Gustave Doré, Canto XV.

This winter, we’re recapping the Inferno. Read along!

As Dante continues to descend through hell, guided by Virgil, I too read with a guide of my own—Robert Hollander, whose annotated edition of the Inferno I’ve been using to write about Dante every week. I’ve read the Hollanders’ notes on Canto 15 many times over, but I still find myself getting lost in it—Dante’s encounter here is unlike any other.

Pulling at the pilgrim’s hem is a scorched, unrecognizable sinner. After a few moments, Dante realizes the man is his old teacher Brunetto Latini, who is now among the sodomites. Siete voi qui, ser Brunetto? Dante asks. Are you here, ser Brunetto? This warm, perhaps even affectionate question is underscored, Hollander explains, by something else: “I think he is also asking ‘Are you, wonderful man, down here among the scum?’” It seems, at first, a tender scene: Dante asks if Brunetto will sit with him, and for the first time we see Dante speaking to a sinner about himself and his journey, not standing idly by as a sinner tells his story. It even seems as if the two are catching up. For this reason, Hollander says, readers and critics are often charmed by this scene, but they never examine the relationship between Dante and Brunetto as carefully as they should. Dante’s treatment of Brunetto is colder than it appears.

First, consider the literary tension between Dante and Brunetto. Dante’s relationship with Brunetto may have been warm, but Dante’s decision to write a long poem in Italian, rather than in Latin, introduced an element of competition between the two poets. “Brunetto beat him to it,” Hollander says. “Brunetto was the first Italian author of a long poem … the first Dante, in a sense. But he failed because he died before finishing his poem.” In fact, because Brunetto was Dante’s teacher, Dante may feel—even as his teacher is punished in hell—that Brunetto still sees himself as the master. Hollander described the scene to me as one that deals with “the anxiety of influence and the acknowledgment of a predecessor.” If the encounter is tense, it might be because Dante doesn’t wish to deal with Brunetto on those terms.

Hollander points out that what we fail to understand about canto 15 is that it’s not only a canto of beatitude, but one of anxiety. Dante loves Brunetto, but he knows that it he may not be right to.  After all, Brunetto has been placed with sodomites, and some scholars argue that Brunetto’s subsection of sodomites is the one reserved for pederasts; and yet Dante and readers both find it difficult to despise Brunetto because he’s both gracious and wise. The scene, as a result, is underscored by irony. The more we feel love for Brunetto, the more we engage with a sympathy and affection that, stirred by his story and his manner, allows us to see an unrepentant Brunetto.

Someone like Francesca is easy to see this way—her excuse for her infidelity is flimsy. (Hollander went on to imitate a sobbing Francesca: “Oh, I couldn’t help it, we were reading a book and he was very handsome.”) An excuse like that wouldn’t hold up in court. And Pier, as beautiful as his passage is, ends up being one of the most pathetic figures in all of literature; his self-loathing is almost over the top.

But the division between the pilgrim’s sympathy and the poet’s ironic disagreement with it is less obvious in Brunetto’s case—here, the sympathies of Dante the poet and Dante the pilgrim are almost aligned. We see a teacher meeting an old student, not a sinner speaking with a man on a holy quest. But, ultimately, Brunetto presents as a positive figure, which, with his burnt and charred appearance, allows the reader to see how misguided and wrong he is.

Dante the poet faces a greater challenge than his pawn, the pilgrim. The pilgrim deals only with sympathy, but the poet must fumble his way around a love that is not only old, but one that almost forgives sin, and one that is also irritated by literary anxiety. How does he end up facing it? He loves in a way that appears unconditional, but uses irony for judgment. He walks elevated beside Brunetto, but still bows his head in reverence; he praises Brunetto’s poem and even imitates it, but is not nearly as warm to an old teacher as he should be; he thanks Brunetto for teaching him and says that he wishes Brunetto were still alive, and yet here, he writes a scene in which Brunetto’s face is charred by falling fire. Dante allows himself to remain divided—he uses his pilgrim for love and his poet, a lightly antagonized literary heir to Brunetto’s work, for theology.

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.