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A lot. Chow’s first 100 days in office have been wildly busy, due to the massive challenges facing Toronto, the fact that she replaced John Tory midterm with council business underway and her own drive to get things moving.

“I think it’s going well,� Chow, 66, said of her nascent mayoralty, looking relaxed in her second floor city hall office overlooking Nathan Phillips Square.

The former city councillor and NDP MP, who became mayor July 12, seems content to leave it there rather than talk up her accomplishments. With a laugh she declines to grade her own performance running Canada’s biggest city.

Others, however, are willing to rate her early days and the reviews are mostly positive. The Star interviewed city councillors of all political stripes, Chow transition team members and office staff, officials who worked under Chow’s predecessor John Tory and other city hall observers.

The consensus is that contrary to fears raised by her opponents in the June 26 byelection — that she would seize city hall and impose radical leftist rule — Chow has emerged as a pragmatic progressive advancing the city’s interests by building relationships with politicians of all persuasions.

While that approach has earned Chow early success — most significantly Premier Doug Ford’s surprise pledge to help pc28¹ÙÍøfix its finances — the avid kayaker faces choppier waters in the coming months. Ahead is a gruelling budget process, crucial negotiations with the other levels of government and council rivals ready to sink her if she veers off course.

Those waters could get even rougher for the consensus-building Chow with the threat of an opposition bloc forming if she can’t keep former Tory backers happy, one representative accusing her of “ideologically driven policies� and some allies already breaking ranks with her on key issues.

Chow earns praise for her approach

Jon Burnside, a right-leaning councillor who in February unsuccessfully begged Tory to not resign after the ex-mayor acknowledged he’d had an improper relationship with a staff member, said so far Chow has “hit it out of the park.�

The Don Valley East representative said the mayor has been incredibly responsive to councillors — his text to Chow about a grocer in his ward displaced by Metrolinx construction triggered immediate help — and surprisingly effective dealing with the Ontario Progressive Conservative and federal Liberal governments.

But, Burnside said, “the rubber hasn’t hit the road yet,� noting the mayor will be judged on how she handles issues like the 2024 budget with its massive revenue shortfalls for transit and other services.

The early days of any mayoralty are hectic. Many procedures for running the city of more than three million people aren’t formalized. Each administration figures out basics like how to deal with council members, the media and the municipality’s vast bureaucracy. It took weeks for Chow’s team to start issuing daily itineraries.

Tory faced unique challenges when he took office in 2014 after the scandal-plagued years of Rob Ford. According to insiders, Tory’s team had drug-sniffing dogs sweep through the mayor’s office in case Ford had left behind any contraband, either accidentally or as a prank.

But while Tory’s most pressing problems were inadequate transit and snarled traffic, Chow is also grappling with a generational housing crisis, a billion-dollar post-pandemic budget shortfall and a shelter system so overburdened refugee claimants are sleeping on the streets.

Chow opted to take office less than three weeks after the election, rather than the traditional five weeks, and plunged into staff briefings to get up to speed.

“What sticks in my mind is the fact that she was ready to go in and work from Day One — there was never a day she wasn’t there early and stayed late,� said Nadine Tkatchevskaia, who worked on Chow’s campaign and the transition team.

Chow’s team has received guidance from former Tory chiefs of staff Luke Robertson and Courtney Glen as well as Jane Karwat, who ran David Miller’s office when he was mayor.

Also key was Coun. Jennifer McKelvie, the Scarborough-Rouge Park representative and Tory’s deputy mayor who took on his responsibilities after he quit in February.

McKelvie was a faithful Tory ally who burst into tears when he informed her he would resign. She later joined him in endorsing former councillor Ana Bailão — not Chow — as the best candidate to succeed him.

But Chow made McKelvie ceremonial deputy mayor for east pc28¹ÙÍøand kept her on as chair of the infrastructure and environment committee.

“I’m really delighted to be part of the administration,� McKelvie said, adding her work to ensure a smooth transfer of power has been rewarded with collaborative efforts to ensure the city meets its goals for housing and climate change.

“Mayor Chow is building upon that and accelerating that and I think there is a recognition of that from my colleagues,� she said.

Opposition holds fire — for now

Not all council colleagues give Chow rave reviews. After she organized a council vote earlier this month to cap the number of ride-hailing licences issued by the city, Brad Bradford criticized the decision in a news release as reckless, contrary to staff advice and “a glaring example of ideologically-driven policy rammed through at (Torontonians’) expense.�

The Beaches-East York councillor, who finished eighth in the byelection, was one of five right-leaning members who held a Sept. 5 call to talk about how to resist aspects of Chow’s platform. That group has yet to coalesce into an organized bloc.

Bradford said how much opposition the mayor faces will depend on convincing members like him she’s prioritizing residents’ day-to-day needs, not left-wing ideology.

“I think the mayor will continue to enjoy a lot of support from her colleagues, including me, when she is focused on the issues that matter most to everyday Torontonians� like housing, congestion and affordability, he said.

Stephen Holyday, another councillor on that September call, said Chow should not be fighting the Ford government’s Ontario Place redevelopment plan or spending millions of dollars to get 25,000 rent-controlled homes built when the city is in financial crisis.

But the Etobicoke representative, who backed former police chief Mark Saunders for mayor, said he’s also found “common ground� with Chow, who has asked him to lead a new committee dedicated to improving city customer service.

