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Author Josh O’Kane.Handout

  • Title: Sideways: The City Google Couldn’t Buy
  • Author: Josh O’Kane
  • Genre: Non-fiction
  • Publisher: Penguin Random House Canada
  • Pages: 320

Humans have lived in cities for thousands of years. It’s unclear which location can lay claim to being the world’s oldest city, but a handful of places – Beirut, Jerusalem, Varanasi, Aleppo, and others – prove urbanization goes back, way back. As a species, we gather to share benefits and burdens, to cooperate and compete. Together, we build things that outlast us. Life in cities echo the words of former Governor-General Adrienne Clarkson, who said, “Each of us is carving a stone, erecting a column, or cutting a piece of stained glass in the construction of something much bigger than ourselves.”

Collective undertakings such as cities may be grand, but they rarely exist without tension, miscommunication and disagreements. In Sideways: The City Google Couldn’t Buy, Globe and Mail technology reporter Josh O’Kane recounts the story of Google’s sister company Sidewalk Labs and the public-private development organization Waterfront Toronto as they navigate local, provincial and national governments; activists; industry titans; and their own relationship. The book explores how the two tried to work out the future of Quayside – a development site in the city along the shores of Lake Ontario – as a smart-city neighbourhood.

Sideways is a detailed, meticulously researched study of the affair and the future of cities. In the context of Google founders Sergey Brin and Larry Page’s – especially Page’s – vision for smart cities, it’s also a study of the power and limits of Big Tech. Ditto the risks and pitfalls that come with reimagining settlements that have slowly evolved over time. Moreover, it’s the story of how billionaires with big egos and big pet projects sometimes run up against reality. That reality check includes a lesson in how cities work, especially in a country with three orders of government and academic and activist communities that can, at times, rise to the occasion to resist undertakings that beg for resistance.

As O’Kane writes of the company, “Nothing ever seemed to be enough for Sidewalk Labs.” Central to the tale is the never-ending push by Sidewalk for more: more land, more control, more data. These are the keys to a healthy return, information that drives “innovation” – and yields patents. Bound up in that push are risks to democracy we have become familiar with throughout decades of neoliberal governance and putting the private market ahead of the public good. Privacy is shunted aside. Favourable tax breaks are offered. Public things are privatized. Citizens are treated as vessels of value production and capital accumulation. Surveillance powers are given – or taken. It’s bad news for democracy, especially when a company seeks to become a de facto government. That’s been done. It didn’t go well.

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The organizations central to Sideways read like characters. Sidewalk Labs is a bullying megalomaniac. Waterfront Toronto is a well-meaning local do-gooder in over its head. The real-life participants are written in three-dimensions, their actions and motivations detailed; they aren’t caricatured. In that way, we learn about Dan Doctoroff, former deputy mayor of New York and head of the city’s failed Olympics bid, who led the Sidewalk effort as he faced a shifting public increasingly wary of tech companies. We meet Bianca Wylie, who helps spearhead the campaign against Sidewalk in the name of good governance and democracy, even as she faces, cliché as it is, a David-versus-Goliath struggle. We encounter Ann Cavoukian, privacy watchdog and pioneer of Privacy by Design, who tries to keep Sidewalk honest from the inside. We also come across plenty of others who, for years, were part of the Quayside development effort, a local project with global implications – one that reads a bit like a Greek tragedy, in case anyone might be thinking of Icarus.

Sidewalk Labs never did build its smart-city neighbourhood at Quayside. Doctoroff blames the pandemic. “The only thing that ended up making this project not happen was COVID,” he says. It didn’t help, of course, that Page and Brin retired, deflating the Sidewalk bubble as they did. But there was more to it. As O’Kane concludes, “Though the people who loudly questioned Quayside didn’t cancel the project, they changed the math that did. They chipped away at Sidewalk’s glossy veneer, separating niceties from intentions and truth from marketing.”

As a couple of asides, O’Kane tells the stories of Amazon’s HQ2 defeat in Brooklyn and Google’s failures to launch its startup campus in Berlin. Those asides are central to a key takeaway of this book. Big Tech has the privilege of time. These fights aren’t over. They’re just beginning. Reflecting on the Quayside struggle, Wylie notes, “The thing that carried right to the end, that carries right to this day, is that this can happen again.” It can. Indeed, it will. And hopefully O’Kane will be around to document the next struggles, too.

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