Walter Benjamin said that "the realization of dream elements, in the course of waking up, is the paradigm of dialectical thinking. Thus dialectical thinking is the organ of historical awakening." This Benjaminian search and his longing for historical awakening serves as the driving force of this book. And if we are going to explore the mysteries of dreaming and the possibilities of awakening, who better than Freud to accompany us in that journey. One of my main contentions is that by bringing together Sigmund Freud and Walter Benjamin, the interpreter of dreams and the interpreter of history as dream, we encounter a productive constellation of concepts and ideas on history, politics, dreams, and their dialectical interaction. I argue that if we think about Freud and Benjamin together we will find that the historiographical proposal that comes out of this encounter can shed light on how we look at the relation between history, politics, and dialectical thinking. More importantly the Freud/Benjamin encounter provide us with an approach to history and politics that renders our understanding of the historical as a primary political problem. This book will be of interest to social scientist, political theorists, and those interested in the relation between politics and history.