Machiavelli's chapter on fortuna, which distills the teachings of The Prince, promises success to the prince who will adapt to the times. But when Machiavelli adds that one can never adapt, he implicitly withdraws the promise and leaves the prince naked before fortune. While others view this chapter as the shoal on which the text's optimistic teaching runs aground, I argue that the failure is strategic; like Machiavelli's anomalous treatment of Cesare Borgia, it points to the coherence underlying an apparently inconsistent text. In appropriately Machiavellian fashion, the work is not, as it purports to be, a handbook on princely success. Instead, it represents a characteristically audacious attempt to reconcile self-serving aims: to secure the author employment, to spur the Medici on to the task of unifying Italy, and, paradoxically, to draw his prospective employers and the potential instruments of Italian glory—once they have served his threefold purpose—to their ruin.