Blayne Haggart's Orangespace

Last Friday, I attended a preview performance of The Master Plan, a play about the Sidewalk Labs-Waterfront Toronto Quayside debacle. The evening, which was hosted by Jim Balsillie, one of the higher-profile opponents of the Quayside project, served as a reunion of sorts for many of the (many) critics who opposed the project.

The gathering was long overdue: because Sidewalk Labs abandoned the project at the beginning of the pandemic, in May 2020, the activists who had spent three years of their lives fighting this deal never had the chance to celebrate in person.

It felt like a reunion. Since I’m based down the road in St. Catharines, and because I was primarily involved via this blog and other public writing on the project, it was a chance to meet for the first time many of the people whose names I recognized from news reports, blog posts and Twitter activism. It was a delight, the mood valedictory.

As for the main attraction, well, I have some notes.

The Master Plan does a lot of things very right. Its staging and use of video screens are excellent and fit the story perfectly. Mike Shara as Sidewalk Labs CEO Dan Doctoroff is a force of nature, his character perfectly written. That he didn’t have the opportunity to receive a final applause break during the play itself (his final “appearance” occurs off-stage) was a shame. The other actors do well in their (necessarily) less-flashy parts. The play adeptly covers two-plus years of craziness, and at 2.5 hours with one intermission, it never drags.

It’s also very funny. I laughed throughout, not least because of my intimate familiarity with every angle of the play. When they finally revealed The Master Plan (aka the Master Innovation and Development Plan), my laughter was definitely cathartic. One cannot emerge unscathed from devoting an entire a working month (Monday-Friday; I took a day off for my birthday) deciphering a document that was designed to be seen, not read. I imagine the rest of the audience, many of whom spent three full years being dismissed, ignored and lied to, felt much the same way.

While it was definitely a hit in the room, I don’t know how an audience unversed in the intricacies of Quayside bureaucratic infighting will take to it.

And, on reflection, I’m not sure how well it hangs together as a play. It gets the details right but the story wrong, both as a coherent work of fiction (on its own terms) and as an argument about what actually happened.

Waterfront Toronto’s lack of agency

Its biggest problem is that while playwright Michael Healey, working from Josh O’Kane’s book, Sideways: The City Google Couldn’t Buy, has a very good grasp on Doctoroff and Sidewalk Labs, his portrayal of Waterfront Toronto, in the characters of Kristina Verner and Meg Davis (fictionalized but based on real people), is surprisingly inert. In the context of the play, Sidewalk Labs is something that just happens to them. They have no agency. They simply react to the latest weird thing that Sidewalk Labs does, without really considering deeply own roles, and the ongoing role of the company they work for, in contributing to their own misery. Without that second half, the satire loses a lot of its bite.

All fault on Waterfront Toronto’s side is placed on the head of the bumbling, out-of-his-depth CEO Will Fleissig – resembling no one so much as Jack Lemmon’s take on Glengarry Glen Ross’s Shelley Levine – and to a lesser extent, members of the Waterfront Toronto board who won’t let our brave head bureaucrats talk to the public. (The play at times seems to posit that the biggest problem with Quayside was its comms plan.) They are presented as our heroes, the ones who just want to provide environmentally sustainable housing for Torontonians.

This pose, though, only works (in the play and in real life) if there was even the slightest chance that Google/Sidewalk Labs could deliver on its promises. But as I detailed in my month of blog posts on the MIDP, success was never on the table. This was never going to work, because Sidewalk Labs had no experience in building a neighbourhood and no workable plan for constructing anything on Quayside’s 12 acres. That they were, in the play’s words, “clowns” is made very clear throughout. In the beginning of the play, Doctoroff effectively says that the company had done nothing of consequence. In the end, the MIDP, their Master Plan, is revealed (correctly) to be a steaming pile of overreaching nonsense.

But Sidewalk Labs isn’t just something that happened to Waterfront Toronto, in the play or in real life. Sidewalk Labs, in the play, is a force of nature, the vampire that needs to be invited in to cause chaos. But it was Waterfront Toronto that set everything in motion, and was complicit in keeping things moving right up until the very end.

Waterfront Toronto, and its staff, drafted a flawed RFP. Waterfront Toronto continued to negotiate with Sidewalk Labs after it became manifestly clear that they were a bad actor incapable of playing straight with anyone.

