Sideways

NATIONAL BESTSELLERA GLOBE AND MAIL BEST BOOK OF THE YEARFinalist 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 AwardLonglisted for the National Business Book AwardNominated for the Heritage Toronto Book AwardA 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

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.