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In this article I examine how prison conditions litigation in the 1970s, as an outgrowth of the civil rights movement, inadvertently contributed to the rise of mass incarceration in the United States. Using Florida as a case study, I detail how prison conditions litigation that aimed to reduce incarceration was translated in the political arena as a court order to build prisons. Drawing on insights from historical institutionalist scholarship, I argue that this paradox can be explained by considering the different historical and political contexts of the initial legal framing and the final compliance with the court order. In addition, I demonstrate how the choices made by policy makers around court compliance created policy feedback effects that further expanded the coercive capacity of the state and transformed political calculations around crime control. The findings suggest how “successful” court challenges for institutional change can have long-term outcomes that are contrary to social justice goals. The paradox of prison litigation is especially compelling because inmates' lawyers were specifically concerned about racial injustice, yet mass incarceration is arguably the greatest obstacle to racial equality in the twenty-first century.