Scholarship has attributed to the Italian teachers of rhetoric of the central Middle Ages a very significant role in the development of political discourse, but their testimony concerning the momentous conflict fought from 1226 to 1250 between the Lombard League, the Papacy and Emperor Frederick II has largely been overlooked. This paper approaches it by focusing on the works of Guido Faba, comparing them with the production of his main colleagues, Boncompagno da Signa and Bene da Firenze, and considering the impact of the conflict upon the schools to which they belonged. It first examines a papal privilege issued to the Lombard cities that only features in Faba's Dictamina rhetorica, arguing that it is most likely a verisimilar work of fiction supporting the contested validity of the Peace of Constance (the settlement reached between the League and Frederick Barbarossa in 1183) and its recognition of the League. The second half of the enquiry then shows that the conflict between Empire and League attracted considerable attention among contemporary teachers of rhetoric, whose schools were directly involved in it. That Faba's works are particularly rich in evidence for the conflict and the engagement of the Papacy should be attributed to his Bolognese background.