The article proposes a cosmological reading of the Fortuna theme in Niccolò Machiavelli's fictional and non-fictional writings. Within the framework of a cosmological order of spheres, the ‘many wheels’ of Fortuna cited by Machiavelli can be understood as a quantitative extension of the traditional analogy between the Earth’s round and Fortuna’s wheel. The success of an enterprise is therefore determined by the stars and consequently by Fortuna and can only be achieved when the cosmic influences harmonize with human action. As the comparison of the author's political writings with the play ‚La Mandragola‘ shows, man, according to Machiavelli, only hypothetically and in fiction is able to influence the stars and shape his own fate, while, in reality, he remains subject to the course of the stars and the rule of Fortuna.