- Montresor twice pretends to think Fortunato is expected somewhere that evening. For example: “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—” Fortunato finally says, "I am not engaged;--come!" Montresor does not want people out looking for Fortunato that night if he is expected at home or somewhere else and doesn't show up. He wants to leave a cold trail and not have people inquiring about his victim until tomorrow morning at the earliest. His mention of Luchesi is intended to motivate Fortunato to accompany him to his palazzo immediately. He can't make an appointment for Fortunato to come to his palazzo at some later time--even an hour or two later--because Fortunato could easily tell someone he was going to Montresor's home. Then when Fortunato turned up missing and the police started making inquiries, they would want to question Montresor and even search his premises. He wants to be above suspicion--which is why he has conditioned himself, not only to call Fortunato his friend, but actually to think of him as "my friend," "my good friend," and "my poor friend," as shown throughout his narrative.
- Montresor tells Fortunato he bought the Amontillado impulsively because he didn't want to lose a "bargain." "Bargain" is the key word. Now he wants to make sure it is genuine. Why? He has already paid for it and had it delivered to his vaults. Obviously he would buy more at a bargain price if only he could be sure it is genuine Amontillado. A lot of us can have second thoughts about "bargains." We find out there is something wrong with whatever it was we purchased. Fortunato is not interested in helping Montresor or in showing off his connoisseurship. He is interested in the "bargain." He wants to get in on it.
- Montresor constantly uses what is called "reverse psychology." When he and his victim are down in the catacombs, he keeps suggesting that they turn back. Fortunato is drunk, and drunkards are notoriously contrary and stubborn. If your friend has been drinking too heavily and wants to drive home, you will have a very hard time getting him to let you drive his car. Montresor's fake concern about Fortunato's health makes him seem completely innocent. Why would he be suggesting that they turn back if he had any ulterior purpose in moving forward? Here is an example of his 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—”
Montresor has never given Fortunato reason to doubt his goodness. Therefore, Montresor has no problem luring Fortunato to his death. But the number one strategy Montresor uses on Fortunato is to use his (Fortunato's) pride against him.
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 tells Fortunato he is not sure about his wine being Amontillado. Montresor knows Fortunato will not be able to resist showing off his knowledge of wines, so he insists on going to Montresor's vaults in order to test the wine.
Montresor also continues to encourage Fortunato to drink as they descend further into the vaults. This keeps Fortunato drunk enough to ignore his cough, to continue to suspect nothing sinister about Montresor, and to continue his proud quest to prove his superior knowledge of wine.
Montresor continues to use Fortunato's pride against him. Although the light is too dim for Fortunato to proceed, Montresor mentions Luchesi, another wine connoisseur; Fortunato proceeds in order to prove his superiority over Luchesi.
Crazy though he may be, Montresor certainly uses his wits in his revenge on Fortunato. First, he hides his true feelings in order to lure Montresor into a false sense of security; he doesn't let on that he has experienced any change of feelings.
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.
Montresor also chooses his bait well. He picks something he knows Fortunato cannot refuse: the chance to inspect a very valuable old wine—a cask of Amontillado.
He also is very clever in recognizing his friend's vice: his pride. He knows that if he appears to give preference to another wine expert's advice, Fortunato will be anxious to prove himself and prepared to go anywhere and drop anything to do so.
"Luchresi cannot tell Amontillado from Sherry."
"And yet some fools will have it that his taste is a match for your own."
"Come, let us go."
He also chooses carnival time to get his revenge, when the streets are crowded, people are less attentive, his servants are out making merry, and he himself can wear a disguise: "a mask of black silk and ... a roquelaire." It also helps ensure that Fortunato isn't thinking clearly—he's already drunk, since his eyes betray "the rheum of intoxication." He also cleverly works to keep his friend that way: "A draught of this Medoc will defend us from the damps."
What's more, he has clearly prepared the scene; he has the chains ready so that it is "the work of a few seconds" to loop them around Fortunato and lock him in.