Fortunato appears to be an extreme extrovert. He likes to get drunk. He has a lot of money and evidently enjoys spending it on his own enjoyment. He is wearing a jester's costume when Montresor encounters him on the street. People generally choose costumes that represent what they think of themselves, how they would like others to perceive them, and/or what they would like to be. Fortunato would like to be thought of as a very funny fellow, but if he has really injured Montresor a thousand times, then he is the kind of "funny fellow" who likes to inflict pain. The court jesters of old were often cruel in their jests because they had the protection of a powerful patron. The grave digger in Hamlet says that Yorick, the king's jester, poured a bottle of wine over his head one time. That may have amused the king and his guests, but the victim would not have been amused. King Lear's fool is constantly saying hurtful truths to Lear and to others. Many of the "injuries" Montresor suffered from Fortunato may have been painful digs that hurt his pride. Montresor describes Fortunato as "a man to be respected and even feared."