The human being is freely ‘self-determined’ rather than determined through some external authority (whether theological or teleological). This dichotomy conveniently expresses the usual understanding of modern political thought’s divergence from preceding tradition. By comparison, pre-modernity is teleological, anthropomorphic, realist; in a word, naïve – with its substantively rational nature, dictating essential ends to which we are subject. These received truths are past due for a re-examination. Just how naïve or dogmatic was the Greek understanding of freedom and nature? In this chapter, I argue that Plato’s view of man as naturally political is more complex and multivalent than our historical categorizations allow. Nevertheless, there is a sense in which, for him, politics does indeed depend upon a natural model. That model, however, is the Idea of the Good. And here, where Plato seems furthest from us, lies his greatest challenge to contemporary understandings of nature and freedom.