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Business & Economics Computer Industry


The City Google Couldn't Buy

by (author) Josh O'Kane

Random House of Canada
Initial publish date
Sep 2022
Computer Industry, City Planning & Urban Development, Urban & Regional
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    Sep 2022
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From the Globe and Mail tech reporter who revealed countless controversies while following the Sidewalk Labs fiasco in Toronto, an uncompromising investigation into the bigger story and what the Google sister company's failure there reveals about Big Tech, data privacy and the monetization of everything.

When former New York deputy mayor Dan Doctoroff landed in Toronto, promising a revolution in better living through technology, the locals were starstruck. In 2017 a small parcel of land on the city's woefully underdeveloped lakeshore was available for development, and with Google co-founder Larry Page and his trusted chairman Eric Schmidt leaning into Sidewalk Labs' pitch for the long-forsaken property—with Doctoroff as the urban-planning company's CEO—Sidewalk's bid crushed the competition.
But as soon as the bid was won, cracks appeared in the partnership between Doctoroff's team and Waterfront Toronto, the government-sponsored organization behind the contest. There were hundreds more acres of undeveloped former port lands nearby that kept creeping into conversation with Sidewalk, and more questions were emerging than answers about how much the public would actually benefit from the Alphabet-owned company's vision for the high-tech neighbourhood—and the data it could harvest from the people living there. Alarm bells began ringing in the city's corridors of power and activism.
To Torontonians accustomed to big promises with little follow-through, the fiasco that unfolded seemed at first like just another city-building sideshow. But the pained battle to reel in the power of Sidewalk Labs became a crucible moment in the worldwide battle for privacy rights and against the extension of Big Tech’s digital might into the physical world around us.
With extensive contacts on all sides of the debacle, O'Kane tells a story of global consequence fought over a small, forgotten parcel of mud and pavement, taking readers from California to New York to Toronto to Berlin and back again. In the tradition of extraordinary boardroom dramas like Bad Blood and Super Pumped, Sideways vividly recreates the corporate drama and epic personalities in this David-and-Goliath battle that signalled to the world that all may not be lost in the effort to contain the rapidly growing power of Big Tech.

About the author


  • Short-listed, Shaughnessy Cohen Award for Political Writing

Contributor Notes

JOSH O’KANE has been a reporter with the Globe and Mail, Canada’s largest national newspaper, since 2011. He won Germany’s Arthur F. Burns Award for transatlantic political and cultural reporting in 2019, for his coverage of that country’s broad pushback against Big Tech. O’Kane’s reporting has also won numerous Best in Canada awards from the Society for Advancing Business Editing and Writing. His first book, Nowhere with You, was a Canadian bestseller. He lives in Toronto.

Excerpt: Sideways: The City Google Couldn't Buy (by (author) Josh O'Kane)

