The Antebellum South is often remembered in stark terms: a society rigidly divided along racial lines, where white planters held power over enslaved Black people. Yet, history reveals a more complicated reality. While most slaveowners were white, a small but significant number of free Black individuals also owned slaves. This little-known fact unsettles common assumptions about race, power, and agency in pre-Civil War America. By examining the experiences of Black slaveowners, we gain a deeper understanding of the social and economic complexities that shaped the South—a story more nuanced than many realize.