Just about two years ago, I was hired on a three-month contract to help write a giant public planning document on what Sidewalk Labs, an urban planning company owned by Google's parent company Alphabet, was proposing to do in Toronto.

It was a fascinating world and job. I was ushered up into what I started to privately call "the god realm." In a glass-walled skyscraper in New York City's newest urban district, Hudson Yards, I worked in airy offices overlooking the city. It was a space where talented people thought big thoughts and worked hard, while partaking of copious quantities of free food and drink.

But the project we were working on, in essence a new city in part of Toronto, would come to naught, a victim of irreconcilable differences between the city and the company. It would seem informative to examine why this was the case and to ask what any city or company could do differently next time.

The group up in the sky, in a way, was trying to bring the god realm to Toronto, Canada's largest metropolis. The city had been struggling for decades to do something with an 800-acre piece of land created from fill a century ago as part of a failed industrial bid. The enormous parcel, called the Port Lands, sits right off downtown. It's as if Manhattan had a vast swathe of vacant land sitting right off 42nd street. But various attempts to develop the Port Lands over a century had largely failed.

A New Model for a New City

The latest attempt had begun in 1998, when the Toronto City Council voted to go after the 2008 Olympics and use the Port Lands as the principal site. Toronto was attempting to copy Barcelona, which used its 1992 Summer Olympics to develop an underused section of its waterfront. But in 2001, Beijing won the Olympics. Toronto came in second.

Not wanting to let the work go to waste, Toronto turned its Olympics task force into the Toronto Waterfront Revitalization Corp., which eventually was renamed Waterfront Toronto. The national, provincial and city governments all had a hand in it. After more years of work, the agency produced a series of plans for the Port Lands and adjacent areas that sketched in 190 acres of new streets and business, residential and recreational areas, with the urging that it all be environmentally and climate conscious. In 2017, Waterfront Toronto entered into a partnership with Sidewalk Labs to carry the vision out.

Sidewalk Toronto’s offices in Quayside. (David Kidd)

Sidewalk had been working on its own to create a new model of what a city could be. Dan Doctoroff, relatively fresh from his position as deputy mayor under Michael Bloomberg in New York City, had created the company in 2015 with Google co-founder Sergey Brin. It was a marriage of urban planning with government, business and technical expertise. Doctoroff was building on what he had learned from forming Hudson Yards, which, coincidentally, grew out of an unsuccessful Olympics effort he had led. The marriage with Toronto seemed fated for success.

Sidewalk Labs took Waterfront Toronto's 50-year plan for the area and turbocharged it. The final 1,500-page Master Innovation and Development Plan, which I worked on, showed curbless streets mostly for walking, bicycling, streetcars and autonomous vehicles. There would be no private cars, and little parking. There would be lots of new, more affordable housing in different shapes and sizes, which Toronto was desperate for. The streets would use the latest technology to keep them free of snow and ice; the energy to warm them as well as the buildings would come from tapping into geothermal sources far below ground. There would be automated package delivery systems. The buildings themselves would be timber-framed of modular construction, a developing technology considered not only beautiful but also environmentally friendly. And, fitting for a Google sister company, the whole area would be wired, with broadband connectivity everywhere and smart city technology used to adjust energy usage, open doors for disabled people and monitor traffic patterns.

To top the plan off, it would include a new Canadian headquarters for Alphabet. Sidewalk pledged to commit more than a billion dollars to get the plan started. The project was predicted to produce tens of thousands of jobs.

"Surveillance Capitalism"

Yet, presented with this glittering jewel of a modern-day urbanist's dream, much of the city reacted not with enthusiasm but with suspicion and distrust. Some used the term "surveillance capitalism," theorizing that Google was pioneering a new system of control where one's every movement and entire online life would be captured and profited from. And there was an uproar over a Sidewalk proposal, later dropped, to receive a share of property taxes and development fees generated by rising land values.

As the public pushback intensified, Waterfront Toronto over two years scaled back the scope of the project, consigning Sidewalk to a 12-acre parcel called Quayside and repeatedly delaying final approval. Then, months before another approval vote was set to be held, the COVID-19 pandemic hit. Faced with so many obstacles, this May, Doctoroff pulled the plug on Quayside, writing that the smaller project wasn't worth doing, particularly in light of the "unprecedented economic uncertainty" the virus had added.

