Brownfield redevelopment has become increasingly popular in the first part of the twenty-first century (Hollander, Kirkwood & Gold, 2010) because of the environmental, economic and social benefits realized from remediating and redeveloping brownfields. There has been little research conducted regarding the redevelopment of brownfields in smaller cities that do not have the strong market forces that have spurred brownfield redevelopment in locales such as Toronto and other large population centres. Municipalities with mid to low markets may need to take different approaches to redeveloping their brownfields and the current Provincial policies may not meet their needs. The purpose of this study is to investigate brownfield case studies in the cities of Sault Ste. Marie and Brantford, Ontario and offer explanations as to why some redevelopment plans have failed to occur in these communities and yet nearby sites have had success.