Sidewalk Toronto: The Plan. A Final Note on its History, Method, and Trajectory.

Prepare for another round of psychological tolerance testing and revisionist history. This is a long one, please settle in.

“Within weeks” Sidewalk Labs will give its plan to Waterfront Toronto. In a final and fitting act of democratic disrespect, they refuse to provide a delivery date. What this does is disrupt the public consultation process yet again — no one can plan dates, no one can book venues, no one can prepare communications, and the City moves into summer vacation mode.

Setting this aside, “within weeks” the plan will arrive. And before history gets rewritten, as Sidewalk Labs (and/or their strategic communications firms) are working hard to do, it’s critical to ground this next phase of assessment in the context of the project’s history and the firm’s operating methods.

This is important history to keep present and alive, both for the residents that have engaged in the process to date and for the residents and decision-makers that have not joined in yet but are due to get engaged soon.

Phases of Work

The first phase of the experiment has come to an end, the second one will start soon. Sidewalk took 19 months to learn what would and would not be permissible or allowed and 19 months to tag in as many people, organizations, and institutions as possible to appear in their proposal and to legitimize their work. This way, if you don’t like the broad plan, it means you are not rejecting Sidewalk Labs, you are rejecting the organizations and local businesses and people they have made agreements with or worked with. Now that’s not a very Toronto thing to do, right? You don’t want your friends to thrive?

Creating division within the city. This is psychology and this is a well-known and old control tactic. You think Sidewalk Labs couldn’t have provided a plan without filling out all the procurement and partnership pieces and left that to democratic process? Of course they could have. But it wasn’t to their strategic advantage.

Sidewalk Labs will walk back all or most of the things that were troubling when they landed in the press. This does not mean these things will never happen, this means they will not happen in this first phase of work, the plan phase. Separate from, say, implementation agreements (important legalese in the current contract that no one is talking about) or physical build-out phases.

The psychology of this is nasty. As has been evidenced by Sidewalk’s behaviour, they want to push people and find the limits of what they can do. This is steamroller style. So while they will seek to say that people were speculating or telling lies or creating myths, it was only in a vacuum that this kind of speculation could occur. Sidewalk Labs created that vacuum and forced the people here to fight into a void to protect themselves. There have been several times lately when Sidewalk Labs’ has charged the community with speculation or myth creation, with judging the plan without knowing what’s in it.

After 19 months, 7 months late, I can hardly believe they think the public could be doing anything else. It’s Sidewalk Labs’ fault entirely for not explaining exactly what they’re doing. They have not revealed exactly how they are making money and what the trade-offs are for the roles and influence they want to have. You cannot divorce all the playground fun and whimsy from municipal finance and operations but they have done just that.

Rather than accept that error, (and it’s a big one, truly a big flag for a broken process, to have a consultation end in a surprise at the end), they spin it and blame the people that live here for trying to stitch together what is happening from the media, the hundreds of documents and events, and the company’s work globally.

Let’s step further back and interrogate how much cognitive dissonance this communications strategy displays. Let’s take a handful of items, this is not all of them but a few cases: data, scope creep, CEO departure, secrecy, delays, lobbying, and experimentation. After these cases I’ll close with some thoughts on what might be in the plan.

Illustration credit: Scott Rankin

The Data Dare

Sidewalk Labs announced back in 2017 that they wanted to build a neighbourhood from the internet up, with extensive data collection. They hired Ann Cavoukian to help them on privacy. Clearly, data was central to this project. Or so they were signalling.

Then they took a full 11 months, yes — 11 months!, to share their data trust idea. Meaning they let residents sit in uncertainty about collection, ownership, and usage models for almost a full year.

This was unreal. And while the company likes to tell you it “was consulting” what they did was take a run at seeing what they could get away with, let it fester, then when it all got too hot, punted the data trust term over the fence, which they have refused to engage with in any meaningful way since.

Lest anyone think this data/digital infrastructure issue is solved, it’s not, yet. But consider that behaviour. Can you imagine a sister company to Google and a company that has been making urban software for two years rolling into town to build a data-heavy neighbourhood waving its hands above its head like “so what do we do?” with the data “I wonder if we should control it all?”. It’s ridiculous. And yet, that happened.

So, apart from exposing itself for what it is and how it operates, it was good that people showed up for that conversation because who knows how it would have gone otherwise.

