One of the celebrated features of the emergence of ‘complexity thinking’ on the research scene is its acclaimed ability to cut across disciplinary boundaries, offering potential explanations to pertinent issues that have haunted ‘experts’ and bureaucrats for a long time. In the field of urban studies, such vexing questions revolve around the notoriety and reluctance of the urban system to be harnessed into our-own-made, control-oriented predictive models. Despite the prevalence of copious volumes of literature on the subject, there are still more questions than answers in the understanding of the urban system. This paper attempts to view urban regeneration through the lenses of complexity theory. The task involves a historical narrative that weighs the evolution of the regeneration processes of a once highly deprived inner city area of Hulme in Manchester against the characteristic features of complex adaptive systems. A premium is placed on the analysis of the design platform and processes that saw Hulme emerge from worst slum in Manchester to one of the exemplars of regeneration in England. The analysis goes beyond mere explanation by making a commitment to securing potential areas for better-informed intervention. The fundamental argument that is championed is that even prior to central intervention, there is usually a resilient prior reality that characterizes that particular setting and that successful intervention is a function of how well a programme conforms to these natural tendencies.