The book explores Oakeshott’s thought on the key role human imagination plays in relation to the political. It addresses four main themes: imagination, foundational narratives, the question of political societies’ identities as well as that of human living-together, to use Hannah Arendt’s expression. The book’s main objective is to show that Oakeshott may be rightfully understood to be a philosopher of the imagination as well as a foundationalist thinker in the Arendtian narrative constructivist tradition.