Don’t forget this little snippet of history, courtesy of a recent piece by Josh O’Kane: “Early on, however, Mr. Fleissig [ex Waterfront CEO] raised concerns that have continued to dog the project. “Google has purportedly told other candidate communities that they want to control ALL data in this demonstration project area. Could present privacy issues and control issues,” he wrote in an internal e-mail in July, 2016, according to a later report by Ontario’s Auditor-General, Bonnie Lysyk.”

So when Sidewalk Labs chides and derides the community for speculating and getting engaged without the plan, don’t forget how critical doing exactly that was to getting data issues to where they should have been since day one. They made people fight for that when they could have just announced out of the gate. It was a game of unnecessary chicken. That’s not engagement, that’s bullying.

Scope Creep — The 12 Acres that Wasn’t

Sidewalk Labs can go on all day about how the RFP asked for ideas to scale beyond the 12 acres of Quayside. It’s true. So it’s funny how the only time they started to be more clear about this with the public was after a document leak. Look back to this map from the first public meeting:

Slide 13:

Yes, two slides later the presentation says (in words only) that the ideas might be scaled up and out. But the real estate transaction was organized to look like 12 acres. Maps and visuals matter.

And so yes, you can delve into words and defend the idea that much larger scope was always plausible but it most certainly was not the intention of these visuals to convey that possibility to the public. How about maps that showed that at public meeting number one? How come they didn’t exist?

Despite all the hand waving about innovation and smart neighbourhood, there has always been a very real part of this deal focused on real estate. That part of the plan needs focused public attention in review.

Another false narrative that Sidewalk Labs has put forward is that it’s them or nothing happens in the Port Lands, complete with stories about land undeveloped and photos of the empty site. Very rarely does the story touch on the 1.2 billion dollars that the governments have recently put into flood protection to enable development. It’s not Sidewalk Labs or nothing. Sidewalk Labs somehow got bumped to the head of the line.

Waterfront Toronto Still Doesn’t Have a CEO

The CEO that was the architect of the deal was gone mid- project (Jul 2018), and the organization has yet to find a replacement. This, from Amanda Roth — “Less than three years into the role, Will Fleissig offered his resignation as CEO of Waterfront Toronto following pressure from the organization’s board of directors.”

Nothing more to say than this is a red flag. The organization still has no CEO, this project is going on without a CEO at the organization that is the public steward. Red flag. Governance red flag.

Secrecy Has Been A Hallmark of this Project. A Public Project.

The secrecy started with a failure to disclose the initial contract, the Framework Agreement (which seems to have disappeared from the Sidewalk Toronto website unless I just can’t see it, please help me if I’m wrong here…) between Sidewalk Labs and Waterfront Toronto. This secrecy went on for months and months, and was not resolved until a second contract was signed between the two in 2018. Then the second contract, the Plan Development Agreement, is so convoluted/impossible for a layperson to parse that it’s still unclear as to how the deal(s) between the two organizations may shape up.

Then there was the NDA drama with Waterfront Toronto’s advisory council, as Reported by Amanda Roth and Sean Craig. “Waterfront Toronto faces opposition from Sidewalk Toronto advisory panel over strict confidentiality agreement.”

Then they created a closed advisory council, a group of “influential city-builders”, the only one member of the group that self-identified is Richard Florida. Sidewalk Labs is, with a straight face, publishing advice or opinions about the project from a group without revealing who the group is. When questioned about the existence of this closed group, here’s Sidewalk again: “the fact that our opponents find fault in even having this dialogue tells you everything you need to know. If these conversations were not happening, they would be criticizing us for that.”

Most recently, and most importantly, there was the document leak in February, as reported by both Marco Oved and Fatima Syed that showed Sidewalk had plans for revenue schemes it hadn’t shared publicly and a larger real estate deal it also hadn’t been clear about fifteen months in.

Again, this company is daring to shame the public for trying to guess at its plans?

Delays — Or, the Political Psychology of Invested Time and Personal Capital

I don’t know what it’s called, but there is a phenomenon where if you have waited in line for 20 minutes, you’re unlikely to leave on the 21st because you’ve already waited so long. This project and all of its delays are essentially creating this condition, one where the governments, the project supporters, and a whack of others feel so vested in the time spent to date, and the reputational investment they’ve made, that it’s getting harder every day to imagine taking that back.

It’s also why the structure of the deal is corrupt because anyone could have foreseen that the $50 million dollar budget was to make this fait accompli. A done deal. No was never an option, it was always how. And this is psychology.

