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What precipitates the collapse of seemingly durable social orders like segregation in the American South? Prior research suggests education played a key role in the decline of Jim Crow but Black schooling in the South was designed to maintain the status quo racial hierarchy. We propose a model of “path divergence” in which an intervention contributes to a long-run process that shifts society away from the entrenched equilibrium toward a new social order. Drawing on data from a remarkable educational intervention in the 1920s, we test this model by estimating the long-run effects on civic engagement of introducing 5,400 schools into mostly rural Black communities in the South. Counties exposed to “Rosenwald schools” in the 1920s, which increased Black school enrollment, were more likely to engage in civil rights protests in the 1960s. In addition, we show that these counties saw greater increases in voter turnout after passage of the Voting Rights Act in 1965. Using both mediation analysis and distance from railroad lines to approximate random assignment of schools, we provide suggestive evidence of causal relationship between Rosenwald schools and greater Black civic engagement. We find major investments in African American education, despite its separate and unequal status, nurtured a generation of equality-minded citizens who helped dismantle Jim Crow.