Sideways: The City Google Couldn't Buy

by Josh O'Kane

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.

Genres: Nonfiction, Politics, Urbanism, Technology, Urban Planning, Business, Canada

415 pages, Kindle Edition

First published September 13, 2022

About the author

Josh O'Kane has been a reporter with The Globe and Mail since 2011, and has covered the technology sector for much of the past five years. His coverage focuses on the relationships between tech companies and human beings, governments, economies, and each other.

His latest book, Sideways: The City Google Couldn’t Buy, investigates the failed effort by Google sister company Sidewalk Labs to build a future-focused neighbourhood in Toronto, the many institutions that company won over, and the consequences of Big Tech’s push into the physical world.

O’Kane won the 2019 Arthur F. Burns Award for transatlantic political and cultural reporting from Germany’s Internationale Journalisten-Programme for his coverage of that country’s broad pushback against Big Tech. His reporting has also won numerous Best in Business Canada awards from the Society for Advancing Business Editing and Writing.

He has written widely on music, entrepreneurship, and Atlantic Canadian culture; his first book, Nowhere with You, examined all three subjects, and was a Canadian bestseller. O’Kane has extensively reported from Berlin, Halifax, Fredericton and Saint John, and is based in Toronto.

Reviews

[Hugh · Rating 5 out of 5]

I’m definitely the target market for this book. I followed the story fairly closely as it happened, lived and worked close to it all. I even joked when the official announcement was made that “Dan Doctoroff has the perfect name for a comic book villain”.

Well.

This book is great. O’Kane does a great job of bringing the players to life and weaving the narrative with the broader cultural developments (Cambridge Analytica, The Age of Surveillance Capitalism, and others) that evolved public perception of the project. He skewers the public figures that used the project for political gain without caring about the on-the-ground reality.

It’s great, and useful in a much larger context than just Toronto. Anyone with an interest in the intersection of private tech companies and public policy should pick this up.

[Michael Donolo · Rating 3 out of 5]

It's more about the boardroom drama and political theatre than Sidewalk's plan. Still an interesting story that exemplifies big tech's poor understanding of the public interest.

[Simonas · Rating 5 out of 5]

Sužinojau iš "The Economist" geriausių knygų sąrašo ir tiesiog - puiki. Man visiškai negirdėta istorija kaip "Google" įkūrėjų finansuotas "pet project" bandė gauti teisę tiesiog vystyti ir statyti realiai naują Toronto priemiestį. Knyga pasakoja visą istoriją "nuo-iki", tad tikrai įdomu nieko negirdėjus apie tas peripetijas - apie verslo ir valdžios santykį, politines priemones, privatumo problemas ir t.t.

Įvykiai labai nauji, knygos pabaiga siekia net 2022 m. pradžią.

[Deborah · Rating 3 out of 5]

The book is an interesting behind-the-scenes look at local politics in Toronto and the way it fits into the broader Canadian political and cultural narrative. It strives to present all facets of the Sidewalk Labs saga. In doing so it has the side effect of being long winded and following numerous tortuous side quests before getting to the actual point.

The book could have been half its current size and packed twice the punch if it didn't detail every single email exchange between bureaucrats with the feverish excitement of a breaking news story.

[Dorottya · Rating 4 out of 5]

At times this book lost the plot and wandered a little too far off but for the most part it was a fascinating read. Equal parts terrifying and inspiring to see Toronto fight back! #FuckOffGoogle

[Abigail · Rating 3 out of 5]

*snaps fingers approvingly*

I really enjoyed the book! A boardroom/political drama that revolves around the urban fabric of the waterfront that had the potential to reshape how cities across the world work.

When the book opened with explaining how Larry Page was a ‘pod’ guy, I knew it was going to be bad. Like with the premise of essentially selling a chunk of the city to one of the mega tech companies to do whatever they want with, obviously it’s going to be bad, but still. Tech just does not understand the built environment or communities in any way and it’s infuriating. The thought process every time seems to be ‘We’re very cool and smart, and we solved X software problem one time, so we can definitely apply the same concepts to every other problem society is facing if only these pesky governments and activists would get out of our way.’ There are a lot of problems with our governments, but the answer is never privatization, that’s just swapping a somewhat accountable organization for a totally unaccountable one. Any company seriously considering sea steading as a viable solution for cities because they think all problems stem from the existence of a local government is just trying to create a libertarian hell.

