Are the limits of psychoanalytic politics the limits of the politics of psychoanalysis’s founding father, Sigmund Freud? This article offers an answer to this question by discussing Freud’s political affinities and then recounting a short history of the “Left Freudians,” psychoanalytic thinkers who broke with Freud’s old-style liberalism. Freud was neither a communist nor a political radical, but he was the figurehead of a tradition of inquiry and body of knowledge that lent itself to radical political thought and practice. How does psychoanalytic thinking justify this ideological break? Beginning with anarchist Otto Gross, this article traces a genealogy of radical psychoanalytic thinkers through the historical depoliticization and repression of political psychoanalysis, unearthing its more radical proponents and critiques and substantiating Gross’s assertion that psychoanalysis is preparatory work for the revolution. At the end of the genealogy, the article turns to psychoanalyst Jacques Lacan’s infamous and emblematic encounter with provocateurs from the radical student movement. Neither as domineering nor paternalistic as he seemed, Lacan’s diagnosis of the revolutionaries as hysterical helots should be read as his own provocation for them to clarify their desire, because the purpose of political psychoanalysis is to understand the unconscious desire involved in political acts.