This paper assesses the complex debt of Machiavelli’s moral and political thought to Aristotle and the Aristotelian tradition, especially in its Scholastic variant. My claim is that Machiavelli’s attitude vis-à-vis Aristotle is twofold because it reflects two different aspects of Aristotle’s moral and political theory that are closely intertwined and that were selectively developed by subsequent Aristotelian Scholastic commentators: a teleological and a realist aspect. On one hand, Machiavelli provides a model that dramatically breaks with Aristotle on, for example, the (...) question of the origin of human society and the moral prudence of rulers. On the other hand, Machiavelli’s engagement with Aristotle amounts to something more complex than a simple rejection. The Florentine appears to read Aristotle rather selectively, and emphasizes the realist dimension of certain Aristotelian ideas that suit his own original overturning of classical moral and political ideas. I use two paradigmatic themes in which the Aristotelian teleological-realist divide is most evident, i.e. the account of the origin of human society and the case of prudence, in order to prove the dual relationship of Machiavelli’s thought with Aristotelianism. (shrink)