Gentrification is often described metaphorically as a form of ‘colonization,’ however in this paper I argue that gentrification comprises one strategy in the continued historical colonization of Indigenous peoples in the Canadian context, and more specifically in the settler city of Toronto. I propose that the colonial relationalities, both symbolic and material that give rise to the settler city, persist as a discipline on poor and Indigenous bodies, spaces and lands, through the capitalist way of life. Colonial relationalities are again heightened through gentrifications role in Toronto’s strivings for global city status in a neo-imperialist global economy. Gentrification is based on moral investments in the capitalist ideology of private property and monetary investments in shifting of property values. Investment in private property is fraught with the ethical contractions of land theft, exploitation, ongoing original accumulation, and displacement, which form the basis of homelessness and Indigenous marginalization in the city. However, gentrification theory and Marxist geography do not fully or consistently account for the implications of colonial history in the current understanding of gentrification. Neil Smith, for instance, relegates Indigenous history and epistemologies to an irrelevant past failing to unsettle or decolonize the notion of gentrification. Other Marxist theorists, who have attempted to connect issues of gentrification and colonization offer a way forward to a decolonized understanding, however, more engaged dialogue with Indigenous scholars and communities are necessary to continue this discussion in a more liberatory direction.