The enormous parcel, called the Port Lands, sits right off downtown. It's as if Manhattan had a vast swathe of vacant land sitting right off 42nd Street. (David Kidd)


And so it goes. Another big, ambitious project that was not to be. Although Waterfront Toronto and Toronto's mayor pledge to soldier on in some fashion, I suspect that if I visit Port Lands a generation from now, it will still be a largely empty and underused piece of land. It seems a sad legacy that an innovative company like Sidewalk, backed by the deep pockets of Alphabet and working in concert with three governments — the city of Toronto, the province of Ontario and the nation of Canada — couldn't make it happen.

Are there any lessons to be drawn from this failed effort, not only for Toronto or Sidewalk but also for other places that might want to undertake a project on the scale of the original Port Lands vision? It's an important question, because other cities will face what to do when a big corporation comes calling. Cities usually want to be receptive, but on the other hand don't want to be seen as suckers giving away the store.

Fears vs. Hopes

In the case of Toronto, it's hard not to conclude that the city and region unwisely let their fears outweigh their hopes. There was little evidence that Sidewalk wanted to engage in "surveillance capitalism," but the term itself and the imagery it evoked, combined with the power of Google's name, overwhelmed rational thought. These fears caused Toronto to look a gift horse in the mouth too closely, until ultimately the horse's owner led the animal away.

While I worked on the project, I saw nothing to suggest that Sidewalk was engaging or thinking about making money from capturing people's data. Mostly, the staff seemed addicted to cool urban planning. Doctoroff occasionally reminded the staff that the company did eventually want to make some money, but he pointed to things like a new timber-frame construction industry and "generative design," which is basically computer-assisted urban design.

To me, these potential profit generators were fascinating, but seemed like longshots as far as being money makers. As did the entire endeavor. No normal corporation would have spent millions of dollars up front designing a new city, in preparation for spending billions more, with only vague ideas about how it would recover the investment. But it seemed par for the course for Brin and Larry Page, the eccentric academics who founded Google and who had spent lots of money in an effort to digitize all the world's books, on "Google glasses" and self-driving cars, and on many other projects that have generated little to no return. Google makes most of its profits from Internet advertising. It and its parent company could afford to spend vast sums on other projects that caught the founders' fancies. It didn't need to build a new kind of city to get people's data; it already had their data, through its dominance of the search engine business and the Android operating system for mobile phones.

The critics in Toronto seemed to not understand this. They had a chance to let a mega-corporation pay for a substantial share of its city's long-contemplated urban design vision. They let that opportunity slip away.

An Amazon Strategy

If Toronto fumbled the ball, how about Sidewalk? Could Sidewalk have proceeded in a way that made it more likely its work would have been realized, if not in Toronto then somewhere?

As it happened, in 2018, while I was working at Sidewalk, Amazon announced that it would build a new campus in New York City in the waterfront district of Queens called Long Island City — it turned out that New York, along with a Virginia suburb across the Potomac from Washington, D.C., had won the company's frantic HQ2 competition. Although Amazon withdrew the New York offer after receiving what, by that contentious city's standards, was relatively mild criticism, it was clear that the company could have proceeded if it wanted to. Amazon was in a different position vis-a-vis New York than Alphabet/Sidewalk was in Toronto. Amazon was clearly in the driver's seat in New York. Sidewalk clearly wasn't in Toronto.

Sidewalk should copy Amazon, I found myself thinking, and have cities around the world compete for its participation, perhaps dangling a Google headquarters as an incentive. By going all in early in Toronto, including opening a large office there and proceeding with design and engineering work, Sidewalk left itself at the mercy of local officials and politics. Better to have gotten some assurance or a near-guarantee before teaming up with the city.

So that's my conclusion about a new city that was not to be in Toronto. The city and region let an opportunity slip away. Sidewalk should have demanded more up front before committing to the endeavor.

This is not to suggest that everything Alphabet, Google or any big company does is good. Quite the contrary. I'm a fan of reviving antitrust law against Google and other tech companies when it comes to their core businesses, and said so in my last book. But at a time when giant corporations bestride the earth, there are moments when, almost by chance, they may end up offering to do something for a city or region with relatively few strings attached. In 2011, for example, Google wired Kansas City for high-speed Internet service to launch its Google Fiber project. If such an offer is made to a city, my advice is, after checking it out thoroughly, to take it.


Governing's opinion columns reflect the views of their authors and not necessarily those of Governing's editors or management.