https://www.thestar.com/news/toronto-election/2022/10/15/john-tory-is-the-middle-man-but-is-he-bold-enough-to-lead-toronto-out-of-its-post-pandemic-crisis.html

When John Tory, the fourth mayor of the megacity of Toronto, was an executive at Rogers Communications Inc., he developed a method for bringing ideas to his boss, the company’s irascible and detail-obsessed founder, Ted Rogers. The key, Tory said, in his elliptical, run-on way — his sentences have a habit of beginning in one place then branching off, like tunnels in an ant colony, into unexpected passageways and dead ends — was to hit Ted at the exact right time with the exact right amount of information.

“If you went too early and hadn’t done your homework, or he wasn’t ready to talk about it, then that was a problem,” Tory said, leaning forward over a low table set up in front of a couch in his city hall office. “If you went too late, he’d say ‘Why didn’t you do this some time ago?”

It was just before 7 a.m. in the dying weeks of Tory’s second term as mayor. From outside, in Nathan Phillips Square, it looked as if the light in Tory’s office was the only one on in City Hall. Inside, he drank black coffee from a Starbucks cup. On his left wrist, he wore a yellow bracelet with the word LEADER spelled out in white blocks along the string.

You couldn’t give Ted too much information, Tory continued. “The more information you gave, the more questions you got.” At the same time, you couldn’t give him too little either, or he wouldn’t believe you’d thought the idea through. “We drew up a diagram,” Tory said, sketching it out with his hands in the air. It had four circles on it, on the four corners of the page, representing the four ways things could go wrong: too much or too little; too early or too late.

To get Ted to agree to anything, Tory said: “You had to find the spot in the middle.”

For more than 50 years in politics, and over the last eight years as Toronto’s mayor, Tory has been homing toward that middle. “He tends to campaign to the right and govern to the center-left, which works because it wedges both out,” said one long-time adviser. “Look at him today, right? He’s got effectively no opponent.”

While that’s not exactly true — Gil Penalosa, an impish and talkative urbanist, has run an eye-catching campaign against Tory — most pundits and pollsters agree that Tory should waltz to victory on Oct. 24. “He’s going to win overwhelmingly,” said John Filion, a retiring city councillor who has been largely shut out of the Tory administration.

But if the outcome of the election looks to be in little doubt, the future of the city Tory governs seems, increasingly, a lot less certain. There are growing signs that the next four years will be pivotal for Toronto, no matter who ends up as mayor. And more critics are questioning whether Tory, who believes in consensus and incremental change — in staying, in other words, in the middle of the page — has the vision and the makeup to see the city through.

“There is a distinction between management and leadership,” said one city hall insider who has worked closely with Tory for years. “And he is a manager.”

If Tory does win, he will enter office with more political capital than any mayor in the history of amalgamated Toronto. He is set to have a massive mandate, a council shorn of many of his most effective foils — including outgoing downtown councillors Kristyn Wong-Tam, Mike Layton and Joe Cressy — and a new set of strong-mayor powers that should in theory allow him to unleash more big ideas, in more consequential ways than any municipal leader since David Crombie in the 1970s.

The stakes for Toronto are high. Even as interest rates soar, the city’s housing calamity shows no signs of waning. “Every point along spectrum below, basically, luxury housing is in a state of crisis,” said Alex Mather, who ran communications for Jennifer Keesmaat’s mayoral campaign in 2018 and now works in the affordable-housing industry.

Homelessness remains endemic. The city’s public infrastructure, from parks, to water fountains and garbage bins, looks increasingly rundown. The TTC is facing a ridership “death spiral.” Social services are overburdened. Municipal finances are a mess: There’s a projected $850-million hole in the operating budget for next year; an infrastructure deficit; an aging population; inflation; rising interest rates; and a shrinking list of viable ways for the city to raise more cash.

