carnival season and initially feigns his friendship. He then proceeds to tell Fortunato an elaborate story of how he managed to acquire a pipe of rare Amontillado wine before having an opportunity to consult him. Montresor also mentions that he is not sure if the wine is authentic or not. Knowing that Fortunato takes pride in his connoisseurship in wine, Montresor mentions that he plans on consulting Luchresi about the matter in order to make Fortunato jealous. Fortunato reveals his pride by criticizing Luchresi and insisting that he try the Amontillado in order to tell if it is authentic or simply Sherry. It is also implied that Fortunato would be interested in acquiring a pipe of Amontillado for himself while the opportunity presents itself, which is why he agrees to follow Montresor into the catacombs. Inside his family's vaults, Montresor gives Fortunato several glasses of wine to further impair his judgment before eventually shackling him to the back wall and burying him alive.

Montresor's plot for revenge hinges on a critical fact; Fortunato believes himself to be an expert on the taste and authenticity of wine. Because of this, Fortunato will be not only willing but insistent on verifying Montresor's fictional cask of Amontillado wine, in order to prove himself superior to Luchresi, a locally-accepted expert.

He had a weak point... He prided himself on his connoisseurship in wine. Few Italians have the true virtuoso spirit.
[...]
"The cold is merely nothing. Amontillado! You have been imposed upon. And as for Luchresi, he cannot distinguish Sherry from Amontillado."
(Poe, "The Cask of Amontillado," xroads.virginia.edu)

Montresor needs to get Fortunato into the catacombs of his own free will; note that each time Montresor asks Fortunato to return, Fortunato insists on continuing to find the cask. Because of this, Montresor doesn't need to do anything drastic, such as drugging Fortunato or knocking him out; Fortunato willingly goes to his doom, assured that Montresor has only his best interests at heart. Had Fortunato not been so egotistical (and also drunk), he would have not been so eager to one-up Luchresi; however, his ego forces him to prove his expertise, as Montresor expected from the start.

The above answer to the question concerning Poe's "The Cask of Amontillado" is certainly correct in identifying Fortunato's weak point as his belief in his expertise as a judge of wines. However, it seems unlikely that his strong motivation to taste Montresor's Amontillado is merely based on a desire to prove his superiority to another connoisseur or to demonstrate his own connoisseurship to Montresor.

The story Fortunato has been told is that Montresor just bought a "pipe" (126 gallons) of gourmet sherry at a bargain price. Why is he now going to Luchesi (spelled Luchresi in some texts) to confirm the authenticity of his wine? As intended, this strongly suggests to Fortunato that Montresor would have bought more if he had been sure it was genuine and that he intends to buy more if an expert reassures him. Fortunato is interested in buying some bargain-priced gourmet wine himself. If a boatload of Amontillado sherry has recently arrived in Venice, he could easily find the newly arrived Spanish ship without going to Montresor's palazzo. Fortunato could taste the wine on board and deal directly with the captain.

The only thing that forces Fortunato to go with Montresor is that if he pleaded some prior engagement, Montresor would go directly to Luchesi, as he says (falsely) he was doing when he ran into Fortunato. Luchesi could also find the Spanish ship and compete with Fortunato in bargaining for perhaps the entire cargo.

But Montresor has no intention of going to Luchesi. He doesn't want to kill Luchesi, and the Amontillado does not exist. Montresor only says he is going to Luchesi because this forces Fortunato to accompany him to his palazzo rather than putting Montresor off with some excuse and going to find the Spanish ship directly.

Montresor expects Fortunato to be planning to sip his wine, tell him it is just ordinary sherry, then find the source and buy up the entire shipload. Fortunato is a rich man. This would be only one more injury added to the "thousand injuries" he has inflicted on Montresor. And Fortunato would regard it as "an excellent jest."

Montresor is a connoisseur himself. Poe chose Amontillado because Montresor might not be a connoisseur in Spanish wines, as he is in French and Italian wines.

