I spent much of the fall of 2017 in the archives room of a magazine combing through 50 years of award-winning Canadian design for a retrospective issue. The inaugural vintage didn’t disappoint. In the afterglow of Expo 67 and Centennial celebrations, the 1967/1968 laureates featured Canadian icons in the making – including Moshe Safdie and Raymond Moriyama – and a collection of bold, forward-thinking architecture that reflected the optimism of a country ascendant. But one winning project stood out from the pack for very different reasons: Clifford & Lawrie’s proposed scheme for Toronto’s Spadina Expressway.

It would have changed the city forever. As part of the new highway that would connect Highway 401 with downtown, the design envisioned an imposing pedestrian interchange at the proposed expressway intersection with Eglinton. According to the jurors, the project represented a “harmonious” integration of people and automobiles, demonstrating that “we no longer have to fear the car.” The colossally misguided vision would entail demolishing large swathes of downtown neighbourhoods – including Chinatown and Kensington Market. It was the future once, but not for long.

Fiercely opposed by the likes of Jane Jacobs and Marhsall McLuhan, plans for the sprawling highway were halted in 1971, sparing Toronto’s downtown the worst of the butchery performed on many North American cities. But among the projects of the past half-century, the Spadina Expressway struck me as the most influential of all Toronto winners, precisely for the fact that it was never built. (For my money, it’s infinitely preferable to imagine a Toronto without the Royal Bank Plaza or the Eaton Centre – both award-winning designs – than it is to stomach a highway in place of Spadina Avenue’s eclectic urbanity.)

Then, in October of 2017, the announcement that Google affiliate Sidewalk Labs had won the RFP to develop a prominent parcel of the waterfront made global headlines. Suddenly, the five near-barren lakefront hectares at Quayside were the locus of urban discourse the world over, with the tech giant promising to build the first-ever neighbourhood “from the internet up.” Excitement and backlash soon followed in seemingly equal measure. While the project was championed as a cultural and economic coup that – in urbanist Richard Florida’s words – would propel Canada’s biggest metropolis to “the top of the heap in…‘urban tech,’ ” the optimism was countered by urgent concerns about data collection, lack of oversight and a fundamentally undemocratic regulatory structure.

The problems with Quayside started well before Sidewalk’s involvement. The optics of Google as a sort of digital Robert Moses sat uncomfortably, but the terminally flawed terms of Waterfront Toronto’s RFP also jeopardized the project from the beginning. The RFP sought an “innovation and funding partner” for the site, one that would also “create the required governance constructs to stimulate the growth of an urban innovation cluster.” In other words, Sidewalk Labs was tasked with developing not only the technology of urban data farming but also the legal and regulatory frameworks that govern it. As an agency comprising three levels of government, Waterfront Toronto effectively offloaded the creation of public policy to a for-profit tech giant. While fears about individual data privacy dominated our public discourse, the fatal problem was rooted less in privacy than privatization.

For all the controversy, it still looked like utopia. From the beginning, Sidewalk’s slick notional renderings promised a city of the future with all the trimmings. From heated “smart” sidewalks to underground servicing and waste management and sensor-equipped laundry machines, nothing was off the table. As the plans coalesced, the level of ambition only rose. Mass timber. Affordable housing. Modular design. Pedestrian- and cyclist-driven urban design. Lots of parks. By the time Sidewalk released its 1,500-page Master Innovation and Development Plan in 2019, it had performed enough community consulting to devise an unprecedented level of urbanist wish-fulfillment – or box-checking.

Some of it was genuinely thoughtful and innovative, a great deal of it was fanciful, unfocused and half-baked, and the rest was relatively obvious (it doesn’t take much “innovation” to figure out that bike lanes and street trees are a good idea). Even so, concept renderings courtesy of Thomas Heatherwick and Snøhetta drew the eye, while the street-level sensitivity of the project evoked the “sidewalk ballet” famously described by Jane Jacobs. In New York magazine, architecture critic Justin Davidson wrote that “Quayside is the new city that Hudson Yards might have been: mixed, flexible and humane.” Hell, maybe it actually would have been.

