In Canto 21, Dante and Virgil encounter a group of devils collectively referred to as Evil Claws. The meeting that ensues portrays Virgil as being an overly confident master who takes the word of a devil despite being in a subcircle of the circle of fraud and the inherent evil nature of the beast-like creature. Virgil questions one of the devils: ” ‘Do you think, Evil Tail, that you see me here,’/said my master, ‘once already safe from all your tricks,/without God’s will and favorable fate? Allow us/ to walk on, for it is willed in Heaven that I guide/ someone on this savage journey,’ ” (79-83, 323). In other words, Virgil reminds the devil that he has already journeyed on this path through Hell on his own without the trickery or deceptions of the devils harming or affecting him in any manner. He is able to get past them and does not imagine how or why it should happen otherwise this time. Virgil also wishes to express that part of the reason he is traveling through Hell with the pilgrim and must be allowed to continue to do so, is because God is allowing it to happen through His own will. Virgil’s bold demeanor appears to be effective for the time being when Evil Tail lets his guard down, orders the rest of his group not to abuse Virgil or Dante in any manner and to guide them on through their next path.

This reaction that Evil Tail presents seems to be a positive sign on the surface. However, the reality of the situation is that Evil Tail is deceiving Virgil by allowing the latter to believe that Evil Tail is bowing down to Virgil’s reasoning and self-assured tone. Barolini elaborates on this point by claiming, “Malacoda [Evil Tail] weaves truth with falsehood into a perfectly designed trap, giving instructions and information that seem straightforward and helpful to Virgilio but that his troops can decode as deceitful and hostile,” (Barolini). The escorts that Evil Tail sends along with the two travelers have evil intentions in mind and are aware that they are allowed to carry them out because of Evil Tail’s clever manner of speaking with Virgil. The ‘trap’ that Barolini mentions refers to the deceiving approach Evil Tails uses in making his three statements. The first and the third one are true while the second one, claiming that there’s an unharmed bridge that will ease Virgil and Dante’s path, is the false statement. As Barolini points out, this cleverness of throwing in a false statement in between two true ones effectively distracts Virgil from the fact that he is being deceived thanks to the self-assurance present in Virgil’s attitude.

Such deception supports the idea that Virgil’s ability to reason with the demons of Hell is not always successful as Virgil, and especially, Dante hopes. Dante’s lack of trust and his overwhelming fear of the demons is influenced by a moment in canto 8 where Virgil is unable to carry out his word. Virgil takes an assertive stance against a group of demons that protect the gates of the city of Dis. He fails to sway their stubbornness in any which way resulting in Virgil and Dante inability to cross the gates. This, in turn, discourages Virgil immensely. Consequently, Dante marks this as a significant failure that must be kept in mind throughout the rest of the journey. Although Dante has faith in Virgil’s intelligence and ability to deal with the creatures of Hell, he does not wish to forget this moment for the sake of eluding danger which Virgil fails to do so in canto 21. Furthermore, Virgil fails to recognize the idea that simply because Evil Tail complies with his demands, this does not signify that Evil Tail will stay true to his word. After all, as mentioned before, in a circle that contains sinners of fraud, it should be remembered that the demons, though they punish those sinners, are not restrained themselves and are free to carry out their evil nature as they please. Virgil must also keep in mind that it is self-centered to believe that he is incapable of failure in his dealings with demons. There is obvious evidence otherwise which justifies Dante’s dread of the situation and it should be taken seriously, especially in an environment where it is understandable to have such sentiments.

Secondary Source: https://digitaldante.columbia.edu/dante/divine-comedy/inferno/inferno-21/