This essay explores W. E. B. Du Bois’s evolving sense of disillusionment with the liberal paradigm in an effort to stimulate critical thinking about an American political culture consumed by both the fear and purported legitimacy of private competition. Du Bois always encouraged sustained critical appraisal of an American society torn between winners and losers, the favored and the damned. As his thinking developed into the 1930s, he focused more squarely upon the logic of capital accumulation, or the structural imperative to expand power in the service of private interest, and always in response to a suspicion or fear of the other—the competitor. I suggest that Du Bois’s claims about the racially biased character of the competitive society, as well as his argument, put forth in a series of speeches and writings on “Negro education,” that Black colleges ought to facilitate the critique of this society, may have some normative import today as widespread, often unreflective acquiescence to the principles of competitive liberalism seems poised to exacerbate and further legitimize racial and economic inequities.