The air was filled with excitement and optimism. It was 2017 and Waterfront Toronto had just announced a partnership with Sidewalk Labs, the urban tech arm of Alphabet, Google's parent company, to develop a 12-acre plot of land along Toronto's eastern harbourfront known as Quayside. The premise of the project was to deliver an innovative new 'smart' neighbourhood, dubbed Sidewalk Toronto, that was infused with revolutionary technology and which would herald a new era of urban development for the digital age. Dan Doctoroff, star CEO of Sidewalk Labs and former deputy mayor of New York City, was leading the project and arrived in Toronto with much fanfare, along with the vocal support of Google founder Larry Page and Alphabet CEO Eric Schmidt. But less than three years later, after countless scandalous headlines, high-profile resignations, audacious land grabs, and mounting public distrust, the partnership crumbled and Sidewalk Labs left Toronto with next to nothing to show for it. What happened?

Conceptual rendering of former Sidewalk Toronto proposal, image via submission to Waterfront Toronto.

Globe and Mail reporter Josh O'Kane weaves together the complex web of characters, events, and documents that make up the Sidewalk Toronto saga in his new book, aptly named Sideways: The City Google Couldn't Buy. O'Kane paints a comprehensive picture of what went wrong and why, and connects the events in Toronto to the wider global struggle between data privacy, intellectual property rights, and the grossly underestimated powers of Big Tech. The book is not just an historical account of events, it is a stark warning for the future of our cities and the future of our individual privacy, and how woefully unprepared we may be in the battle for both.

Book cover for Sideways, image courtesy of Random House Canada 2022.

O'Kane was one of the primary reporters at the Globe and Mail who followed the Sidewalk Toronto story from start to finish and had a front row seat to all the ensuing drama. Pieced together from more than 150 interviews of people close to both sides of the project along with years of investigative reporting, O'Kane's account of events is likely to be the most complete we may ever have of the Sidewalk Toronto saga. 

Portrait of author Josh O'Kane, image courtesy of Random House Canada 2022.

Sideways presents a captivating story that reads like a boardroom TV drama. The book assembles an unexpectedly diverse cast of characters, from Prime Minister Justin Trudeau to former BlackBerry CEO Jim Balsillie, each of whom had a role to play that influenced the course of the Sidewalk Toronto project. The story even stretches to Berlin, where a group of activists successfully pushed a planned Google development out of their neighbourhood to resist gentrification, and to the Cambridge-Analytica scandal that shocked the world in 2018. The book details the pressing issues of the digital age, and offers a fresh perspective on the messy complexity of urban life.

Conceptual rendering of former Sidewalk Toronto proposal, image via submission to Waterfront Toronto.

With big egos, bold personal ambitions, frustrating bureaucracies, backroom politics, consequential miscommunications, and unexpected external forces, Sideways is a story of political intrigue, drama, hope, and frustration, with an uplifting air of David-versus-Goliath storytelling mixed with an eye-opening window into what a digital future might hold. It is a story with consequences that extend far beyond the muddy shores of Lake Ontario, but which also hits close to home in a city changing at a breakneck pace. All things considered, it is a story worth reading.

Sideways: The City Google Couldn't Buy by Josh O'Kane will be released on September 13, 2022, and can be picked up online or at your local bookstore.

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