Do you see how much the notion of saying no is challenged? Do you see how much of an edge position saying no is interpreted as? Do you see how saying no is being “critical/negative/early”? This is a very savvy and profound psychological maneuver. It worked. Consent = purchased.

And do you see how much of this coy “big reveal” rhetoric has made it so most people lack adequate information to weigh in? Which means they are either supportive of component parts or silent?

Part of this strategy has also been to do the usual tech thing where the public gets sold a vision of pretty pictures and get rich fast schemes and if the governments don’t want to do it, they’re just too conservative and don’t “get it”. Blame the institutions for not wanting to be edgy or disruptive enough. Pit the public against the government at a tech conference of two and in the media. This hasn’t been landing well over at Waterfront Toronto, as reported by Donovan Vincent in March, here’s Chair of the board Steve Diamond:

“I can advise the board that we have all been somewhat frustrated over the last few months that Sidewalk Labs has chosen to continually provide the media with elements of the plan … but yet has not delivered that plan, particularly the business terms, to Waterfront Toronto as has been promised,” Toronto developer Steve Diamond told the corporation’s board meeting Thursday. “These concerns have been communicated both verbally and in writing to Sidewalk Labs,” Diamond went on to say.

But the strategy has been working, so they can afford to disrespect Waterfront Toronto. City officials have been heard wondering about the impact of saying no to the deal, another sign that this was never going to be allowed. That saying no would pose a reputational risk. Nevermind that the no option was how it was sold to the public at the beginning.

From Nov 2017, both CEO’s wrote: “At the end of this year-long process, if the outcome doesn’t live up to our shared aspirations, both partners have the chance to walk away.”

That no was supposed to be on the table. It’s been taken away somehow.

This concern is, in itself, the most damning evidence that this was a project designed as fait accompli. Nevermind that this concern is grounded outside of reality: Toronto is booming, the real estate would have many other interested parties, and the governance mess this is in means stepping back would be pro-democracy and pro-moral business. But “reputational risk”. Ok.

Lobbying, Lobbying, Lobbying

Quick note to remind everyone how this work and plan has been created. With incredible and undocumented (content wise) access to elected officials and City Staff. As Thorben Wieditz shared in his recent deputation, and thanks also to solid reporting on the City as always from Matt Elliott, the City’s lobbyist registry shows at least 1,638 lobbyist points of contact by subsidiaries of Alphabet in the last 14 months.

And that’s just the City.

The company is also lobbying the province and the federal government. From Anna Desmarais in Nov 2018:

“A subsidiary of Google’s parent company is lobbying a dozen federal departments for their help after its Toronto project was criticized publicly by a former Ontario privacy commissioner. Sidewalk Labs Employees LLC, a subsidiary of Google-parent company Alphabet, filed 19 communications reports with federal departments that had CEO Dan Doctoroff’s name on them. Among the departments lobbied were: Employment and Social Development Canada (ESDC), Environment and Climate Change Canada (ECCC), Finance Canada, Infrastructure Canada, Innovation, Science and Economic Development (ISED), the Prime Minister’s Office, Privy Council Office, the Public Health Agency of Canada (PHAC), and Treasury Board.”

At the provincial level, Sidewalk has reportedly recently hired Loyalist — which is described in this Macleans piece.

Is lobbying bad? No. Is the extent of this lobbying normal and are its impacts benign? Would also argue no.


Because of the work of our communities in speaking up, from many angles, a range of harmful things have already been mitigated. And given the extreme pressure there appears to be to “make a deal” let the many victories achieved to date not be minimized or misunderstood should some version of this deal go through.

When Sidewalk Labs seeks to do a renewed round of gaslighting by saying “see! nothing here to worry about, you had it wrong, etc. etc.” feel no shame or concern for the work done or the concerns you might have raised. They have set everyone up to look the fool and this is also by design. Be grateful for the many global voices that have been speaking up and out about the company, its past, its status, its other lines of business, and more.

Sidewalk Labs has zero social license to operate here nor has it earned one ounce of trust. Treating it any differently would have been a big error, be sure of that. And shame on the firm, and its supporters, for their condescending reactions to the people of this city that have shown up to voice concerns.

To fail to understand, in this climate in 2019, why people would be concerned about any flavour of this deal is to live a life that is removed from any of the potential harms it may bring. Which brings us to the final note, this has always been about governance and privatization, not only privacy, and those areas will also need vigilant attention in the months to come.

