Amos Nattini, I Consiglieri Fraudolenti, date unknown.

We’re recapping the Inferno. Read along! This week: the price of wheeling and dealing with the Pope.

In Canto 27, just as Ulysses’s incandescent spirit departs, another burning sinner approaches Dante. This time, because the spirit is Italian, Dante speaks with him, instead of allowing Virgil to interpret; and though the sinner is never identified by name, the biographical information he offers suggests that he is Guido da Montefeltro, a well-known Ghibelline captain who fought a good many battles.

Much like Vanni Fucci, Guido is not eager to speak with Dante. He decides to speak only because he believes that Dante is one of the damned, and will never again be among the living—he feels secure that his story will never be heard again. Oops.

Guido says that Pope Boniface VIII solicited him for guidance on conquering Palestrina, a Ghibelline fortress. Guido demurred, but the Pope assured him his soul would be saved in exchange for his help—and that convinced Guido to help out, even if he had his doubts about the pope. Upon Guido’s death, St. Francis came to escort him to heaven, as promised, but a demon intervened on the grounds that no man can be pre-absolved for a sin he hasn’t yet committed. The Pope’s promise was thus null, and Guido was led instead to Minos, who deemed him guilty of fraudulent counsel.

Guido is a lot like Ulysses, whom we heard from in the last canto—he’s just as cunning, and he nurses the same sense of restlessness:

When I saw I had reached that stage of life
when all men ought to think
of lowering sail and coiling up the ropes,
I grew displeased with what had pleased me once.

Guido’s similarity to Ulysses raises a few questions about these two cantos. Namely: why is there so much ambiguity in the nature of their sin? The strongest theory for cantos 26 and 27 is that the sinners are guilty of some form of fraudulent advice—which covers all manner of evil or duplicitous counsel. But it is never fully explained what exactly the sin is.

Is it that Ulysses’s sin is the plan he hatched at Troy, and Guido’s is helping Boniface quell a rebellion? This seems a bit strict: Guido and Ulysses are not so much giving fraudulent advice there, after all. They’re simply strategizing. If we consider that for a general, the nature of commanding an army in battle is outsmarting or overpowering the enemy—what Aristotle calls necessary and probable behavior for men of their nature in their situation—the manner in which they accomplish their victories seems insignificant. We may begin to suspect that Ulysses and Guido gave fraudulent advice not in their military and political stratagems, but in their advice to themselves. In a broader sense, their sin is hubris—they thought they could beat the system. They set off in their own way once more, even at an age when men should lower their sails and coil up the ropes. They acted as their own fraudulent advisers.

To catch up on our Dante series, click here.

Alexander Aciman is the author of Twitterature. He has written for the New York Times, Tablet, the Wall Street Journal, and TIME. Follow him on Twitter at @acimania.