Frederick Douglass’s relationship to education was multifaceted and at times paradoxical. Douglass’s accounts of his denied access to education while enslaved, his history of unsanctioned self-education, his role as an activist-educator and promoter of Black education, and his evolution into an iconic subject for education on U.S. slavery and Black history more generally demand that a discussion of Douglass and education be addressed from several angles. This essay traces the consonance of and tensions between the various ways we must consider education’s place within Douglass studies. Douglass’s overrepresentation in educational materials for children further compounds tendencies to view Douglass in more simplistically individualistic terms. Though exceptional in his ability, learning methods, and educational circumstances, Douglass is best understood within the larger historical context of Black education. Moreover, Douglass himself recognized that education was not a simple cure for racism and criticized the educational elitism attached to prestigious institutions and occupations.