Josh O’Kane is a technology reporter with The Globe and Mail, Canada’s most widely read national newspaper, where he covered the Sidewalk Labs saga for more than two years. His book “Sideways: The City Google Couldn’t Buy” was published by Penguin Random House Sept. 13.

Before Sidewalk Labs staff spent two-and-a-half years defending a controversial smart city in Toronto, they were under pressure from then-Google CEO Larry Page to dream up a fantastical urban future. By the start of 2016, Page had made it clear to the employees of his Google side-project that they should think about the pieces of a city in wholly new terms. Every piece, every unit, could be movable or rearrangeable. They shouldn’t be restrained by governments, real estate prices or people—they should abide only by the constraints of physics.

The company’s CEO, Dan Doctoroff, wanted to make an ambitious VIP product. A city, he wrote in his memoir, was “like any other product. It had customers. It had competitors. It had to be marketed.” While he was working on New York’s Olympic bid in the ‘90s, he had become determined to find the detailed bid books for the 1992 Games in Barcelona and Atlanta’s 1996 Olympics. In the run-up to the Atlanta Games, a member of his team pressed used-book dealers to pin down a copy of that city’s bid, eventually spending $800 to get a copy. Storytelling meant everything to Doctoroff. Changing the world meant everything to Page. So Sidewalkers set out to build a bid book that suited them both.

Some of the staff and consultants started with feasibility studies. Others began diving into data collection. Water recycling. “Street mesh” road grids. Utility tunnels. A massive dome to cover part of the community. It took more than a year to build out the vision. Dozens of staff, contractors and consultants worked late nights and weekends to synthesize the details they’d gathered and brainstormed, preparing a 437-page document that would become known as the Yellow Book.

Peppered with references to Disney and the dome-obsessed futurist Buckminster Fuller, the Yellow Book declared that Sidewalk would help cities “overcome cynicism about the future” and build “a city from the internet up.” The plans proposed a massive community that could house 100,000 people across 1,000 acres. It viewed people through the lenses of efficiency and profit, even as it promised residents better lives through novel technologies. And the document was sheathed in whimsy, in a bright-lemon jacket adorned with a tribute to a 1935 Frank Lloyd Wright exhibition called Broadacre City.

Much of the Yellow Book reimagined society in progressive ways, proposing schools that would account for different learning styles and social backgrounds, and outlining a justice system that could divert people from prisons and into programs to address substance abuse or mental illness. But it also described a dome-covered dream world built on principles that were deeply skeptical of government. “Fearing risk, bureaucracies stifle innovation,” the authors wrote, several pages after Dan Doctoroff’s introductory letter, in which he lamented “how difficult it is to get anything done in a city.” Though Sidewalk promised to build an inclusive world, it proposed handing enormous power to the private sector. It would resemble a kind of fiefdom—one where people would be monitored from the moment they looked in the mirror in the morning.

No, really. The mirror would collect data on residents using a hidden sensor to monitor for stress marks on a person’s face or changes in skin colour that could indicate fluctuations in blood oxygen levels. Like many other technologies proposed in the Yellow Book, this “smart mirror” didn’t exist, but many of the components to make one did. The mirror was framed in the language of kindness and care: It would give doctors a clearer picture of a person’s health.

But the city the Yellow Book envisioned would also be a for-profit enterprise. Users would be encouraged to share as much data about themselves as possible, collected by everything from those smart mirrors to their smartphones. Project Sidewalk would create “a new market for data” to learn more about city living, and Sidewalk and other companies would reap economic rewards from learning about people’s day-to-day lives. Insurance company executives, for example, would trip over themselves for the type of smart-mirror data Sidewalk wanted to collect.

The Yellow Book took Silicon Valley’s typical disdain for government bureaucracy a step further, weaving data collection into many of its plans. It wanted power on par with government—and in some cases, even more power than that. It wanted to levy its own taxes, track and predict people’s movements, and control public services, including law enforcement. The ideas were dressed as progressive but gave unprecedented control to Alphabet and its partners. For instance, a police accountability system that tracked cops’ movements and included a rating program, like a “Yelp for police officers,” might help officers build trust in their community. But the system would only work because the cops would be working under constant surveillance.

It’s not that privacy was entirely an afterthought in the early days of Sidewalk. The company promised to follow Privacy by Design, a set of principles meant to ensure that privacy protection is built into systems and technologies from the jump. Some of the Yellow Book’s data-sharing ideas had the potential to be very helpful—like a smoke alarm that, when alerting the fire department to a fire, would give the resident the option to automatically let first responders know other crucial details, such as if anyone in the household had asthma.

Yet despite a promise to let residents opt into data sharing, people living in a Project Sidewalk community would also have to endure tiered access to their own neighborhood based in large part on how much data about themselves they were willing to share.

