In October 2017, an Alphabet subsidiary named Sidewalk Labs announced that it was going to build a brand-new neighborhood, “mixing people-centered urban design with cutting-edge technology,” on a sliver of Toronto’s waterfront known as Quayside. The company, originally founded as Google’s urban-planning arm, promised a beautiful “carbon-positive” city: A 1,500-page, four-volume document featured full-color illustrations of kayakers paddling along packed beaches, families strolling leafy streets, and workers sipping coffee in golden-lit outdoor cafés in the dead of winter. It would also utilize a dizzying array of fantastical tech: pneumatic trash cans, snow-melting pavement, retractable rain canopies, its signature self-driving cars (of course), and sensors to track everything from foot traffic to air quality to food waste, which, by interfacing with the smartphones of residents, would produce quantified data snapshots of daily life. “The most innovative district in the entire world,” said Dan Doctoroff, a former deputy mayor under Michael Bloomberg, who led Sidewalk’s contingent of urbanists and architects. Alphabet was putting up the funds but expected a return on its investment: The neighborhood would double as a kind of urban-tech theme park to help the company sell its innovations to other municipalities. The project would be so well conceived, so perfectly livable, that Sidewalk Labs assumed the people of Toronto would flock to its meticulously designed, hypersurveilled boundaries.
Within 18 months of the announcement, the Canadian Civil Liberties Association called the plan a “non-consensual, state-authorized mass capture of Canadians’ personal information.” Leaked documents also revealed that Sidewalk Labs had much grander aspirations than the single neighborhood it was selling to city leaders. The Quayside parcel was relatively small, only 12 acres, yet Sidewalk Labs was secretly planning to acquire 800 acres of adjacent properties with the intention to site a new Google campus. The reason for the land grab, Sidewalk Labs claimed, was that it needed scale in order to make the grandiose project truly work.
Then, in May 2020, less than a year after the official $1.3 billion draft master plan had been released, Sidewalk Labs suddenly abandoned Quayside, blaming the pandemic for derailing its plans. What actually happened was a bit more complicated. Sideways: The City Google Couldn’t Buy is Globe and Mail reporter Josh O’Kane’s effort to piece together why the tech company’s attempt at building a smart city, complete with hypersustainable mass-timber towers filled with much-needed affordable housing, failed so miserably. Curbed spoke with O’Kane about the seasteading origins of Sidewalk Labs, the battle over its existence, and whether it’s possible to build an ethical smart city in the first place.
Can you speak first to the ambition of the project? The most powerful company in the world suddenly decides it wants to build a utopian city. Where did this come from?
There was a smart-cities movement in the late 2000s, early 2010s, that was very hardware focused — these legacy technology companies becoming interested in infrastructure and centralized operations: We’re going to streamline, streamline, streamline. This is also the time when Larry Page ascended to CEO of Alphabet, and he is this restless character who is constantly thinking about innovation. So what’s next?
In 2014, this secretive moon-shot group inside Alphabet called Javelin was formed to change the physical world and improve cities. They decided that in order to test their theories, they needed freedom from regulation. They looked into building a dome-covered, effectively libertarian city on the sea. Well, then it turns out that there are laws governing the sea. So they scale it back but keep the dome idea, which was basically about how the world’s climate is getting harsher, so: What if we could shield ourselves from the elements? This is when they started to build a team that eventually spun out and became Sidewalk Labs.
Let’s talk about this team. Were these credentialed urban thinkers? Grifters? Both?
Dan Doctoroff built his name as this larger-than-life power broker, first in the private-equity world, then as the mastermind of New York’s failed 2012 Olympic bid and Michael Bloomberg’s deputy mayor for economic development. After launching Sidewalk Labs with Google in the mid-2010s, he brought on a handful of Bloomberg alumni, some Googlers who’d been involved with Larry Page’s earlier urban-fantasy ideas, and some urban-tech experts like Smart Cities author Anthony Townsend. On paper, it was a smart mix of people. In practice, there were a lot of quiet disagreements over what directions to take Sidewalk.
And you unearthed this secret 437-page document produced in this time. Their plan for “a city from the internet up.”
The Yellow Book. It was filled with a bunch of really interesting and wacky ideas; notably, data was treated as a form of currency in the city they imagined. If you didn’t share a certain amount of your personal data while you’re going around the city, you wouldn’t have access to services. Then they present it to Larry Page, and depending on who you’re talking to, Larry Page either loved the idea or asked if it was innovative enough. Six weeks later, Doctoroff receives an email from a former employee that says, “Hey, we’re working on this project in Toronto. Would you be interested in looking at it?” Over the course of reporting the book, I learned that, in fact, Toronto was sort of a secondary plan. What they wanted to do was actually host Olympic-bid-style contests for cities to have the privilege of working with Sidewalk Labs.
Why didn’t they just build their own smart city right on their property in Mountain View?
There was a very big push within Sidewalk Labs to not look like it was this big boulder rolling into a city and making all these changes. They at least wanted the optics of building trust with a local community and to show that they are willing to work with governments in terms of execution. They did take a lot of time and effort to put together a bid, and learn about Toronto, and try to work with Toronto. And whether that was genuine or whether that was for the optics will change depending on who you’re asking. If they had just bought a bunch of land here in Toronto, it would have been very different. But it was thought of as an opportunity to build a partnership.
What were the vibes in Toronto as this was happening? Did you get a sense you were being turned into an experiment?
