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SidewaysBy: Josh O'Kane 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
By: Josh O'KaneNATIONAL 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 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.
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4.3 ★★★★★
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Product Reviews
★★★★★ 5
Good for 1Ls to know
Format: Paperback
Very useful
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Reviewed in the United States on May 7, 2025
★★★★★ 5
For law students
Format: Paperback
Great resource for literal thinkers entering law school.
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Reviewed in the United States on July 25, 2024
★★★★★ 3
Needs to be more concise to weed out extraneous crap in your arguments
Format: Paperback
It’s very wordy and could be a lot more concise and be even more effective. “Getting to maybe” is not an exercise in dissertations but finding the right points to create an effective argument. There are better resources out there.
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Reviewed in the United States on May 25, 2026
★★★★★ 2
This book made me angry
Format: Paperback
I was excited about this book. Many law-related blogs and forums highly recommended this book. It's a "must read" for law students, they said.
I was angry when I read the introduction. I was angrier when I began reading the chapters. What happened to brevity? Law students are already swamped with course readings. Why write a book intended to be read by law students in such a long and voluminous way? Much of the text can be removed.
"Get to the point," I found myself telling the author as I read page after page. I hated it. It is the rare law student who will pick up this book for its narrative value. The typical law student will pick this book for its value on navigating through law school exams, not for its story-telling. Yet that student will be left disappointed.
I wish the author would have considered writing a "Get to the Point" book, which would serve as a shorter version of 'Getting to Maybe.' Perhaps it is not too late. "Get to the Point" could serve as an alternative or accompanying version, maybe? I ask that the author considers this.
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Reviewed in the United States on August 2, 2025
★★★★★ 5
Great overview!
Format: Paperback
Well worth the price for basic overview of Employment Law. Wish there was more information on co-employment risk.
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Reviewed in the United States on August 31, 2023