This paper examines historical and contemporary processes of urban (re-)development and displacement in Uganda. Particular focus concerns the often conflicting strategies employed by urban managers and residents to plan, govern and live in both the late-colonial and early twenty-first century city. Both eras can be considered significant, even momentous, for the prominence of strategic projects of socio-spatial urban reconfiguration that incorporate(d) powerful discourses fusing land and housing development with societal progress and national development. The former project putatively centred on orchestrating African development and welfare, the latter on the more ambiguous project of re-development. The ‘Good City’ and the ‘Good Citizen’ are used as heuristic devices to examine the planning ideals and rationalities that inform(ed) these projects and the conflict of rationalities they provoke(d), particularly in terms of competing visions of the good city and good citizen. The paper emphasizes that current projects of redevelopmentalism do not take place in politically inert or historically benign space. Rather, it is shown how historical and place-based specificities articulate with and mediate the process of redevelopmentalism in Kampala and Jinja.