Gloria Naylor’s 1985 novel Linden Hills employs Dantean allegory to examine the relationship between material success and cultural identity within African American middle-class communities. This article analyzes how Naylor constructs a moral geography that maps social ascent onto spiritual descent, revealing class mobility as a process of racial self-erasure. Through close reading of the novel’s structural architecture, characterization, and thematic preoccupations, this study demonstrates that Linden Hills critiques bourgeois assimilation by staging material acquisition as incompatible with communal belonging and cultural embeddedness. The analysis situates Linden Hills within Naylor’s broader fictional project, contrasting its vision of alienated prosperity with the culturally grounded communities depicted in The Women of Brewster Place and Mama Day. This comparative approach illuminates Naylor’s sustained interrogation of identity politics, gender, and the costs of respectability.