As for the BlockSidewalk campaign, we are committed to supporting the City’s process as per its recent staff report, as well as Waterfront Toronto’s upcoming process (the timeline for which will be announced once they receive the plan) and we invite you to join us to continue along in this work.

Finally, What to Expect with the Plan

So the plan, here are my guesses — all could be off but here you go: It will appear to be mostly fine. It will be delivered with a smug “you had us all wrong, the critics were wrong” tone . The problems with it will need to be dragged up and out of the complexity, they will not be clear or in plain sight.

More confusingly, the problems and business models may not manifest as problems immediately. This is one of the hardest things to get one’s head around but is vital to understanding how the tech industry operates. Problems related to privatization and and governance and implementation, tying them into any infrastructure, may not surface for years (see: Uber). There is also the under-discussed nightmare of using data sources or infrastructures that governments can’t properly see into (black boxes, such as the Replica software product, if you will) as policy inputs, which this plan seems to be speeding ahead into.

The component parts of this plan, including all the community benefits, are the magician’s hands. The framing role of how a city should operate and the role and place that Sidewalk Labs wants to assume within local governance is a major thing to focus on. That will not be explicit in the plan. It falls outside. It’s the anti-democratic nature of what they’ve done already. They’ve worked hard to normalize what they’re allowed to do, and they’ve been decently successful at it. There is also something to look out for when people say their business model is as complicated as a 50-sided Rubik’s Cube (Doctoroff). When you look at the history of business models that were described like this the precedents are alarming.

The plan will be very pretty, they aren’t going to scrimp on presentation. It will include some if not many good ideas. It will include over 400+ technologies, only about 10 of which are Sidewalk Labs’ (according to the company’s recent deputation — it’s unclear if they mean that many different firms have been integrated into it, tbd).

Part of the plan may suggest that Sidewalk Labs should be the beneficiary of the “uplift”, or gain in value, of real estate. This particular piece of the action is one of the major points to keep an eye out for when the thousand pages of obfuscation emerge.

The plan will be full of scope creep, it will include answers to questions that weren’t on the test. so to speak. The plan will be also be designed with announcements for each level of government.

At the City level, it’s a) financing the Light Rail Transit (LRT) and b) revenue sharing of intellectual property (IP) with Waterfront Toronto (aka you’ll all get rich), in addition to Google on the waterfront and the urban innovation show. For the province, it’s the promise of the tall timber industry, and maybe the autonomous vehicle industry, and the jobs that go along with both. Federally, both the jobs and the “Google is growing with us” announceable moment. The last part also appeals to the City.

There are going to be more, but those form part of the probable appeal for each government and other stakeholders. And what happens through this fragmentation, each government and community looking at its component parts as stand-alones, is that no one is looking at the whole — the potential long-term impact on democracy. That has emerged at exactly no-one’s problem or concern. This has been confirmed by every politician and stakeholder that is ignoring the backwards process of vendor framing policy and the outright purchase of access and consent.

Many politicians may not even be in power anymore when the potential problems with this deal manifest. The people working at Sidewalk Labs understand all of this, as they like to remind people, they used to work in government.

Finally, the plan will argue that Sidewalk Toronto is an eco-friendly undertaking. You’re not against the environment, are you? It may be light on surveillance that is easy to see/understand. This company is not stupid. The plan will not, as Roger McNamee wrote in his important letter, include facial recognition at this stage of the work — Jesse Shapins of Sidewalk Labs confirmed this several weeks ago.

But the thrust of McNamee’s letter is what matters. He is, it seems, as many are, throwing spaghetti at the wall to see how to make the threat of this project stick, to shake people out of the boiling frog-ness and inevitability that has set in. He and others are taking big swings with words to try and get people to sit up and take notice of what is happening and what could happen years from now. People in the tech industry are trying to do what should have been done ten years ago, making the warnings that surveillance scholars and many others have been making for decades.

In ten years, where will this all be? Just like Facebook wanted to bring people together, Sidewalk Labs wants to “improve quality of life”. How might that go sideways when it’s done as a for-profit venture, through a sister company to Google, acting as a government? And how might that go sideways when the project is tied to an under-regulated monopolistic firm?

This is the piece to keep in mind from McNamee: “No matter what Google is offering, the value to Toronto cannot possibly approach the value your city is giving up,” he wrote, pleading with officials to abandon the project. “It is a dystopian vision that has no place in a democratic society.”