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Dante opens this canto with an invective against simonists (clerics who sell absolution and other priceless heavenly favors for money). He calls them sinners who "fornicate for gold and silver!"
Dante and Virgil are now in the third pouch.
So how are the Simonists punished? In the rocky ground, they are buried upside-down in holes the size of baptism basins and their feet protrude, only to be burnt by flames. Eternal suffocation and immolation.
Biographical aside: Dante puts a great deal of emphasis on the likening of the holes to baptism basins, and recounts a story where he accidentally broke one in the church of San Giovanni.
Moving on… one sinner is subjected to redder flames than any of the others and Dante asks who it is.
Virgil suggests they go down and find out. And Dante agrees.
At the feet (literally) of the sinner in question, Dante calls out to him—whoever he is—to name himself.
How’s this for some interesting imagery: in standing next to the inverted sinner, Dante (unconsciously?) takes on the role of a friar at the confession of an assassin.
Hilariously, this sinner mistakes Dante for his successor in simony, Pope Boniface VIII, now come to take his place in Hell. After all, the sinner has his head buried in bedrock; he can’t see the guy standing up there.
But you’ve got to give the guy some credit: he realizes that Boniface is a few years early; in actuality, at the time of Dante’s writing, Pope Boniface was still alive.
Like anyone else accused of being their arch-enemy, Dante is shocked silent.
To prevent any mischief, Virgil strictly orders Dante to correct Nicholas’s mistake and to reveal his name. Meekly, Dante does so.
Then, the Pope changes his tone, irritably asking what they want from him and twitching his feet accordingly.
He launches into a boastful description of how he once wore the mantle of the papacy. He attempts to justify his simony by claiming he was just trying to fatten the purses of his family.
He explains to them what happens to simonists once their successors show up in Hell: they drop further into the stony ground so that the whole third pouch (of the eighth circle) is full up to the bedrock with buried simonists.
Pope Nicholas prophesies that after Pope Boniface goes to Hell, he will be followed by an even more evil churchman, Pope Clement V, who will bargain with the French king to guarantee his election and later abduct the papacy and spirit it away from Rome and into Avignon.
But Dante’s heard enough about how wicked everyone else is.
He sassily asks Pope Nicholas how much Christ charged St. Peter before giving him control of the keys to the Kingdom of Heaven. Or how much the Apostles charged Matthias for taking Judas’s place amongst the Apostles after his betrayal. (The answer, of course, is nothing.)
With this rhetoric of righteous indignation, Dante pronounces Pope Nicholas’s punishment just.
Only Dante’s respect for the papacy or papal office, keeps him from talking even more smack about simonists.
But he goes on anyway, depicting Rome (the papal seat) as a whore who fornicates with kings for money. This makes the popes into idolaters just as heinous as the heretics they condemn.
Dante even goes so far as to accuse Constantine for ever funding the Church after his conversion to Christianity.
Pope Nicholas, upon hearing Dante’s rant, kicks hard—either out of indignation or his guilty conscience.
Virgil is so pleased with Dante’s temper that he picks him up in his arms and carries him like a baby across the bridge to the fourth pouch.
Having been set back down again, Dante must watch his feet because the way down into the next valley is very steep.