A vital policy initiative fails due to skilled opposition. A fine program disintegrates under pressure of an unanticipated backlash. A powerful and strong institution collapses when its long-time leader departs. A new leader full of good intentions soon flees office overcome by frustration and ineffectiveness. These all-too-familiar examples highlight haunting reality that good intentions, moral conviction, and even technical competence do not guarantee success in political and administrative life. This disjunction of ethics and achievement has inspired many to despair of relationship between ethics and leadership, best summed up by Niccolo Machiavelli, the man who wants to act virtuously in every way necessarily comes to grief among so many who are not virtuous. Therefore if a prince wants to maintain his rule he must learn how not to be virtuous (Machiavelli, 1973, 15). This realist view argues that leaders cannot afford ethics in a world of serious responsibilities, powerful institutions, and committed adversaries (Morgenthau, 1959; Watz, 1957; Cohen, 1987). The realist view competes with an alternative moral conception of leadership in natural law and Kantian traditions, which argues that leaders should follow requirements of ethics (Gierke, 1934; Kant, 1957). The leadership literature reflects this split between realpolitik and moralism. Classic studies focus upon tactical and personality dimensions of successful leadership (Neustadt, 1976; Tucker, 1995). A number of writers, however, call for an explicit recognition of moral nature of leadership (Burns, 1978; Gardner, 1990; Terry, 1995). These studies succeed in identifying moral nature of leadership but seldom provide consistent guidelines about where leadership ethics should focus. Recent theorists have argued that a virtue based ethics focuses upon moral quality of person and can inform an ethics of leadership (Galston, 1991; Norton, 1991; Cooper, 1987; Cooper and Wright, 1992). From time of Aristotle, theorists have argued that of all virtues, prudence represents linchpin of political judgment and that any theory of leadership needs to develop an account of prudence (Coll, 1991; Dunn, 1985; 1990, esp. 199-215; Dobel, 1990). Building on this tradition, I will argue that political prudence is a central moral resource for political leaders. This article presents an account of political prudence focusing upon its operational requirements. These requirements provide a moral framework to guide and evaluate actions. This article will discuss relationship between virtue and leadership, prudence as a virtue derived from requirements of political achievement, and normative responsibilities and obligations that flow from political prudence. Virtue and Leadership Leadership entails ethics because leaders have responsibilities. Persons in positions of leadership make a difference; they can bring about changes in behavior that would not occur without their presence and actions. Leading is not always linked to official authority; in fact, leadership opportunities exist throughout political and organizational life. Individuals or institutions rely on leaders to accomplish tasks. Fellow citizens, colleagues, and subordinates depend on leader and arc vulnerable to consequences of his or her actions. They rely on leader's competence and promises. Citizens depend on official leaders to protect their security, welfare, and basic interests. Colleagues and other officials depend on leaders to enable them to perform their work. Leaders who hold office are responsible for respecting that reliance, vulnerability, and dependence. The ethics of responsibility requires leaders to attend to consequences of their actions (Weber, 1969).(1) Their first responsibility, however, resides in what Adam Smith called self-mastery. All virtues and personal capacity to live up to promises, obey law, and follow directives depend upon this primary moral capacity (Smith, 1976, III, 6, 3). …