Another flame approaches, roaring and crackling. It is from a Lombard — it speaks in the Romagnol dialect. Guido da Montefeltro: a great Ghibelline military captain, famous for cunning rather than force, who late in life became a Franciscan friar in genuine repentance. But then Pope Boniface VIII came to him with a problem: he needed to destroy the Colonna family's stronghold at Palestrina, and needed a counsel of fraud to do it. Guido refused. Boniface told him: I give you absolution in advance; now counsel me. And Guido — believing the papal power capable of pre-forgiving sin — gave the counsel: promise much, keep little.
The counsel worked. Boniface promised the Colonnas safety, then destroyed Palestrina utterly. And Guido died shortly after, expecting the Franciscan habit he had worn as a friar to save him. But a black cherub appeared at his deathbed to claim him — Francis of Assisi could not carry him off because a man cannot repent and will a sin simultaneously. The absolution was void: it is logically impossible to intend to sin and to repent of it at the same moment. The devil's logic is impeccable: "perhaps you did not think I was a logician." Guido is here not for his military career but for trusting that a pope could sell him a ticket to sin.