This article examines the political, psychological, and moral challenges of senior public service in the executive office. The study uses memoirs published by members of the Clinton administration. The memoirs discuss the consistent background conditions of senior public service as the personality of the chief executive, the vagaries of election cycles, the tension between staff and agency executives, and the role of the media. Senior executives adopt a number of stances to address the tension between the realities of public service and the ideals they bring. The memoirs suggest several stances, such as politics as original sin, seduction, hard work and compromise, and game. The memoirs demonstrate the high cumulative cost that public service exacts on the health and personal lives of senior officials. Finally, the study reveals a number of consistent themes about how senior appointed public officials can navigate the dilemmas and challenges of senior public service at all levels of government.