In a largely previously untold story, Melissa Milewski explores how, when the financial futures of their families were on the line, black litigants throughout the South took on white southerners in civil suits. Between 1865 and 1950, in almost a thousand civil cases across eight southern states, former slaves took their former masters to court, black sharecroppers litigated 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. But they also found that, in the kinds of civil cases that they could litigate in the highest courts of eight states, they were also surprisingly successful. In a tremendously restricted environment in which they were often shut out of other government institutions, seen as racially inferior, and segregated, African Americans found a way to fight for their rights in one of the only ways they could. This book examines how African Americans adapted and at times made a biased system work for them under enormous constraints. 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 had to make to have their cases heard.