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From the tech reporter who most closely pursued the Sidewalk Labs fiasco in Toronto, an uncompromising look into what the Google sister company's failure in urban development reveals about Big Tech, data 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 underdeveloped lakeshore was available for development, and with Google co-founder Larry Page and 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. Hundreds more acres of undeveloped former port lands kept creeping into Sidewalk's plans, and questions were emerging about how much the public would benefit from the company's vision for a high-tech neighbourhood—and the data it could harvest from residents. The ensuing fight to reel in the power of Sidewalk Labs became a crucible moment for the worldwide battle for digital rights and against the extension of a digital behemoth's corporate might into the physical world. In the tradition of boardroom dramas like Bad Blood and Super Pumped, Sideways signals to the world that all may not be lost in the effort to contain the rapidly growing power of Big Tech.