Montresor shows his cleverness in several places throughout "The Cask of Amontillado." When he first encounters Fortunato celebrating in the street, he wants to make sure that he is not expected anywhere that night. He would like to lure Fortunato to his palazzo and leave a cold trail. If Montresor's victim were expected at home, for example, then relatives, friends, and servants might go out looking for him that very night, and there would be many people who would remember seeing him and who would at least be able to tell in which direction he was going. But if Fortunato were not missed until the following morning, everybody would be sleeping or hung over and would not remember anything of use. So Montresor cleverly ascertains that Fortunato is not expected anywhere by pretending to believe he is expected.
“As you are engaged, I am on my way to Luchesi. If any one has a critical turn it is he. He will tell me—”
“Luchesi cannot tell Amontillado from Sherry.”
Montresor does not get the information he wants, but at least he plants the idea that he is on his way to Luchesi and suggests that he is in a big hurry to have his Amontillado judged by a connoisseur. So he tries again.
“My friend, no; I will not impose upon your good nature. I perceive you have an engagement. Luchesi—”
“I have no engagement;—come.”
That was what Montresor wanted to find out. Fortunato will not be missed anywhere that night. Even tomorrow his family will assume that he is sleeping it off at a friend's home, or spending the night with a mistress. It will be some little time before people start wondering what on earth could have happened to Fortunato.
Montresor shows his cleverness by his use of "reverse psychology," a method of persuasion by telling a person to do the opposite of what you want them to do. Montresor must realize that Fortunato, as drunk as he is, will begin to wonder why the big "pipe" of wine is stored at such a distance from the foot of the cellar stairs. Here is an example of Montresor's reverse psychology.
“Come,” I said, with decision, “we will go back; your health is precious.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. We will go back; you will be ill, and I cannot be responsible. Besides, there is Luchesi—”
“Enough,” he said; “the cough's a mere nothing; it will not kill me. I shall not die of a cough.”
There is a natural human tendency to resist being told what to do. This is especially observable in drunks. By pretending to want Fortunato to turn back, Montresor suggests that there could be no danger ahead and that he could not have any ulterior motive for leading Fortunato onward.
There are many other examples of Montresor's cleverness. For instance, he has honed his entrapment story so that it will be nearly foolproof. He says he bought a cask of Amontillado without consulting an expert because he was afraid of losing a bargain. It is the bargain that interests Fortunato and not the prospect of sipping a glass of wine in a dank underground setting when he has a bad cold and is not adequately dressed for it. If Montresor got a pipe of 126 gallons of gourmet sherry at a bargain price, then Fortunato would like to buy some himself and sell it at a profit. Montresor knows his man. He understands that Fortunato is only going with him to his palazzo in order to prevent him from going to Luchesi. Fortunato assumes there must be a Spanish ship in the harbor carrying a cargo of Amontillado and offering it at a bargain price because it is hard to find buyers during the carnival when everybody is neglecting business. Montresor has been injured by his friendly enemy a thousand times, and he knows Fortunato is planning to tell him his nonexistent wine is only ordinary sherry, whether it is or not; then, if it is genuine, go to find the nonexistent Spanish ship and buy up the whole cargo.
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