O'Kane lifts the lid on Google's failure to build a city of the future on Toronto's waterfront

A year into its quest to build a neighbourhood “from the internet up” in Toronto, Google sister company Sidewalk Labs was doubling down on Canada. Chief executive Dan Doctoroff and his colleagues embarked on a vast influence campaign that month, meeting with tech CEOs in Waterloo, Ont., visiting the Fortune Global Forum at the Ritz-Carlton to pontificate on cities, and launching a secret advisory panel of influential Torontonians. On Oct. 25, 2018, the company pulled off perhaps its most important meeting yet: a dinner with 12 of the most powerful unelected officials in the federal government. It was co-hosted by the office of Innovation, Science and Economic Development Canada and the Privy Council Office, the nerve centre of Canada’s government. Securing the meeting was a coup for Sidewalk. The country’s corporate elite pitched meetings to public servants all the time, but rarely did a comparatively small American firm command such attention. Four top innovation department officials were on the guest list, as were the secretary of the Treasury Board of Canada, the president of the Public Health Agency of Canada, and a handful of deputy ministers, including Kelly Gillis, whose portfolio at Infrastructure Canada meant overseeing Waterfront Toronto—the tripartite agency that Sidewalk was partnering with. It was a chance to sell Sidewalk’s brand of optimism to the very people who would advise legislators on any regulatory or policy changes that the company desired as it sought to build a community called Quayside on the shore of Lake Ontario, if Waterfront ever gave it permission to break ground. It was also a chance for Doctoroff’s team to get in front of the reputational damage that been piling up for months. As innovation department staff briefed meeting co-host Paul Thompson, an associate deputy minister, they warned him about Sidewalk’s vague proposals around data and privacy, about rumours that the company was pushing for more land than Quayside, and about the resignations of influential advisers such as privacy expert Ann Cavoukian and venture capitalist John Ruffolo. Canadian intellectual property was at stake, too, and federal staff warned about a contract I’d discovered months earlier that showed Sidewalk wanted full control of design partners’ IP. In the talking points they drew up for Thompson, he was told to press Sidewalk to ensure that Canadians would realize the benefits of their ideas, and to bring up the importance of strong privacy measures and good data governance. But the associate deputy minister was also told to strike a balance—one rooted in a growing global insecurity. That same day, a Berlin politician declared that Google abandoning a startup campus in the city would be “fatal” for the German capital. Thompson’s colleagues feared the same thing: that if Sidewalk left Toronto, it could send a message to other tech companies that Canada was anti-innovation. Thompson was given specific instructions on how to address this, by saying: “I hope that Sidewalk Labs’ experiences with the Quayside project could act as a positive test for additional product development and investment in innovation by Alphabet in Canada.” The country’s official stance on the Sidewalk project was to attract as many new and shiny things as possible. So the October dinner with bureaucrats was, by all accounts, pretty banal. Doctoroff gave his usual sales pitch, flanked by policy chief Micah Lasher and communications leader Lauren Skelly. They talked about a proposal to host data in a third-party trust, and how Sidewalk’s model for data would promote Canadian innovation. No one in attendance raised much fuss. “It’s senior bureaucrats,” says one person who was there. “No one really gets into fights.” To many people in Ottawa, Sidewalk Labs was a Toronto problem. Yet this was one of the highest-profile efforts in human history to rethink how cities were built. And because government responsibility fell to an obscure agency, it was easy for officials with actual power to absolve themselves of accountability for the outcome. That marked one of the project’s greatest flaws. The most consequential decisions to be made around Quayside were about data governance: those choices could have set global standards for who prospered, how fairly wealth would be shared, and how privacy would work in the world’s increasingly sensor-laced cities. But Waterfront’s own governance was broken. Its allegiances were to the city, the province, and the country in equal measure. With no majority shareholder and three very different sets of interests, it was a fundamentally paralytic organization—a superficial symbol of government co-operation that lacked any of those governments’ authority. Waterfront was forced to wait for those governments to write policies that would regulate data collection at Quayside—policies they hoped would be world-beating and privacy-protecting, and would stand up to the scrutiny such a widely watched project would inevitably get. Rather than listen to Waterfront or to the project’s opponents, who were begging for leadership around data and privacy protection, the lawmakers and policy advisers in Ottawa did extraordinarily little. After the Cambridge Analytica data-misuse saga changed the world’s view of corporate technology and Quayside was beset by months of scandals, the political opportunity