One of the most clever things Montresor does in entrapping Fortunato is to make sure that his intended victim is not expected at home or anywhere else that night. Montresor twice pretends to believe that Fortunato has an engagement. First he says:
This also introduces the idea that if Fortunato should refuse to accompany Montresor to his palazzo for any reason, Montresor would immediately go to Luchesi to ask him to judge his wine. Fortunato responds to the mention of Luchesi but not to the supposition that he is "engaged." Montresor must find out. He wants to leave a cold trail. If Fortunato is expected anywhere that night, Montresor will probably postpone his revenge. Again he brings up his enemy's supposed engagement, and this time he gets the information he wants:
“I have no engagement;—come.”
A second clever thing Montresor does at the beginning of the tale is to repeat that he has "doubts" about the authenticity of the Amontillado. If Fortunato does not come to Montresor's palazzo that night for any reason, such as an engagement or his bad cold, then Fortunato will certainly want to know more about the wine the next time he sees Montresor. Since the wine does not exist, Montresor will bring Fortunato a bottle of ordinary sherry and tell him it came from the cask he just purchased. Fortunato will, of course, judge it not to be true Amontillado, and that will be the end of the matter.
Montresor shows great patience and foresight in his revenge scheme. When he has Fortunato chained to the wall and his victim pretends that he is expected that night by his wife and a houseful of guests, Montresor cannot be frightened into unlocking the padlock. A third clever thing he did, which shows his patience and foresight, was to condition himself to think of Fortunato as his "friend" and to address him and refer to him as such repeatedly over a long period of time. When it is discovered that Fortunato has disappeared, there will be a big investigation. Naturally people will suspect foul play--but no one will suspect Montresor because he is known to be Fortunato's very good friend. Montresor himself will undoubtedly continue to inquire after Fortunato for a long time after his mysterious disappearance. In fact, the uproar occasioned by Fortunato's disappearance, along with the pain it causes Fortunato's wife and relatives, will contribute to Montresor's enjoyment of his perfect revenge. Fortunato himself has been lulled into trusting Montresor by being repeatedly addressed by him as "my friend," as Montresor does throughout his narrative.
Montresor pretends to believe that Fortunato has an "engagement"; that is, that he is expected somewhere that night. He hopes Fortunato will either confirm or deny it. The first time Montresor mentions a presumed engagement, Fortunato does not respond. The second time he mentions an engagement, Fortunato gives Montresor the information he requires when he says, "I have no engagement. Come!" Much later when Fortunato is chained to the rock wall, he will try to frighten Montresor into releasing him by asserting two things: (1) that people have seen him and Montresor together on the streets and supposed they were on their way to Fortunato's palazzo, and (2) that he is expected at his home by Lady Fortunato "and the rest." Fortunato also treats his entrapment as a big joke, offering Montresor an excuse and an alibi at the same time he is trying to plant a grain of fear in his captor's mind. If Fortunato is really expected that night and doesn't show up, then servants, relatives and guests could all be out searching for him with torches. Montresor wants to leave a cold trail. He doesn't want Fortunato missed until the next morning at the earliest, by which time everybody will be recovering from hangovers. If Montresor were foolish enough to release his captive and go along with the fantastic pretense that this was all a big joke, Fortunato would act as if they were the best of friends until he got out of those dreadful catacombs--but later Montresor would be found in an alley with his throat cut. Montresor describes his friendly enemy as a man to be respected and even feared. Fortunato does not succeed in unnerving his captor because Montresor had the foresight to find out that Fortunato had no "engagement."
Montresor's only excuse for pretending to believe Fortunato has an engagement is that he supposedly has had a hard time finding him. If Fortunato were to ask, "What makes you think I have an engagement?", Montresor would probably reply, "I have been searching all over for you and had decided that you must be on your way to a celebration of some sort at a private home." Something of that sort. Montresor has been fine-tuning his revenge plot for years. He has formed the habit of speaking of Fortunato as his friend, his good friend, etc., and has even conditioned himself to think of Fortunato as his good friend. He knows this will create a strong impression that he and Fortunato are very good friends. He probably never mentions Fortunato's name without saying, "My friend Fortunato," "My old friend Fortunato," or "My good friend Fortunato." The only purpose for this is that, when Fortunato turns up missing, no one will have the slightest suspicion that Montresor could have had anything to do with his disaappearance. Montresor knows that the inquiry will be large and long. Fortunato is an important man. People will be talking about the mystery for years. Montresor himself will have to be one of the people who shows the most concern for the longest period of time. He will be continually asking if there is any news about his good friend Fortunato.
