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Earlier studies of Canadian inner‐city gentrification, especially in Toronto, project an image of the process as being emancipatory: a middle‐class reaction to the oppressive conformity of suburbia, modernist planning and market principles. This paper, a case study of gentrification in South Parkdale, Toronto, questions this image by illustrating the role of local context in theory and policy and the consequences of gentrification for vulnerable inner‐city populations. Once a desirable residential neighbourhood, South Parkdale experienced disinvestment following the construction of the Gardiner Expressway in the 1960s and also experienced further problems in the 1970s and 1980s following the deinstitution‐alisation of psychiatric patients from adjacent hospitals. Discharged patients suffered from a shortage of affordable housing options, and many ended up in substandard rooming houses and bachelorettes, of …