There was a strange tension in the air by early 2019, where Toronto was splitting into stubborn factions: people who were warning of the potential for massive surveillance, people who were warning that the project could run off the rails without clearer government oversight, and people who saw those groups as blindly against economic development. Each one of them was worried about a different aspect of the future of cities, and there were a lot of wars of words. It seemed like no one was happy. But by mid-2019, Sidewalk dropped its draft master plan, revealing a bunch of details that even its government partner, Waterfront Toronto, was frustrated with. Then even fewer people were happy. It was a strange mood at a moment that should have felt full of potential.
What was the beginning of the end?
Sidewalk Labs’ ambition for the Toronto property always hinged upon a hope that they would get more than the 12 acres they were allotted by Waterfront Toronto. If you look at Sidewalk Labs’ bid for that land, it was very clear from the very beginning they wanted much more; they wanted to scale. This 1,500-page catalogue that they released in June 2019 explained how they were going to do that. Doctoroff was obsessed with Olympic-bid books. He carefully studied these bid books as he worked on his own Olympic bid, and that obsession carried forward into Sidewalk Labs’s Yellow Book as well as this enormous, four-book draft master plan for Toronto. Waterfront Toronto had been asking Sidewalk to hold off, saying, “Let’s not publish this. Let’s talk about these details.” And then Sidewalk publishes it anyway. This is where the controversy really begins. Waterfront comes out and says, basically, “We don’t endorse this plan.”
So when Sidewalk Labs blamed the economics of the pandemic, saying the plan had become infeasible — really, it had always been. From the beginning, Sidewalk Labs did not embrace the reality of what they had been offered in the first place. Toronto and Sidewalk Labs both wanted a city of the future. But Sidewalk Labs didn’t want Toronto to get in the way of its ideas.
One example of this is how they brought in these big-name architects like Thomas Heatherwick and Snøhetta to draw up renderings of mass-timber buildings that looked like these towers made from popsicle sticks. But Sidewalk didn’t mention that their mass-timber renderings would require an overhaul of the entire municipal code.
There are other people within Canada that are pushing governments to amend building codes to allow mass-timber buildings; this is something that a lot of people wanted to do. But what a lot of Torontonians were frustrated about was the brazenness with which there were these expectations laid out. Another example: The company also envisioned its energy-use and conservation plans as creating “the largest climate-positive district in North America,” which could have set a whole new standard for urban sustainability. There are so many truly forward-thinking ideas that were proposed by Sidewalk Labs that were just completely knocked down by the way the company chose to execute its plans.
Sidewalk Labs dissolved in 2021. Where are some of the major players now?
By the time Sidewalk Labs announced it would disband at the end of 2021, many of its key leaders had already left the company or were in vague advisory roles. Policy head Micah Lasher became policy director for New York governor Kathy Hochul. Joshua Sirefman returned to Detroit to become CEO of Michigan Central, which has been pitched as the centerpiece of what locals are referring to, familiarly, as an innovation district. Alyssa Harvey Dawson, Sidewalk’s head of legal, privacy and data governance, became chief legal officer of the tech company Gusto. When Dan Doctoroff stepped down amid the tragic news that he very likely has ALS, he returned to an old habit, raising money, as he sought to do his part in eradicating the disease.
You mentioned how the original Yellow Book proposed using personal data as currency, and that was one of the biggest criticisms of Sidewalk Toronto: that people would not own their own data.
There’s some really interesting ways that you can embed sensors in urban infrastructure to learn about how people move about their city — and how they live their lives in cities. And you can do this in a really privacy-protecting way. You can do this in a way that when those new technologies are developed, the people who are walking around the city can actually get a stake in the return on their investment. Because if you’re sharing your data, why shouldn’t you have a return on that investment? That’s a mistake that was made in the early days of the internet that we’re still trying to figure out how to deal with. This is what the people who were opposing Sidewalk Labs were saying. These weren’t Luddites opposing everything; these were people who said, “This is going to happen. Let’s figure out the right way to do this.”
Is there a way for this to work — for a company like Sidewalk to equitably share its profits?
This is not necessarily a widespread phenomenon right now, but it was baked into what Waterfront Toronto wanted to do for the Sidewalk project. It wanted Torontonians to have a stake in the intellectual property (IP) generated in the neighborhood. It was a people-focused reimagining of how the digital economy was built, where a handful of companies currently profit immensely from IP built upon data that everyday people generated online.
Sidewalk eventually backed away from things like requiring biometric scans to enter buildings. But can we have tech interwoven into every aspect of daily life without this kind of nightmare trade-off? Is it possible to build a city from the internet up?
It’s totally possible to build a city from the internet up. But it requires a lot of thought about what a city from the internet up even looks like. And when you take a top-down corporate approach from a project perspective, with a parent company that expects a return on its investment, you’re not necessarily going to take the time that’s probably required to really satisfy all of the issues that people think about.
The biggest lesson I learned while working on this book was there is no one great answer for who should design the future of cities other than everyone should get a say. Sidewalk Labs had a lot of great ideas — they were important to most people that I interviewed, who were in a great rush to execute them. What was interesting was that the main theme from the people who opposed it was, Let’s slow down. Let’s not look at this as a great big market opportunity. Why don’t we consider these ideas on a one-by-one basis and think about what’s best for the people who live here? That was not really a consideration.
This story seems to infer there’s just no way to reconcile the profit-seeking part.
I don’t think there’s a clear answer because I think a lot of people see an enormous market opportunity in the future of cities. And there are a lot of people who see cities as the No. 1 battleground for the future of human rights. And I think there will continue to be these major, major clashes between the two.
This interview has been edited and condensed.
