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Recent developments in Machiavelli scholarship have led an increasing number of scholars to reevaluate Machiavelli’s relationship to Platonism. It is not that recent advances in the field have revealed that the consensus according to which Machiavelli mostly rejects Platonism had been wrongly held for so long. It is more that in the detail of that disagreement we find philosophically interesting nuance that helps us further understand Machiavelli’s thought. This paper aims to pursue this line of inquiry and add to the growing body of scholarship on the topic by examining how Machiavelli’s mostly understudied (with the exception of the “Mandragola”) plays and his short story “Belfagor Arcidiavolo” reveal his critique of the Platonic notion of eros. Since the plays have been regularly addressed in the literature and Belfagor has, to be knowledge, almost never been researched, this paper expands more on the contributions of the latter than of the former to the field of Machiavelli studies. This paper aims to show that Machiavelli’s literary works reveal (a) his agreement with Plato and Savonarola that literature should be used a vehicle for philosophically useful concepts, (b) an implicit critique of Christianity and of the potential of a positive relationship between love, lust and knowledge, and (c) that Machiavelli inscribes himself in a line of politically astute manipulators who capitalized on low mass intelligence by using pretensions of supernatural insight to reach their philosophical and political goals.