This book explores the meaning of freedom through its fundamental relationship to the experience of slavery. It makes transparent a central insight on the human condition often ignored or disavowed by philosophers and political theorists by examining a specific, highly overlooked form of flight from slavery, marronage, that was fundamental to Caribbean and Latin American slave systems and has widespread application to European, New World, and black diasporic societies. The theory derived from such flight is freedom as marronage. The text deepens our understanding of freedom not only by situating slavery as freedom’s opposite condition, but also by investigating the significance of the equally important liminal and transitional social space between slavery and freedom. It argues that we must pay more attention to the experience of the process by which people emerge from slavery to freedom. The study investigates ideas in Hannah Arendt, Philip Pettit, W.E.B. Du Bois, Angela Y. Davis, Frederick Douglass, Samuel Taylor Coleridge, the Haitian Revolution, Édouard Glissant, and Rastafari to develop a theory of freedom that offers a compelling interpretive lens to decipher the quandaries of slavery, political language, and the experience of freedom still confronting us. Its contributions to freedom’s meaning, and by extension unfreedom, include a cautionary tale on the limitations of disavowing slavery and slave agency in conversations about flight. This work is significant for scholars in black studies, Caribbean thought, interdisciplinary philosophy, American studies, critical theory, contemporary political theory, and all those interested in the idea of freedom between past and future.