There are few psychoanalysts more closely associated with the notion of freedom than Erich Fromm. In 1941, Fromm published Escape from Freedom, which established him as a pioneering psychoanalyst and a public intellectual of global renown. The central chapter of Escape from Freedom was entitled, “Psychology of Nazism,” and in it, Fromm applied the principles of a social psychoanalysis to explain why people would be willing to give up their individual freedoms and embrace an authoritarian leader and a totalitarian regime. With the rise of far-right political parties throughout Europe and the United States, the importance of Fromm’s interdisciplinary study of freedom, and the responsibilities that a positive notion of freedom creates for us, has not diminished. This article revisits Fromm’s Escape from Freedom, focusing on both his social psychoanalytic approach, and on his contributions to understanding the limits of freedom, agency, and dangers posed by the reemergence of a fascist mind-set in the present day.