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We introduce the concept of the “Long-Brown” through a careful study of the life and work of Ruby J. Gainer, a Black educator in Alabama and Florida between the 1930s and 1980s. Gainer’s life and work exemplifies that dialogical relationship. Her activism in salary equalization and integration in schools and teacher professional associations were directly tied to the issue raised by NAACP litigation, but she pursued these battles without their direct support and from her own ideological perspective. Her activism and organizing, over the course of a half-century, reveals not only the grassroots organizing of Black teachers that made the NAACP’s national educational campaigns successful, but also the nuances of how Black educators navigated the world that Brown helped create.