It would have been nice if we’d never awarded Sidewalk labs the contract to plan out Keyside in the first place, but it can be very hard to resist the shiny allure of big tech. They put a lot of time and money into the window dressing of their ideas. And at the time the mainstream narrative was still that the tech giants could do no wrong. But it was really entertaining to hear them slam up against the slow moving giant that is city politics over and over against.

The main thing I would’ve liked to hear more of is an analysis of the actual ideas Sidewalk was proposing, because I know a few and they are comically bad. Like having the entire city be made of modules that will be swapped out throughout the day in a ‘just in time’ fashion so that you theoretically have exactly what you need at any moment but in practice just live in Daedalus’ labyrinth and can never find anything because the walls are constantly moving. That’s probably out of scope for a technology reporter, and he did do a good job of explaining the big concepts that grabbed the public’s attention, but I can never really have enough urbanism talk so would’ve loved to go a few levels deeper on it.

Thanks for coming to my Ted Talk

[Daniel Perry · Rating 3 out of 5]

All the details are here, if you want to know them, but that's both good and bad; myself, I found I had trouble separating the most important revelations from the more mundane, but your mileage may vary.

[Jeremy Mutton · Rating 4 out of 5]

Josh O’Kane’s well written, well researched book echoes classic tales of hubris, in this case from a tech giant that in 2017 could do no wrong. They learned quickly what a shit show development and politics are in Toronto. I enjoyed some of the smaller details that made clear what a fiasco the sidewalk labs project really was. Like buildings wearing raincoats… only these protective covers would be hazards for blind people. Or heated sidewalk tiles that would crack in the winter. There was no modicum of local knowledge that Sidewalk, Larry page’s dystopian entry into the billionaire tech bro dick measuring contest, did not ignore.

Spoiler alert: google dies at the end

[Todd Friars · Rating 5 out of 5]

Being a Torontonian, I certainly was aware of the excitement on the Sidewalk and Waterfront Toronto joint project announcement which turned into frustration and anxiety as the project plodded along. In the end I was relived to hear that the project was being cancelled but without really knowing why. This book does a good job of explaining key players, and there were many, and the factors and decisions that led to the project being cancelled.

It feels like this was the right direction but it would be nice to see the 3 levels of government take the learnings from this process and introduce legislation to address the data collection and privacy issues / roadblocks that arose. These issues could arise again.

[James Pasternak · Rating 3 out of 5]

While this book argues that “Sidewalk Labs” was bad news for a good city, it’s really just another chapter of a timid city that doesn’t want to be bold, to be creative and to be world class. Toronto’s civic leaders regularly give into the Twitter mob and the profits of doom. Toronto had a chance to be the focus of the new lakefront urbanism that would have made up for failed Olympic bids, the inability to host a Commonwealth Games or an international exhibition. Toronto doesn’t need anyone to kick sand in it’s face on the waterfront, it does such on its own. Toronto wants to be a world class city but never fails to miss an opportunity (OK we hosted a very successful PanAm games). A the end of the day other cities will hold the title of “Smart Cities” while Toronto looks in the rear view mirror to another lost opportunity, one that came with risks and weaknesses but one that makes cities great. More evidence backing the school of thought that Toronto has an inferiority complex and will constantly leave the new urbanism to other cities.

[Becca Latto · Rating 4 out of 5]

Super interesting story (@libbay) buti found the text style a bit slow and repetitive. A lot of good info abt local government

[kanchan · Rating 5 out of 5]

A detailed play-by-play account of what went down from the municipal politics to the design and data privacy issues. Especially interesting for those of us who worked in fields adjacent to this circus and its grand promises.... while the show was going on.

[Carlosfelipe Pardo · Rating 4 out of 5]

Incredibly thorough, but almost to the point of exhaustion. A thousand names made it tough to follow the story. But it was incredibly illustrative of how tech struggles to work on urban projects.

