This article explores the puzzling behavior of tyrants who undermine themselves once in power. Therealpolitik perspective and a variety of psychological frameworks are used to try to resolve this puzzle in the cases of several ancient and three contemporary tyrants. Although all the frameworks used have explanatory power, the one that most closely fits the tyrants studied here is that of the narcissist with severe superego deficiencies. An individual with such psychological characteristics may have some advantages in rising to power, and his behavior may be an effective response to some real-life factors, but once he has consolidated his position his reality-testing capacities diminish. Fantasies held in check when his power is limited are apt to become his guides to action. As a consequence, his behavior becomes more erratic, he runs into difficulties in meeting his goals, and his paranoid defenses become more exaggerated. The finale of a tyrant’s career depends on the particulars of his political and social situation.