From 1865 to 1950, when the financial futures of their families were on the line, black litigants throughout the South took on white southerners in civil suits. In almost a thousand civil cases across eight southern states, former slaves took their former masters to court, black sharecroppers litigated disputes against white landowners, and African Americans with little formal education brought disputes against wealthy white members of their communities. As black southerners negotiated a legal system with almost all white gatekeepers, they displayed pragmatism and a savvy understanding of how to get whites on their side. They found that certain kinds of cases were much easier to gain whites’ support for than others. In the kinds of civil cases they could litigate in the highest courts of eight states, though, they were surprisingly successful. In a tremendously constrained environment where they were often shut out of other government institutions, seen as racially inferior, and often segregated, African Americans found a way to fight for their rights in one of the only ways they could. This book examines how black southerners adapted and at times made a biased system work for them. At the same time, it considers the limitations of working within a white-dominated system at a time of great racial discrimination and the choices black litigants made to have their cases heard.