“It’s a problem,” said Enid Slack, the Director of the Institute on Municipal Finance and Governance at the Munk School of Global Affairs and Public Policy — one even some of Tory’s closest confidants believe could blow a big hole in his legacy plans. “I would have told him not to (run again),” said one Tory adviser. “I think a third term post COVID with no money is going to be hell on wheels.”

But there’s a lot more than the mayor’s legacy at risk. “I think that the next four years are going to be the critical moment in my lifetime in the history of Toronto,” said Gord Perks, who is running for re-election in Parkdale—High Park. “We either wind up like so many American cities where nothing works and there’s litter blowing across the cracked pavement, or we come to an understanding of what municipal governments are for and how they’re funded. There’s really no middle ground. And my worry is I have yet to see the John Tory who could lead that fight.”

Over the past two months, the Star has spoken to more than 30 city insiders, Tory confidants, and on multiple occasions Tory himself, about the last eight years in the city and what we can expect from the next four if, as widely expected, Tory wins on Oct. 24. We have granted anonymity to some sources to allow them to speak frankly about their experiences with the mayor.

The portrait that emerged from those interviews is of a man of sometimes baffling contradictions: a deeply committed, often thin-skinned public servant who, depending on who you ask, is either the only person capable of wedding the megacity’s many factions together or a leader too afraid of being hated, and too tied to his suburban base, to push through the difficult reforms it is increasingly clear the city needs.

“He was somebody that came in here to stabilize the city in that first term, to bring some peace, to bring decorum,” said Ana Bailão, a retiring councillor who worked closely with Tory on housing issues and is one of his re-election campaign co-chairs. “He’s done that. He came into the second term, launched a whole bunch of things the first year and then he got hit by a pandemic, which his leadership style was incredibly successful in managing.”

But not everyone believes that kind of steady, nudge-it-forward-leadership is enough for Toronto anymore. “I can’t think of a single service we’re delivering to the same standard we were 10 years ago,” Perks said. “And I think he realizes the problem. I don’t think he yet realizes that the path to solving the problem involves really shifting gears.”


On a Friday afternoon in early fall, Gil Penalosa, a Colombian-born consultant, urban strategist and parks obsessive, stood next to his bicycle outside a fenced-in rectangle of ragged green space east of Yonge Street near the city’s core. George Hislop Park has been closed to the public since the summer of 2020, when city workers evicted a large homeless encampment that had settled there in the early months of the pandemic. The city has a plan to redevelop the space, part of a series of linear parks that run from Charles Street to Dundonald Street. But officials say construction won’t begin until next spring; until then the park remains closed.

For Penalosa, a voluble father of three who has lived in Toronto for 23 years, George Hislop Park is a physical representation of the many failures of the Tory mayoralty. “I honestly feel that the city today is less affordable, less equitable, and sustainable than eight years ago,” Penalosa said. “I think that the city is falling apart. People tell me the streets are dirtier, the garbage bins are not clean. You take the subway and the escalators are broken. You go to the park and the water fountains are not working. I think the symptoms are everywhere.”

For Penalosa the mayor had one thing going for him when he first ran for mayor: timing. “I think his biggest asset, or luck, is that he came after Rob Ford, probably the worst mayor ever,” Penalosa said. “Anybody, even a donkey, would have looked good after that administration.”

That, in a nutshell, is the case against John Tory today. He brought the city calm after Ford. He was a steady hand during COVID. But at this point, Toronto needs more.

“When it comes to symbolism and communications, I think he’s extraordinary,” said Josh Matlow, an incumbent city councillor and one of Tory’s most persistent critics. “But when it comes to the behind-the-curtains, substantive managing of the city… he failed.”

Matlow cited everything from Tory’s failure to back drinking in parks to his now-forgotten SmartTrack plan and his handling of homeless encampments in parks as examples of the kind of mayor he thinks Tory has been.

“He will not move forward with I think some of the more important objectives of the city because they’re risky or controversial,” he said. “And what we’ve been left with is a lot of people on our streets … We have garbage cans that are overflowing. We have water fountains that aren’t turned on until June.”


