This qualitative analysis describes the parallels between Carolyn Heilbrun’s nonfiction writing, her Amanda Cross novels, and Heilbrun’s real-life experiences as the first woman tenured at Columbia University amid the social movements of the 1960s and 1970s. Heilbrun’s nonfiction insightfully deconstructs gender issues in society. She turned to fiction as Amanda Cross, however, to expose the unrelenting differential privilege in the academy. Conflict theory, although not identified as such, permeates her writings, both novels and nonfiction. The underlying theme, differential privilege, is examined through four manifestations: response to war, women’s perspectives on women, the attitudes of the privileged toward others, especially men toward women, and the institutionalized privilege in the highly stratified practice of higher education. These observations remain relevant and applicable for dealing with today’s issues with differential privilege.