This essay examines various intellectual affinities between Dewey and Baldwin, including their pragmatic and tragic conceptions of history. I argue in the first section that Dewey’s attention to the precarious dimensions of experience and his critique of dominant modes of inquiry that prioritize the stable over the precarious pay insufficient attention to race, though this focus on the precarious over the stable aspects of experience is enough to show that pragmatism does acknowledge the tragic dimension. The subsequent section argues that this insufficiency might be rectified through a reading of Baldwin’s work. While Dewey and Baldwin both acknowledge that existence is finite and precarious (and hence the tragic), Baldwin shows that racism and the promotion of white identity is essentially an attempt to disavow the precariousness of existence. Baldwin’s writings should supplement Dewey’s theory of experience and his account of history because we find in them an acknowledgement of the deep institutional roots of racial oppression and various forms of resistance to this oppression as a key dimension of American history.