From our Greek sources, one of the most oft-cited reasons for Greek resistance to Persian westward expansion in the 5th and 4th centuries BCE is the question of freedom, perhaps best described in the conversation between the Spartan emissaries and their Persian host Hydarnes in Herodotus 7:135, where the Greeks, we are told, are “free” and the Persians are not, lacking even an understanding of the term. An examination of Persian sources, however, as well as other textual material from the Ancient Near East, demonstrates that freedom was an important part of Near Eastern culture, appearing in texts as far back as the third millennium BCE (the reforms of Urukagina; the Law Code of Hammurabi), and was present as well in Achaemenid royal ideology (the Cyrus Cylinder). This indicates that the conception of freedom as seen by both these cultures was actually far more complex than the Greeks believed, reflecting different views that wound up being seen as mutually exclusive and thus contributing to the ideological reasons for political conflict. These conceptions of freedom, which can be summarized as “freedom to” for the Greeks and “freedom from” for the Persians and their Near Eastern subjects, are examined in this paper, reflecting the different histories of each culture and their fundamental social evolution, notably the contrast between the polis and the development of the state in the Near East. Since the Greeks and the Persians interacted throughout antiquity, any understanding of the frequent conflicts between the two must consider these fundamental cultural differences, and how they manifested themselves both in ideology and the actual political policies of both groups.