But so what? Even if the promises of architectural utopia came true, the terms of Waterfront Toronto’s RFP created a structural impasse that was never adequately resolved. As Brock University’s Blayne Haggart puts it, “Quayside mattered not because it was a terrible urban-development project, but because it was an exercise in designing data-collection standards and promoting a particular vision of digital economic development.” What’s more, Sidewalk’s stymied ambitions to scale up the Quayside project to eventually include 77 hectares of Toronto’s adjacent Port Lands – one of the largest development projects in North American history – eroded the tech giant’s potential for profit. Then came COVID-19, and that was that.

Last week, when Sidewalk Labs quietly announced that the experiment was at an end, it felt like a loss to some. As Martin Regg Cohn wrote in the Toronto Star, “Google has given birth to peerless infotech and innovation that could have boosted Toronto’s global brand, so this is a missed growth opportunity.” For Toronto, a first-of-its-kind experiment in smart city urbanism would have meant international cachet – though perhaps of the dubious sort lately generated by New York’s High Line and Hudson Yards.

In the Globe and Mail, Marcus Gee echoed a more pointed iteration of the sentiment, writing, “The Toronto that showed its face during the Sidewalk saga was a smug, self-satisfied, suspicious, weakly led rather provincial town that is afraid of the big and bold and is quite happy with the second rate. It is not an attractive look for a city with hopes of being a top-tier global metropolis.” It’s a mentality that Siri Agrell more caustically and concisely summed up (again in the Toronto Star): “Sidewalk Labs left because Toronto is a timid, backwater nanny state that rejects innovation.”

But, as Agrell argued, Sidewalk more likely “walked away because they were stifled in their actual objective, which was, to put it plainly, a land grab.” After the Google affiliate’s plans to oversee the much larger 77-hectare Port Lands site were continually rebuffed, Sidewalk “was not interested in deploying its nascent subsidiary to secure a large parking lot on which they could develop condos with iPad-enabled garbage chutes.” In all likelihood, we’ll never know the full scope of Google’s internal decision-making, which means that speculation about the true reasons for the tech giant’s departure will continue for some time yet. But in a project so fundamentally flawed from the earliest RFP stage, the self-flagellation seems unnecessary to begin with. And besides, what if the well-warranted skepticism that greeted Sidewalk Toronto was not a symptom of small-mindedness but of robust civic engagement?

According to Spacing‘s John Lorinc, Sidewalk Labs and Waterfront Toronto (then led by CEO Will Fleissig) misunderstood both the city’s decentralized “weak mayor” council government and Toronto’s political culture. “The Sidewalk crew and Fleissig didn’t bother to internalize what, to my mind, was the single most defining moment in the city’s recent past, which was the resounding defeat of then councillor Doug Ford’s cynical 2012 bid to hijack the Port Lands’ planning and development process,” writes Lorinc. “That episode demonstrated that Torontonians feel a sense of ownership towards the waterfront,” and that “all that lakefront land wasn’t just a bunch of brownfield waiting to be claimed. It wasn’t for sale. And it wasn’t some kind of zone for experiments.” So much for a bunch of provincial rubes.

Insofar as all local politics tend to be just as parochial as Toronto’s, the broader accusations of provincialism also seem at odds with the city’s socio-economic reality. Even without Sidewalk Labs, the city is a global financial capital, and one that already boasted the fastest-growing pre-pandemic tech economy (not to mention the fastest-growing population) on the continent. We’re also arguably the most diverse place on the planet; a North American metropolis where a majority of the population is neither white nor Canadian-born.