Early on a recent Monday morning, Tory himself came into the Toronto Star office for an interview, accompanied by a member of his campaign staff. The Star is in the process of moving, and leaning against the wall in the meeting room where Tory sat was an old, blown-up front page from Sept. 11, 1987, the day after a provincial election that saw Tory’s Progressive Conservative party reduced to 16 seats.

Tory served as PC leader Larry Grossman’s campaign chair in that campaign. It was one of the hardest elections he was ever in, Tory said, in part because he knew it was all but doomed from the start. An internal poll commissioned the day the election was called had the PCs at about 15 per cent. “It was the worst result I’ve ever seen.” And he had to go to Grossman’s house to let him know.

Tory has been involved in PC politics since he was 15 years old. He was once described in the Star as a “20-year-old political veteran.” From the late 1970s through to the early 1990s, he was one of the most influential backroom players in the country, working behind the scenes for Brian Mulroney and Ontario premier Bill Davis.

To this day, Tory subscribes to Davis’s brand of pragmatic, big-city progressive conservatism. But he rejects the idea that those moderate instincts have prevented him from getting things done at City Hall. “I believe most people believe that while we have problems in the city — which there will always be in a big city, any big city in the world, including ours — the city has moved forward on my watch,” he said. “I’ll get you a list and you’ll say ‘None of these are gigantic things that revolutionize the world. (And) I’ll say ‘Maybe it’s a whole series of things that (I’ve) done, that have just generally made life better for different groups of people, and for all the people.’”

Despite his five decades in politics, Tory remains remarkably sensitive to criticism about his record. At the Star, I read him a list of things Penalosa and others had told me for this piece. As the quotes unfurled, he became visibly frustrated.

When he’s relaxed, Tory tends to twist his body, leg over leg, then tilt his torso in the opposite direction with his arms folded over his chest. As I read that morning, he straightened out, uncrossed his legs and swivelled to face me directly. When I played back the tape of the interview, I could hear the thump, thump of his hands banging on the table to emphasize each point of his response.

“I wouldn’t be running if I thought I hadn’t done anything, and accomplished anything including, especially for people who are of lesser means in the city and people who are marginalized,” he said. “And I’m running because I want to do more to build up the city and to make sure that those same people can get a better job, because the city’s economy is expanding, and make sure that the city remains affordable to them, that we have transit to get them to a job, and that we have affordable housing for them.”


On a hot late summer morning, on the patio outside a coffee shop near George Brown College, Joe Cressy sat enjoying life outside of politics for the first time in eight years. Cressy, a lifelong New Democrat, resigned his city council seat earlier this year to take a job as vice-president at George Brown.

Between 2014 and 2020, Cressy was perhaps the most effective critic Tory had on city council. He was on every progressive’s shortlist for mayoral candidates in 2022. But then the pandemic happened, and for Cressy, everything, including his relationship with the mayor, changed.

Cressy and Tory worked side-by-side for the first two years of the pandemic, as mayor and chair of the Toronto Health Board. For a time, they were in a COVID bubble together, away from their families, meeting every morning, making decisions that would affect the lives of millions of Toronto residents. “You cannot go through that type of experience, of relentless day in and day out trauma and struggle and challenge and not develop a bit of a brotherhood,” Cressy said.

What struck Cressy is that, through it all, Tory never cracked. After one particularly grim COVID modelling session in 2020, Cressy went to the alleyway behind councillor Mike Layton’s house, sat 12 feet away from his old friend, and broke down in tears. But the mayor, he said, just carried on. “He never broke. He never wavered,” Cressy said.

“He has this deep love for the city and this belief that we need to go through all the division and strife and resentment and angst that exists, (and) hold it together,” Cressy said. “I came to understand that. And you know, that’s a rather uniquely and helpfully positioned perspective to have in a pandemic.”

People who have worked closely with Tory, even critics like Cressy, tend to speak about him with something that goes beyond admiration. “If John said to me, ‘I want you to run through that brick wall.’ I wouldn’t hesitate,” said Alek Krstajic, who worked under Tory at Rogers and went on to found Public Mobile. “And the reason I wouldn’t hesitate is I would (know) he has my interests at heart above all.”

