Community organizations are increasingly turning toward the arts and historic preservation to catalyze community economic development, although both strategies have complex histories related to gentrification and placemaking. In the late twentieth and early twenty-first centuries, the arts and historic preservation have been variously framed as victims, bystanders, and instigators of gentrification. While policymakers have hailed the arts and preservation as cutting-edge economic development strategies, scholars have criticized economic developers, large arts organizations, and historic preservation advocates for art and preservation as strategies that prioritize exogenous urban renewal rather than endogenous community development. There is minimal research, though, on organizations that have intentionally pursued a nexus of arts and preservation, particularly within the context of shrinking/declining cities. This article begins to fill this gap through a qualitative case study of Cleveland's Detroit Shoreway Community Development Organization (DSCDO) and its signature effort to revitalize the Gordon Square Arts District. DSCDO evolved from a low-capacity organization focused on basic maintenance, public safety, and community organizing into a high-capacity community development corporation that embraces the nexus of arts and preservation to propel both the neighborhood and organization forward.