Michael Oakeshott's concerns about political developments in twentieth-century Europe seem to shape his philosophical writings. Yet Oakeshott persistently portrays himself as a philosopher who has little practical interest in politics. This essay argues that Oakeshott's genteel conception of the good life leads him to develop a political doctrine for practical reasons while disclaiming any practical motives. His diagnosis of collectivist politics in the 1930s reluctantly solicits a philosophical defense of a pluralist political order that is hospitable to his ethical ideal. His writings concerning the self, society, and state develop such a defense. Yet for Oakeshott, political engagement is incompatible with gentility because it conflates worldliness with spirituality. Oakeshott, therefore, disavows the practical aspirations that shape his work.