This essay examines the theme of masochism in the metapsychological work of French psychoanalyst Jean Laplanche. One of the most distinctive aspects of Laplanche's work as a whole is its recursiveness: it advances by repeatedly retraversing the same themes and rereading the same Freudian texts, often after intervals of years and each time from a deepened critical perspective. The approach taken in this essay is therefore diachronic. That is, rather than seeking to present a reduced summation of Laplanche's position on masochism, it tracks the recursive evolution of his thinking about masochism, from the 1960s through to the development of his celebrated "general theory of seduction." The essay locates each of Laplanche's key interventions on masochism within the broader frameworks of his theoretical enterprise, and positions masochism as a point of orientation for understanding a number of the essential claims of his metapsychology, particularly the relationships among fantasy, pain and the drives; the economic dimensions of human desire; and the intersubjective origins of psychosexuality. Finally, the essay suggests that masochism might have a particular pertinence to psychoanalytic thinking as Laplanche conceives and practices it: that is, as a pains-taking labor whose very stimulus is the "wound" of the Freudian breakthrough.