This article examines the place of Machiavelli’s Prince in the history of ethics and the history of leadership philosophy. Close scrutiny indicates that Machiavelli advances an ethical system for leadership that involves uprooting corruption and establishing rule of law. He draws on history and current affairs in order to obtain a realistic understanding of human behavior that forms a basis for a consequentialist ethics. While he claims a good leader might do bad things, this is in situations where necessity constrains a prince to choosing the “least bad” course of action. Furthermore, Machiavelli advocates winning the goodwill of followers through leadership as a source of power. Machiavelli’s leadership ethics has a sophistication not fully enjoyed by his reputation in management scholarship. He would not score as especially “Machiavellian” on the Mach IV. Many of his ideas contain seeds for theories that are now considered important for leadership today.