Chow governs with shifting coalitions

Tory’s office had a command-and-control approach to council, lobbying allies on key votes and sometimes using cheat sheets to remind them at council. Chow, so far, is using a more fluid approach, with shifting coalitions issue by issue.

“I don’t control council. I won’t call it that,� Chow said. “I see it as a team and building strong relationships with each other so that everybody can achieve what they’re most interested in.�

But she and her allies recently lobbied colleagues to cap the number of Uber and Lyft drivers. “Uber was lobbying too. I saw highly paid lobbyists,� she said in response.

The most recent council meeting also saw Chow grill a senior civil servant over undelivered reports on the correct number of drivers in a way that shocked some colleagues.

“She’s quite forceful,� said Coun. Gord Perks, like Chow a longtime NDPer, who added that she has gained more ground in key files including housing and finances than Tory and Rob Ford did in 13 years.

Chow’s co-operative approach to council could be soon tested. Coun. Shelley Carroll, her budget chief, has broken ranks on important issues, including a proposed parking tax and a ride-hail driver cap. Some close to Chow believe that level of public disagreement from a key administration figure isn’t sustainable.

Mayor’s office staffing raises eyebrows

Behind the scenes, more than three months in, Chow is still one or two positions short of a full complement of staff after outreach to progressives as far away as British Columbia. There are challenges to onboarding employees midterm, but those close to the mayor acknowledge her staff has been stretched thin at times.

Many of her senior staff are New Democrats, which has raised concerns outside the office that she could be pushed further left with ideological advice.

“Not all the best people in city building are NDP. There’s some great city builders that are more neutral,� said Richard Peddie, who worked on Chow’s 2014 mayoral campaign.

Michal Hay, the mayor’s chief of staff, said her office has moved “incredibly quickly� and has “very clearly demonstrated� that staff are committed to “the collaborative approach that (the mayor) wants to take.�

Chow makes early missteps

Chow stumbled weeks into her tenure when she made no public statement about a police officer being seriously injured and a police dog killed in action. The pc28¹ÙÍøPolice Association, which put out a statement criticizing her, now says a meeting with the mayor, and her subsequent actions, have allayed officers’ concerns.

Chow also came under fire for sounding resigned, in a CBC Radio interview, to Ford’s plan to build a large spa at Ontario Place. She said she still opposes the plan and is trying to convince the province to put the spa elsewhere. However, she’s facing a tough fight: the city has limited ability to decide the fate of the facility on provincial land.

On her biggest misstep, two tweets following Hamas’s attack on Israel that managed to enrage pro-Israel and pro-Palestinian Torontonians, Chow said social media “is really hard to capture something with so much anger and emotions in a few words.� She apologized and released a single revised statement.

Chow said she’s not bothered by those “bumps� on the road. “If I messed up a major housing file — that’s not a speed bump, that’s a big problem,� she said.

“There are bumps along the way on different issues, but it’s a pretty complex job. Apologize and continue to move forward.�

Doug Ford becomes an unlikely ally

Asked how she got Ford to acknowledge Toronto’s structural budget deficit and pledge to help fix it, Chow traces it back to her election night phone call with the premier and their previously unreported informal meeting a short time later.

While the pair are unlikely allies, Chow noted they’ve aligned before — they both criticized Tory’s SmartTrack transit plan running against him for mayor in 2014 — and years later, they realized that “there was a lot of things we could work on.�

Chow said she went into their first formal meeting, at Queen’s Park, knowing she had won Ford over with help from “an almost bulletproof� city staff report laying out the funding gap.

While she got some money from the Prime Minister Justin Trudeau government to help shelter refugees — a sum quickly used up — she’s still waiting for Toronto’s share of the federal $4 billion “housing accelerator� fund.

“We did everything (Housing Minister Sean Fraser) wanted,� she said, adding with a wry laugh: “Accelerate the decision.�

Larger pc28¹ÙÍøissues loom

Chow remains an unabashed progressive leading a council that collectively leans more right. Issues ahead that threaten her extended honeymoon include the east Gardiner Expressway, which she promised to tear down rather than rebuild aloft, and a pledge to forge ahead with renaming Dundas Street.

While Chow doesn’t want to pre-empt the work of the group advising the city on Dundas, she said: “There might be ways that are not as much financially, but one way or another it will come through the budget cycle, respecting the process that was put in place,� she said.

Chow said her predecessor’s record offers some insight on how to avoid adding to the city’s already considerable problems. She expresses amazement at Tory and council’s decision to agree to host the 2026 FIFA Men’s World Cup at a cost of at least $300 million, before getting provincial and federal funding commitments for the event.

“Are you kidding me?� she said. “We should ask, have them say yes — then you sign the bid.�

Chow notes, more than once, that FIFA is among potential headaches she inherited after Tory resigned and her plans for a major canoe trip went out the window.

She is still getting out on the water, in a kayak or on an inflatable paddle board, but only after busy days at city hall and sometimes in the dark. The lake is safer now in cooler weather because the jet skis are gone, she adds.

“It’s beautiful, it’s very quiet,� she said, adding she was recently alone one night — a rarity for a busy mayor usually surrounded by people — on the Rouge River.

“I didn’t see anyone. It’s safe. I have big lights.�

David Rider is the Star’s City Hall bureau chief and a reporter covering city hall and municipal politics. Follow him on Twitter:

Ben Spurr is a Toronto-based reporter covering city hall and municipal politics for the Star. Reach him by email at bspurr@thestar.ca or follow him on Twitter: @BenSpurr