In this regard, data would be a kind of currency: People who chose not to share anything about themselves when they visited a friend’s apartment in Project Sidewalk might not get access to its self-driving “taxibots” or be able to buy items from certain stores. Data could ultimately be used to reward “good behaviour,” too. Business licences could be more easily renewed for those offering good customer service. Interest rates on loans could be determined by “digital reputation ratings.” A nightclub could be instantaneously fined if sensors found it was too noisy, and people could be automatically blocked from accessing certain kinds of housing if someone filed a complaint about them.

And yet the Yellow Book vision for a Sidewalk city did not appear to pay much heed to neighbors, or what holds neighborhoods together.

Anthony Townsend was staring at Google Earth and thinking about churches. It was the fall of 2015, and the smart-city consultant was sitting in a northeast-facing conference room at Intersection’s offices in the Woolworth Building, overlooking City Hall Park. It was a sunny day, and he was clicking around satellite images from a different sunny day in Detroit. After publishing the book “Smart Cities: Big Data, Civic Hackers, and the Quest for a New Utopia,” Townsend had been swept in by Sidewalk Labs to help bridge the worlds of urbanism and technology. On this day in 2015, he was trying to figure out what a hollowed chunk of the city might look like if Sidewalk had its way with it.

The company was plotting out a potential neighborhood there that would be built around what staff called a “street mesh”—city blocks divided by a mix of avenues, laneways and promenades, with various levels of access for people and self-driving cars. At 1,000 feet long by 1,000 feet wide, each city block could ostensibly house about 3,500 people amid a mix of park space, apartments and offices.

With help from outside consultants, Sidewalk staff were working on feasibility studies to show what a “Project Sidewalk” community might look like in a real city. They were studying a few sites, including one on the outskirts of Denver and the site of a former naval air station in Alameda, California, across the bay from San Francisco. If the company put in a $2 billion investment and gradually reinvested some of its proceeds, the team calculated that Denver could give Alphabet a return on its investment of 11.9% over 30 years from real estate alone. Thanks in part to the Bay Area’s soaring land values, Alameda could deliver 28.4%.

Detroit had the least potential estimated return for the company, at 10.5%, and staff freely admitted that it would take longer there to achieve their goals. But they also saw it as a chance to shake the rust off the Rust Belt and revive one of America’s lost cities of industry. Detroit was also home to huge swaths of underused land close to its core and remained the centre of gravity of America’s legacy automakers. Given Alphabet’s massive cash reserves and valuation— at nearly half a trillion dollars in February 2016, it was worth more than 10 times what Ford or General Motors were—some Sidewalk staff thought the company could buy one of those manufacturers to help accelerate Alphabet’s self-driving dreams.

After studying the whole city, Sidewalk staff had found what they were looking for: a 1,307-acre site they believed to be nearly 85% vacant, more than half of which was owned by the city itself, wedged between downtown Detroit and GM’s Detroit-Hamtramck Assembly. Much of it was in a neighborhood called Poletown East. At the corner of the site sat the Packard Automotive Plant, considered the largest abandoned factory in the world, its 40,000 employees long gone. The company mulled buying the plant and repurposing some of the structure into Project Sidewalk, which staff wrote in an internal document would “provide an eloquent opportunity to bridge Detroit’s past and future.”

They had run the numbers, too: Among the 7,132 parcels of land on the site, only 1,132 were believed to be occupied. That wasn’t even 16% of them. It couldn’t be that hard to move people out, raze the neighborhood and build out a street mesh.

But as Townsend clicked around Poletown East on Google Earth, he couldn’t stop dwelling on something it seemed no one else had bothered to consider: the churches.

Townsend counted at least a dozen of them. They all had names: Faithway United Ministries, Harper Avenue Church of God in Christ, Sweet Kingdom Missionary Baptist Church. A few were historically Polish churches. Many had Black congregations, and were still active. These were people’s spiritual sanctuaries. Even though thousands had left the community, many still returned weekly to the place they once called home.

Townsend was stunned—not because of the controversy that would clearly emerge if Sidewalk tried to displace the churches, but because no one at Sidewalk had raised this as an issue. They hadn’t considered how real people might be hurt by the utopian city they were planning to satisfy their billionaire patron. Many of the New Yorkers and Silicon Valley residents who shaped Sidewalk were so hell-bent on making ordinary cities better that they’d overlooked what made people come together in cities in the first place.

Excerpted from Sideways by Josh O’Kane. Copyright © 2022 Josh O’Kane. Published by Random House Canada, a division of Penguin Random House Canada Limited. Reproduced by arrangement with the Publisher. All rights reserved.