As diverse as the sins punished in the eighth circle of Hell may be, Malebolge reveals a structural balance that may not be immediately apparent. The third bolgia (Simonists, Inf. 19) and the eighth (Ulysses, Guido da Montefeltro, Inf. 26-27) share several stylistic and thematic features, among them the introductory apostrophes, the contrapasso, and the mention of the Emperor Constantine first in Dante’s invective and later in a simile. Most importantly, Pope Boniface VIII figures prominently in both bolge even though he is still alive at the time Dante makes his fictitious journey through Hell.

The poet places “road signs” along the way to guide the reader towards an awareness of the symmetry. When Dante descends into Malebolge on Geryon’s back he sees nothing but the beast, is unaware of his surroundings, and knows that he is moving slowly downward only because he feels a wind from beneath blowing on his face. Soon he sees fires below him, then hears laments. Disoriented at the start of his flight, he is reoriented by the fires visible to him, which appear in bolge three and eight and are the only ones in Malebolge. While Dante recovers his sense of place, the reader may be oriented in advance to a connection between these two bolge, each portraying sinners punished by flames and each centrally located in the first and the second halves of the ten ditches of Malebolge.

The exact dividing line between the two halves is the ridge between bolgia five (Barrators) and bolgia six (Hypocrites). Unlike any other ridge in the entire eighth circle, this one sets the stage for fear and action and presents a barrier to Dante’s progress on his journey. After having observed the military-style skirmishes and reciprocal trickery practiced by the sinners immersed in pitch of the fifth bolgia and by the Malebranche, the devils who torment them, Dante and Virgil are themselves involved in a dramatic scene of perceived danger and escape. As they walk slowly along the ridge searching for a way across the sixth bolgia, whose passageway is complicated by a broken bridge, a squad of devils goes off in the same direction ostensibly to inspect the sinners below. Dante, suspicious of the vengeful Malebranche, pleads with his guide to hurry. Virgil quickly clasps Dante to his chest and slides on his back down the rocky slope into bolgia six. In an undignified, quasi-comic “coda” to bolgia five, Dante and Virgil enter the second half of Malebolge. Among the Hypocrites they are safe, as the devils cannot proceed beyond their own territory.

The transitional bolgia of the Barrators (Inf. 21-23) allows us to look backward and forward in Malebolge. “Barratry” (baratteria) has civic and nautical connotations that relate to the Simonists as well as Ulysses. It can refer to the purchase and sale of public office or to fraud perpetrated against a ship’s owner by its captain or crew. The Barrators therefore refer us in retrospect to their ecclesiastical counterpart, the Simonists, while the vivid nautical simile at the beginning of Canto 21 foreshadows Ulysses’ shipwreck. Here the pitch in which the Barrators are submerged is compared to the pitch boiling in the Venetian shipyard in winter, where workers repair their vessels. Moreover, the reciprocal tricks played by the Malebranche and the Barrators prefigure the deceitful military stratagems for which Ulysses and Guido da Montefeltro suffer in Hell.

In the third bolgia the Simonists are wedged head first into holes that cover the floor and sides of the ditch, their legs protruding, flames flickering on the soles of their feet. Dante descends into the ditch to address the flames burning the feet of a sinner, Pope Nicholas III, who in great astonishment thinks Dante is Pope Boniface VIII, another simonist pope destined to suffer a similar fate but arrived before his time. He inveighs against Boniface for deceiving the Church for material gain. Once Dante corrects the error, Nicholas relates his own cupidity as pope and the greed of Clement V who will push Boniface farther down the hole. Now it is Dante’s turn for a passionate invective against Nicholas and Simonists in general, as well as the Emperor Constantine. According to the “Donation of Constantine,” a forged document accepted at Dante’s time as genuine, the Emperor had given civil authority over the Western Empire to the Papacy, a gift that in Dante’s view contributed greatly to the contamination of the spiritual powers of the Church with temporal power.

