Entering the Fifth Pouch of the Eighth Circle of Hell, Dante sees “an astounding darkness.” The darkness is a great pit filled with a kind of boiling tar similar to what the Venetians used to patch their ships (XXI.6). As Dante examines the pitch to determine its composition, Virgil yells for him to watch out: a demon races up the rocks on the side of the pit, grabbing a new soul and tossing him into the blackness. As soon as the sinner comes up for breath, the demons below—the Malabranche, whose name means “evil claws”—thrust him back underneath with their prongs.
Virgil now advises Dante to hide behind a rock while he tries to negotiate their passage. The Malabranche at first act recalcitrant, but once he tells them that their journey is the will of Heaven, they agree to let the two travelers pass. They even provide an escort of ten demons—a necessary accompaniment, they say, as one of the bridges between the pouches has collapsed. Malacoda, the leader of the Malabranche (his name means “evil tail”), informs them of the exact moment that the bridge fell: 1,266 years and nineteen hours (or, as he puts it, five hours later than the same time yesterday) before the present moment. Malacoda adds that a nearby ridge provides an alternate route.
The group goes forward, with Dante carefully watching the surface of the pitch for someone with whom to converse. He has few opportunities, as the sinners cannot stay out of the pitch long before getting skewered. Finally, Virgil manages to talk to one of the sinners who is being tortured outside of the pit. The soul, a Navarrese, explains that he served in the household of King Thibault and was sent to the Fifth Pouch because he accepted bribes—this pouch, then, contains the Barterers. The conversation breaks off as the tusked demon Ciriatto rips into the soul’s body. Virgil then asks the soul if any Italians boil in the pitch. The soul replies that it could summon seven if the travelers wait for a moment. A nearby demon voices the suspicion that the soul merely intends to escape the demons’ tortures and seek the relative relief of the pitch below. The other demons turn to listen to their coworker, and the soul races back to the pitch and dives in, not intending to return. Furious, two of the demons fly after the soul but become mired in the sticky blackness. As the other demons try to free their comrades, Virgil and Dante take the opportunity to make a discreet exit.
As he and Virgil progress, Dante worries that they may have provoked the demons too much with this embarrassment. Virgil agrees. Suddenly, they hear the motion of wings and claws from behind, and turn to see the demons racing after them in a mad pack. Virgil acts quickly. Grabbing hold of Dante, he runs to the slope leading to the Sixth Pouch of the Eighth Circle of Hell. He then slides down the slope with Dante in his arms, thus foiling the demons, who may not leave their assigned pouch.
Now in the Sixth Pouch, Virgil and Dante see a group of souls trudging along in a circle, clothed in hats, cowls, and capes. Dante soon notices that lead lines their garments, rendering them massively heavy. One of the shades recognizes Dante’s Tuscan speech and begs Dante to talk with him and his fellow sinners, as they include Italians in their ranks. These are the Hypocrites. The sight of one of them in particular stops Dante short: he lies crucified on the ground, and all of the other Hypocrites trample over him as they walk. The crucified sinner is Caiphus, who served as high priest under Pontius Pilate. Virgil asks one of the sinners for directions to the next part of Hell. He finds that Malacoda lied to him about the existence of a connecting ridge, and now learns the proper route.
Although Malacoda intentionally misinforms Virgil and Dante about the passage along the ridge, his statement regarding the collapsed bridge appears truthful. The date he gives for its destruction matches that of the earthquake that Virgil describes in Canto XII. With this detail, Dante gives an elegant clue as to the timing of his journey: from it the reader may not only verify the year of this expedition as 1300 but also construe the specific day and hour during which it takes place. Malacoda says, “It was yesterday, five hours later than now, / That the twelve hundred and sixty-sixth year fell / Since the road here was ruined” (XXI.110–112). We know from Virgil’s earlier comments that Hell shook with an earthquake not long before the Harrowing, or upon Christ’s death. Figuring forward from Christ’s death (according to the Gospels, with which Dante was familiar, Christ died at age thirty-three, at the hour of noon), we know that Dante’s journey must have begun at midday on April 8, 1300—Good Friday. Thus, Dante follows Christ into Hell on the anniversary of His death, though the poet keeps this fact from the reader until the character has penetrated nearly to the bottom of the pit. As Dante leaves the Fifth Pouch, it is around seven in the morning on Holy Saturday, April 9.