Dan Doctoroff is here to listen. In the opening moments of the stage play The Master Plan, actor Mike Shara’s fictionalized Sidewalk Labs CEO takes pains to present himself as a humble servant of the public good. It’s just that, in making his point, he can’t help yelling and interrupting everyone else. Written by Michael Healey, directed by Chris Abraham and based on Josh O’Kane’s book Sideways: The City Google Couldn’t Buy, the play chronicles the Sidewalk Toronto saga, which saw the global tech giant make a bold (and ultimately unsuccessful) play to build a neighbourhood “from the Internet up” on the city’s waterfront. This past fall, the production sold out a seven-week run at Toronto’s Crow’s Theatre (and scripts can now be purchased through Playwrights Canada Press). The development process was always full of drama. Now, it’s the stuff of theatre, too.

Filling seats for a play that mines the minutiae of civic procedure for raucous laughter is no small feat. Artfully translating the jargon of municipal governance and public procurement, The Master Plan situated the personalities (and civic aspirations) that lay behind a convoluted boardroom bureaucracy. Sidewalk Toronto’s barrage of facts and context — from city hall protocol to RFP regulations — was delivered via a deft combination of self-consciously explanatory monologues and a set of screens above the stage, framing the action below. The six-person ensemble cast played a wide variety of roles, performers rapidly switching from John Tory and Justin Trudeau to public governance activist Bianca Wylie and Josh O’Kane himself. But it was Doctoroff, storming in and out of meetings, who dictated the story’s frenetic pulse, seldom stopping to take a breath — let alone to listen.

The Master Plan enjoyed a sold-out seven-week run at Toronto’s Crow’s Theatre.

On the political and theatrical stage, Doctoroff draws a striking parallel. Described as a prospective “Robert Moses of the Bloomberg era” in the New York Times during his prolific 2000s tenure as New York’s deputy mayor, the former Sidewalk Labs CEO arrived in Toronto with city-building ambitions powered by the mix of hubris and ego that also drove his mid-century counterpart. Moses, too, has recently had his turn on the stage: He was played by Ralph Fiennes in 2022’s Straight Line Crazy (which ran first in London, then in New York). But while Shara’s Doctoroff relied on a veneer of corporate equity jargon, Fiennes’s Moses was an old-school tyrant.

As historical figures, the two men stand generations apart. As theatrical characters, however, they are contemporaries, taking the stage at a moment of heightened public interest in urbanism. From a growing awareness of the North American geographies of exclusion and institutional racism to a housing crisis that increasingly shapes urban life the world over, understanding how — and why — we’ve built our cities feels more timely than ever. On the stage and in the public imagination, Moses and Doctoroff give us a rough draft of a bigger story.