In order to consider the interaction between psyche and history, this chapter addresses the role of German Kaiser Wilhelm II in the period directly preceding the start of the First World War. The first part of the chapter examines the Kaiser’s rise and fall through the contemporary German public’s eyes – a history that is seldom told. The second part of the chapter considers Thomas A. Kohut’s psycho-historical analysis of the young Wilhelm. Kohut’s study was published a quarter of a century ago yet still challenges historiography today because it provides essential historical and psychological insights into the Kaiser’s actions and avoids reductionist explanations of the First World War. The development of a psychoanalytic perspective on the role of the Kaiser enables us to appreciate the complex history of the time and the entanglement of political and psychological factors that led to the end of the Kaiserreich and the July crisis of 1914.