Schwab, Leisa ElizabethNo system of laws and political institutions is without gaps, and leaders are required—often in the face of uncertainty and under a heavy burden of risk—to fill them. This project adopts a view of individual leadership that finds its roots in the ancient world with Plato, but which speaks to modern problems like the role of appointed administrative officials in a complex democracy and the problems of autonomous weapons. It is composed of a series of papers exploring this gap-filling leadership activity in a modern democratic state from both normative and descriptive perspectives. The first paper, “Making Ourselves Accountable: An Ethics for the Administrative State” addresses the discretionary decision making by un-elected officials through which many of our society’s important leadership decisions are made. It argues for the necessity of these leaders and recommends criteria to guide their decision making in conformity with contemporary democratic ideals. The second paper, “Seeking Standards for Leadership Reasoning in the Executive Branch by Analogy to Representation and Judicial Reasoning,” looks deeper into the work of such leaders to better understand the place of their role in shaping the law alongside legislative representation and judicial discretion. The third paper, “A Different Kind of Responsibility Gap: Trust and the Burden of Risk as a Limit on Military Automation” considers the problem of autonomous weapons in the context of this theory of the individual leader as a necessary component within the legal and institutional system. Inspired by ancient notions of the activity of governing as an activity fundamentally about leaders before it is about laws, it argues that even fallible human leaders who fall short of the ideal remain necessary no matter how sophisticated or accurate an automated system we may devise.enDissertationPhilosophyLawPolitical scienceAdministrative StateAutonomous WeaponsDecision MakingExecutive DiscretionLawLeadership