After the overthrow of Jim Crow and the reelection of our first Black president, how should we conceptualize the tasks of a racially progressive politics in the United States? I address this question through (1) the lens of recent philosophical work on the relation between narrative and the justification of political hope and (2) a comparison of two autobiographies, Barack Obama’s Dreams of My Father and W. E. B. Du Bois’s Dusk of Dawn. In light of this comparison, the paper also evaluates some recent contributions to the American Political Science subfield of American Political Development.