The aim of this paper is to examine Cioran’s interpretation of Maistre’s reactionary thought. Cioran judges the philosophical work of De Maistre as a useful instrument to investigate the Twentieth century ideological debate on Revolution, with specific reference to the issue of the engagement of philosophers in politics. Through the analysis of Maistre’s criticism of revolutionary thought at the time of the Enlightenment, Cioran proposes an insightful deconstruction of the ideological dichotomy between Reaction and Revolution. Indeed, the paper will show that Cioran’s understanding of De Maistre implies both a radical criticism of Sartre’s existentialism and an original interpretation of Schmitt’s Political Theology.