This article investigates the impact of public land ownership on long-term processes of urban development by comparing the political histories of waterfront redevelopment in Chicago, Vancouver, and Toronto. The study is driven by two research questions: Why have redevelopment efforts in Chicago and Vancouver apparently succeeded whereas those in Toronto failed? And what was the impact of public land ownership on these outcomes? Drawing from archival, interview, and geospatial data, I argue that land ownership conditions had a defining and enduring impact on the shape and scale of waterfront redevelopment in each city. What separates Toronto’s waterfront from Chicago and Vancouver is not how much land was historically controlled by public versus private owners, but rather the relative distribution and concentration of these assets. Early political events involving the consolidation or fragmentation of land ownership established institutional arrangements that either enabled or inhibited effective implementation.