Montresor is the narrator of "the Cask of Amontillado" by Edgar Allan Poe, and he holds a serious grudge against his friend Fortunato. Montresor is intent on getting his revenge against Fortunato for some imagined insult, and to do that he creates an elaborate plan to kill Fortunato.
Montresor is not a sane man but he is clever, and the plan he devises necessitates some creative thinking on his part. First of all, Montresor must hide his feelings of hatred for Fortunato. He does this so successfully that throughout the entire plan, and even at the end, Fortunato has no clue that Montresor wants to kill him.
Second, Montresor chooses Carnival time to enact his plan; this guarantees that Fortunato will not be immediately missed, buying Montresor some time if he needs it. Brilliant.
Third, Montresor must be able to bring Fortunato to his empty house. To do that, he does the simplest and most clever thing he can think of to do during Carnival time:
I had told them [the servants] that I should not return until the morning and had given them explicit orders not to stir from the house. These orders were sufficient, I well knew, to insure their immediate disappearance, one and all, as soon as my back was turned.
It is an ingenious move to tell the servants that he will not be home but he does not want them to go anywhere; it is human nature for them to disobey under such circumstances, and they do.
Next Montresor has to lure Fortunato away from the Carnival festivities. Montresor determines that the only way he can get Fortunato to leave the celebration is to appeal to his pride as a wine connoisseur. Montresor lies and tells Fortunato he has a cask of Amontillado, a nearly impossible feat during Carnival time. When Fortunato is dismissive of the claim, Montressor argues that he needs someone to test it and then suggests Luchesi, Fortunato's rival, should be the one to test the wine. Of course Fortunato does not want to be outdone by his competition, so he insists on going to taste the wine. Every time Fortunato wavers, Montresor mentions Luchesi and that is enough to keep Fortunado moving. It is an ingenious strategy.
Finally, Montresor has to lure Fortunato into the lowest point in his home, the crypt. To do that, he feigns (pretends) concern for Fortunato's health and keeps giving him medicinal draughts of wine. This keeps Fortunato drunk or tipsy enough to keep moving without too many questions or hesitations.
In short, Montresor is successful in developing and executing a clever plan to lure Fortunato to his death; however, it may have been just a bit too clever, since Fortunato never realized why Montresor wanted him dead.
In “The Cask of Amontillado,” Montresor plays upon Fortunato’s ego in order to lure him into his trap. “He had a weak point—this Fortunato….He prided himself on his connoisseurship in wine.”
Fortunato plays upon this pride. First, he tells Fortunato about the Amontillado, which he says he doubts is authentic. Next, he tells Fortunato that he is on his way to see Luchesi, another connoisseur, to ask his opinion. Montresor then gives reasons why Fortunato should not go with him to examine the wine—a previous engagement and Fortunato’s obvious illness. Fortunato dismisses these things and insists he go with Montresor to taste the wine. All the while, Montresor alludes to imposing upon Luchesi instead of Fortunato. Finally, Fortunato says, “And as for Luchesi, he cannot distinguish Sherry from Amontillado.” Fortunato's ego will not permit him to allow his friend to consult another connoisseur. They then hurry to Montresor’s palazzo.
As they proceed to the vaults, Montresor continues to implore Fortunato to leave because of his health. He also continues to say that he can request Luchesi’s aid to authenticate the Amontillado. Because of the nitre which is causing Fortunato to cough, Montresor gives him Medoc to drink, proceeding to get his friend drunk. In his intoxicated state, Fortunato is easily fooled into his grave, still in search of the illusive Amontillado.
Montresor certainly is ready with his bag of tricks when it comes time to lure Fortunato into the catacombs. First, he introduces the prospect of a rare bottle of Amontillado when it is, in fact, nonexistent. The possibility of sampling the vintage is enough to keep Fortunato interested until it is too late. Secondly, Montresor has chosen the "supreme madness of the carnival season" to use as a background for his murder. The noise, costumes and alcohol provide a screen for his plan; additionally, he has told his servants that he will be out for the entire evening, knowing that it would
... insure their immediate disappearance, one and all, as soon as my back was turned.
With no witnesses, Montresor and Fortunato alone descend deeper into the tombs. Again, Montresor has planned ahead. He tells Fortunato that the Amontillado is near, at "the most remote end of the crypt." But instead of finding Amontillado, Fortunato finds his final resting place. Montresor has already visited the area, hiding mortar amongst the loose stones; he has chains attached to iron staples in the granite in which to subdue Fortunato. He even carries a trowel with him, the final tool of his perfect crime.