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This article makes the argument for a reframing and a reconceptualization of the urban-suburban divide which can inform the options and possibilities for transformative practices in urban schools. Drawing primarily from a Canadian, and more specifically a southern Ontario context, the article explores the changing realities of urban within this region; examines the extent to which the suburban and the urban realties have become enmeshed; and explores the educational opportunities that can emerge through that reframing. Reconceptualizing the "urban" is a vital aspect of contemporary and future schooling given the shifting context of actual urban spaces and the people who inhabit them in many of the major city centers of the world. The article also addresses the need for the development of leadership in these urban/suburban school settings that is collaborative, transformative, and moves beyond hierarchical conceptions.