This paper examines W.E.B. Du Bois’s John Brown as a turning point in his thinking about the use of force in the struggle for African-American liberation. I call it a “turning point” not only to mark a periodized transition in Du Bois’s developing socialism but also to underscore the ways Du Bois wrestles with the question of violence in this work, turning on it from a plurality of imagined perspectives. Du Bois portrays John Brown alternatively as a prophet, a slave in revolt, a laborer exploited by industrial oligarchs, a member of the talented tenth, and a white outsider to the struggle of African Americans to model the vicissitudes of political judgment concerning the use of force. Confronting John Brown’s ultimate conclusion that “the cost of liberty is less than the price of repression, even though the cost be blood,” I argue that Du Bois’s perspectival approach to judgment marks an important alternative to both a political moralism that abstracts from questions of consequences and a political realism that brackets claims of right. This essay demonstrates how taking Du Bois’s repudiation of both moralism and realism seriously troubles not only his own earlier attempts to domesticate the politics of revolt in Souls of Black Folks, but also more recent attempts to police the boundaries of violence and non-violence in contemporary political theory.