[Morgan Gariepy · Rating 3 out of 5]

Thorough, but repetitive. There are some tangents that felt like unnecessary padding. This is surprising given how short the book is.

[Annie · Rating 4 out of 5]

Rating: 4.0/5.0
Format: Audiobook

I live in Toronto and I have no idea how Google/Sidewalk Labs project could have changed the trajectory of our city. This book, while very verbose/data/name heavy, helped articulate the impacts, the story, and the consequences of this whole political debaucle. I learned a lot and am happy I read it!

[David Wood · Rating 5 out of 5]

Thorough account of the Sidewalk Labs/Waterfront Toronto ordeal that gripped the city’s urban and data thinkers from 2017 to 2020. Josh O’Kane offers the necessary context to better understand the project’s inception, profiles of the personalities and governance systems that shaped its trajectory, and details the growing global skepticism of unfettered private sector ambition that ultimately contributed to its failure to take root.

One clear question I ask after this book is who should lead city/province/nation building? A private company with private motives or a messy but accountable public process? I feel more certain than ever that this task should be for the public to tackle - though certainly public processes should be updated to make positive change more achievable.

[Liz · Rating 4 out of 5]

Chock full of facts, maybe too many. But it did clarify what went on with Sidewalk Labs, which at the time was very vague and muddy. I guess as citizens we should never get too excited or complacent when big tech comes to town.

[Kathy · Rating 4 out of 5]

Government is always complicated but when you combine a tech company with government, well that’s at a whole other level of complicated. It is easy to get lost in the details and the timeline but there are two big take aways for me. Government should still manage city design and infrastructure even though it is slow and tech companies are always going to be in it for the data. It a good thing that Sidewalk Labs didn’t happen on our waterfront but surprisingly as the Toronto develops the waterfront today, as citizens, we still don’t know what the vision is for that invaluable piece of shoreline.

[Cal Lee · Rating 4 out of 5]

The story of Sidewalk Labs is quite interesting and reflects a lot about tech in the 2010s, as well as working with government and business in Canada. I wish the author wasn't so definitively negative against Sidewalk, but it does paint a picture of a very messed up internal environment of big egos, inflated sense of purpoose and zero actual accomplishments. The fact that Sidewalk took so long to accept what was patently not negotiable, that the area was limited to 8 blocks. Sidewalk's unwillingness to play by the rules, no matter how excruciating the rules were, was pretty revealing.

The aspect this book misses on is imagining what was the best case scenario? What would the Waterfront District look like if Sidewalk had carried out their amazing vision? I think the best case would probably be pretty subdued, some sleek mass timber buildings with smart recycling pickups and battery energy to reduce peak loads? Unlikely to be that game changing.

[Michael · Rating 5 out of 5]

This actually ended up being one of my favorite reads of 2024. I'm working on a pet theory about pie-in-the-sky projects like Sidewalk Labs: that they're not actually exceptional cases, but rather simply the points at which the underlying ridiculousness of ordinary things becomes concrete and visible. Put in one sentence: "it was privatization, of all the things people in a democracy want governments to do, that was at stake."

What strikes me is how powerful the forces behind the initiative must have been in order to get it as far as it went, because when you spell it all out, it clearly does not work. Fundamentally, Sidewalk Labs needed to make a lot of money. They “needed a rate of return they could justify—and had to justify it to Alphabet,” their parent company. Alphabet had begun to feel pressure from shareholders to justify its "moonshots", a category that included Sidewalk: "Alphabet’s revenue for what it called these “other bets” in its financial statements was $659 million that year [2019], 0.4 percent of its total income, yet they lost $4.8 billion." These things can last a while under the charisma of a founder like Larry Page, but eventually an organization has to rationalize its strategy.

