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Drawing from a large research study of school desegregation in Mississippi from 1964-1971, this presentation examines the role of superintendents in the desegregation process, paying close attention to both the micro (e.g., the daily decision that had to be made) and the macro (the unique social, cultural, historical, and economic contexts of individual schools districts). Oral histories of four superintendents who successfully led 8 school districts through desegregation provide the data for this presentation. We use the following descriptive themes to organize the presentation: the enforcer, the mediator, the negotiator, and the maverick.