illustration of Fortunato standing in motley behind a mostly completed brick wall with a skull superimposed on the wall where his face should be

The Cask of Amontillado

by Edgar Allan Poe

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What makes Montresor an effective enemy to Fortunato? Can you give an example of a similar villain from a book or film/TV show?

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What makes Montresor such an effective enemy of Fortunato is his resolve to get revenge, attention to detail, and ability to act amicably to Fortunato's face while plotting his death. Montresor begins by mentioning he has vowed to get revenge on Fortunato for causing him to suffer a thousand times and laughing at his respected family name. Montresor then elaborates on his feelings concerning the perfect revenge and is careful not to get caught. After carefully plotting his revenge, Montresor conceals his hatred and is friendly to Fortunato's face, which allows him to convince his enemy to follow him into his family's catacombs. Montresor says,

"I gave Fortunato no cause to doubt me. I continued to smile in his face, and he did not understand that I was now smiling at the thought of what I planned for him, at the thought of my revenge" (Poe, 1).

Montresor is also aware of his enemy's weaknesses, which are pride and a love of alcohol. By mentioning that he will consult Luchesi about whether or not he has purchased amontillado, Montresor is able to pique Fortunato's interest and provoke him simultaneously. Montresor also makes sure his estate is empty by lying to his servants, which leaves him alone with his vulnerable enemy. After Montresor successfully buries Fortunato alive, he keeps his secret for half a century, ensuring that he will not be punished for his crime.

The character Iago in Shakespeare's Othello is similar to Montresor in that he carefully plots revenge and feigns friendship to Othello's face. Although he does not directly kill Desdemona, he accomplishes his goal of ruining Othello through manipulation and lies. 

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Montresor is an especially effective enemy to Fortunato, because Fortunato completely trusts Montresor.  

A person could be an effective villain by being supremely powerful or by having some amazing awesome plan.  But being an effective villain is made harder, if anybody that you are trying to be a villain toward is always suspicious of you.  I imagine that Darth Vader has a really hard time being a sneaky villain.  He looks suspicious, sounds suspicious, and has a history of being evil.  

Montresor has none of Darth Vader's problems.  Fortunato assumes that they are still "buddy-buddy."  Fortunato has no previous encounters with Montresor in which Montresor made Fortunato's life miserable.  Basically, Fortunato has no reason to suspect Montresor of anything except honesty and good will.  And Montresor knows it.  

Montresor also knows exactly what to say and offer to Fortunato to get him to follow Montresor anywhere.  Montresor name drops "Luchesi" to goad Fortunato.  Montresor also knows that the allure of an Amontillado is too great of a temptation to be ignored.  

Any episode of CSI would fit the bill for this kind of "bad guy," because in that show the bad guy is always the best friend that you would least suspect. I have a film example.  It's the movie "Predestination" with Ethan Hawke.  It's based on the short story "All You Zombies."  It works as an example because the main protagonist and antagonist know each other completely . . . because they are the same person.  There are lots of weird paradoxes in the movie, since time travel plays a big part.   

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Montresor makes a really effective enemy for Fortunato because he is proud, diabolical, and very intelligent. He understands people very well, and he is able to exploit this highly developed understanding in order to manipulate everyone around him. For instance, he knows just how to get Fortunato to come, willingly, to his home and down into his family vaults. Montresor knows that Fortunato will not be willing to pass up an opportunity to show that he knows more about wine than Montresor; Fortunato insists, even before they see the supposed amontillado, "You have been imposed upon." Montresor also knows that, by telling his servants that he would be away until the following morning and that they should not leave the house, he could "insure their immediate disappearance, one and all, as soon as [his] back was turned." There will be no one home to observe his arrival with his enemy.

It is tricky to think of a contemporary villain who is always one step ahead of his victim and who is ultimately successful in his plot to overcome that victim. At the very least, we will have to consider villains who are capable of intricate plotting and are very good at "reading" other people. I think Professor Moriarty from some of Arthur Conan Doyle's stories about Sherlock Holmes is a good candidate. He is proficient at manipulating people, is emotionally detached, and does not seem concerned about the morality of his actions, just as Montresor—at least at the time he killed Fortunato—was not concerned about the morality of the action either.

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First, Montresor knows an ultimate weakness of Fortunato:

He had a weak point—this Fortunato—although in other regards he was a man to be respected and even feared. He prided himself on his connoisseurship in wine.

Montresor is thereby able to exploit this weakness in his plans to kill Fortunato while also maintaining a keen ability in holding the man's trust:

It must be understood that neither by word nor deed had I given Fortunato cause to doubt my good will. I continued, as was my wont, to smile in his face, and he did not perceive that my smile now was at the thought of his immolation.