How could Sidewalk Labs make money? Their entire business model was dependent on "partnering" with a city, meaning that the city government would hand over valuable public assets. These assets would include 12 acres of waterfront land in downtown Toronto, but crucially would also include nonphysical assets: the massive amounts of data generated by Torontonians, as well as any intellectual property developed from the planning process or from insights generated by the data. The land had been appraised for $590 million CAD, but the nonphysical assets could potentially be much more valuable. O'Kane quotes writer and advocate Bianca Wylie: "Fifty million dollars is a rounding error in the conversation about the value of our data. We cannot undervalue this asset." O'Kane himself points out the "hundreds of billions of dollars that technology companies were raking in from learning how people behave online," so how valuable could it be to gather an unprecedented amount of data about how people behave in cities?

On top of all this, Toronto would create the conditions for Sidewalk to extract greater profits by exempting it from existing regulations, "amending the City of Toronto Act, the city’s municipal code, and the Ontario Highway Traffic Act", and possibly giving Sidewalk the power to levy its own taxes. No matter how this is framed, it is tantamount to ceding the city's legislative authority to Sidewalk Labs. Fundamentally, though, Sidewalk Labs could only make money from being handed public assets: land, data, and intellectual property.

If you want public assets belonging to Toronto, Ontario, Canada, you have to deal with all three layers of government. Toronto is regarded as having strict procurement policies; or at least, if you have any dreams about circumventing them, you are going to have to have some exceptional advocates within the government. Sidewalk wasn't able to find such a patron. A source tells O'Kane: "The land questions came up in Sidewalk’s occasional meetings with Mayor John Tory... Offering a subsidiary of one of the richest companies in the world hundreds of acres of extremely valuable real estate wouldn’t just break procurement rules. It would be political suicide."

Hundreds of acres? Right: I forget to mention that the 12 acres that Waterfront Toronto was actually authorized to develop wasn't enough for Sidewalk's plans to be profitable, by their own internal projections. Sidewalk would at least need access to 20 acres at Villiers Island, if not a total of 190 acres. This core contradiction in the plan culminates in this beautiful exchange:

“As you say, you’ve worked in government, and real estate, and you can’t have been surprised that attempting to short-circuit a procurement process—”
Doctoroff interrupted him. “The procurement issue for Villiers was always complicated.”
It wasn’t. There hadn’t been a public procurement process for Villiers West...

The gears turned slowly, our institutions mostly did their job, and pressure from private citizens, activists, and journalists (including O'Kane) played a crucial role in turning the tide of public opinion. Waterfront Toronto, a small municipal office, was unsurprisingly not prepared for the sorts of things that an Alphabet company would try to slip past them. Here is a paradigmatic example: Sidewalk tried to invent a legally novel category of data called "urban data". Without legal expertise in this area, you wouldn't necessarily know that this was Sidewalk asserting that it would not be subject to existing privacy regulations. It has been frequently observed that "tech" "innovation" tends towards moves of this form (think of Uber calling its workers "contractors").

I remember conversations about Sidewalk Labs mainly focusing around the changing concept of privacy in an era of new technology. The notion of privacy involved was typically an individualist one, at that: "Who cares if Google knows my location? That's just the direction technology is headed in." The main lesson I would want people to take away is that flashy technology and privacy concerns were a "red herring". It's not new technology, and it's not entirely that you should be worried that Google knows where you are; it's that Google is profiting off this data that you produce, and you're not seeing a dime of it.

The details of the struggle are super interesting in both their resonances with history and their general insanity. Of course behind Sidewalk Labs is the same guy who brought us Hudson Yards, with its eyesore suicide magnet and tax increment financing. Of course Waterfront Toronto's chief development officer was the daughter of Bill Davis, the Ontario Premier who joined with Jane Jacobs to lead the defense against one of the other great urban design boondoggles in Toronto's history: the proposed Spadina Expressway which would have cut downtown Toronto in half (the finished part is now known as the Allen Road). Of course Sidewalk pitched building a giant dome so people could sleep outside, not as a measure to protect the unhoused, but to lure "progressive types.. using the example of Occupy Wall Street encampments", without any sense of ironic awareness that the protestors didn't just love sleeping outside but were protesting against companies like them. Of course Larry Page listened to Sidewalk Labs's initial pitch and ignored their market research to ask out of the blue why they hadn't considered making buildings on wheels. Of course Sidewalk invited Indigenous groups to make recommendations for the project, ignored all of their recommendations, continued to name-check the involvement of Indigenous groups in publicity, and all the while completely sidestepped the Missisaugas of the Credit, the actual parties to the treaty involving Quayside- and internally "some of Sidewalk's employees had been privately descibing the company's work as 'colonial'". Of course the whole affair ended in an anticlimax after Waterfront Toronto held their position and Alphabet realized they wouldn't make enough of a profit in the wake of Covid.

