This article examines the Chicago Brownfields Initiative and its effect on the communities in which brownfield redevelopment has already occurred. After examining the many federal, state, and local brownfields programs, it critically examines both the successes and concerns of the Chicago Brownfields Initiative. The successes include job creation and retention, residential redevelopment, improvements to quality of life, services and amenities provided, encouragement of additional investment, increased tax revenues for local governments, and increased environmental health and safety. The concerns include whether the jobs generated benefit the members of the brownfield communities, whether the new services and improvements benefit members of the brownfield communities, whether brownfield redevelopment led to gentrification, and if the site remediation was sufficient to protect community health and safety. The article concludes that the Chicago Brownfields Initiative has been very successful, but can be strengthened to encourage economic and environmental improvement within the surrounding brownfield communities.