This article investigates some of the various ways in which theorists have used Machiavelli (and more specifically The Prince) in a business and management context and suggests that the two most common approaches, the use of metaphor and the use of analogy, are both flawed. Metaphor often relies on a reading of Machiavelli that cannot be sustained, whereas analogy takes Machiavelli too far out of historical context. This article discusses how business and management can more usefully incorporate Machiavelli’s ideas by placing them within a tradition of discourse, along the lines of Lockyer’s historical method. We outline three potential discourses: those of humanism; of guides to leadership; and of power. In so doing the article suggests that historical texts (in particular Machiavelli) can prove useful to students and practitioners of business and management.