Very little is made, for example, of the insinuation in the play that the only reason Sidewalk Labs was awarded the project over an infinitely more experienced and capable Siemens was because Sidewalk Labs was willing to pony up $50 million to undertake the initial planning. It reminds me of a perhaps apocryphal story about how the most convincing thing about the Ottawa Senators’ 1992 expansion bid was simply that it had $50 million to give to the NHL.

In the play, up to the very last minute, Waterfront Toronto is looking for loopholes that will allow Sidewalk Labs to stay on the project, despite literally no proof that Sidewalk Labs could be trusted on anything.

At the very least, there’s a lot one could unpack about the constant bad decisions that Waterfront Toronto itself made. Waterfront Toronto, including its staff, were active participants in their own misfortune. Unfortunately, its motivations, including that it’s facing a decision on its renewal as a corporation, are never seriously unpacked in the play.

Instead, the overall impression of Waterfront Toronto is of an entity concerned solely with doing the right thing, especially for the environment, which, as in Sidewalk Labs’ promotional materials, gets trotted out every now and then to burnish their bona fides.

The real enemies: Pesky activists and faceless bureaucrats

In making Waterfront Toronto the heroes, the play commits to a surprising choice of villains. Probably the most fascinating thing about the play is its rock-bottom opinion of the public, the activists who kept trying to bring some accountability to Waterfront Toronto, a highly unaccountable organization (being a tripartite quasi-governmental organization, residents and citizens have no direct way to influence its decisions) over an obviously bad deal.

The play has a very strong opinion about whether the public should be involved: basically, no, not at all. If Sidewalk Labs is a force of nature, the two main villains in Healey’s play are the public and City of Toronto bureaucrats.

It’s weird.

What makes it particularly strange is that the play’s argument, which surfaces mostly in the second half, is not supported by the play itself.

Anti-Quayside activists do not come off well at all in this play. Public opposition to Quayside is presented as a bunch of misinformation-driven NIMBYism.

The play illustrates this point with a Jon Stewart-esque takedown of the many media outlets and activists who used this quote from Alphabet CEO Eric Schmidt: “We started talking about all of these things that we could do if someone would just give us a city and put us in charge,” without reporting the rest of the quote: “For all sorts of good reasons, by the way, it doesn’t work that way.”

Schmidt, you see, was just joking! And paranoid, biased activists refused to recognize the joke. Paying attention only to the first part, they sowed misinformation and needless fear about Quayside, raising unfounded questions about Google’s and Sidewalk Labs’ bona fides.

Having DESTROYED these ignorant activists, the play gets back to the real heroes, the good folks at Waterfront Toronto who are pushing back against this misinformation to get the Sidewalk Labs deal across the finish line. For climate change. And stuff.

Remember that saying, Many a true word is spoken in jest? Healey’s play apparently doesn’t.  

As an audience member, to say nothing of someone who watched this nonsense unfold in real time, this supposed dunk was incredibly frustrating because it contradicts practically everything that happens in the play. Doctoroff spends literally every second of stage time running roughshod over Waterfront Toronto. In the play, Doctoroff’s final speech (brilliantly delivered) is nothing less than a plan to create a self-funded entity within the City of Toronto. He practically says, Here are the things we will do when someone gives us a city and puts us in charge.

Going into the project, they thought that Waterfront Toronto had more autonomy than it did, kind of like the Triborough Bridge Authority in New York, whose self-financing was the foundation for Robert Moses’ autocratic powers. Back in Toronto, as I detailed in my examination of the MIDP, Sidewalk Labs wanted to create several management entities with themselves at the centre. Even within the universe of the play, the assertion that Google thought it shouldn’t be put in charge of a city makes no sense whatsoever.

The activists – we – were right to be suspicious of Google. Their – our – analyses has been vindicated, both by reality and within the play.

To repeat: The activists were RIGHT. About Schmidt’s quote, and in their suspicion of the project.

(As was Mariana Valverde’s, one of the few academics to speak out publicly against the Quayside project, including in peer-reviewed and academic articles, raising among other things, relevant questions about the project’s governance structure. She deserves better than to have her work dismissed by O’Kane (p. 233) as a “University of Toronto law professor [she’s actually a criminologist] who was writing sharp-tongued screeds about how governance oversights could cause trouble at Quayside.”)