was gone. Officials who dealt with or closely followed the file now privately admit that Justin Trudeau’s government had previously approached Sidewalk and other tech giants with naïveté. One told me, jokingly, that Sidewalk became “inconvenient.” Others were more blunt. “Why would you run into that fire?” says Matthew Mendelsohn, a former high-level Privy Council official. “You only run into the fire if you’ve got a hose.” The abdication of responsibility happened not just between governments, but within them. Because Waterfront was, at its core, an infrastructure agency, it reported to the federal Infrastructure Department. But big decisions about how Canada would handle the future of citizens’ data and privacy fell to the innovation department. With the Prime Minister’s Office by this time deferring to Infrastructure Canada for any public comments on a project that Trudeau had once so eagerly embraced, the infrastructure and innovation departments fell into an awkward dynamic that did little to answer the big-picture questions Quayside posed for the future of data and privacy rights. The Personal Information Protection and Electronic Documents Act, Canada’s mouthful of a privacy law for private-sector companies that’s usually shortened to PIPEDA, was nearly two decades old. It was woefully under-equipped to deal with the mass data collection practised by technology firms in the late 2010s. By the time Sidewalk came to Canada, federal officials were struggling to balance the duelling imperatives of data protection and their government’s pro-Alphabet stance. Infrastructure Canada was hesitant to take ownership of the project’s big-picture questions; the department says it didn’t believe the Quayside project necessitated policy change on its own, since the government had already promised to overhaul PIPEDA entirely. The innovation department was trying to make that happen. But for years, the overhaul was hit with delays, in large part thanks to territorial jockeying: numerous senior staff and politicians wanted a say in digital regulations, which would ripple through departments from the Treasury Board to National Defence. And innovation minister Navdeep Bains was a deeply cautious politician—a team player to a fault, willing to dodge meaningful questions about Quayside as they related to his department’s digital policy work, to avoid stepping on the toes of his colleagues in infrastructure who actually had responsibility for overseeing Waterfront. As one person who watched it all happen describes it, Sidewalk had become a political hot potato. Since they were unable to get meaningful privacy and data governance reforms through Parliament quickly, the two departments discussed helping Waterfront fight for privacy and data protections in their agreement with Sidewalk, which would reflect the modern world better than PIPEDA did. Effectively, they hoped to protect Canadians’ interests contractually, rather than legally. Frozen by complex internal politics and afraid to take responsibility for a controversial project, a government with the power to write a country’s laws was addressing one of the most complicated city-building efforts in its history by avoiding laws altogether. Sideways: The City Google Couldn’t Buy, by Josh O’Kane, is published by Random House Canada. The book is one of five finalists nominated for this year's Shaughnessy Cohen Prize for Political Writing. Established by the Writers' Trust in honour of the late MP from Windsor, Ont., the $25,000 award is given annually for an exceptional book of literary nonfiction that captures a political subject of relevance to Canadian readers. The award will be handed out in Ottawa on Wednesday, May 10. Two questions for Josh O'Kane Why did you write this book? "After more than two years reporting on the failed attempt by Google sister company Sidewalk Labs to build a neighbourhood in Toronto, I realized that what I'd seen said so much more about power is exerted between the public and private sectors in the 21st century than I could have possibly imagined. The pandemic gave me plenty of time to put the story in its many important contexts." Why is your book important and who should read it? "Digital giants have spent much of the past 15 years trying to expand their dominance into the physical world, and governments the world over are woefully underprepared for grappling with what this means for their citizens. Anyone interested in how Big Tech really works, how public-private partnerships fail, or how Canada sees itself in the world will find it a compelling tale." The Hill Times

O’Kane lifts the lid on Google’s failure to build a city of the future on Toronto’s waterfront

The following is an excerpt from Sideways: The City Google Couldn’t Buy, by Josh O’Kane, one of the five finalists for this year's Shaughnessy Cohen Prize for Political Writing.

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O’Kane lifts the lid on Google’s failure to build a city of the future on Toronto’s waterfront

The following is an excerpt from Sideways: The City Google Couldn’t Buy, by Josh O’Kane, one of the five finalists for this year's Shaughnessy Cohen Prize for Political Writing.

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In-Depth Features

The following is an excerpt from Sideways: The City Google Couldn’t Buy, by Josh O’Kane, one of the five finalists for this year's Shaughnessy Cohen Prize for Political Writing.