Fortunado is wearing a Joker costume, which represents what Montressor actually thinks Fortunado is; a clown and a fool.
Montressor says that he will drink to Fortunado's long life, yet Montressor knows that Fortunado will not live much longer.
The Cask of Amontillado The thousand injuries of Fortunado I had borne as I best could, but when he ventured upon insult, I vowed revenge. I must not only punish, but punish with impunity.
Montressor knows that Fortunado will not die of a cough, but by his arrangements.
"Once more let me implore you to return. No?"
Poe shows Montressor's tone is angry and unhappy. He is also determined to get his revenge on Fortunado.
I again paused, and holding the flambeaux over the masonwork, threw a few feeble rays upon the figure within.
Poe does a good job at describing Montressor's actions, and the state that Fortunado is in.
On their way to the catacombs, Montressor would repeatedly ask Fortunado if he wanted to leave the catacombs. With Fortunado chained to the wall and unable to move, Montressor askes Fortunado again, knowing that he will regret his earlier decisions to move on.