The outcomes of urban redevelopment projects are never predictable, nor do they conform perfectly to any single ideological expression of contemporary development approaches, whether that of rational master planning for the public interest, a market-driven neoliberal approach in the name of the competitive world class city or some other vision of utopia. We argue here that a critical pragmatic analytical lens can be applied usefully to improve our understanding of the justifications, qualifications and compromises that contribute to shaping such projects in their contexts. The critical pragmatic approach, deriving from the work of Laurent Thévenot, Luc Boltanski and others, is offered here with illustrative applications to the case of a major redevelopment project in Vancouver, Canada. The approach is situated within planning theory related to governmentality, communicative action theory and American pragmatic philosophy. We establish the utility of studying disputes in the public sphere surrounding development projects, in terms of the objects and actors involved in particular contexts (as opposed to a pure discourse approach) and in terms of the nature and trajectory of compromises attempted and attained in the process (as opposed to consensus-seeking or governmentality approaches).