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From the left: Globe and Mail reporter Josh O’Kane, Director of the play The Master Plan Chris Abraham and playwright Michael Healey, at the Crow’s Theatre on Sept 12.Fred Lum/The Globe and Mail

I was reading a script in a Brazilian hotel bar last May while on assignment, and I was thinking about trees. Specifically: a Norway maple wearing an Adidas track suit, narrating Toronto’s long clash with a Google urban-planning project called Sidewalk Labs. I’d spent five years investigating that clash. Was the tree me? Or if not, was the tree running away with the story I’d written?

The script was for The Master Plan, a play that just debuted at Crow’s Theatre in Toronto. It’s based on Sideways, my 2022 book on Toronto’s long saga with Google’s city-building experiment. The playwright Michael Healey had kindly passed along a draft script for me to give notes on. I was trying to limit my comments to factual accuracy; I’d signed away the stage rights to the story months earlier. But I became fixated on the arboreal narrator. Was this the story I first sought to tell?

Sideways was an investigative postmortem of the failed attempt by Sidewalk Labs to build a neighbourhood on the Toronto waterfront; it doubled as an exploration of tech companies’ intrinsic incompatibility with how cities are run. The book was expressly a work of journalistic non-fiction, examining cities as the next battlefront for the private sector’s role in society and democracy. Healey was writing the play as a comedy, narrated by a tree.

I put aside my feelings and tapped out some notes on facts and pacing. On how Healey introduced light-rail transit, I wrote: “Having a newspaper guy aneurysm you can ignore here, but on the off chance someone doesn’t know what LRT is, you could either spell it out or just say transit?”

He didn’t take the note. I spent the next few months thinking about what happens when non-fiction becomes fiction, and when a story you obsessed over for so long floats out of your hands.

Books are often the start of storytelling for the stage and screen. There would be no Hamilton without Ron Chernow’s Alexander Hamilton. All the President’s Men is the story of Carl Bernstein and Bob Woodward’s newspaper reporting on the Watergate scandal that led them to eventually publish a book called, well, All the President’s Men. Non-fiction adaptations take the heavy lifting done by historians and journalists and reshape it into entertainment.

It’s rarely an easy transition. Even Susan Orlean, whose 1998 book The Orchid Thief became the definitive book-to-film adaptation – quite literally Adaptation, the 2002 Spike Jonze and Charlie Kaufman movie starring Nicolas Cage and Meryl Streep (and Nicolas Cage, again) – ceded full control of the story she told. As I tried to grapple with my own adaptation, she was the first person I reached out to.

Her initial reaction to Adaptation’s screenplay was trepidation. I’ve learned, too, that it’s easy to wrap yourself in a cocoon of defensiveness when you’re handing a story to someone else.

“I met with the costume designer to show him my closet, and I sat for some interviews with Spike,” she told me. “But I wasn’t involved at all with the actual screenplay.”

When Chris Abraham, the artistic director of Crow’s Theatre, contacted me last year expressing interest in Sideways, he threw me a curveball: He wanted to adapt it as a comedy. And the first name Abraham had in mind was Healey, who in the years since his play The Drawer Boy swept the awards circuit has produced a fine stream of satires. The playwright agreed to come out of semi-retirement, and we began a year-long text thread, trying to transmute a 316-page investigation into a two-act comedy.

He did a remarkable amount of research beyond just reading Sideways, interviewing enough key players from the Sidewalk project that he managed to talk with at least one person who wouldn’t pick up my calls. He clearly cared for getting the story right.

To a point, anyway. Healey made it clear over texts, coffees and beers together that he expected to rigidly adhere to what actually happened – except when it was necessary to fake things to drive the plot. Some of his ideas made for good comedy, including a prop we’ll call Chekhov’s cake and a scene interrogating Sidewalk staff’s selective readings of Jane Jacobs. Others made me feel wary; in one scene, the script attributes a news scoop to me that the Toronto Star and National Observer actually broke. Elsewhere in the script, buttoned-up executives uncharacteristically swear like sailors as their real-life words and actions are twisted into satire. And there was still the matter of the tree.

While I was sitting at the Rio de Janeiro hotel bar, fellow Globe and Mail reporter Sean Silcoff was walking red carpets for the premiere of BlackBerry Matt Johnson’s comedic adaptation of Losing the Signal, which Silcoff co-wrote with our former Globe colleague Jacquie McNish.

