Modern city planning theories were widely accepted in the early twentieth century producing many ‘City of Towers’ neighbourhoods throughout Toronto and the world. Although cities in the twenty-first century are being planned with the inclusion of human needs, remnants of the twentieth century city planning are still present within our built environment. The current methods of revitalizing existing City of Towers neighbourhoods are band-aid solutions that are not sustainable in the long run. This thesis investigates how alternative strategies can provide a more integrated solution without taking the tabula rasa approach. Architecture and other built forms are used to propose strategies that will produce a new relationship between existing buildings and their surroundings to meet the needs of residents today and in the future. St. James Town located in Toronto, Ontario is selected to investigate the hypotheses of this thesis to give expression to the topic of Bridging Divides|Creating Connections.