Heidegger is often said to be the most important philosopher of the twentieth century, but the political import of his thought is by no means easily discernible. He has been associated with a striking variety of political positions, from left to right, West to East, peaceful to violent. This dissertation argues that this variety is best understood as deriving from two discreet inflections: a particularist-revolutionary inflection and the quietist-awaiting inflection. The 'paradox' of Heideggerian politics is the necessary proximity of these two inflections to one another. The proximity derives from the treatment of actually existing 'everyday' arrangements and institutions as at once essentially paltry, ephemeral, and evanescent and yet also constituting the only available route to the most important question, the question of being. Of the two inflections, the 'particularist-revolutionary' treats the everyday as the product of arbitrary and willful historical human activity and thus calls for a revolutionary retrieval of unexhausted resources from a people's 'ownmost' history. The 'quietist-awaiting' inflection, however, regards the existing status quo as having been granted by the unfathomable endowments of Being and therefore entails a submission to the political order as it has been determined and a quietist waiting for a new dispensation of Being. Through supplying textual interpretations of several of Heidegger's most important writings, the dissertation argues that the ambiguous political import of Heidegger's thought derives from his characteristic approach to fundamental ontology. It concludes that Heidegger's bequest to his successors is the requirement, for which his thought does not supply adequate means, to negotiate the tension between the demand for the revolutionary transformation of politics and the retreat from politics.