOT SUPPOSED TO AGREE!!!
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