After the Gold Rush

The Berliners couldn’t tell whether to be excited or disappointed. It was just after noon on a late-October day in 2018, and their screens were lighting up in and around the neighbourhood of Kreuzberg, just east of the city’s core. The loosely connected crew didn’t all call themselves activists, but they sure acted like activists, and they were frantically texting and e-mailing each other, trying to figure out if they’d just won a two-year campaign against one of the world’s most powerful companies. If they really had, they’d learned the news in the most mundane way possible: from a blog post.
“Campus in Kreuzberg substation becomes house for social engagement,” the post began in German. Big changes were coming to the neighbourhood just east of Berlin’s core. “Everything is different,” the post continued. “Google is handing over the space to us as social experts to unleash the full power of social action.”
Was the post some kind of hoax? The link the Berliners were bouncing around was from betterplace, a relatively unknown local online-donation platform, which would get access to a large space in a converted electrical substation instead of Google, the Californian corporate giant that had become a household name by making the world’s information easier to find. It was Google that had the lease on the space. Giving it away would mean the company was abandoning a long-planned incubator-style “campus” for start-ups that had faced two years of pushback from digital rights campaigners, anti-gentrification advocates and plain-old frustrated neighbours from Kreuzberg and Neukölln—the communities that met where the building sat on the Landwehr Canal.
The allies were unlikely: young and old, graffiti taggers and lawyers, recent immigrants and long-time Berliners. But their concerns about Google’s plans for Kreuzberg, first announced in late 2016, were all variations on the same themes. After watching Big Tech spend two decades concentrating power in the digital world, they had noticed its power spilling over into the physical world. A tech company’s data collection can give it market power, market power can become purchasing power, and purchasing power can price people out of neighbourhoods. And affordability was only part of their concern: unregulated data collection can morph into surveillance, surveillance can chip away at the right to privacy, and the decline of privacy can constrain other rights and freedoms. Google’s enemies in Kreuzberg and across the rest of Berlin weren’t just challenging an annoying new neighbour—they were contesting the way the world’s richest companies were reshaping the world’s cities and democracies.
Kreuzberg’s anti-gentrification factions had a history that stretched back to before the fall of the Berlin Wall. But against Google, ordinary neighbours with no history of protest found themselves suddenly working alongside anarchists to defend their neighbourhood against an encroaching giant with unfathomable resources. Their flyers and pamphlets were augmented by a loose crew of self-described nerds who took the battle into territory that Google had long ago claimed—the internet—to bring global attention to their campaign. Some of those opponents branded their battle as a movement with a name few would forget: Fuck Off Google.
Tens of thousands of stickers bearing their campaign’s name were slapped across Berlin’s courtyard walls, train station halls and bathroom stalls. Just a month before the blog post was published, dozens of the movement’s supporters had occupied the old electrical substation, with a handful getting taken away by the police.

Their tactics had worked. Or, well, maybe they had.
Some of the Fuck Off Google crew weren’t sure they could believe the post. They traded messages furiously. There was a poorly staged photo attached to the announcement, of a Google executive in a grey sweater handing the keys over to the new tenants; one member of the crew zoomed in as close as possible to see if the image had been photoshopped. “Doesn’t look fake,” the Berliner e-mailed in English to the rest of the group. “Have we won already?? We were only starting having fun!!”
Eventually, headlines began proving that the news was real. In Europe, the Guardian, BBC and Le Monde covered the end of the Google Kreuzberg campus. So did Bloomberg, the New York Times, CNN and the Wall Street Journal. The coverage came with new details: Google would spend €14 million to cover five years of rent, utilities and retrofitting costs so that betterplace and a social co-operative could take over the company’s space. For the Berliners who’d fought the campus, this carried a subtext that seemed much more consequential than corpo­rate benevolence. It looked like Google was willing to spend €14 million just to get rid of a nuisance—to rid itself of them.
Soon, night had fallen in Berlin, and some of the Fuck Off Google crew decided they should mark the occasion. A few dozen of them gathered in front of the substation, cheering and popping bottles of cheap sparkling East German wine named after Little Red Riding Hood—Rotkäppchen—as the canal glistened in the dark behind them.
But the celebration was muted. The day had at first seemed cathartic, but some of the crew began worrying about what came next. The new tenants had the space for only five years—just a third of the length of Google’s lease at the substation. The California company could easily outwait the opposition and come back to Kreuzberg. And Fuck Off Google’s battle wasn’t just about Berlin. For many of them, shutting down the start-up campus dealt with only a symptom of what they felt was wrong with the company, not the cause. Google was still everywhere.
Ten or fifteen people were still hanging around when one of them pulled a bedsheet out of their bag and laid it on the grey cobblestones in front of the substation. As empty bottles of Rotkäppchen clinked and rolled around next to the sheet, someone pulled out a can of spray paint. The dwindling crowd began to call out the names of distant cities where like-minded counterparts were still fighting Google.
The painter lifted the can from the bedsheet, now a makeshift banner. Solidarity from Berlin to SF, to San Jose, to Rennes, it read.
The group gathered around for a picture—but then someone remembered another city that shared in their fight. It wasn’t with Google, but with a lesser-known sister company funded by Google’s money: one facing accusations of sidestepping democratic oversight and plotting a sensor-filled neighbourhood that some worried would be rife with surveillance.
The painter lowered the spray can back to the sheet, filling out the banner’s bottom-right corner: to Toronto.
They hoisted the banner and threw their fists in the air.

