In the field of political theory, few authors have spurred intellectual tirades and triggered collective fantasy as much as the sixteenth-century Florentine Secretary Niccoló Machiavelli. Despite all controversies, in the discipline of International Relations (IR) Machiavelli and his The Prince have been almost exclusively associated with classical realism. This largely unchallenged association contributed to the edification of the myth of The Prince as the ruthless symbol of raison d’état, carrying transcendental lessons about the nature of politics and a set of prescriptions on how helmsmen should behave to seize, maintain, and reinforce their power. The realist hijacking of Machiavelli is at the core of the foundation of classical realism as an IR theory and its location at the very epicentre of IR as a discipline. This appropriation has, in turn, obscured alternative myths of The Prince, which depart from Machiavelli’s reflections on the Principati nuovi to read The Prince as a radical manifesto for political change. The opening of the semantic space in the field of IR – spurred by the so-called interpretive turn – offers an opportunity to break this monochromatic reading. This article delves into two competing myths of The Prince: the classical realist myth and Gramsci’s ‘progressive’ one to demonstrate its contested nature.