Recent scholarly work on the relationship between Hannah Arendt and James Baldwin have sought to reconcile their differences by demonstrating how Baldwin’s writings on love can complement Arendt’s concept of amor mundi (love of the world). Rather than seek common ground, I aim to shed new light on this relationship by focusing on a divergences in their later writings on the connection between thinking and action, especially the activity of judgement. Analyzing their different uses of the figure of Socrates as a compelling model of moral and political responsibility, I argue that Baldwin’s enacts a form of judgement rooted in a creative, productive imagination, that, for all its uncanny resemblances to Arendt’s understanding of judgement, contrasts sharply with her understanding of political imagination as primarily reproductive. This contrast is illustrated most clearly in their different figurations of the conscience, the relationship between past and present, and in Baldwin’s distinctively musical mode of speech and writing. Though each turns to the Socratic example of the examined life in the aftermath of civilizational crisis, Arendt’s thinking on judgement is premised on the possibility of reconciling oneself to the unprecedented through judgement’s capacity to orient our actions and affirm the free actions of others. Baldwin’s vision for the examined life is, in contrast, premised on the impossibility of reconciliation. Paradoxically, accepting and, in a specific sense, embracing that impossibility is, for Baldwin, the only hope for future reconciliation. The affirmation of freedom in the present requires reckoning with the power of past over the modern imagination, with the traumatic precedents of white supremacy. In Baldwin’s eschewal of the theorist’s desire for comprehensive analysis and conceptual simplicity, he is more Socratic, and provides a more developed, clear picture of Socratic citizenship by his example.