What are some things that show that Montresor is cunning in "The Cask of Amontillado?"
Montresor uses Fortunato's pride to entice him to go and try the Amontillado. Montresor notes Fortunato's weakness in the third paragraph:
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.
Knowing this, Montresor intended to exact his revenge on Fortunato by exploiting that weakness. He first mentions that he has the Amontillado but has his doubts about it, encouraging Fortunato to brag about his connoisseurship. Montresor then adds that he's going to ask Luchesi to sample the Amontillado in order to give him a judgment on it. Montresor knows Fortunato will say that he is the more seasoned wine taster. Fortunato adds, "And as for Luchesi, he cannot distinguish Sherry from Amontillado."
As they go further in to the catacombs, Montresor continuously suggests that they go back to save Fortunato's health and nagging cough. Fortunato, in his pride, takes this as a dare, as if Montresor is daring him to continue on. Fortunato urges them to continue on; thus, Montresor makes Fortunato the captain of the journey that will lead to his end (Fortunato's).
Montresor further displays his capacity for cunning deception by boldly placing evidence of his crime in plain sight. He begins the story haughtily telling of a murder he was never caught nor convicted of committing. In this sense he announces his guilt openly and boastfully knowing that the only proof of crime lies in his questionable narration.
This continues to the end to the story when Fortunado asks for a sign to confirm that Montresor is a mason.
I looked at him in surprise. He repeated the movement --a grotesque one.
"You do not comprehend?" he said.
"Not I," I replied.
"Then you are not of the brotherhood."
"You are not of the masons."
"Yes, yes," I said; "yes, yes."
"You? Impossible! A mason?"
"A mason," I replied.
"A sign," he said, "a sign."
"It is this," I answered, producing from beneath the folds of my roquelaire a trowel.
Monstresor inflates Fortunado's ego by reminding him of his mason status. This gesture places within Fortunado a false sense of security making him all the more susceptible to his horrible end. Furthermore, Monstresor cleverly utilizes the double meaning of this word. He blatantly shows Fortunato his murder weapon of choice, the trowel, before sealing him in the catacombs.