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Despair is often understood as the absence of hope, the wilting of agency, and the closure of struggle. In short, as we typically understand it, to be in despair is to be already defeated by the world and one’s circumstances in it. But in this paper, I am interested in understanding what kind of political work despair does in the black radical tradition, especially in the face of resurgent white populism. I situate my investigation in the mid-twentieth century, at a time when white populism took the form of white citizens' councils and "massive resistance" to Brown v. Board of Education. Writing in the face of these and other challenges, James Baldwin offers a unique window into the peculiar role despair plays in critiquing the politics of innocence embraced by white populists and offering insurgent visions of black democratic challenge. Drawing on the use of popular black music (the blues and jazz in the early to mid-twentieth century) in James Baldwin’s political thought, I argue that contrary to our popular understandings, despair can be a critical and paradoxically galvanizing force in the black radical tradition. It offers both a critique of mainstream narratives of racial progress and an opening for radical, sometimes militant and triumphant, re-imaginations of black freedom and agency.