This essay examines the US literary publisher Grove Press from 1951 to 1970. During this period, Grove promoted an aesthetic that Susan Sontag termed the “new sensibility,” one that valued impersonal sensations over personal expression. Grove thus became a key mediator between humanism and antihumanism, publishing many of the major literary works cited by poststructuralist thinkers. This editorial sensibility found its roots in the class character of the press, which was headed by affluent radical Barney Rosset. Drawing on close readings of key publications, as well as of editorial discourse such as advertising and marketing surveys, this essay argues that the masochistic fantasies of self-shattering featured in Grove’s publications allowed its imagined audience of professional-managerial class radicals to appear to transcend their economic positions. In the pages of Grove publications, white-collar masochists styled themselves as revolutionary suicides or self-destructive saboteurs squandering the human capital of the organizations in which they worked. Nevertheless, this imaginative solution failed to overcome the press’s own class contradictions, which came to a head during the unionization drive and feminist protest occupation of Grove in 1970.