A hit show on Toronto’s failed smart city project returns to the stage

What happens when one of the most controversial and visible unrealized smart-city developments becomes a piece of theater?

“The Master Plan” dramatizes Toronto’s fractured relationship with then-Google subsidiary Sidewalk Labs and its effort to implement smart city infrastructure in one city neighborhood. The play sold out its first Toronto run in 2023 and earned playwright Michael Healey a Dora Award (Canada’s equivalent of a Tony Award) for Outstanding New Play. The show is returning to Toronto in November at Soulpepper Theatre in the East End’s Distillery District. 

Based on the Josh O’Kane book “Sideways: The City Google Couldn’t Buy,” the show captures the conflict between two main players: Waterfront Toronto, the government agency in charge of developing the city’s lakeshore, was seeking to bring forward-thinking ideas to a 12-acre parcel of land in a populous city that rarely took risks with urban tech investments. Sidewalk Labs won the bid, but it wanted more data and less bureaucracy than Waterfront Toronto would provide. Privacy and surveillance concerns affected public perception of the effort and relationships between the two parties during negotiations. 

The project faced some dramatic turns of events: An adviser on the project resigned, Ontario fired Waterfront Toronto board members, and an outspoken critic of the project, former BlackBerry co-CEO Jim Balsillie, said Sidewalk’s parent company Alphabet would be the project’s only beneficiary.

Ultimately, Sidewalk Labs scuttled the Toronto waterfront project in May 2020, attributing its demise to “unprecedented economic uncertainty” in the early days of the COVID-19 pandemic.

Finding drama in the smart city

Toronto’s residents were divided over the smart city project falling through. Critics expressed relief, while advocates for the project were disappointed by the city’s risk-averse attitude. That central conflict is at the heart of the book, the author said in an interview.

“I wanted to write about the massive power of Silicon Valley and the slow, sluggish pace of the Canadian government, and how the clash between those two [parties], who really wanted the same thing, resulted in them still not fundamentally understanding each other,” O’Kane said. “I didn’t think it would make great theater, but it does.”

Healey threaded his stage play with O’Kane’s narrative of how the Sidewalk Labs partnership with Toronto began smoothly but quickly soured. 

“Josh’s book is so vivid, and the way he described those meetings between Google tech bros and the incredibly conservative Canadian bureaucrats made me think from the outset there were dynamics here to exploit for humor,” Healey said in an interview. 

Fact and fiction

Healey said he deviated from the facts of the story to add his own take on the nervous breakdowns he assumed many executives involved in the project suffered during negotiations, which included screaming matches documented in O’Kane’s book and bad press. 

In the play, the resignations and negative headlines cause Waterfront Toronto Chief Development Officer Meg Davis to do violent things to a dessert in the middle of a meeting — also fictional, Healey said. 

O’Kane applauds Healey’s adaptation, saying it captured how “consistently Sidewalk Labs shot itself in the foot and how its own ambitions got in the way of its own goals.”

Lessons in the aftermath

In 2021, Sidewalk Labs folded its products into Google. A year later, cities including Philadelphia experimented with Pebble, a Sidewalk Labs parking and curb management technology that allows drivers to reserve spots through an app and city officials to track violations.

For Sidewalk Labs to survive the well-publicized Toronto saga would have been challenging, said Ben Green, author of “The Smart Enough City: Putting Technology in Its Place to Reclaim Our Urban Future” and assistant professor at the University of Michigan School of Information. “They wouldn’t have been able to find receptive audiences in any other cities [because of what happened in Toronto],” he said.