This article uses historical scholarship on Guido da Montefeltro and medieval Romagna (Franceschini and Vasina) alongside Ovid’s Metamorphosis and the Serventese del 1277 to contextualize the question asked by the soul of Guido (about peace or war in Romagna) and the catalog of tyrants provided by the pilgrim in Inferno 27. It examines how Dante held Guido accountable for the intensification of warfare in Romagna and made an argument for the responsibility of military strategists in the consolidation of urban signorie. Dante’s assessment coincides with current historiography and shows his concerns about the formation of regional states. A recontextualization of Guido’s question reveals the targeted nature of the pilgrim’s response, in which the pilgrim presents Guido with the triumph of his enemies.

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