This article concerns the nature of reason in the work of the Twentieth Century Catholic theologian Erich Przywara and Georg Wilhelm Friedrich Hegel. The discussion centers on three interlocking issues: (a) the question whether proper thinking submits to or transgresses the principle of non-contradiction; (b) the relationship between reason and history; (c) the theological concern with distinguishing the “history of reason” and the divine life. It is argued that both Hegel and Przywara give an account of reason where there are moments of contradiction, and that this is a necessary feature of historical existence. Further, while Przywara and others are concerned with Hegel’s making reason’s reconciliation of contradiction in history identical with the divine life, I argue that although this is a real concern, Hegel’s account is more equivocal than normally admitted. Finally, I argue that the distinguishing feature between Przywara and Hegel is what happens after the moment of contradiction; that is where we see the most important difference between an analogical and a dialectical account of reason.