If Fortunato was not incapacitated as he was, would Monstresor's calculated revenge plan have worked? Does Montresor actually "win" in the end? After all, it is not very difficult to chain up a drunkard (I would know; I've bound an intoxicated someone with duct tape in revenge for squirting ketchup at me, but that's a story for another day). Montresor also claims that a wrong is unredressed "when the avenger fails to make himself felt as such to him who has done the wrong," but the inebriated Fortunato clearly had no clue that he was being punished from the very start right until his hiedous end. Thus, Montresor's injury was not redressed because he failed to make it clear to Fortunato what crime he was being punished for. Montresor therefore is a murderer, not an avenger of his injury nor even a bearer of his family's motto: "Nemo me impune lacessit".
Another detail lies in Montresor's coat of arms: a foot crushing a serpent with its fangs embedded in the heel of the foot. Montresor would certainly like us to think that he is the foot, crushing the insulting serpent with impunity. That is what he wants us to think, but does he really believe that deep down inside? Or does Fortunato gain some measure of victory with a twisted mind game he plays with Montresor at the end?
"For the love of god, Montresor!"
"Yes, for the love of god."
And then there was silence, save for the jingling of Fortunato's jester cap. This clearly unnerves Montresor; his heart grows sick, perhaps at a sudden realization of the ramifications of entombing his friend alive, but he covers it up by claiming it was the doing of the dank air. His hurried work on the last stone betrays his nerves. We don't know if he comes to regret his action over the course of half a century. Although no regrets are implied, this could be a conscious act to prove that he was not a coward or a weakling. Perhaps Fortunato was instead the foot that crushes the serpent Montresor; although the serpent bites and kills him, Fortunato leaves a lasting footprint upon the serpent's conscience.
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