And again, these are not exceptional circumstances. The spectacle of it all is nothing but rhetorical cover for ordinary greed that is nowadays structurally channeled into taking this strange form.

""It's so seductive to say 'I'll start over' rather than just pay my taxes," said Sarah Moser, a McGill University professor studying these projects... "Then they present themselves as a beacon of hope for humanity." She and her research colleagues came to describe this philosophy as 'unicorn planning'."

This is another way of phrasing Fredric Jameson's observation that "all class consciousness of whatever type is Utopian insofar as it expresses the unity of a collectivity"; even the anarcho-capitalist dreams of an impossibly out-of-touch billionaire class necessarily take the form of a hopeful vision for the future. It's important to take the right lessons from this. The Unicorn Planning vision of Utopia, while on its face a complete lie, is built on the reality of the human value of the data that our cities produce. Sideways is a call for our institutions to take responsibility for the stewardship of this resource, resist privatization, and project a competing vision of what is possible.

[Melissa · Rating 5 out of 5]

I was a member of BlockSidewalk and I'm an urban planning/policy nerd, so my appetite for this kind of investigative account of what actually went on with a fairly dry and very technical urban development project is probably larger than most people's. That said, I found the way Josh told this story really engaging (I binged the whole book in two days!) although he jumps around in time a lot which makes it a bit difficult to follow. He did a fantastic job investigating it: he provides really important background and context and sheds a lot of light on a very complicated and very opaque story with a lot of moving parts. A lot of what he presents here was new to me and he found answers to a lot of questions that have plagued me for years now. This book gave me a sense of closure that I didn't know I was looking for and wasn't expecting.
(I do wish the book provided in-text citations or in-text numbered endnotes--the format chosen was not user-friendly.)

[Justine · Rating 2 out of 5]

Very much focused on the main players at Google/Sidewalk Labs and Waterfront/CA gov. A bit more insider-y than I think it needed to be to be interesting. Missed an opportunity to talk bigger picture about how transformative (both good and bad) the project could have been and the way it would have reshaped the way cities are governed (by private companies in this case, likely). In many ways I think this failure means we as a society dodged a bullet, and learned a lot in the process about data governance, smart city tech, business’s role in society, importance of government institutions and public consultation, etc.

[a.m. kozak · Rating 3 out of 5]

I was expecting a lot more technical elements of urban design, but this book is mainly an in-depth report of private-public partnership negotiations amidst a sea of bureaucracy and governance. The conversations around data and privacy were the most interesting, and the look into how giant projects develop had interesting components as well, but the subject matter got dry after awhile - for half the book I was waiting for it to "start" until realizing this was all the book was going to be about. The author did a good job at capturing the details and painting a picture of the project - it's just more about bureaucracy and politics than urban design.

[Rishav Agarwal · Rating 3 out of 5]

Overall interesting book about the Waterfront-Sidewalk fiasco. On how big tech with its saviour complex and government with its general ineptitude can’t play nice, and regular people suffer. The book is repetitive at points and too long for the subject matter it covers.

[Jason Zhang · Rating 4 out of 5]

There's a certain mediocrity pervasive in Canada. It invades our governments and their policies, stifles our innovation, and makes our cultural presence weak at best. This mediocrity was a key cause of the failure of Sidewalk Labs in Toronto.

Sidewalk Labs (SWL) was a subsidiary of Google, who won a bid to develop a coveted and underdeveloped part of Toronto's waterfront — a site called Quayside. Toronto's eastern waterfront has suffered greatly in the years after industry evacuated the city. The shell of factories and refineries has left a hole in Toronto's core that is still unfilled properly to this day. This presented an obvious opportunity to Toronto's stakeholders to provide a model for how we could use underutilised land.

