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Byline: Saeed Parto This paper examines the causes of the failure by the Region of Waterloo (Ontario, Canada) to meet its objectives on sustainability. The analysis shows that in such macro matters as sustainability, scale does indeed matter, as do numerous other factors including the degree of trust in interrelations, perceptions and convictions, conflicting interests and competing agendas, the manner in which discourse occurs on policy formation and implementation, and ideology as expressed through partisan politics. This paper contributes to the discourse on sustainability in two ways. It proposes an evolutionary, multi-dimensional analytical framework to study sustainable development. The framework is then applied to a case study to underline the political implications of operationalising sustainable development