This book examines the complex philosophical relationship between Martin Heidegger and Leo Strauss. It argues that both thinkers provide searching analyses of the philosophical tradition’s origins in radical questioning. For Heidegger and Strauss, the recovery of the original premises of philosophy cannot be separated from rethinking the very possibility of genuine philosophizing. Common views of the influence of Heidegger’s thought on Strauss suggest that, after being inspired early on by Heidegger’s dismantling of the philosophical tradition, Strauss took a wholly separate path, spurning modernity and pursuing instead a renewal of Socratic political philosophy. The book rejects this reading and maintains that Strauss’ engagement with the challenges posed by Heidegger—as well as by modern philosophy in general—formed a crucial and enduring framework for his lifelong philosophical project.