The relevance of Machiavellian theories of political leadership to school administration is examined in this paper, with a focus on the superintendent/school board relationship. As the first modern political theorist, Machiavelli used empirical observation and generalization to understand that perceptions are more real in their consequences than reality itself. Themes include security over virtue and the usefulness of being feared. He argued that politics is about the power and security of the state. From this viewpoint, the school superintendent is a political leader who addresses the political realities of the job. In a time of educational controversy, Machiavellian thought may prove to be interesting reading material for school superinttendents. (LMI)