Heidegger’s pivotal impact on Leo Strauss’s thought is widely acknowledged. As one commentator notes: “One could almost say that Heidegger is the unnamed presence to whom or against whom all of Strauss’s writings are in large part directed.” This view is confirmed by Strauss himself, who proclaimed that “the only question of importance … is the question whether Heidegger’s teaching is true or not.” While much has been written on Strauss and Heidegger, here I wish to focus on the intersections of Strauss’s understanding of Heidegger and Judaism. The chapter’s argument is threefold: first, that Strauss’s lifelong grappling with matters Jewish are importantly marked by the philosophical, theological, and political challenges reflected in Heidegger; second, that his engagement with Heidegger unfolds within the context of his reflections on the Jewish engagement with modernity, understood as a project indebted to the Christian horizon; and third, that while he sees Heidegger as representing the “danger” and high point of the modern crisis in both philosophy and religion, it is, paradoxically, Heidegger who offers the theoretical breakthrough that directs out of the crisis.