What cities can learn from Sidewalk and Toronto's failed city of the future

A new book digs deep into Google and Toronto’s infamous smart-city project.
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Josh O’Kane

· 5 min read

In 2017, an underdeveloped 12-acre neighborhood on Toronto’s waterfront became a canvas for the city of the future, as imagined by Sidewalk Labs, a Google affiliate specializing in smart-city development.

Sidewalk had a $1.3 billion high-tech vision to remake the way that cities were developed by using tech from automated vehicles to underground waste management. But the project fell apart in 2020 due in part to economic uncertainty in the wake of the pandemic and after criticism from residents and privacy advocates. Sidewalk Labs ultimately pulled out of the project entirely before being reabsorbed into Alphabet in 2021.

The project was arguably the most high-profile failure in the short history of smart-city projects, with ripple effects for smart-city endeavors beyond Toronto.

In a new book published last week, journalist Josh O’Kane took an in-depth look at how the project broke down. O’Kane covered the partnership between Waterfront Toronto and Sidewalk for the Canadian newspaper the Globe and Mail for two years.

Emerging Tech Brew talked with O’Kane about Sideways: The City Google Couldn’t Buy to learn more about how the splashy project failed and the broader challenges of deciding who shapes the future of cities.

This interview has been edited for length and clarity.

Throughout the book, you can see trust beginning to fall apart between Sidewalk Labs and Waterfront Toronto. Why was there so much miscommunication and dysfunction between these partners, and how did it affect the way this project developed?

Sidewalk Labs did not truly grapple [with] or understand the fact that Waterfront Toronto was this agency that was fundamentally paralytic, because it reported to three governments in equal measure, which means it had no majority shareholder, which means that if they wanted to address something that perhaps required a policy change, say around surveillance and privacy, they would have to get the federal government to do it, because Waterfront Toronto didn’t make policy. If they wanted to make a change to zoning laws or bylaws, that was a municipal issue. Building codes? Municipal issue that is also sort of under the jurisdiction of the provincial government.

And so Sidewalk Labs, when they approached the project, did not necessarily understand that Waterfront Toronto was not a one-stop shop. It created the appearance of being a one-stop shop, but in fact, it was sort of a layer of bureaucracy in front of three different governments because of not being able to get anything else done.

Who bears the responsibility for the way the Sidewalk deal fell apart? Was it Sidewalk or the government?

Each of them [the federal, provincial, and municipal governments] hid behind the fact that Waterfront Toronto was the agency that basically put forward the contract…the agency was powerless to actually engage with the requests and the needs of Sidewalk Labs, which led to the imbalance and then frustration with the power dynamic…The fundamental lesson of the book is “Who gets to decide what the city of the future looks like?” Sidewalk Labs had some really interesting ideas but Sidewalk Labs was also beholden to Alphabet, which over the course of its lifetime, was putting increasing pressure on the company to fundamentally be a profitable organization.

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What lessons can be taken from Sidewalk and Toronto going forward for other smart city enterprises or initiatives?

I think that there needs to be some pretty serious questions asked right from the get-go of: What are the consequences of the kinds of technology you want to deploy? Should there be public policy written to protect any data that is collected, used, or disseminated from that sensor? And if there should be public policy, should [the] government be out there racing around the world trying to develop this public policy so that citizens’ rights are protected? That’s just a single example. But I think it’s sort of a fundamental one, because privacy looms very large on the minds of everyone who’s discussing this project.

Was this a case of Sidewalk Labs dreaming too big? Could this have worked better if Sidewalk was able to tailor its mission to maybe, let’s say, only focusing on garbage collection?

Yeah, I think if Sidewalk Labs had focused more on specifically what Waterfront was asking, or focused on a narrower set of individual technologies, I think it would have had a greater amount of success. It also would have had a greater amount of success if they just went out and bought land in some city, it doesn’t need to be in Toronto, said they wanted to build something and then lobbied a government to say, “Hey, we have this opportunity. Would you consider amending these regulations?” That could certainly happen.

But to Sidewalk’s absolute credit, they did want to partner with a city. They saw this as an opportunity to do this kind of city design in tandem with the government. But, that also came with a lot of bureaucracy, a lot of hurdles, and in the end, that agency that they partnered with didn’t necessarily have the power to do all the things that would be required to make a city of the future.

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