Justin Van Dette, a well-known conservative organizer in Toronto, credits Tory with changing his life. It was Tory who convinced a young, closeted Van Dette to attend a program at the 519 community centre in the Church Street Village called Coming Out, Being Out. When Van Dette kept skipping meetings, he said Tory called his bluff. “He said to me, ‘Justin, you’re going to be there next Wednesday night. And we’re going to go together.’”

After our first interview, Gil Penalosa called me back to say one more thing about Tory: “I don’t think he cares at all about immigrants. He plays a lot. He loves to have photos with Black celebrities. He loves to go to the ethnic festivals. But I don’t think he’s really truly committed to that part of it.”

When I read that back to Tory, he openly seethed. “Go and ask the people,” he said. “Go on, ask people. See the relationships I’ve developed with all those communities, which are very genuine.”

For Van Dette, the idea that Tory is a phoney, that he shows up in marginalized communities just for votes, is absurd. “He was coming here for the Gay Men’s Softball League fundraiser at Woody’s,” he said recently at a bar in the village. “He never went there looking for fanfare or cameras. That was not him. He was very, very authentic then, as he is today.”


One of the reasons staffers and executives who have worked under Tory, in both business and politics, cited when I asked them why they liked working for him so much, is that he empowers the people beneath him. He trusts them to find solutions and carry them out. But there is a flip side to that equation. Because of that trust, the quality of what Tory delivers can vary a lot based on the kinds of people he empowers — and even some of his closest advisers don’t think he always empowers the right people.

That was especially true in Tory’s first term, according to multiple city hall and mayoral insiders. “It always seemed to me that what the mayor wanted and what his senior staff wanted were often kind of the same, but different,” said one former Tory adviser. “If you talk to the mayor, you could hear his commitment to all kinds of really progressive and helpful initiatives, whether it’s housing or harm reduction. … But (his senior staffers) weren’t necessarily quite as interested in those things.”

Another former Tory insider put it more bluntly: “The first term was s—.” “Most of us, including the mayor, didn’t know where the f—ing bathroom was at city hall,” said another member of that team.

Tory expended a huge amount of political capital in his early years on what one former staffer said the left sees as “the original sins” of his administration: rebuilding the eastern leg of the Gardiner Expressway, supporting the one-stop Scarborough subway and appointing Mark Saunders as chief of police. He also stuck to his campaign pledge to keep property tax hikes at or below the rate of inflation, a decision critics have long blamed for the city’s increasingly ragged finances.

“It’s almost like shooting yourself in the foot to not raise taxes,” said one senior bureaucrat who recently left the city. “You’re already behind the eight ball when you’re starting your budget process. And I think that he realized quite late that he’s hamstrung by that problem.”

Filion, for one, thinks both the mayor’s office and the mayor himself improved dramatically after the 2018 election. “I thought he did a fantastic job in his second term,” he said, especially on the pandemic. “It wasn’t just the leadership on vaccinations and masking or other restrictions. It was also the opening up of public spaces and creating more bike lanes and outdoor cafes.”

Filion was one of at least half a dozen city hall insiders from across the political spectrum to cite Tory’s second term chief of staff, Luke Robertson, as a big reason for the improvement. “Luke is brilliant and very pragmatic,” Filion said. “He works well with everybody.”

But while Tory’s office staff turned over significantly between his first and second terms, his informal “kitchen cabinet” of largely conservative advisers has remained mostly the same. According to multiple sources, he still leans on controversial pollster Nick Kouvalis, Chris Eby, his former chief of staff, Amanda Galbraith, a consultant at Navigator, and Liberal Bob Richardson for political advice.

