This book examines Oakeshott’s political philosophy within the context of his more general conception of philosophical understanding. The book stresses the underlying continuity of his major writings on the subject and takes seriously the implications of understanding the world in terms of modality. The book suggests strongly that Oakeshott’s philosophy of political activity cannot be reduced to a branch of conservatism, liberalism, or postmodernism or a theory or set of doctrines which fit neatly into any conventional school, like that of Idealism or Skepticism. Rather, Oakeshott’s philosophy of political activity is a provocation to all of the currently dominant schools of political theory and political practice. It questions their presuppositions and exposes as ambiguous, arbitrary, or confused all of the supposed certainties which they take for granted. It does all this by offering profound insights into the character and limits of both political activity and political theory in the modern world.