It’s kind of hard to follow the play’s logic. Toronto City Hall is being run by pedantic bureaucrats who won’t let Torontonians have nice things, the nice things here being Sidewalk Labs’ plans. They’re responsible for thwarting Waterfront Toronto, an organization run by unaccountable bureaucrats, that is doing business with a company, Sidewalk Labs, which has demonstrated time and again that it can’t be trusted.

I might be a tool of Big Bureaucrat, but if I were a Toronto employee, I’d be very suspicious of the entire thing, too.

And yet the play ends with a condemnation of Toronto’s culture, city hall, and anti-Quayside activists as the faceless forces thwarting Sidewalk Labs’ desire to fight climate change. And not, say, with a condemnation of Waterfront Toronto for wasting three years of everyone’s time by getting into bed with a company that was obviously from day one not up to the task. Time that could have actually been spent addressing climate change. Would working with Sidewalk Labs really have helped move the needle on anything? Where would you look for evidence to prove that assertion?

(Stepping outside the play for a moment, the play quickly dismisses surveillance concerns as a nothingburger. But as we’ve seen with Google’s DeepMind, Google can easily bring supposedly independent entities in-house, changing the rules on how data is used. And if you think Google is just interested in data for advertising, let’s chat about a little something called AI. Plus, once you’re hooked into a company’s tech, it becomes hard to change horses. This type of power is not really on the play’s radar, though.)

Sidewalk Labs and the dream of success

Which brings us to another structural problem: the play begins, and ends, on a note that suggests that Sidewalk Labs could actually do all the things it says it wants to do. Healey creates a composite character to reflect the optimistic part of Sidewalk Labs’ mission: that they would solve homelessness, climate change and much else. Presented in a sympathetic light, this character, along with Verner’s and Davis’s paeans to fighting climate change, speak to the heart of the play’s argument, that the Quayside project was undone because of narrow-minded Toronto NIMBYism and the intransigent, faceless, overly powerful bureaucrats who run City Hall like low-rent Illuminati.

This conclusion is at least partially true to O’Kane’s source material, which ends on a note of cautious optimism about what could have been:

If implemented carefully, many of Sidewalk Labs’ individual ideas for Toronto could have changed countless lives for the better. Though few of its ideas were truly new, they had rarely been sold in such a lucrative-looking package, and could have set new standards around the world for energy-efficient buildings, home ownership models, garbage reduction and, eventually, maybe neighbourhoods destined for self-driving cars. Sidewalk hired dozens of employees who brushed aside all the drama the company courted and really tried to make these things happen. But Sidewalk bid for a project from a relatively unknown public agency in a city it didn’t know well that was asking for innovation it couldn’t really define. And Dan Doctoroff built a company that couldn’t stop sabotaging its own great ideas, repeatedly asking for more than anyone could offer it – against the advice of the agency he partnered with, the city he wanted to work in and even the people he courted for support. Sidewalk Labs wanted to win so badly that it just kept losing.

“If implemented carefully,” does a lot of heavy lifting in that paragraph. It assumes that a company whose main calling card, as mentioned in the play, were street-based internet kiosks that delivered porn al fresco to New Yorkers, was actually capable of delivering everything that they promised. And they promised everything.

Putting aside the unsupportable hyperbole of “countless lives,” in the play as in life actually existing Sidewalk Labs – the inexperienced tech start-up that Waterfront Toronto foolishly got into bed with – never demonstrated the capacity to pull off any projects at the scale of the neighbourhood.

Literally everything they said and did indicated the opposite, in the play as in reality. Sidewalk Labs gave us no reason to believe that they could deliver on any of the things they promised. Like so much of what passes for innovation in Silicon Valley, they were selling a form of technological solutionism that was more focused on creating markets for technology than actually addressing climate change. Then again, that’s just something that we egghead academics have been researching and writing screeds about for over a decade now.

As for Waterfront Toronto, at the end of the day they were saved from being tied to a company of “clowns” (to quote the play), not by any decisive move on their part, but by Sidewalk Labs walking away in May 2020. From the play’s Sidewalk Labs’ urban-development composite character:

I used to go to bed at night praying you wouldn’t notice we were clowns until there was a hole in the ground. We had unserious leadership – we were a fucking mess – yes. We were clowns. But we came here not knowing that NIMBYism is a way of life here. It’s bigger than ice hockey [NOTE: I’m pretty sure Americans just call it “hockey”]. You might have warned us.

