This paper aims to present the main ideas of Claude Lefort's political theory with the goal of determining the relationship between his interpretation of Machiavelli and his reflection on democracy and totalitarianism. In order to achieve this, Lefort's specific methodology for interpreting classical texts and his reflections on Machiavellianism are firstly considered. After that, the focus of the paper moves towards Lefort's interpretation of Machiavelli's works The Prince and Discourses on Livy. Lastly, Lefort's conception of democracy, which is inextricably linked with the theme of totalitarianism, is considered. Lefort's interpretation reveals Machiavelli as a theorist of class conflict who, in the clash of the people and the grandees, takes the side of the people. Given that class conflict is insolvable, Machiavelli calls for its regulation and openness of the political community towards the event, that is towards contingency. Machiavelli's theory is thus shown to be similar to Lefort's conception of democracy as a regime which recognizes conflict and separates power, knowledge and law. Totalitarianism appears as a counter-revolution which aims to abolish democratic indeterminacy. Lefort opposes totalitarian negation of conflict as Machiavelli criticized the negation of class conflict characteristic of Sparta and the Republic of Venice.