One year and eight days earlier, a Toronto real estate executive named Julie Di Lorenzo was in a teal-and-orange cab heading south through the city’s core, racing to the office of a public land-development agency called Waterfront Toronto. She was deeply, deeply worried. She was supposed to be doing due diligence with a corporate lawyer, not rush­ing to a board meeting that had been rescheduled to help accommo­date the schedules of some of the world’s most influential men. Worse, the Waterfront board was meeting to vote about the project she wanted to talk through with the corporate lawyer: a partnership with a Google affiliate called Sidewalk Labs to develop an ambitious, sustainable, high-tech community on the shore of Lake Ontario in Canada’s biggest city.
It was a little after 8 a.m. on Monday, October 16, 2017. A veteran property developer with an anxious attention to detail, Di Lorenzo was on the phone with a different lawyer—one she’d hired to advise her on corporate governance—just as she had been until 10 p.m. the night before. She was trying to figure out if she should vote against the project, abstain or leave the Waterfront board altogether.
Taken at face value, the partnership meant Toronto would gain access to both brand affiliation with Google and the deep pockets of its parent company, Alphabet, to build a first-of-its-kind neighbourhood. The company promised to “set a new standard for downtown communi­ties and help relieve the pressures of the city’s remarkable growth.” Sidewalk had put enormous effort into its bid for the project, promising energy-efficient building designs, self-driving taxis, garbage-moving underground robots and sensors that would use artificial-intelligence software to track traffic flows. Modular building components could be assembled quickly, and Sidewalk promised that those buildings could have a “radical” mix of retail, office, residential and gathering spaces. Clever construction and financing ideas could even make the cost of living more affordable, meaning Sidewalk could potentially solve some of the problems that the Berliners were battling, though through a more overtly capitalist approach than they may have liked.
Much of Waterfront’s management was smitten with Sidewalk’s pitch to plan out this neighbourhood on 12 acres of underused lake­shore property. The agency had tentatively agreed on the partnership a month earlier. As a partner, Sidewalk would bring more than just Google’s clout; it was ready to cut a $50 million cheque to help with planning and consultations.
Waterfront had never taken on a project like this. The agency was launched by the federal, provincial and Toronto governments a decade and a half earlier to make the city’s once-industrialized slice of Great Lakes shoreline less barren. Each of the three governments appointed directors like Di Lorenzo to make sure the agency was following this mandate. And now, after weeks spent finalizing the deal, Waterfront was asking those directors to vote on it four days earlier than planned, in large part because prime minister Justin Trudeau, Alphabet chair Eric Schmidt and Sidewalk CEO Dan Doctoroff had a narrow window of opportunity to be in the same place for a celebratory announcement.
That opportunity was on Tuesday. Several armies of schedulers were trying to make that event happen, and all that was left was for Waterfront’s directors to sign off on the project. But Di Lorenzo didn’t want to. The developer saw herself as a shrewd, professional dealmaker, one both experienced and fortunate enough in life to dedicate her spare time to public service. On this October day, she felt she was being forced to vote on a project without enough time to make a fair decision on the public’s behalf.
Di Lorenzo chaired a Waterfront board committee that was supposed to parse these kinds of deals for the rest of the directors, using her decades of experience in development to guide the board’s decisions, and something about the deal she was being rushed to vote on didn’t feel right. Waterfront had a duty to ensure that its projects were in the best interests of Torontonians, of Ontarians, of Canadians, yet in her mind the agreement had raised more ques­tions than answers. It wasn’t quite clear who would be accountable if something went wrong, and the company had no real track record. Though Sidewalk executives had development and planning experi­ence in New York, the company itself hadn’t built anything before. New York had a very different political climate than Toronto’s, too, and a mayor endowed with greater powers. Pushing such a project through would be harder here: as happy as Toronto would be for a Google co-sign, caution was built into the fabric of its politics.
Sidewalk’s wildly rich parent company did have a track record, however, in building technology. It had changed the world through internet searches, advertising auctions, mobile computing and data collection, and at the time was worth nearly $700 billion—more than double the Canadian government’s budget for the year. Waterfront had no experience in going into business with a company with that kind of money and technical savvy. The power imbalance would be profound.
Di Lorenzo’s cab slipped down Bay Street, past the curving twin towers of City Hall and into the business district, as her lawyer, Carol Hansell, coached her on her options for the vote. Hansell was a well-regarded governance expert who’d been a director at Canada’s central bank and on countless other boards. She was just as baffled as Di Lorenzo: forcing a board to vote early on a deal of this magnitude so the prime minister and corporate executives could announce it the next day was no way to reach a sound decision.
Resigning was an option, Hansell told Di Lorenzo. But Di Lorenzo didn’t want to do that. Even if the project went forward, she wanted to be in a position to fix problems, or at least warn the public of what might go wrong. And merely abstaining from the vote wouldn’t send a clear message. So Di Lorenzo asked about dissenting. Given every­thing she was worried about, would it be appropriate?
She had every reason in the world to dissent, Hansell said, and she could make sure to ask that her position be recorded.
They got off the phone, and Di Lorenzo’s cab arrived at the foot of Bay Street just before 9 a.m. She stepped out and into the cloudy, chilly morning and walked into the office tower.
She took the elevator to Waterfront Toronto’s offices, turned to the south door and stepped into its boardroom, where a thirteenth-floor view of Lake Ontario was blocked by a generic-looking office tower that Waterfront’s design team probably would have frowned upon. The other directors and staff in the room seemed calm. Di Lorenzo wasn’t. As she took her seat, she was shaking. Her mind was racing. Did Waterfront have enough savvy to make sure they weren’t getting screwed by one of the world’s most powerful tech companies?

