While Niccolò Machiavelli’s political theory generally focuses on the subject’s power of action, a large part of his writings arises from a situation of enforced leisure and thus, at least ‚prima facie‘, political powerlessness. On the basis of selected letters from the correspondence with Francesco Vettori, the present article examines the specifically political scope for action of this Machiavellian leisure. The latter gains its power and its potential Machiavellian effectiveness precisely by permanently deconstructing the seeming opposites of activity and passivity, ‚vita activa‘ and ‚vita contemplativa‘, political and private, power and powerlessness. Finally, by analyzing a broad spectrum of ‚otium‘ and leisure practices that ultimately transcend such oppositions, a new model of political practice can be developed in and through leisure.