Focusing on the work of Stuart Dybek and a case study of the literature of South Shore, this chapter considers how the neighborhood literature of Chicago has taken shape in response not only to literary antecedents but also to historical changes in the city’s neighborhood order. The emergence of the New Chicago, a post-industrial metropolis that developed through and around the old familiar industrial city, created new possibilities for the city’s writers. Stuart Dybek’s stories of Pilsen/Little Village have made him the dean of the New Chicago’s writers, putting him at the head of a cohort that ranges from Gwendolyn Brooks to David Mamet, Nelson Algren to Gabriel Bump.