And – if this type of thing butters your toast – we also regularly rank at or near the top of global indices of livability and economic vitality, with the likes of Frank Gehry, Renzo Piano and Bjarke Ingels now plying their trade in Hogtown. For all that, our most fundamental problems are not some abstract lack of “innovation” or “world-class” aspiration, but our society’s failure to harness the enormous wealth already generated in our city to reduce inequality, end homelessness and ensure an adequate standard of living for our most economically vulnerable people.

Nonetheless, as Lorinc points out, the political culture of the city is decidedly “decentralized and ponderous,” with a lack of streamlined and aggressive decision-making. Part of the reason is structural – the weak mayor council is a contrast to many American cities – but civic culture and urban history also play an important role. In his 1995 book Accidental City, Robert Fulford argues that Toronto’s rapid 20th century growth was largely unplanned. While the threat of Quebec separatism spurred the country’s big banks to transplant from Montreal, Canadian immigration policy suddenly – and somewhat unexpectedly – transformed a quiet Protestant city into a radically diverse global capital.

Twenty-five years later, the accidental city is an accidental metropolis. Picking up Fulford’s thread in 2019 in his book Perfect City, urban planner Joe Berridge writes that – until very recently – “Toronto has never been comfortable thinking of itself as a great city.”

Maybe that’s not altogether a bad thing. While Sidewalk’s three-ring circus has left town, Quayside and the Port Lands are hardly left for dead. An unprecedented – and much-needed – plan to transform the sprawling Port Lands into a dense, mixed-use neighbourhood is already well underway. Meanwhile, a $1.2 billion project to naturalize the mouth of the Don River will create a revitalized and resilient new urban waterway, while some 80 hectares of new green space will help revive the once-industrial eastern waterfront. It may not (yet) draw the eyes of the world, but a forward-looking new Port Lands is poised to rise in one of the most lucrative development sites in North America. In our understated, Torontonian way, we are assertively building a city for the future.

Finally, it does our civic culture a disservice to conflate the outspokenness of Sidewalk Labs’ critics as a symptom of timidity or fear. It takes courage to embrace new ideas, but it can take even greater courage to reject them. After all, when Jane Jacobs et al. contested the Spadina Expressway, the activists faced accusations of halting progress and selfishly failing to see the bigger picture. While a 1960s expressway and a proposed 21st century “smart city” are hardly analogous, they jointly illustrate that a city is shaped by saying “no” as much as “yes.” (Indeed, when Amazon announced – and later aborted – a North American search for a second headquarters, Toronto earned plaudits as one of the few shortlisted cities that did not offer the tech giant egregious subsidies or tax breaks in exchange for its presence.)

It’s possible (if unlikely) that the next iteration of a Sidewalk Labs future city, if there ever is one, will resolve the problems faced in Toronto. If an equitable and inclusive neighbourhood rises from the internet up, it will be another city’s gain. For the time being, however, the Sidewalk era has demonstrated the resilience of Toronto’s activists and civic institutions in the face of unprecedented corporate and institutional pressure. In lieu of what was likely to be an iconic and attention-grabbing new neighbourhood, the city is left with a quieter but equally meaningful watershed moment. Just as the cancellation of the Spadina Expressway shaped Toronto for decades to come, so too could the cancellation of Quayside. And though there will never be postcards or awards or Instagram Stories for a neighbourhood not built, its legacy will linger.

It all ends with a peculiar, unresolved grace that’s quintessentially Torontonian in its subtlety. But look carefully, and the evidence of saying “no” is already all around us. For my part, the first post-pandemic stop on my list is a walk through my old neighbourhood, Kensington Market. The place is a vestige of an eclectic and unfettered pre-war urbanism now largely extinct in North America – demolished for highways like the Spadina Expressway in the last century or gentrified into another kind of oblivion in this one. But not yet here. For now, Kensington’s spontaneous (albeit endangered) vitality makes for a neighbourhood like no other. When I step onto Augusta Avenue, I’ll remind myself to feel thankful for the city Toronto still is, and for everything we did – and didn’t do – to embrace it.

This essay is excerpted in Designlines magazine.