Over the next two and a half years, the deal that terrified Julie Di Lorenzo would explode into a battle for the future of cities, privacy, wealth and democratic decision-making. For all of Sidewalk and Waterfront Toronto’s vaunting talk of innovation as a vessel to make cities better—and for all the accusations of embracing surveillance that they were about to face—technology and data were almost after­thoughts in the calamity that unfolded.
The story of Sidewalk’s Toronto project is also the story of the failed ambitions of powerful men who deployed the language of collective progress as they tried to build their personal legacies and influence. Once Sidewalk walked into Toronto, those men largely stepped back and let others fight their battles for them.
Left to manage a project that routinely spun out of control, Waterfront and Sidewalk’s staff spent years trying to convince the public that the neighbourhood they were planning really had the public in mind. Working against them were droves of unexpected allies who used whatever means they had to call out what could go wrong. Digital activists found themselves working alongside tenured professors, patent lawyers, start-up executives, an erstwhile smart­phone magnate, a backroom-loving venture capitalist, a former attor­ney general whose life had nearly collapsed, an auditor general with a flair for drama, an ex-punk parliamentarian, and a mayor and a provincial leader who might have wanted each other’s jobs. Some of these people fought against what Sidewalk wanted to build in Toronto. Some of them fought against each other. And some of them simply wanted to make the project better. But they each managed to tell the world what could happen when one of the world’s biggest companies tried to reinvent cities in its own image.
Nothing went according to plan. And over the course of four years, I spoke with nearly everyone involved as I tried to figure out why. What started as a series of stories in 2018 looking at Sidewalk Labs and the economic consequences of data collection for the Globe and Mail—Canada’s most widely read national newspaper—led me to dozens of investigations and news stories about the company that reached into every corner of Canadian business and politics, into the great American centres of influence, and into the long shadow of an old electrical substation across the Atlantic Ocean. When Sidewalk pulled out of Toronto in May 2020, I realized I’d witnessed some­thing that said more about how power works in the twenty-first cen­tury than a sensor-filled 12-acre neighbourhood flooded with garbage-hauling robots ever could.
This book is based on interviews with more than 150 people, conducted in Toronto, New York and Berlin—and over pandemic phone and video calls—as well as thousands of pages of documents, some of which Sidewalk and government officials spent years try­ing to shield from the public. It’s a story about technology, ego, influence and failure, and how the rest of the world began asking the same questions as Julie Di Lorenzo was asking herself that October morning.

Editorial Reviews


Sideways is a detailed, meticulously researched study of the [Sidewalk Labs] affair and the future of cities.” —The Globe and Mail

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