Ontario Place in Toronto has a long legacy of unfulfilled plans, conflicting interests and missed opportunities. Its evolution is punctuated by myriad socio-cultural, political and economic shifts. Landscape biography, an empirical research strategy, is used to capture the diversity, complexity and the transformational character of this landmark site through archival research and oral histories over five phases of development. With origins in cultural geography and social anthropology, landscape biography is a compelling analytic tool to study the evolutionary dynamics of landscape change. Ontario Place is closely examined within the broader context of Toronto’s post-industrial waterfront to highlight and explain contingent moments in this cultural landscape’s historical trajectory. Findings reveal that Ontario Place, like waterfront itself, is the aftermath of political indifference and short-term expediency multiplied over several years. A road-map is created to visualize long-term evolutionary cause-and-effect relationships and a framework is developed to provide guidance for future transformations of this public asset based on historically grounded research.