This article examines the transformation of community development in Chicago in the last three decades from a predominately grassroots movement for social change to a much smaller and fragmented one led by professionalized groups. It focuses oil Harold Washington's and Richard M. Daley's mayoral regimes and the ways they helped to shape the context and implementation of community development. The major theine in the article is that this movement lost most of its capacity to be innovative and to contribute to progressivism (most evident under the Washington administration) when it lost its basic connections to grassroots leadership under the subsequent Daley administration. As a consequence, problems like poverty, homelessness, poor schooling, and greater racial and class divisions have resulted. The discussion and analysis is based oil interviews of people involved with both regimes and a review of changes in policies and practices between the Washington and current Daley (Daley II) period. The article concludes with a sober overview of how community development has been absconded to serve the interests of progrowth and corporate interests rather than used as a tool to promote fairness, access, and equity in low-income neighborhoods.