This chapter offers a critical appraisal of two dominant approaches to pluralism, conflict, and difference in contemporary political theology, both of which draw on the thought of Augustine. Postliberal Augustinianism, represented by the “Radical Orthodoxy” of John Milbank, develops a highly sophisticated account of the metaphysics of human sociality, grounded in a creative reading of Trinitarian theology which construes political community in terms of harmonious difference. Augustinian civic liberalism, represented by Charles Mathewes and Eric Gregory, draws on Augustine’s understanding of love and difference in order to propose an ethics and ascetics of liberal citizenship. Both, however, thematize political community and difference in essentially oppositional terms, privileging one or the other, and reading conflict in decidedly negative terms. The limits of these political theological strategies reveal a need to reconceptualize the nature of political community and the place of conflict therein.