Edgar Allan Poe often seems to be a writer obsessed with blurry intersection of mentally disturbed exhibitions of violence and sheer, unadulterated evil. Is the narrator of “The Tell-Tale Heart” really as guilelessly driven by guilt as he seems…or is he a something of a prototype for Keyser Soze, leading the police down a confessional hole straight to an insanity defense that gets him out of jail? The typical reading of that particular killer in the Poe canon is generally one of a soul driven over the edge first by greed and then by remorse. Poe’s other great killer is usually not the recipient of such bleeding heart liberalism. In fact, Montresor in “The Cask of Amontillado” remains one of American literature’s great psychopaths.
And yet, Montresor seems every bit as much the unreliable narrator as that guy who suddenly goes mental over the image of the beating of the hideous heart. It may be that readers have been far less forgiving about Montresor’s crime due to the heightened rationality of his monologue. A coldly lucid assertion that “a wrong is unredressed when retribution overtakes its redresser” (340) is, after all, something that the hysterical narrator of “The Tell-Tale Heart” seems almost incapable of formulating. And Montresor’s continuing monologue follows along the same path of highly functioning sociopathy throughout his tale of perceived insult and overwrought retribution.
It is that overwrought ambition to right the perceived wrongs of insult that creates a bizarre irony in “The Cask of Amontillado.” The killer driven to madness by his imagination in “The Tell-Tale Heart” ultimately becomes something of a pathetic figure almost worthy of sympathy whereas those who feel sympathy toward Montresor might find themselves subject to a psychological evaluation. In reality, these opposite emotions would seem to be reversed. After all, few can truly empathize with much of that other great Poe killer, but who cannot sympathize with Montresor’s justification for murder? “The Cask of Amontillado” is, ultimately, a story of vengeance. We don’t get to know exactly what it was that Fortunato did to tick off Montresor to such a degree, but the imagination can certainly take most people to a place where they side with Montresor. Then there is the fact that from the kidnapping victim in “Oldboy” to meth kingpin Walter White, modern day readers of the story have been fully conditioned to root for the guy seeking vengeance, regardless of the nature of the wrongs they are seeking to right or the method by which such revenge is achieved.
Another paradox at work in the fact that Montresor rarely gets the sympathy that other patently deranged killers throughout literary history have enjoyed is that he remains at such an emotional distance despite possessing that one trait that separates the legendary serial killers from the grotesque crowd. Montresor is genuinely charming. In fact, it is not unreasonable to assume that were Montresor lacking in charm, his plan might never have come to fruition as it is not without reason to assume that Fortunato would not be as quick to follow Montresor to his own doom if Montresor were not the master of such lines as “You are rich, respected, admired, beloved; you are happy, as once I was. You are a man to be missed. For me it is no matter” (Poe 342).
Ultimately, it must be admitted that Montresor’s charming sociopathy is the key to succeeding at his plans for vengeance, but without Fortunato’s utter lack of all those things that allow Montresor to succeed in his nefarious plot, that plan would likely have fallen apart at some point. Perhaps Montresor is that rarest of birds: the killer who is just a little too coldly calculating in his charm to win the hearts of an American public all too willing to embrace otherwise nice guys who break a little too badly for comfort.