Reading Politics with Machiavelli is an anachronistic reading of certain key concepts in Machiavelli’s The Prince and The Discourses (as well as some of his correspondence). In 1513, soon after the Medici returned to power in Florence, Machiavelli lost his position as First Secretary to the Republic, and he was exiled. On his family farm, he began a self-consciously anachronistic reading of great political figures of antiquity, and, in combination with his own experience as a diplomat, crafted a unique perspective on the political crises of his time. At our own moment of democratic crisis, as the democratic imagination, as well as democratic habits and institutions face multiple attacks from neoliberalism, white nationalism, and authoritarianism, I argue that a similar method, in which we read Machiavelli’s work as he read Livy’s and Plutarch’s, can help us see the contingency, and the increasingly forgotten radical potential, of our politics. Louis Althusser argued that Machiavelli functions for us as an uncanny authority, one whose apparent familiarity is dispelled as we examine his epistolary yet opaque account of history, politics, and authority. This makes his readings a potentially rich resource for a time of democratic crisis. With that challenge in mind, we will examine the problems of conspiracy, prophecy, torture, and exile and use a close reading of Machiavelli’s work to make out new perspectives on the politics of our time.