Dante’s Inferno: Canto 27 Retelling — Guido da Montefeltro

Chapter 27: Guido da Montefeltro

The flame punishing the souls of Ulysses and Diomed moved away, and another flame came toward Dante and Virgil, both of whom directed their attention toward this flame because of the roaring sounds that came from its tip.

These roaring sounds remind me of another roar, Virgil thought. Phalaris was a cruel ruler of the city Agrigentum in Sicily. He commissioned Perillus to construct a hollow bull of metal to be used as an instrument of torture. The victim would be placed inside the bull, and then the bull would be heated. As the victim roasted, the victim screamed. Phalaris ordered that the bull be constructed in such a way that the screams of the victims would sound like the bellowing of a bull.

After Perillus used his great abilities to construct the bull — something that he ought not to have done — Phalaris made him the first victim to be placed in the bull and roasted. This is poetic justice, and contrapasso is very much concerned with poetic justice. Additional poetic justice occurred when Phalaris was overthrown and also became a victim of the bull.

In this story, we see a person being punished for the misuse of great abilities, and of course, the sinners in this bolgia are being punished for that sin.

I know the story of Guido da Montefeltro, who is like Perillus. He sinned at the request of another person, and he pays for that sin.

The sinner inside the flame had recognized Virgil’s dialect and now spoke to him, “It has taken me a while to reach you. Please wait a while and speak to me. If you are a newcomer to Hell, can you tell me news of whether the inhabitants of Romagnol are at war? I come from that region.”

Virgil told Dante, “You speak to this sinner — he is Italian.”

Dante said to the sinner in the flame, “The leaders of Romagnol always have war in their hearts, but their country is not presently at war, although Romagnol has a troubled past.

“But who are you and what is your story? I did you a favor by answering your question, so do me a favor and answer my question. I can make your fame long-lasting in the Land of the Living.”

“If I thought that you would ever leave the Inferno, I would not answer your question,” the sinner in the flame answered, “but since I have heard that no one ever leaves here, I will answer your question.

“I am Guido da Montefeltro. I had two careers: First I was a soldier, and then I was a monk. I blame Pope Boniface VIII for my being in Hell. While I was alive, I was wily like a fox. I was shrewd and had great abilities. I was a warrior, but I was also known for trickery. I became world-famous.”

Guido is overstating his fame, Virgil thought. He was important regionally, but he was hardly famous throughout the world.

“When I grew old, I became concerned about the afterlife,” Guido continued. “I confessed my sins, and I became a Franciscan monk — it could have worked!”

It could have worked, you think, Virgil thought, but obviously it didn’t. You are in the Inferno. God does not make mistakes, so you are where you belong. You tried to scam God by becoming a Franciscan monk, but obviously it didn’t work. Repentant sinners don’t end up in the Inferno, so obviously you did not sincerely repent your sins.

“Pope Boniface VIII chose to make war on a family of Christians instead of making war on the Jews or the Muslims,” Guido continued. “Pope Boniface VIII became Pope when Pope Celestine V resigned, but the Colonna family did not believe that the resignation of Pope Celestine V was valid; therefore, the Colonna family opposed Pope Boniface VIII. Pope Boniface VIII ran into a problem. He was fighting the Colonna family, and the Colonna family was barricaded inside Palestrina, a fortified city at the top of a mountain in Italy. Because of the location of the fortified city, it was going to be very, very difficult to take.

“Pope Boniface VIII came to me to give him advice about how to conquer the Colonna family. I stayed silent — Benedictine monks ought to be concerned with peace, not war. They should not give advice about how to conquer Christians.

“Pope Boniface VIII then said to me, ‘Don’t worry about the fate of your soul. I am the Pope, and I have two keys. These keys will unlock the gates of Heaven. I tell you now that the sin you will commit by answering my question is forgiven.’”

Dante, pay attention, Virgil thought. Guido da Montefeltro was a scammer while he was alive, but in his story he is now being scammed by Pope Boniface VIII, who is still alive, but who will be damned to Hell when he dies. We know that he will be punished with the other Simonists in the third pocket of Circle 8. Pope Nicholas III, a sinner there, told us that.

“I was impressed by Pope Boniface VIII’s reasoning,” Guido continued. “I said to him, ‘Father, since you have assured me that my sin is forgiven, this is how you may conquer the Colonna family: Make a promise to them, but do not keep your promise.’”

Guido knew that he was sinning by offering this advice, Virgil thought. His advice to Pope Boniface VIII was to make promises, then not keep your promises — tell the Colonna family that you want to be friends and that you will give them what they want, and then when they come out of the fortified city, destroy the city so that the Colonna family no longer has this stronghold. In other words, arrange a truce, and then break the truce as soon as it is advantageous for you.

In fact, Pope Boniface VIII followed this advice. When the Colonna family left the fortified city, the Pope had it destroyed.

“When I died, Saint Francis came to escort my soul away from Hell,” Guido continued, “but one of the black Cherubim also came to get my soul. The fallen angel cried, ‘Don’t touch this soul! He is mine! Unrepentant sinners go to Hell! He must go down into the Inferno because he did not repent sincerely. A sin cannot be forgiven unless the sinner is repentant, and one cannot repent a sin at the same time that the sinner is committing it! The “repentance” is cancelled out by the deed! Examine my logic for flaws, and you will see that my logic has no flaws.’

“The fallen angel took me to Minos, who wrapped his tail around himself eight times and sent to this place of fire. And here I will stay forever.”

Guido spent his life scamming others, yet he did not recognize the scam when Pope Boniface VIII scammed him. He has lost the good of intellect, Virgil thought. In addition, Guido tried to scam God with a fake repentance. Obviously, that scam failed.

Ulysses also lost the good of intellect. He should have known that he should have stayed home with his family now that he was old and tired. He should have also realized that it is better not to experience and not to know some things. However, he went on a final voyage and got his men and himself killed.

Dante, we have spent a lot of time in this bolgia because you have something important to learn here. Ulysses and Guido da Montefeltro are very intelligent people. Both felt a temptation to misuse their intelligence and their powers of persuasion. Both scammed other people.

As a very intelligent man, you, Dante, may feel the temptation to misuse your intelligence and your powers of persuasion. Here in the Inferno you need to learn not to do that. If you, Dante, misuse your great abilities, you can end up in the Inferno just like Ulysses, Diomed, and Guido da Montefeltro.

The flame moved on, and Dante and Virgil continued their journey, moving on to the ninth bolgia, where the sowers of discord are punished.

Copyright by Bruce D. Bruce

This is an excerpt from Dante’s Divine Comedy: A Retelling in Prose by David Bruce, available here:






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11 Responses to Dante’s Inferno: Canto 27 Retelling — Guido da Montefeltro

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