In this paper we argue that Niccolò Machiavelli has little to do with Realism in International Relations theory. By concentrating, as Machaivelli did, on the walls that define political relations—both inside and outside the polity—we find his insights deeply rooted in the specific political contexts of Sixteenth century Italy. Others may wish to generalize from them, but Machiavelli did not. In fact, as we show, Machiavelli was mindful of the difficulties of generalizing about walls and acknowledged the dangers political actors faced in navigating between the internal and external walls of the polity. We examine the geopolitical contours of Machiavelli’s walls and seek to demonstrate how morality is present in these historical spaces. In contrast to Realists, Machiavelli was ready and willing to make ethical judgments. We argue that theorists of international politics should exercise care in reaching for Machiavelli as the iconic thinker for making sense of anarchy in world politics. This article concludes by suggesting that the ideology of Machiavellianism has obscured deeper understanding of the particular contexts of Machiavelli’s own world.