On the Subject of Masochism interrogates the changing meanings of masochism in late nineteenth and twentieth century psychiatric and philosophical discourses. I merge queer theory, feminist theory, and the history of psychiatry by historicizing the valorization of passivity, shame, and negativity, probing the liberal subject's naturalized desire for freedom, and uncovering relationships between gender, race, psychiatry, and theory. In tracing masochism's movement from the clinical to the critical, I argue that masochism, which originated in Austrian psychiatric literature as a pathology to describe those who desired submission, is a flexible term that describes hierarchies of power, gendered and raced relationships, and concepts of rational and irrational subjectivity. Taking Richard von Krafft-Ebing, Sigmund Freud, Frantz Fanon, Simone de Beauvoir, Michel Foucault, Gilles Deleuze, and Judith Butler in turn, the dissertation uses masochism as an analytic to understand their articulations of freedom, governmentality, and subjectivity. Through historicizing questions and concepts in critical theory using a methodology that I term empathetic history, the dissertation focuses on the situated and embodied nature of reading theory thereby illustrating the contingent and political nature of knowledge, theory, and science.