Through the contextualized biography of a previously unknown African American immigrant to Africa, this book illuminates slavery and freedom in multiple parts of the nineteenth century Atlantic world. A decade before the American Civil War, James Churchwill Vaughan (1828-93) set out to fulfill his formerly enslaved father’s dying wish: that he should leave his home in South Carolina for a new life in Africa. Over the next forty years, Vaughan was taken captive, fought in African wars, built and rebuilt a livelihood, and led a revolt against white racism, finally becoming a successful merchant and founder of a wealthy, educated, and politically active family in Lagos, Nigeria. Tracing Vaughan’s journey from South Carolina to Liberia to several parts of Yorubaland (present-day southwestern Nigeria), the book documents this “free” man’s struggle to find economic and political autonomy in an era when freedom was not clear and unhindered anywhere for people of African descent. By following Vaughan’s transatlantic journeys and comparing his experiences to those of his parents, contemporaries, and descendants in Nigeria and South Carolina, the book reveals the expansive reach of slavery, the ambiguities of freedom, and the surprising ways that Africa, rather than America, offered new opportunities for people of the African diaspora.