This is fundamentally a story about the tech industry trying to do non-tech things. Sidewalk wanted to propose a new paradigm for how cities are planned and built. They proposed a techno futuristic smart city full of sensors and big data and always-running algorithms. Their manifesto, a Yellow Book, was comically dystopian. It's like they never thought about non-tech perspectives. Who really wants mass data collection or lives dictated by an algorithm? Part of the big problem of the digital world is that things are dictated by things out of our control — network outages, data loss (in the storage sense), and data breaches (in the security sense) — and there's often not much we can do about it.

Tech is hyper-individualistic, so its solutions are too. Sidewalk proposed pod housing and self-driving cars. They assumed a fast deadline, because timelines in big tech move incredibly fast. But the reality is that timelines in the real world run comparably slower. Objectively, this mismatch results in the inevitable downfall of SWL. Their ideas could've worked in practice, but we'll never know because they would've had to put up with years and possibly decades of slow change.

In fact, I'd argue that for a city of the future to come into form, we have to be brave enough to try one out, to prototype the ideas, and to stress and strain them. Indeed, the future won't come into fruition if we don't try things out or if we rule things out before they even get off the ground.

Of course, things don't have to be slow. The government is inefficient sometimes, and there are often lots of assessments for no reason. There's lots of institutional inertia that prevents good projects and good change. But the overarching rationale behind these checks is that decisions that impact people should be thoughtful and executed not by incompetent actors.

And that's not to say that the private sector (and big tech) holds a monopoly on incompetence. The Sidewalk Toronto saga has revealed the staggering incompetence of Toronto's municipal government and of Canada's federal government during the 2010s.

Let's start with Toronto itself. Sideways diagnoses correctly why Sidewalk came to Toronto in the first place. Chapter 5 defines two of "Toronto's defining, competing attributes — ambition and insecurity". For the first, we desire the prestige and wealth that comes with big tech investment and being a cultural powerhouse of the world, but without diagnosing what makes cities like New York or London or Chicago so attractive. For the latter, we compare ourselves with these global cities on grounds that no reasonable person can agree to, or to cities we are decidedly not in the same tier with. A pervasive cultural mediocrity. Waterfront Toronto decided to choose a CEO from Colorado Springs during this vital time. Because we emulate America so often, we import their worst aspects.

"Sidewalk Labs' original sin" is arguably solely on the part of Waterfront Toronto, the multi-government organisation that ran the show. They couldn't bother giving enough detail about what they wanted. In fact, I'd argue this objectively proves it's not ultimately fully on Google that Sidewalk Toronto failed. For every failure on SWL's parts, political mediocrity and bureaucracy has made another misstep.

Sideways also correctly predicts the direction the data collection was going (so well that the book will have aged well in 5-10 years) — already in the 2010s, big data and algorithmic frameworks were controlling an unprecedented amount of the Internet. It's notable, in this respect, that Canada is still not ready for the Internet age. While Europe and California have adopted reasonable data privacy measures, Canada's baseline is PIPEDA, originally adopted in 2000 in a much different world. It's telling that the federal government could not even step up to such a basic challenge. This could've been an easy win, but our overwhelming political mediocrity has forced everyday Canadians to be surveilled on with no protections of our own.

I will end on this note. It is truly infuriating to see incompetence at a scale like this. Not only in Waterfront Toronto (who were incapable of clear communication), and in Google (who couldn't figure out a cohesive vision for what they wanted), and in the federal government (who flip-flopped on regulation so much that SWL would've been unviable even if everything else went as planned). Quayside could've been much more than what we got — but we will never know.

4.5/5

[Louise de la Vallière · Rating 4 out of 5]

Was putting this off for a while and finally got around to finishing it.

- the style is a play by play narrative from the very conceptions to the end of the politics around the sidewalk toronto initiative a few years back which ultimately was canceled. The information was pieced together from interviews, public records, and documents thay the author was able to get access to as a reporter (the author is a reporter with The Globe And Mail)

- storytelling / narrative structure which makes the events not seem dry, with useful side stories about big tech, city building, and individual history of some of the players in order to give the reader more possibly relevant background information as a supplement for understanding of decisions made.

