Enmeshed in the exploitative world of racial slavery, overseers were central figures in the management of early American plantation enterprises. All too frequently dismissed as brutal and incompetent, they defy easy categorisation. Some were rogues, yet others were highly skilled professionals, farmers, and artisans. Some were themselves enslaved. They and their wives, with whom they often formed supervisory partnerships, were caught between disdainful planters and defiant enslaved labourers, as they sought to advance their ambitions. Their history, revealed here in unprecedented detail, illuminates the complex power struggles and interplay of class and race in a volatile slave society.