Despite their widespread influence, Martin Heidegger's works have rarely been assessed for their own direct significance as political theory. In this article I undertake such an assessment by drawing out the political implications of Heidegger's understanding of freedom and community in two of his early works. Specifically, I argue that, although Heidegger's thought has been interpreted as advocating political conservatism, it in fact propounds a new kind of radicalism which is neither precisely conservative nor progressive, although decidedly revolutionary. When this is brought to light, it is easier to see the connection between Heidegger's works and the earlier Philosophy of Freedom, as well as ways in which they anticipate important trends in contemporary political thought.