This article examines Niccolò Machiavelli’s account of virtues in his famous work The Prince. The Italian philosopher uses three different stages or steps of argumentation. All these steps are analyzed in this paper. It is argued that in each step, Machiavelli makes partial conclusions which are neglected in the next step. In the last step, Machiavelli concludes that not only some virtues lead to failure, but all virtues are harmful to a successful leader. Instead of an honest and just way (...) of acting, Machiavelli proposes the slyness of a fox – the most effective and successful way of acting. Cicero’s De Officiis effectively helps to understand the radicality of Machiavelli’s account of virtues. Cicero’s work enables one to explain all the central metaphors and analogies used in Machiavelli’s The Prince. Comparing Cicero’s and Machiavelli’s radically different accounts of the same virtues and vices shows that Machiavelli changed the traditional understanding of virtues, thus refuting traditional moral and political philosophy. -------------------------- Received: 05/01/2023. Reviewed: 20/02/2023. Accepted: 30/03/2023. (shrink)