Sideways

The City Google Couldn't Buy

By: Josh O'Kane

Narrated by: Ian Lake

NATIONAL BESTSELLER

FINALIST FOR THE WRITERS' TRUST SHAUGHNESSY COHEN PRIZE FOR POLITICAL WRITING

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 neighborhood—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 listeners 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.

©2022 Josh O'Kane (P)2022 Random House Canada

Critic reviews

2023, Heritage Toronto Award - Historical Writing: Book: Short-listed

2023, Legislative Assembly of Ontario Speaker's Book Award: Short-listed

2023, National Business Book Award: Long-listed

2023, Shaughnessy Cohen Award for Political Writing: Short-listed

2023, Shaughnessy Cohen Award for Political Writing: Short-listed

2023, Society for Advancing Business Editing and Writing (SABEW) - Best in Business Book Award: Short-listed

NATIONAL BESTSELLER
A GLOBE AND MAIL BEST BOOK OF THE YEAR

Finalist for the Writers' Trust Shaughnessy Cohen Prize for Political Writing
Finalist for the Ontario Speaker’s Book Award
Finalist for the SABEW Best in Business Book Award
Longlisted for the National Business Book Award
Nominated for the Heritage Toronto Book Award
A Hill Times Top 100 Best Book of 2022

“Sideways is a detailed, meticulously researched study of the [Sidewalk Labs] affair and the future of cities.... The story of how billionaires with big egos and big pet projects sometimes run up against reality.... Reads a bit like a Greek tragedy, in case anyone might be thinking of Icarus.” —The Globe and Mail

“In Sideways, Josh O’Kane presents the engaging, comprehensive tale of Google’s collision with Waterfront Toronto, a federal-provincial-municipal government development agency, as it seeks to cash in on the love affair with Big Tech. Packed with insightful interviews and tart observations of the zeitgeist, O’Kane deftly combines analysis, telling anecdotes, and a helping of wit to recount how the romance went sour. The result is a definitive chronicle, leaving behind valuable lessons for Canadian policymakers.” —2023 Shaughnessy Cohen Prize Jury

“Big Tech is remaking our physical landscape in ways that we are only beginning to reckon with. In Sideways, Josh O’Kane gives the definitive account of the most ambitious remaking attempted yet: the effort by one of the most powerful companies in the world to build an entire urban neighborhood in its own image, in the fourth largest city in North America. This is the engrossing saga of what happens when our tech overlords let their overweening aspirations get the better of them and finally meet their match.” —Alec MacGillis, author of Fulfillment: America in the Shadow of Amazon

City Building Failure

The story had nothing particularly scandalous or surprising, but I enjoyed the in-depth look at a failed public/private partnership in city building. Additionally, I came to appreciate democracy more.

Good but too long.

The whole of the story could be told in 1/3 the time.

Interesting how the best way to do good government is to simply do nothing at all. Then no one can complain or protest.

Unstoppable force vs. immovable object

If you’re looking for the next Bad Blood or Super Pumped, that is not this. It’s not a book about grift or true crime-like intrigue, but rather an impeccably reported account of what happens when one of the biggest companies on earth tries to bully a city into doing what they want and the activists that stood up to stop them. This is a must listen for anyone interested in tech or business in Canada, and the importance of building cities for people first.

The only thing I would be a little critical of is the narrator; there’s a few places where the narrator pronounces a word phonetically that differs from the way they’re pronounced (“Mattamy”) or spells out acronyms that are read as words (e.g. Canadians don’t spell O-M-E-R-S we just say “omers”) that take me out a bit as a Canadian reader.