While Montresor plots to kill Fortunato by using personal knowledge against the man, he is simultaneously able to never give himself away; Fortunato trusts him, and even as he is led to what will become his tomb, he rejects Montresor's insincere attempts to turn back. Thus, he allows himself to be led directly to his death.

In Shakespeare's Julius Caesar, there is a similar betrayal. Brutus knows that Caesar trusts him, yet he aligns himself with the forces who seek to kill Caesar. It is Brutus's betrayal that pains Caesar most and the one which is the literal final blow:

Et tu, Bruté? —Then fall, Caesar.

[dies] (III.i.89-90)

In this case, the two are closer friends than Montresor and Fortunato, yet Brutus clearly violates a similar sense of trust in order to commit murder.

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Montresor is an especially effective enemy of Fortunato because he has made Fortunato and everyone who knows these two men believe that they are the best of friends. Montresor is cunning, and it is his cunning that enables him to make Fortunato believe he is his good friend. Therefore, Fortunato trusts him, and when Fortunato disappears, nobody will ever suspect Montresor of foul play because they are sure that he and Fortunato were very good friends.

The one character is classic literature who resembles Montresor in this respect is Iago in Shakespeare's Othello. Iago has Othello convinced that Iago is honest and that he is Othello's friend. Even after Othello has killed Desdemona as a result of Iago's villainous machinations, he speaks highly of Iago, who has completely deceived him.

EMILIA:
O mistress, villainy hath made mocks with love!
My husband say that she was false!

OTHELLO:
He, woman;
I say thy husband. Dost understand the word?
My friend, thy husband, honest, honest Iago.

A more modern instance of Montresor's type of villainy can be seen in the excellent 1998 movie The Truman Show, starring Jim Carrey. Truman Burbank discovers that he has been on an internationally popular television show ever since he was a baby, and that the woman he is supposedly married to is a professional actress working for the producers of "The Truman Show." The show relies for its income on advertising inserted in the scripted drama in what is called "product placement." Truman also discovers that the man who has been his best friend since childhood is also a professional actor who works for the show and has only been pretending to be his friend for all these years. This "friend" is as cunning and insidious as Montresor. In fact, everyone in the show is a professional actor except for Truman himself, who has been kept in ignorance all his life while being photographed from countless concealed video cameras in the totally artificial town where he grew up.

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What is it about Montresor that makes him an especially effective enemy to Fortunato?

Montresor is an especially effective enemy of Fortunato for a few reasons, not the least of which are his intense pride and ability to manipulate. As he says early on, "I must not only punish but punish with impunity." He feels the need not only to avenge the wrongs done and insults given to him by Fortunato, but also to exact his revenge without having to endure some punishment for it. His family motto translates to "You will not harm me with impunity"—in other words, no one can harm a Montresor and get away with it. His personal and familial pride make him especially relentless and ruthless when it comes to Fortunato.

Further, Montresor clearly put a great deal of thought into his revenge, and he manipulates his staff and the public, as well as Fortunato, to achieve it. He tells his servants he will be gone all night and that they must remain at home, knowing they will all go to the festival as soon as he leaves (and will claim they were home all night to avoid trouble). He makes sure his costume covers his face so he will not be seen with Fortunato in public, and he concocts an elaborate story about a pipe of Amontillado, knowing Fortunato's pride will compel him to risk his own health in order to prove Montresor has been had. He is so thoughtful and manipulative, which makes him a perfect enemy for the relatively simple and straightforward Fortunato.

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What is it about Montresor that makes him an especially effective enemy to Fortunato?

Montresor claims that he has borne a "thousand injuries of Fortunato" but he never says exactly what they are. He adds that it is an insult that sends him over the edge and propels him toward thoughts of revenge. And this is severe revenge: "I must not only punish, but punish with impunity." 

But even though Montresor is filled with anger and a thirst for revenge, he never lets these hateful thoughts known to Fortunato. He coldly informs the reader that he continued to be friendly to Fortunato and to smile but that "he did not perceive that my smile now was at the thought of his immolation." This is Montresor's first strategy. He acts as if he and Fortunato are still good friends and therefore, Fortunato will never expect anything sinister from Montresor. 

Montresor also knows Fortunato's weakness: his pride in being a connoisseur of wines. 

When Montresor greets Fortunato at dusk during the carnival, he is friendly and then starts to lure Fortunato by telling him he has just bought a cask of Amontillado but is not sure it is genuine. He further tempts Fortunato when he says that since Fortunato seems busy, he will summon Luchesi to taste-test the supposed Amontillado. Fortunato insists that he is the better judge of wine and insists on going with Montresor to judge for himself.

