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The Master Plan

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In 2017, when the public agency Waterfront Toronto decided to put up a parcel of land for development, Sidewalk Labs, a subsidiary of Google’s Alphabet Inc., swept in with a proposal to create the city of the future. Waterfront Toronto jumped at the opportunity to advance housing sustainability and affordability by exploring Alphabet’s innovative technology and data-driven techniques. But the project quickly started to fall apart from uneasy partnerships, sclerotic local politics, and an overwhelmingly negative public response. In this biting comedy about the failure to build a smart city in Toronto, Michael Healey lampoons the corporate drama, epic personalities, and iconic Canadian figures involved in the messy affair between Sidewalk Labs and Waterfront Toronto. Based on the bestselling exposé, The City Google Couldn't Buy by Josh O’Kane, The Master Plan exposes the hubris of big tech, the feebleness of government, and the dangers of public consultation with sharp wit and insightful commentary.

152 pages, Paperback

Published September 5, 2023

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Displaying 1 - 7 of 7 reviews
Profile Image for Alan (the Lone Librarian rides again) Teder.
2,712 reviews255 followers
January 22, 2024
The City Google Couldn't Buy
Review of the Playwrights Canada Press paperback edition (September 2023)

Fleissig (CEO Waterfront Toronto): To be clear, we selected Sidewalk. Sidewalk didn't choose Toronto.
Doctoroff (CEO Sidewalk Labs, a Google subsidiary): Absolutely. Toronto is going to be an amazing host city.
Fleissig: Maybe the term "host," maybe that's not great, host, it kind of sounds like you guys are going to come bursting out of Toronto's chest.
Doctoroff: Ha ha, maybe!


The Master Plan is a theatrical adaptation of journalist Josh O'Kane's non-fiction book Sideways: The City Google Couldn't Buy (September 13, 2022). It tells the story of how Waterfront Toronto sought a partner to develop ideas for an experimental "smart city" to be built on an undeveloped 12 acre plot of Toronto's lakeshore. It goes from the initial partner search of March 2017 to the project's collapse in May 2020. Many of the play's characters are based on the actual people and some are fictional amalgamations of several or dozens of people.

Google's Sidewalk Labs was selected for the project and it becomes evident very early on that the tech corporation's goals are much more wide-ranging than the city's desired experiment in high-tech urban planning. It becomes a case of seeking to harvest personal data and exploit public monies with a plan to extend the project across the entire waterfront of Toronto. Facing increased public protests the project was terminated and Sidewalk Labs pulled a face-saving measure by blaming the failure on the COVID pandemic.

This is all rather cleverly condensed into Healey's bureaucratic social comedy which combines live theatre with screens and projections. The playscript is very effective in getting all of this across.


Photograph of the stage set for The Master Plan at Crow's Theatre, Toronto. Photograph by Dahlia Katz, sourced from the Toronto Star.

Trivia and Links
The Master Plan was commissioned by and premiered at Crow's Theatre, Toronto as the 2023/24 Season Opener in September/October 2023. There is an archived listing of the theatrical performances at Crow's Theatre. This was still active as of January 2024, but the archive listing may not be permanent.

There was a teaser trailer for the theatrical performances which you can see here. The glitches in the video are intentional 😅.
19 reviews
October 3, 2023
This play is based on the book "Sideways" by Josh O'Kane which I found very hard to get through.

Michael Healy has transformed this dull narrative into a work of theatrical beauty. I watched the production of it last month and was amazed by the transformation of the story: from lifeless to effervescent, from rambling to compelling, and from putting me to sleep to having an entire audience on their feet. Amazing!
Profile Image for Jacqueline Keddy.
2 reviews
March 2, 2024
I saw this performed at Crow’s theatre in Toronto for its world premiere and it was just too good. The direction, the set, the acting, and most fundamentally, the script, were incredible. So funny, So thoughtful, so witty, and a gift to Torontonians, allowing us to laugh at just how ridiculous our city can be.

Naturally, i knew i’d have to read it at some point, and what a funny and lovely read it was, I have no doubt i’ll revisit it again at some point.
Profile Image for Jake.
22 reviews
July 26, 2024
really impressive, balanced stuff from healey here. the fact that it was commissioned less than a year before it debuted at crows is fucking nuts
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