Hannah Arendt and Leo Strauss - two major political thinkers of the twentieth century, both of German-Jewish background and forced into exile in America - were never friends or intellectual interlocutors. Yet they shared a radical critique of contemporary idioms of politically oriented discourses and a lifelong effort to modify reflective approaches to political experience. Liisi Keedus reveals how Arendt's and Strauss's thinking about political modernity was the product of a common intellectual formation in Weimar Germany, by examining the cross-disciplinary debates guiding their early work. Through a historical reconstruction of their shared interrogative horizons - comprising questions regarding the possibility of an ethically engaged political philosophy after two world wars, the political fate of Jewry, the implications of modern conceptions of freedom, and the relation between theoria and praxis - Keedus unravels striking similarities, as well as genuine antagonisms, between the two thinkers.