In the eighth bolgia the sinners are totally enveloped in flames. Among them is Ulysses, the mythological King of Ithaca and military hero of the Trojan War. He is in Hell, hidden together with Diomedes within a single two-tipped flame, for three clearly defined fraudulent acts: the invention of the Trojan Horse to defeat Troy, using Deidamia to lure Achilles to war, and the theft of the Palladium to make Troy vulnerable. Yet what makes Ulysses memorable is his folle volo, his mad ocean voyage into the unknown world of the southern hemisphere to seek virtue and knowledge, virtù e canoscenza. Unlike the deceitful wartime stratagems for which he was damned to Hell, Ulysses’ little speech to his companions shows him in a different role from that of warrior. Though crafted with the skills of a persuasive leader well practiced in the art of rallying his troops, his orazion picciola, serves a new purpose: to reach a moral and intellectual goal.

Virtus and sapientia were lofty ideals among the ancients, but for Christian world Ulysses’ refusal to return home to Ithaca and instead embark on a quest for goodness and understanding without divine guidance would constitute the misuse of his temporal powers to the detriment of his temporal responsibilities. As an old man Ulysses used his eloquence to urge his crew on, beyond the Pillars of Hercules into forbidden territory and ultimately to death. He is the antithetical counterpart of the Simonists: instead of misusing a spiritual office for temporal gain, he misused temporal powers for spiritual gain. Ironically, his ship went down in full sight of the Mountain of Purgatory, unknown and unknowable to him. Purgatory alone is the true way for repentant sinners to ascend to virtù e canoscenza, spiritual fulfillment in the knowledge of God.

Dante’s contemporary Guido da Montefeltro, in juxtaposition with Ulysses, illustrates the mutual corruption of temporal and spiritual powers in the context of northern Italian politics. Like Ulysses he is a man of arms, known as “the Fox” for his military cunning. After many successes and later defeats as a Ghibelline captain, he retreats in old age to the religious life as a Franciscan friar, only to be sidetracked by Pope Boniface VIII who is at war with the powerful Colonna faction. Seeking advice from Guido, the pope promises absolution in advance for a sin about to be committed. Guido, unrepentant, succumbs to the pope’s fraudulent promise and reverts to his former trickery with this fraudulent counsel: “Lunga promessa con l’attender corto.” Guido’s failed retreat into religious life parallels Ulysses’ failed expedition on a moral and intellectual quest, and both represent misguided forays of secular leaders into the spiritual realm, actions that reverse the conceptual pattern of the Simonists.

In keeping with the basic theme of the two centers of Malebolge, the misuse of ecclesiastic and secular power, the opening apostrophes denounce respectively the rapacious popes (bolgia three) and Florence with its ambitious and thieving citizens (bolgia eight). Flames or light, a symbol of goodness and knowledge in antiquity and the Middle Ages, perversely lick Pope Nicholas’ feet and obliterate Ulysses and Guido’s identity.

In bolgia three Pope Boniface VIII’s presence is anticipated; in bolgia eight he appears in retrospect, in Guido’s story. In the third bolgia Pope Nicholas III inveighs against Boniface as a prime example of papal greed and deceiver of the Church; in the eighth bolgia Guido denounces him as “lo principe d’i novi Farisei” for his pursuit of political and territorial ambitions. In his account, Guido compares Boniface to the Emperor Constantine and himself to Pope Sylvester I, who cured Constantine of leprosy and was given authority to rule the West in return. But their institutional roles are ironically reversed: Guido the military strategist is related to the figure of a pope, as a “physician” whose advice would “cure” Pope Boniface, who is in turn related to the figure of an emperor. Boniface’s “leprosy” is his desire for victory over the Colonna family at Palestrina, one that Guido’s fraudulent advice helps him to achieve. If Sylvester received authority over the Western Empire, Guido received false absolution but not the Kingdom of Heaven.[1] With this simile the poet once again symmetrically links the third and the eighth bolge in Malebolge. It embodies the intertwining of the powers of Church and State and at the same time casts Constantine in an ambiguous light.*

[1] * For Mark Musa, my teacher.
For a more comprehensive interpretation see Richard H. Lansing, "Submerged Meanings in Dante's Similes (Inf. XXVII)," in Dante Studies, 94 (1976), 61-69.