Urban redevelopment projects persist predominantly within the Downtown central business district of the Kingston metropolitan area. This narrow spatial focus of redevelopment projects and efforts ignores the implication for development of the wider metropolitan area and the national urban structure. Evidence suggests that the efforts put in urban redevelopment have achieved moderate success in a few areas and have failed, in others, to provide the revitalisation and renewal energy needed t\o manage contemporary socio-demographic, spatial and economic dynamics and ensure urban sustainability. Compressing data and information collected over the last 10 years from various pertinent sources the research also draws upon a large volume of intellectual literature. The myriad of negative consequences of the redevelopment efforts since 1907 to date have all ultimately linked to ineffective urban management, lacking both philosophical and technical base. The experiences are valuable tools in improving the future relationship between urban redevelopment and urban development.