In early 2020, Stephen Diamond, Chairman of the Board of Waterfront Toronto, faced an all-too common decision for any major urban development – was his project proposal ready for a board decision or should it be delayed for more public consultation? Waterfront Toronto was evaluating a 1,500-page master plan, eighteen months in the making, titled ‘Toronto Tomorrow: A New Approach for Inclusive Growth.’ The plan was developed by Sidewalk Labs, which was Waterfront Toronto’s innovation and funding partner for the project and a sister company to Google. The smart city initiative, endorsed by the Canadian Prime Minister Justin Trudeau, would be among the largest and most technologically advanced urban development projects in North America.

In 2017, Diamond’s predecessor oversaw a request for a proposal to develop 12 acres of Toronto’s brownfield eastern waterfront land. That request for proposal hinted that the 12 acres would be a test run, with the much larger eastern waterfront open to development by a well- performing partner. Sidewalk Labs took these hints and bid on the project, since scale was exactly what the technology company needed for viability of many of its ideas. 

The unprecedented scale of the project would cause some public and financial concerns, however. Waterfront Toronto needed to coordinate funding to meet the project milestones. Concerns over surveillance and the city’s corporatization also were filling newspaper headlines and dividing the population. Now Diamond’s board must decide whether and how to partner with Sidewalk, or to delay that decision while consulting the public in an effort to preserve trust.