This chapter chronicles the development of the short story as a product of the Program Era from its inception in the 1930s up through the contemporary moment, and argues that its history can be understood in terms of the experiences of the college-educated creative class, whose socioeconomic situation is perennially precarious. As shown through illustrations from the Best American Short Stories, two institutions loom large in this history: the New Yorker and the Iowa Writers’ Workshop, which can stand in for the NYC vs. MFA dialectic that shapes the careers of most American short story writers. It is between these poles that the short story has been negotiated and evaluated during the Program Era. For most writers, it is an apprenticeship form, originally addressed to teachers and students and then to other writers and literary professionals, preparing the field for the novel addressed to the larger reading public.