Silcoff’s concerns about his adaptation centred on the fact that while the filmmakers spell out the movie is a fictionalization, the public could consider that the definitive story anyway. “I’ve been surprised by the number of people who can’t tell the difference between fact and fiction. People have asked me, ‘Did it really happen that way?’” That’s been unsettling to numerous former Research in Motion employees, too, including ex-CFO Dennis Kavelman, who’s lambasted the movie. (Brock University professor Blayne Haggart, a long-time critic of the Sidewalk project, has shared similar concerns about The Master Plan.) But at least, Silcoff says, the filmmakers “picked up and expanded on a lot of the themes we addressed.”

At what point, then, do themes supplant facts in helping the public understand a story?

I’d assumed Orlean, for one, must have been shocked, if not mad, over the final result of The Orchid Thief’s adaptation. I was wrong. Kaufman took a book about obsession and turned it into a movie about obsession – his own – about writing well. About serving an audience. It turned out Orlean was in on the joke.

“I knew it was a gamble, but I just couldn’t resist finding out what it would be like to have the film made,” she said. “I think the movie masterfully encompasses the book’s themes, without being an explicit ‘remake’ of the book. That’s why I think it’s a far better result than a strict adaptation would have been.”

As I read The Orchid Thief after the exchange with Orlean, I came across a line that seemed to almost invite this kind of adaptation. “The flat plainness of Florida doesn’t impose itself on you, so you can impose upon it your own kind of dream,” she wrote.

As I read that line, I started thinking about Healey’s tree again: It was based on a real tree on a residential property whose fate city council once dropped everything to vote on. He wrote it into the play to represent Toronto’s obsession with bureaucracy, with city hall as a “monument to rule-following” – one of the major factors that led to Sidewalk’s failure in Toronto. It turned out I’d planted the seeds of this tree in Sideways.

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Globe and Mail reporter Josh O’Kane (white shirt) is photographed with Peter Fernandes, who portrays O'Kane on stage, at the Crow’s Theatre on Sept 12, 2023.Fred Lum/The Globe and Mail

It was strange, at the first table read at Crow’s in late July, to be a person that professional theatre actors turned to for advice. My “professional” experience in theatre began and ended with teenage boredom two decades ago. I joined the men’s choruses in high-school musicals such as Chicago. I was named office-chair choreographer in a musical adaptation of the Tom Hanks movie Big after convincing the director to let me race across the stage in a Herman Miller knock-off. I played Colonel Pickering in a one-off abridged performance of George Bernard Shaw’s Pygmalion, but couldn’t nail the accent in a play about accents. I was a terrible fit for the medium.

But while Healey had written some of the characters’ dialogue with caricature in mind, the cast nonetheless wanted to portray the very real people they were playing as authentically as possible.

The actor Philippa Domville asked me whether the book I’d written was a comedy or a tragedy. I was stumped for a moment; I’d let the facts speak for themselves. But I had to admit that some of those facts were funny – and that Healey had found the comedy in them.

I’d just watched the cast burst into laughter trying to get through a scene in which Canadians implore an American executive to drop the second “T” when saying Toronto, but the executive can’t figure out why. Healey had built that scene off a single line in my book, in which I describe Prime Minister Justin Trudeau addressing a pair of Alphabet executives with curiously American enunciation. I’d thought the moment absurd. So, too, did the playwright. He’d grown something new with the seed I’d planted.

As I stood up to leave at the end of the day, the actor Peter Fernandes, who plays the tree, stopped me with a question about a secondary character he’d also been cast for: “Anything I should know about playing you?”

I told Fernandes that he’d watched me working all day – that I’d trust his interpretation.

At the first preview of The Master Plan a month later, I brought my parents, who were unaware of the reporter Healey had written into the play bearing my name. As Fernandes marched onstage, he imbued Healey’s goofy jokes – it turned out the playwright had been studying me, too – with a sense of mission and curiosity.

My mom gasped, leaning forward to cover her mouth as she began giggling uncontrollably. Fernandes and I looked nothing alike, but there he was, channelling me in a play that looked nothing like Sideways that managed to feel like Sideways. The tree and I were the same all along.

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