The dramatic rise of remote work threatens the traditional source of urban growth—the unique ability of dense cities to provide a setting in which firms and employees share productive resources, match needs with skills, and transmit knowledge at low cost. These “agglomeration benefits” have induced cities to pursue clusters of related firms that have served as the basis for local economic development and technological innovation. Remote work reduces the necessity for related firms to co-locate, and its popularity has led commentators to predict significant decrease in city business activity, tax revenues, and services as traditional clusters dissipate. It remains unclear how cities will react to the remote work phenomenon. Prior episodes of cluster decline, however, reveal that cities have difficulty pivoting to new economic models when outmoded ones threaten local decay. Instead, cities tend to support existing clusters, notwithstanding that the impending decline is a function of external forces rather than of local policies. This article addresses the potential mismatch between cluster decline that may flow from remote work and city responses. The article theorizes that continued municipal efforts to support a declining cluster emerge from the ability of affected firms to coalesce, exercise political influence, and exploit fragmented municipal decision making to preserve the status quo, maintain or increase municipal subsidies for the cluster, and deter entry by competitors for city resources. Those strategies impede the city’s transition to a more productive economy in the face of looming cluster decline. The article then turns to the history of the garment industry in New York City to illustrate the theory. That history provides a cautionary tale about how cities should and should not respond to the threats they face from remote work.