Fortunato has several character flaws that lead to his death in "The Cask of Amontillado." First and foremost is Fortunato's cluelessness concerning the depths of Montresor's hatred and desire for revenge. Fortunato should have been wary of Montresor's intent due to the "thousand injuries" he had apparently bestowed upon him. Instead, it was Fortunato's other "weak point"--his great love of wine--that blinded him to Montresor's actual motives. Fortunato also made the mistake of following Montresor on a night when he was inebriated due to the "supreme madness of the carnival season." Fortunato's drunken state robbed him of the good sense and reason that he would normally have possessed. Montresor's perfect crime was enacted successfully because he had already planned his actions based on these flaws, faults he knew would successfully allow Fortunato to willingly follow him just about anywhere in order to taste the rare vintage of Amontillado.

Montresor wants to take advantage of Fortunado’s pride in his knowledge of wine in order to trick him to go into the catacombs with him.

Montresor is convinced that Fortunado has insulted him in some way.

THE THOUSAND INJURIES of Fortunato I had borne as I best could, but when he ventured upon insult I vowed revenge. (p. 4)

Although it is not clear what the insult was, we can gather that Fortunado has no idea that he insulted Montresor, or that it was such a big deal.  He still thinks that Montresor is a friend.  Nonetheless, Montresor has been insulted and develops a cunning plan to trap Fortunado.  He is going to take advantage of his love for wine.

In painting and gemmary, Fortunato, like his countrymen, was a quack, but in the matter of old wines he was sincere. (p. 4)

Montresor knows that he can get Fortunado’s attention, even during the carnival, by telling him he has a rare wine.  He can get him to follow him down into the catacombs, and once there they will be alone.  Then he can kill him.

The theme of revenge is a thread throughout the story.  Montresor feels that whatever small insult Fortunado did to him is worth his life.  Yet Montresor is not completely insane.  He is wily enough and sane enough to use Fortunado's love of wine against him.

The way that Montresor lures Fortunado down into the catacombs is by playing on his fondness for wine, and for thinking himself an expert in wine-tasting.  Montresor states, right at the beginning,

"He had a weak point—this Fortunato—...He prided himself on his connoisseur-ship in wine."

So, under the false pretense of having a great cask of Amontillado wine that he paid a heavy price for, he approaches Fortunado.  He tells Fortunado of the wine and that he is worried that he paid too much for it without consulting Fortunado's expertise.  Then, through careful manuvering, he gets Fortunado to insist that Montresor take him down to the tombs so that he can taste the wine and determine if it is truly a good buy.

So, Fortunado's weakness is in wine, but it is truly in the fact that he prides himself on being a wine expert.  And, Montresor plays on that self-pride.  He wonders aloud to Montresor whether he should have consulted another guy, Luchesi, on whether it is a good wine, to which Fortunado insists, "Luchesi cannot tell Amontillado from sherry," and so deems himself the only man capable of determining if the wine is authentic and quality.  Montresor is a cunning villian, in that he plays on Fortunado's vanity and pride to lure him down to his death.  I hope that helps a bit; for your other questions, I suggest submitting them one at a time, as the guidelines of this website allow for one a day.

Here's a new take on Fortunato's "weakness."  Almost everyone thinks it's his overweening pride in his ability to judge wines and this true to a degree, but let's dig a little deeper.

"The thousand injuries of Fortunato I had borne as I best could, but when he ventured upon insult I vowed revenge."  Is this particular insult that seemed to push Montressor over the edge clearly stated?  No! It must searched out.  Once Montressor has Fortunato well into the catacombs and has plied him with wine, the nature of the insult begins to reveal itself.

Fortunato empties a flagon of wine and "threw the bottle upwards with a gesticulation I (Montressor) did not understand."  He repeats the gesture.  Fortunato asks him if he comprehends the motion.  Montressor does not and Fortunato says, "Then you are not of the brotherhood," a reference to The Order of Masons.  Montressor insist that he is, but Fortunato responds, "You! Impossible! A Mason?  Montressor replies that he is and produces a trowel, the symbol and tool of masonry.  Fortunato takes it as a joke.

It is my contention that the insult delivered by Fortunato to Montressor was probably blackballing him or somehow keeping him out of the Masons.  The exquisite irony of Montressor's "masonry" revenge, the walling up of Fortunato, is completely lost on Fortunato.  he doesn't get it and probably doesn't even remember what he had done.  You can assume that Montressor is mad, but it's the madness of a genius.

