This thesis explores the complex life of Armistead Lawless, an enterprising free African American and bawdyhouse owner in antebellum St. Louis. Lawless was also a slaveowner, frequently broke the law, and cheated his friends out of money. His white neighbors rioted and forced him to flee to Illinois in 1832, where he was tricked into signing away control of his property. He sued for his property in the St. Louis Circuit Court, igniting an eight-year legal battle, but he never returned to St. Louis. Lawless fails to conform to conventions about Black freedom. Instead, he illuminates the possibilities of freedom and expands the boundaries of what one Black man could do in the antebellum United States. His story adds an intimate portrait to current interpretations of freedom, violence, formal law, and property ownership, complicating historical narratives about Black freedom and the people who lived it.