Niccolò Machiavelli (1469–1527) never wrote any subtle disquisition on esteem (stima in Italian). Even so, this essay suggests that esteem played an important and hitherto largely unexplored role in Machiavelli’s political thought. Proceeding from an examination of Machiavelli’s use of the noun stima and the verb stimare in their literal and figurative senses, this article discusses Machiavelli’s ideas from three different perspectives. The first section discusses ways of attracting other people’s esteem through virtuous deeds. The second section, in turning to (...) Machiavelli’s notorious advice to princes, explores the ways in which stima may be generated by merely pretending to be virtuous. I argue that Machiavelli’s new prince exchanges the real esteem he must elicit from his subjects (if he wishes to stay in power) with a surrogate: in other words, a psychological economy of stima. It arrests, through a performative spectacle, the rational faculties of the prince’s subjects. The third section investigates Machiavelli’s ideas on esteem in relation to his own person. Even though Machiavelli never uses the phrase stima di se stesso (which would be a literal translation of self-esteem), some passages from his correspondence are highly pertinent to this topic. (shrink)