I think that I would argue that it is his pride both in his ability to know his wines and in his superiority over Luchresi. All Montressor needs to do is keep Fortunado focused on the wine - that rare cask of Amontillado. He is luring him to his death with his weakness for rare, fine wines and with the manipulation of the threat to allow Luchresi to try the wine. No matter how sick he is, Foirtunado cannot let that happen because that would represent an affront to his pride. It is his pride, too, that keeps him from realizing that there is an ulterior motive at play. He does not see that Montressor does not like him because he does not want to see it, He only wants to see himself as he sees himself - arrogant and proud and better than anyone else.

Fortunato's biggest weakness is one of three things -- you picke which.

My first choice for it is that he is vain about his ability to know good wine.  He really wants to go check out Montresor's new wine and see if it's really amontillado.

Second, he hates Luchresi.  All that Montresor has to do is keep mentioning Luchresi and Fortunato is right there.

Finally, I think he must not be all that observant.  All this time, Montresor has been planning to kill him and he has no clue that Montresor doesn't like him?  Sounds like a weakness to me.

So you pick which you think is the biggest -- they all seem important to me.

Fortunato, Montresor's enemy and eventual victim in Poe's "The Cask of Amontillado," is not a very clearcut character to the reader, but he does exhibit a few character flaws according to Montresor's descriptions.

First of all, Fortunato is already drunk when he encounters Montresor, so he may have a weakness for alcohol. Related to his fondness for alcohol is Fortunato's excessive pride in his own knowledge of wine. Additionally, Montresor reports that Fortunato has somehow insulted him, but Fortunato is unaware of his offense. Two possible interpretations of this situation exist: it is possible that Montresor is an unstable person and he is oversensitive and overreactive, or it is possible that Fortunato has done something so hurtful to Montresor that his mistake leads him to his own death. If the second case is true, then another flaw of Fortunato's is his lack of self-awareness.

Fortunato must be a heavy drinker. This is a character flaw in any person and usually leads to serious troubles. The reader must assume that Fortunato is not drunk just because it is carnival season. He shows too much fondness for wine to be moderate for most of the year and then to go wild for just a few days. He is undoubtedly, as Montresor says, a connoisseur of wines, and no one becomes a connoisseur of wines without drinking a lot of them.

Fortunato considers himself a funny man. That is why he chooses to wear a jester's costume during the carnival. A jester in medieval times was a man who was privileged to play cruel jokes on people in order to amuse his master and the courtiers. But a jester could make a lot of enemies. Many of the "thousand injuries" Montresor mentions in the first sentence of his story must have been jokes or jibes.

Fortunato is an egotist. If he were not such an egotist he would not be taken in by his enemy Montresor, who has been flattering him and calling him "My friend" and ""My good friend" for years. Poe gives an example of Montresor's outrageous flattery when the two men are down in the cavern:

"...your health is precious. You are rich, respected, admired, beloved; you are happy as once I was. You are a man to be missed...."

Fortunato is avarious. When he hears about the Amontillado he is anxious to taste it. Montresor says he got a bargain on the wine. Fortunato would like to buy some himself--but he doesn't mention this motive for going to the vaults because Montresor is probably planning to buy more casks for resale if he is assured that it is genuine Amontillado. In that case the two men would be competing and would be bidding the price up. Fortunato is not accompanying Montresor to his palazzo just to accommodate him; he is doing it to taste the wine and to keep Montresor from going to Luchesi, who would be another competitor.

It is of course a reflection on the criminal genius of Montresor that he knows his victim well enough to be able to plot how he can manipulate him through his weaknesses. Of course, his first weakness is his trust of Montresor. Montresor himself tells us that Fortuanto had no reason to doubt his friendship, even though Montresor tells us he had been "insulted" by Fortunato:

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.

Of course, Fortunato believes Montresor and follows him into his catacombs - a very foolish decision.

The next weakness is stated directly by Montresor:

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.

This allows Fortunato to be tempted down into the catacombs with the promise of tasting the eponymous cask of Amontillado.

Lastly, Fortunato's weakness is his susceptibility to dampness, which of course finishes him off. Note how he coughs more and more as he and Montresor descend deeper and deeper into the catacombs.

This story thus charts an act of supposed revenge, but one carried out by someone who is able to use his opponent's weaknesses to help him in destroying his enemy.