By fall 2018, Stephen Diamond was ready to quit. He had been on the Waterfront Toronto board since April 2016 but, in the last year, the job had gotten tense. The organization had initiated a partnership with Sidewalk Labs, the Google sister company with smart-city ambitions for Toronto’s neglected Quayside neighbourhood. The arrangement, which had sailed through the bidding process in 2017, was now attracting fierce scrutiny from policymakers, residents and civic activists concerned with Google’s potential influence on the city. At 67 years old and nearing the later stages of his career, Diamond was ready to spend fewer hours politicking and more time cycling with his wife Karen and golfing with his brother Carey. 

Toronto Mayor John Tory had a different idea. “‘You cannot step off this board,’” says Tory, recalling his phone call with Diamond after learning of his plan to leave. “‘Not only do I see you staying on the board, I see you becoming chair.’”