At the center of the upheavals brought by emancipation in the American South was the economic and social transition from slavery to modern capitalism. This book examines how this institutional change affected individuals, organizations, and communities in the late nineteenth century, as blacks and whites alike learned to navigate the shoals between two different economic worlds. In the aftermath of the Civil War, uncertainty was a pervasive feature of life in the South, affecting the economic behavior and social status of former slaves, Freedmen's Bureau agents, planters, merchants, and politicians, among others. Emancipation brought fundamental questions: How should emancipated slaves be reimbursed in wage contracts? What occupations and class positions would be open to blacks and whites? What forms of agricultural tenure could persist? And what paths to economic growth would be viable? To understand the escalating uncertainty of the postbellum era, the book draws on a wide range of qualitative and quantitative data, including several thousand interviews with former slaves, letters, labor contracts, memoirs, survey responses, census records, and credit reports. The book identifies profound changes between the economic institutions of the Old and New South and sheds new light on how the legacy of emancipation continues to affect political discourse and race and class relations today.