Dante and Virgil are chased by demons into the sixth pouch of the eighth circle of hell that consists of hypocrisy. A hypocrite is someone who pretends to possess virtues, morals, or religious beliefs but in reality do not have them. Punishment for these sinners is to where cloaks that look beautiful on the outside but are lined with lead on the inside. This punishment matches the sinners because they get a taste of their own medicine and have to live in hell crawling around. The eighth circles of hell, Malebolge, consist of sinners that involve conscious fraud. This circle consists of ten Bolgie, or ditches, that pulls people in similar to hypocrites and how they pull people into believing them. Dante has a personal encounter with two people, Catalano and Loderingo. These two noticed that Dante is a living soul and ask him why he arrives to the valley of hypocrites. Catalano and Loderingo were the Jovial Friars and were to fight only in order to protect the weak and enforce peace. However, these two had betrayed the city of Gardingo and it was destroyed by a civil war. .
Dante encounters Caiaphas, a historic character who was the high priest under Pontius Pilate who advised that Christ be crucified. Dante sees Caiaphas as "one crucified with three stakes on the ground. And when he saw me all his body writhed, and through his beard he heaved out sighs of pain" (111. Book XXVIII). Caiaphas organized to have Jesus killed for the benefit of the city of Jerusalem but in reality did not do anything. For his actions, Caiaphas is crucified to the ground and has to suffer being stepped on for the rest of eternity. .
Dante refers back to another historical character when describing the cloaks the sinners have to wear. He states "Dazzling gilded cloaks outside, but inside they were lined with lead, so heavy the capes King Frederick used, compared to these, were straw." (64. Canto XXVIII).
