The Quayside development on Toronto’s waterfront was supposed to be the shining example of a tech-optimized smart city, an urban environment reinvented “from the internet up,” as it was described by Sidewalk Labs. That was a sister company to Google, which won a government bid in 2017 to modernize the 12 acres of former dockland. There would be robotaxis, heated sidewalks, adaptive traffic lights and lots of data collection. But in 2020, Sidewalk Toronto suddenly shut down before a single ribbon had been cut, turning a shining example into a cautionary tale. It’s all chronicled in a new book from Globe and Mail reporter Josh O’Kane called “Sideways: The City Google Couldn’t Buy.” Marketplace’s Meghan McCarty Carino spoke with O’Kane about what went on behind the scenes of the Sidewalk Toronto project.