This chapter provides some basic questions about the psychology of the emerging Clinton presidency. It aims to develop a psychological and, more specifically, a psychoanalytically informed analysis of President Bill Clinton's character, political leadership, and presidential behavior. Relying on several complementary data sources, the chapter first briefly outlines some basic elements of his character and psychology as they emerged in the presidential campaign of 1992 and the first year of his presidency. It discusses some associated psychological traits and traces their impact on Clinton’s approach to the presidency. The chapter also suggests some dilemmas for Clinton's presidency and its ultimate success that flow from these characteristics. It examines the character-based personality traits in Clinton and draws some implications for Clinton's approach to political leadership and the presidency. The evidence appears to bear out the observation that Clinton is both determined and resilient.