Abstract: This dissertation answers two central and related questions: What are some distinct concepts of freedom emerging out of the experience of slavery? What important insights does analyzing the relationship between slavery and freedom provide to political theorists that they either do not know, have ignored, or have not sufficiently investigated? The project examines a specific, highly overlooked form of flight from slavery—marronage —that was fundamental to the experience of Haitian slavery and is integral to understanding the Haitian Revolution. I call the theory derived from such flight freedom as marronage, and I argue that this theory provides a compelling conceptual framework for those interested in understanding both normative ideals of political freedom and the origin of those ideals. The dissertation engages four areas of inquiry. First, it offers a critique of Hannah Arendt and Philip Pettit's neo-Athenian and neo-Roman republican theories, which disavow the relationships among slavery, slave agency, and freedom. Second, the project engages the work of Jean-Jacques Rousseau and the ex-slave Frederick Douglass in order to illustrate theorists who support the claim that freedom must be understood in relation to slavery but do so in ways that still remain insufficient. Third, it focuses attention on the Haitian Revolution to explain a more robust notion of freedom that I contend best describes the dialectic of slavery and freedom. In the process, I highlight the value of the idea of marronage for our modern political vocabulary by redefining its conventional usage and present freedom as marronage as a heuristic device useful also to political theorists working beyond the Caribbean context. Fourth, the project explores the meaning of unfreedom in light of arguments presented in the previous chapters. The conclusion poses the stakes of the dissertation for political theorists and Caribbean scholars concerned with freedom beyond the realms of disciplinary history and anthropology. A primary goal is to demonstrate why political theorists must take seriously political language, the adverse effects of slavery's disavowal, and the dialectical claim that political freedom in its pre-modern, modern, and postmodern formulations is best understood in relation to the lived experience of slavery.