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This paper explores a common characteristic of 1940s black educators—tough kindness—and places this attribute within the context of progressive education and current conceptions of caring. Material is drawn from 140 oral history interview sessions, conducted between 2008 and 2013, with approximately 275 former students and teachers (between the ages of 75 and 102) who were involved in the Rockefeller Foundation’s Black High School Study, staged between 1940 and 1948 and involving high schools in the American southeast. The purpose of the paper is to introduce more complex understandings of black education during the long civil rights/late Jim Crow era and to place the context of black secondary education within the progressive education framework.