Tory’s second term was also not without controversy. He came under heavy fire last year for continuing to serve on the board of his old mentor Ted Rogers’ family trust while mayor. “It’s clearly a f—ing conflict of interest,” said Tory’s old friend and long-time colleague Allan Gregg, but to Gregg it’s a conflict that reveals much about Tory’s sense of loyalty and commitment. “It is not that he’s not aware that it’s a conflict of interest,” he said. “It’s that he is so acutely attuned to the responsibilities and the promise he made to Ted Rogers.”

Perhaps no single issue reveals the enigma that is John Tory more than the people he supports and empowers. In our interviews, Tory kept coming back to his progressive goals for a third term: on housing, on transit, on equity. But he is once again in this campaign actively working against progressive candidates in multiple wards. As he did in 2018, Tory is backing incumbent Mark Grimes in Etobicoke-Lakeshore over Amber Morley, a young, Black community health worker who polls suggest could have knocked Grimes off in 2018 had Tory not intervened.

Grimes, who was found by the city’s integrity commissioner in 2016 to have had an “improper” relationship with developers and who once tweeted at U.S. Vice-President Kamala Harris to “stop talking!!,” seems to represent the kind of politics Tory, who brought up Penalosa’s “donkey” reference repeatedly in our interviews, seems to hate. But Tory makes no apologies for backing him.

“I’ll just say to you, he’s been someone that I can count on to represent his community with great devotion,” he said. When I pointed out that Grimes has also been a reliable Tory vote on city council, Tory cut me off. “Of course,” he said. “There are no parties down here OK? But I do have to get things through.”

When I asked people close to Tory what his priorities would be for a third term, one that could define his legacy in politics and shape the path of Toronto for a generation, the one item that came up more than any other was housing. “I’ve seen him at these public consultations for supportive housing projects that we’ve had. And you can see it comes from inside, the way that he speaks about these issues, that he cares, and that he stands up,” said Bailão, who led the housing file in city council over the past eight years.

When local residents would speak out against supportive housing projects in their neighbourhoods at these hearings, Bailao said, Tory would come back at them, hard. “He pushed back like I had never seen him do before” she said. “I was proud that he came out and he pushed back and that he was standing up for the projects.”

Bailão is retiring from politics this year. To replace her in Davenport, Tory has endorsed Grant Gonzales, a 33-year-old in-house lobbyist for the Ontario retirement home industry. Though he doesn’t list it on his official bio, Gonzales is also a former lobbyist for Airbnb. Between 2017 and 2018, when city council was fighting over new rules for the home-share giant, which has been linked with rising rents in major cities, including Toronto, Gonzales was actively lobbying members of council on Airbnb’s behalf.

(Gonzales said most of his work for Airbnb involved setting up meetings for other people at City Hall.)

Housing is one of several files that represent a growing gulf between how Tory and his critics see the world. Ask Tory about housing and he’ll point to his work legalizing laneway and garden suites, to the city’s housing budget doubling under his watch, to the Housing Now initiative to build affordable housing on city-owned land, and to his ability to keep housing money flowing from other levels of government. His critics, though, will look at all that and say, fine, but the housing crisis is still getting worse. They’ll also point to the fact that, despite months of lobbying last year, Tory failed to get a basic plan to legalize rooming houses through a city council packed with his allies.

In a way, it comes down to philosophy. Tory believes in process and consensus and gradual change. He has throughout his career. “John taught me to slow down and listen and look at all the relevant data,” said Krstajic. “Even though nine times out of 10, my decision would have been the same, he said ‘It doesn’t matter. It’s that one time, Alek. You’d screw everything up.’”

But critics, especially on the housing file, think the problem is too urgent now for slow steps, even if they are in the right direction. “I think the mayor could do more, frankly,” said one senior planner who recently left the city.

He could introduce a motion to comprehensively up-zone Toronto, giving property owners the ability to densify by right (without, in other words, having to apply to the city for permission every time). He could streamline the city’s arduous aesthetic guidelines for building and push back against heritage and other restrictions that have kept two-storey commercial buildings in place along major transit routes. He could “stop listening to the damn residents’ associations so much,” said another ex-planner. But doing any of that would mean making a lot of voters mad, and no one is sure if that’s something Tory, even if he will never face the voters again, will be willing to do.