Using reverse psychology, Montresor continually tries to talk Fortunato out of accompanying him to test the wine. He says that he doesn't want to be a bother to Fortunato and that he doesn't want Fortunato to get sick in the damp vaults where he stores the wine. These friendly protests only make Fortunato more determined to test the wine. As they descend into the vaults, Montresor keeps feeding Fortunato drinks to dull his senses and make it easier for him to continue manipulating Fortunato. 

Montresor continues to alternate these strategies. He is friendly and appears concerned for Fortunato's health. But he keeps him drunk and keeps using Fortunato's pride to lure him deeper into the vaults. 

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Explain why Montresor is an especially effective enemy to Fortunato, and identify a similar relationship in a book/ T.V. show.

You will note that Montresor the narrator continually refers to Fortunato as "my friend," "my good friend," and "my poor friend" throughout the story. He is not being ironic. He wants what he calls impunity. He has conditioned himself to think of Fortunato as his good friend, and he must always speak of him as such to everyone because he wants to be above suspicion when his good friend turns up missing. Even Fortunato thinks Montresor considers him his very good friend. This seems to be what makes Montresor an especially effective enemy. Fortunato trusts him. Nobody will suspect Montresor of having anything to do with Fortunato's disappearance. Montresor is sure to keep asking about him and showing deep concern about him longer than anybody else.

Two parallel examples from classic literature can be found in Othello and King Lear. Iago poses as Othello's best friend, and Othello is completely deceived by him. He calls him "honest, honest Iago." Iago hates him bitterly and seeks to destroy him. Edmund in King Lear shows nothing but brotherly love for Edgar while he is doing his best to turn their father Gloucester against his trusting half-brother. In both these cases the friendly enemies are successful although they both come to bad ends themselves. Shakespeare teaches us that we should be awfully careful about picking our friends. Poor King Duncan thought Macbeth and Lady Macbeth both loved him. King Lear thought Goneril and Regan loved him deeply.

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Explain why Montresor is an especially effective enemy to Fortunato, and identify a similar relationship in a book/ T.V. show.

While Montresor speaks of the "thousand injuries" that he has suffered from Fortunato and vows revenge, there is no explication of what these injuries are. So, added to the fact that Montresor seeks retribution for the supposed wrongs done to him is also the possibility that he is not mentally stable. This condition, added to his clever manipulation of Fortunato's hubrisleads to the power of Montresor as an adversary.

After he accosts Fortunato in the celebratory streets, Montresor catches the reveler off guard by acting as those their encounter is by chance. Casually, then, he mentions that he has received a large cask of Amontillado:

"I have my doubts...and I was silly enough to pay the full Amontillado price without consulting you in the matter. You were not to be found, and I was fearful of losing a bargain."

Here he has captured the attention of Fortunato; then, Montresor acts as though he does not wish to inconvenience Fortunato, saying that he is on his way to Luchesi, who "has a critical turn." This remark certainly ignites Fortunato's pride, "Luchesi cannot tell Amontillado from sherry." Further, Montresor fuels Fortunato's professional jealousy as well as he tells the other man, "And yet some fools will have it that his taste is a match for your own." After this maneuver, Montresor dons a black mask of silk and "suffers him" to hurry together to his palazzo. With feigned concern, Montresor stops Fortunato repeatedly, solicitous of Fortunato's health as the niter causes the other to cough. As they reach the inner chambers, Montresor uses reverse psychology, halting Fortunato along the way out of a seeming anxiety for his acquaintance's health; once they reach a dark recess, Montresor fetters the feckless connoisseur, who is stunned by this cruel act. Then, he laughs, thinking that perhaps this reversal by Montresor is a joke. But, when he realizes that it is not so, Fortunato calls out, "For the love of God." "Yes," replies Montresor coldly, "for the love of God."

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There are many literary works and films that employ a luring of one's victim as a method for horror. One such film has an occurrence that is somewhat similar to the luring of Fortunato to the tomb of his death. In Silence of the Lambs, for example, there is a male predator who tricks young women into helping him as he struggles with a couch, trying to put it into a van. When the young woman steps into the van with the couch prohibiting her exit, he locks the door and kidnaps her. Then, she is thrown into a pit where she cannot escape and will just be sedentary; in the meantime, she is well-fed so that she will get heavy and her skin will stretch. When she gains enough weight, the predator will dispense with her and use her skin for his creative genius. 

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