This article seeks to illuminate the relationship between two of the most important figures in American political thought: the pragmatist philosopher William James, and the pioneering civil rights leader and intellectual, W.E.B. Du Bois. As Harvard's first African American PhD, Du Bois was a critical figure in theorizing about race and identity. His innovative take on double consciousness has often been attributed to his contact with James who was one of Du Bois's most critical graduate professors at Harvard. But beyond the view of the two thinkers as intellectual collaborators, is the fraught history of liberal racial fraternal pairing and its role in shaping national identity. This article examines Du Bois and James's relationship in the context of that history, one marked by troubled associations between friendship and race.