Historical work on the relationship between American incarceration and race is often focused on the Reconstruction era and early twentieth century. This project explores the same nexus before the Civil War. The people, places, and policies connecting the systems of slavery and carceral development in the American South reveal a great deal about how the two were, in some measures, mutually constitutive. To explore the politics of these connections, I pay attention to the presence of free Black sailors arriving to Southern port cities during a time of transatlantic anxiety regarding slave uprisings and Black autonomy after the Haitian Revolution. When was incarceration used as a tool to interrupt liberty? How were people led to auction blocks from prison bars? How were these traditions legislatively codified and legally preserved? Through answering these questions and more, this thesis elucidates how the interplay between slavery and incarceration defined political inclusion and legal freedom in the nation's formative early decades.