I guess the question is: Why are we fucking around like this? [Then he mentions a whole slew of problems, including the climate crisis] So yes, late [in addressing these issues] and yes, clowns, but it would have been a start? Our thing wouldn’t have fixed anything, but it would have been a step?

Clown-delivered public policy

I mean, what do you do with a speech like that? Especially since a Waterfront Toronto employee reacts by giving him a hug, as if she, a representative of the company that kicked off this rolling disaster, can offer some form of commiseration.

Because the answer is, clowns by definition do not offer a start, or a step, on anything but clowning. Just having good intentions isn’t enough if you’re incompetent. When your play steps out of itself to criticize the very people who were pointing out that these people were clowns, you don’t really have a grasp on your subject. People have a right to object to stupid ideas, and the Quayside smart city was full of stupid ideas, from a poorly worded RFP to selecting Sidewalk Labs as a partner, richly deserving in public outrage.

Not nearly enough (by which I mean nothing) is made of the fact that Waterfront Toronto wasted three years of its time working with a company that could never have been a good partner, or vendor. Hoping that your partner agency doesn’t notice that you’re a clown isn’t a business strategy; it’s a con, a scam.

This wasn’t the public’s fault. It wasn’t the fault of culture. Or Bianca Wylie. Or Julie DiLorenzo. Or Doug Ford. Or faceless Toronto bureaucrats. Or any of the other enemies the play posits. Waterfront Toronto wasted everyone’s time.

Consider that, in the play, Waterfront Toronto was willing to concede a piece of public land to keep Sidewalk Labs, a company with no track record, and that had consistently tried to screw Waterfront Toronto over, involved in this project. After watching this play for 2.5 hours, how is the audience member supposed to react? Waterfront Toronto doing what they have to do to get the job done? With this company? A cynic might see these actions as those of a company that, even knowing that Sidewalk Labs could not be trusted, was willing to sacrifice the public interest for its own interest, to save face and preserve its mandate. In the scope of what we’d just been shown in the play, this reading is, at the very least, a fair and plausible one.

But as I said, the play treats Sidewalk Labs as something that happened to Waterfront Toronto, not something that Waterfront Toronto did, and continued to do, to itself and to Toronto.

To say that Sidewalk Labs, or Waterfront Toronto, had some good people working for them, who wanted to do good and be good, is beside the point. It is only as employees of the company or the organization that they are able to conduct their business. An urban developer who works for Google is a Google employee.

Trying to follow the logic

These kinds of thematic inconsistencies recur throughout the play. The attacks on City Hall felt less true to the events of the play and more like an unconnected gripe that’s been bugging the playwright for a while. I’ve no doubt that Toronto bureaucracy can be silly and inflexible. But would it have been better for the City and Waterfront Toronto to partner with Sidewalk Labs? After everything we learned about them, of which the play only scratched the surface? Or for Waterfront Toronto to have more independence? Is the lesson really that the public should have just trusted Waterfront Toronto to do the right thing? And given that they are even less accountable than City Hall civil servants, on what grounds do they deserve our trust? Because they want to do good in the world? You don’t think those awful City Hall bureaucrats believe the same of themselves?

In its dismissive treatment of the activists who raised their voices on Quayside, the play ends up championing Waterfront Toronto’s bureaucrats who, being part of a quasi-government authority, are even more isolated from public pressure than Toronto’s. And, frankly, in a play whose heroes are supposed to be so concerned about climate change, it’s a weird look to illustrate the unchecked power of your enemy – the Toronto bureaucratic Illuminati – by highlighting how difficult it is for Toronto homeowners to chop down trees whenever they feel like it.

But that’s the play in a nutshell: confused on themes, with a predetermined conclusion that doesn’t fit the evidence it presents. Data, intellectual property, technological solutionism and private power – the very heart of the challenges in regulating the smart city, and the heart of the opposition to Quayside – don’t really feature in this play. If you don’t think these are important, maybe it’s easier to see opposition to this type of project as simply garden-variety NIMBYism. But you may also not fully understand what you’re actually looking at.

In Doctoroff and Sidewalk Labs, The Master Plan has one half of a great satire. Widening its target to include not just the vampire, but the organization (Waterfront Toronto) that invited the vampire in would make for a more honest, and more compelling, story.