- Not much overt author opinion / monologuing, reads like a top down view of the events as they took place.

- personally think this would be interesting to read if you either live in toronto, are interested in real estate or city development, or work in tech / faang.

- recommended for tech workers since there is a lot about how the top executives of sidewalk labs interacted with waterfront toronto, the toronto / ontario / canadian governments, and alphabet corp in an effort to essentially get their product to launch. Really interesting insight into negotiation / governance / legal strategies employed and how they turned out.

[Linda Branton · Rating 3 out of 5]

Perhaps you read about this in the Globe and Mail a few years ago - Google has a smaller company called 'Sidewalk' who is trying to develop a portion of the Toronto Waterfront. The Google tech folks are interested in figuring out how to build a new type of city from the internet first and out to smart technology everywhere. This would involve self-driving cars, automatic garbage movement, sensors all over the place for data collection etc...

But, Google can't seem to figure out exactly what their plan is, and Taronna is epically difficult to navigate for pushy American companies. Just keeps going nowhere, and we watch the money and effort just get flushed into the lake.

This book is written by a journalist and seems to be chapters built off of editorials over the years. As such it has a LOT of name dropping and characters, organizations, interviews etc. Occasionally the chapters are interesting, but many keep harping on the same topics. We got it when it said it in every chapter again and again.

Not a great read for me.

BUT -- I read the book because "the Master Plan" is a play about this all. The play is actually fantastic and worth watching. Currently at Theatre Aquarius. Go see it, just don't read the book!

[Richard Cerezo · Rating 5 out of 5]

I read this book in 5 days and really enjoyed the behind-the-scenes look at the failed deal. I'm from Toronto and have a strong interest in business and tech.

The author characterized the tech, business, and government players very well but there was more emphasis placed on identifying the key players and less emphasis on framing/analyzing the deal. The last chapter was probably the most illuminating on the deal.

More specifically, my impression is that the book prioritized breadth over focused analysis. I'm not stating this as a negative critique but as matter of fact. I gained a long list of names of important people and their perspectives related to this deal but not as many insights as I felt there was potential for. It flowed a bit more like a TV show than a business book. (A TV show or doc based on this book would. be great by the way!)

The author did a great job bringing us through the 4+ year timeline and 'character development' of the key players and stakeholders.

I would recommend this book for the information it puts in the spotlight, but the writing style sometimes made me feel lost with the jumping from context to context.

4.5/5

[Dan Watts · Rating 3 out of 5]

I lived in Toronto during the time of Google's Sidewalk project, but it never captured my interest. I remember it as 1) a set of not-terribly-innovative ideas that were lacking in implementation details or explanations of the benefit to Toronto, 2) a magnet for privacy zealots and anti-corporate activists, and 3) an endless series of public consultations that never came close to breaking ground.

I thought that the inside story might be more interesting than that, but sadly that pretty much sums up the contents of the book. It's written in a potboiling style that keeps inserting the author into the storyline, as if the events were as momentous as Watergate. The author is unapologetically biased against the project, but failed to convince me that there was anything nefarious about Google's plans, largely because those plans were far from concrete. It seemed to me that Google "just wasn't that into it".

Policy wonks and those who celebrated the project's demise would get more out of the book than I did, but I think most readers would find it's much ado about nothing.

[Laurent Carbonneau · Rating 4 out of 5]

I was very peripherally involved in this story as it happened so was looking forward to reading this. My reading of it is also completely tainted by my extreme bias.

O'Kane's book gave me a lot of colour of what was happening inside Sidewalk, Waterfront and in Toronto that I didn't know at the time. I read this book asking myself "ok, who was really the asshole here?" I came away with a better appreciation for the fundamentally tough bind Waterfront found itself in and the basic honesty with which the agency and several of its senior stuff conducted themselves. I came out with just about the same low opinion of Sidewalk itself that I went into it with.

His chapter imagining the dark side of Sidewalk was very fun, as well.