In 1995, the U.S. Department of Housing and Urban Development (HUD) took over the Chicago Housing Authority (CHA) on grounds of mismanagement and failure to revitalize a failing housing stock. When the CHA regained independence five years later, in 2000, the agency launched the most extensive redevelopment effort of public housing in the nation’s history. This paper assesses the extent to which the CHA has succeeded in meeting the directive outlined by the Plan for Transformation. It concludes that, despite setbacks in meeting specific goals, the CHA has demonstrated itself to be an effective and accountable housing agency. Nonetheless, the CHA needs to addresses shortcomings in the transparency of management, efficiency of operations, and accessibility of services.