I argue that the leadership task of economic management is possible, as history has demonstrated, yet exceedingly difficult for at least five reasons presented in the chapter. Underlying these reasons, I claim, is the structurally critical but nevertheless anomalous position that the democratic leader must occupy, as the essential hinge linking a democratic polity with a liberal economy. In their democratic role, leaders are agents and representatives of the people, concerned first and foremost with safeguarding the people's welfare; but as economic managers leaders must be solicitous of an economic system whose fundamental principle is founded not in democratic theory but in liberalism. Liberal democratic leaders believe, of course, that ensuring a healthy economy is the surest way to fulfilling their democratic responsibilities, but in times of economic trouble the tensions within the historical marriage of liberalism and democracy become acutely apparent. Leaders find themselves with the dilemma of trying simultaneously to meet the conflicting demands of liberal economy and democratic polity.