As scholars we fail to meet the challenge to speak about politics as occurring in what Hannah Arendt called the condition of plurality when we speak about politics in ways which either, on the one hand, focus on the structural or cultural laws of political change while minimizing the ability of human agency to have an effect at the societal level (e.g. Marxists) or, on the other hand, focuses on the role of individuals but analytically assumes they are identical (e.g. liberals). I confront this challenge by engaging with the work of Niccolò Machiavelli on the question of why and how it is that some political actors are better at politics than others: on their political skill. In my dissertation, The Recovery of Virtù: Imitation and Political Practices in the Works of Niccolò Machiavelli, I present a new interpretation of Machiavelli’s concept of virtù, which is the principal quality he finds in politically successful individuals and states. In the introduction, I show that previous accounts of Machiavelli’s concept of virtù focus on reading carefully to determine his esoteric meaning of virtù, on the gendered implications of his contrast of masculine virtù to feminine fortuna, on his relationship with his political and intellectual contexts, and on a systematic analysis of the various “senses” in which Machiavelli uses virtù. In contrast, I provide a systematic examination of how Machiavelli deploys exemplars of virtù throughout his major political, historical, and military writings. In Chapter 1, I argue that Machiavelli exhorts his readers to learn from political history and to imitate the virtuous practices of successful individuals and states. Chapter 2 identifies variations in how Machiavelli talks about virtù between individuals and peoples and between principalities and republics. Chapter 3 examines the relationship between virtù and the political ends of staying in power and maintaining liberty. I present in depth analyses of all Machiavelli’s examples of virtù in the appendices. I demonstrate that using Machiavelli’s language of virtù allows us to met Arendt’s challenge to speak of politics in the condition of plurality because it forces us to engage with the unique identity of each individual person or polity whose actions are studied.