For a man so associated with gradual change, Tory is, in person, surprisingly kinetic. In public he moves relentlessly from group to group and person to person. Five minutes before the start of a recent parade in High Park, he drifted away from his campaign team and toward the open trunk of a car, where volunteers were blowing up balloons. “I’ll just wander over there,” he told a staffer. From the balloons, he waded into a team of young dancers, before posing for a photo with the Kozaky MC Ukrainian motorcycle club.

Even when he’s sitting down, Tory is always moving. He has a habit of fiddling his fingers — one thumb under the index and then back over. He’s constantly crossing and uncrossing his legs, folding his arms, twisting his hips and checking the refurbished BlackBerry he still clings to for personal use. (“I’m in love with the keyboard,” he said. “I’ll keep it until they pry it from my dead hands … or they stop servicing it.”)

Tory is an odd position heading into the election. Without a mainstream challenger he hasn’t had much need, in public, to focus on the next four years. Instead, he’s been left to pre-emptively defend a legacy he still has time to build.

In our interviews, he didn’t back down from any of his more controversial moves as mayor.

He stands by his decision to serve on the board of the Rogers family trust. “I just felt a moral obligation,” he said. “I said that outwardly at the time. And I’ve made no secret of it.”

He doesn’t apologize for keeping property taxes low for the last eight years. “I just don’t think people can sustain much more than a very modest increase,” he said.

He still believes the city did the right thing by clearing the encampments out of city parks in the summer of 2021. He backed Tracey Cook, the top city bureaucrat in charge of that plan, as the city’s interim city manager in August. This fall, he endorsed another architect of the plan, John Burnside, a former councillor trying to make a comeback in this election.

He also made it clear that he blames activists, not the police or city staff, for any violence that occurred when the encampments were cleared. “The people who were resisting having those encampments taken out of the parks, including a lot of empty tents — empty tents! — were the advocates,” he said. “And these were the very same people, Richard, that I have to tell you, were following the street outreach workers home at night, and shouting at them and spitting on them and bombarding them with terrible emails saying that they were awful people doing terrible things.”

Not one Tory confidante I spoke to expressed much surprise that he chose to run for a third term. “It’s a hard job. It’s a horrible job. He loves it,” said a former staffer. And, perhaps as a result, he’s highly sensitive to any suggestion that he has let the city go backwards on his watch.

“We’re making a change,” Tory said about winterizing park bathrooms, a frequent bugbear of city progressives. “But the thing is that when you make these changes … it’s never fast enough … people want these things fixed tomorrow.”

The same is true for broken garbage cans, he said. “We have actually doubled and tripled the number of times they’re cleaned out by the people that do that for us. But the fact is that the garbage cans themselves are a problem. I didn’t sign that contract. I didn’t invent those garbage cans. But I have begun the process of re-examining those garbage cans.”

Anyone expecting Tory to change over the next four years is likely in for a disappointment. After 53 years in politics, he is who he is.

I asked him at one point, if he was starting out today, if he’d still go into political life. He might, he said, but maybe with a different party.

“It’s not even about parties,” he said. “It’s just about people out there. For some reason they’ve been pulled into this world where they feel they have to put on the red shirt or the white shirt. There’s nothing in between … And I’d say, Well, why? Why can’t we put the red shirt and the white shirt together and find a pink shirt that actually is the best shirt for now, that has everybody feel(ing) that they’re being listened to and mov(ing) forward to some extent?”

With four years left in his political life, Tory is still aiming for the middle of that page he drew up for Ted Rogers. “Are there some who would place the dot not right square in the centre between too early, too late, too much and too little?” he said. “Of course. But you can draw the circle a little bigger in the centre.”

It’s just a question now of whether that centre will ever be big enough for what Toronto truly needs.

Richard Warnica is a Toronto-based business feature writer for the Star. Reach him via email: rwarnica@thestar.ca