Guido da Montefeltro
Guido da Montefeltro: Circle 8, Inferno 27
Whereas Virgil addresses the Greek hero Ulysses in Inferno 26, Dante himself inquires of Guido da Montefeltro--a figure from Dante's medieval Italian world--in Inferno 27. Guido (c. 1220-98), a fraudulent character who may himself be a victim of fraud, immediately reveals the limits of his scheming mind when he expresses a willingness to identify himself only because he believes (or claims to believe) that no one ever returns from hell alive (Inf. 27.61-6). T. S. Eliot uses these lines in the Italian original as the epigraph to his famous poem about a modern-day Guido, "The Love Song of J. Alfred Prufrock":
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S'i' credesse che mia risposta fosse
a persona che mai tornasse al mondo,
questa fiamma staria sanza più scosse;
ma però che già mai di questo fondo
non tornò vivo alcun, s'i' odo il vero,
sanza tema d'infamia ti rispondo.
If I thought my answer was
to someone who might return to the world,
this flame would move no more;
but since from this depth it never happened
that anyone alive returned (if I hear right),
without fear of infamy I'll answer you

Note how the double s's imitate the hissing sound of the speaking flame.
Similar to Ulysses, Guido was a sly military-political leader--more fox than lion--who knew "all the wiles and secret ways" of the world (Inf. 27.73-8). He was a prominent ghibelline who led several important military campaigns in central Italy. In the 1270s and the early 1280s he scored decisive victories over guelph and papal forces before suffering defeat in 1283 at Forlí (in Romagna). Excommunicated, he later captained the forces of the Pisan ghibellines against Florence (1288-92); in 1296 Pope Boniface VIII rescinded the excommunication as part of a political strategy to remove the dangerous Guido from the scene. Thus Dante relates how Guido, unlike Ulysses, made an attempt--at least superficially--to change his devious ways when he retired from his active warrior life to become a Franciscan friar (Inf. 27.67-8; 79-84). In a previous work, Dante praises Guido's apparent conversion as a model for how the virtuous individual should retire from worldly affairs late in life (Convivio 4.28.8); Dante certainly uses Guido's story for a very different purpose here in the Inferno. Now the poet calls into question Guido's pretense to a pious life at the same time that he strikes another blow against the pope he loves to hate: Boniface induces Guido to provide advice for destroying the pope's enemies--a broken promise of amnesty for the Colonna family--in exchange for the impossible absolution of this sin even before Guido commits it (85-111).