This chapter investigates a key tension in the political thought of C.L.R. James, the celebrated Trinidadian Marxist. James believed that the human condition was defined by a search for meaningful freedom through the pursuit of collective self-determination. Yet he was conflicted as to whether peoples of African descent had to depend for this meaning on the European civilization that had enslaved and colonized them. The chapter details James’s unique contribution to Marxist thought: a ‘dialectic of freedom’ that triangulates the struggle between the bourgeoisie, the masses, and the radical intelligentsia. It then considers the impact of colonial education on James’s own development and the ways in which it made Black intellectual production, for him, intrinsically political and contentious. The chapter also explores the dualism with which James treated Blackness as a resource with which to struggle for meaningful freedom. It considers James’s legacy as edifying, precisely because of the intellectual forthrightness by which he lived his split ethical, theoretical, and political orientation towards Europe and Africa.