The 1998 publication of Carla Benedetti’s Pasolini contro Calvino: Per una letteratura impura provoked a series of attacks in the Italian press, mostly aimed at its so-called “banalissima contrapposizione” between authors. Debates in Italy today about the legacy of the Novecento, the state of Italian postmodernism, and the future of Italian literary culture are still haunted by this authorial contraposition, and are often compounded by the perceived opposition, in the field of criticism, between Benedetti’s supporters and her critics. The aim of this essay is to frame these debates by comparing Benedetti’s provocative call for an impure literature in Pasolini contro Calvino with Francesco De Sanctis’ foundational Storia della letteratura italiana. Through this comparison, I argue that Benedetti and De Sanctis are “Machiavellian” literary critics whose future-oriented strategies of expression represent one of multiple ways that the unprecedented challenges Italian culture faces today are being confronted with tools from its past.