Sideways - by Josh O'Kane

About the Book

"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."--

Book Synopsis

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 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.

Review Quotes

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

"A thrill ride of a book, revealing what really happened when Google tried to build a city and Silicon Valley's magical thinking fell to earth. O'Kane delivers the definitive chronicle of the outsized personalities, combative politics, and corporate power driving Google's Toronto experiment, and the citizen pushback that eventually sealed its doom. Sidewalk Labs may be nomore, but its story has lasting lessons for our digital age." --Margaret O'Mara, author of The Code: Silicon Valley and the Remaking of America

"In his crisply written and deeply researched book, Josh O'Kane reveals precisely how Google, one of the most powerful companies of all time, saw its techno-utopian vision for a city of the future foiled by the people who would actually have to live there. A crucial parable for any who finds themselves living more and more in Big Tech's backyard." --Brian Merchant, author of The One Device

"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

"Sideways presents a captivating story that reads like a boardroom TV drama. . . . The book details the pressing issues of the digital age, and offers a fresh perspective on the messy complexity of urban life. . . . [Sideways has] 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 worth reading." --UrbanToronto

"The book is so fantastic and gives such a great insight into this moment, this whole project, how it came to be, and how it collapsed." --Paris Marx, Tech Won't Save Us podcast

About the Author

JOSH O'KANE has been a reporter with the Globe and Mail, Canada's largest national newspaper, since 2011. He won Germany's Arthur F. Burns Award for transatlantic political and cultural reporting in 2019, for his coverage of that country's broad pushback against Big Tech. O'Kane's reporting has also won numerous Best in Canada awards from the Society for Advancing Business Editing and Writing. His first book, Nowhere with You, was a Canadian bestseller. He lives in Toronto.