This essay investigates the political and literary culture of late Duecento Florence as well as the entangled rather than mutually exclusive nature of Dante’s pre- and post-exile political and literary visions. I read Dante’s political vision against the Fiore, a Tuscan form of the medieval French epic Roman de la Rose that appeared in Italy before 1290. Pervasive in Dante’s politics, poetics, and the cultural milieux in which the Fiore appeared are the rejection of French/Provençal cultural dominance, Franco-Angevin political influence in Italy, and mendicants as morally bankrupt threats to civil society. In turn, this essay argues that the Fiore and Dante’s participation in the literary culture that produced it were the consequence of the geopolitical landscape of the late Duecento, which paved the way for his exile and subsequent rancor that pervaded his later works.