What is it about Montresor that makes him an especially effective enemy to Fortunato? Give an example from a book you’ve read or a film/TV show you’ve seen in which this type of villain exists.

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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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