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Contemporary urban political economy emphasizes the role of structural factors in explaining the deindustrialization of cities in the post-World War II era. Urban economic restructuring, by most accounts, has left city officials with few choices other than to pursue corporate-centered economic development strategies emphasizing downtown-area commercial and residential growth. In Chicago, however, a corporate-center redevelopment strategy advanced by a coalition of downtown business leaders competed with a production-oriented strategy articulated by a coalition of neighborhood organizations, manufacturers, and labor. Centrally located industrial districts facing gentrification pressures became contested terrain, and manufacturers ultimately benefited from protective measures put in place by a sympathetic administration. This essay argues that urban economic restructuring is open-ended and politically contested. It concludes that a fuller appreciation of the contingency of urban economic development would help uncover viable regime types featuring governing coalitions that include both community-based organizations and neighborhood business establishments.