This is the first book-length study to provide a structured interpretation of the significance of Michael Oakeshott’s critique of the Enlightenment . By seeing the thinker as a ‘sceptical idealist’ posing a serious challenge to the intellectual positions informed by the Enlightenment , this book attempts to resolve some of the issues debated by Oakeshott scholars. The author argues that Oakeshott’s famous critique of philosophisme and Rationalism in fact expresses a sense of the crisis of philosophical modernity. Moreover, notwithstanding some recent interpretations, throughout his intellectual career Oakeshott has never altered his analysis of these two themes: philosophy as the persistent re-establishment of completeness by transcending abstractness, and the modes of experience as self-consistent worlds of discourse. To apply this philosophy in his moral and political writings, Oakeshott has redressed an imbalance in favour of the Enlightenment ethical position - ‘the sovereignty of technique’, ‘demonstrative moral truth’, ‘the politics of faith’ and ‘enterprise association’ - by revitalising the importance of ‘traditional knowledge’, ‘conversation’, ‘intimation’, ‘the politics of scepticism’ and ‘civil association’. Oakeshott is neither a doctrinal liberal nor a dogmatic conservative, but a philosophical sceptic. Moreover, Oakeshott’s contribution to history not only lies in his effort to transcend the Enlightenment historiographical position - by separating the historical from the naturalised conception of History on which so-called ‘scientific history’ rests - but also in his idealistic solution for the ‘temporal dilemma’ and the ‘epistemic tension’ in history that have long bothered philosophers.