The essay explores the ways in which Edith Wharton’s early work, written as facts were emerging about corrupt insurance industry practices, inspired questions that Wharton would raise throughout her oeuvre about the monetization of life and death, the evaluation of pain and suffering, and the larger consequences of a managed and insured society. By the early twentieth century, insurance was a central institution in the organization and management of modern life, although it is rarely recognized as a cultural force or context in Wharton’s work. This essay corrects this neglect by asking how an early twentieth-century insurance scandal inspired Wharton’s exploration of a growing wound culture intent on regulating and managing pain and suffering, life and death, and by examining Wharton’s representations of a managerial society rather than the society of manners for which she is still best known.