100 days in, Mayor Chow advances agenda but challenges loom at Toronto city hall

Olivia Chow says it's time for the display of congratulatory cards behind her desk in the mayor's office to be put away.

One hundred days into her tenure as Toronto mayor, it could be taken as a sign the celebration -- and the transition -- is over.

Her team is in place, her council appointments have been approved and her office is anointed with handpicked landscape paintings. Above the cards is a piece by Group of Seven painter A.J. Casson, with windswept pines and a blue-grey lake beneath rolling hills.

"I'm usually up in Killarney or Petawawa, you know, on the river, watching the leaves change colour. Since I can't do that -- don't have enough time to do it -- I'm surrounding myself with landscapes," Chow said in an interview this week.

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The first 100 days -- a milestone reached Friday -- have seen Chow look to make her mark on the walls of the mayor's office and city council's agenda.

In recent weeks, she made shelter supports for asylum seekers a priority, boosted transit service, hiked the vacant home tax and promised expedited approvals for CafeTO, the city's seasonal sidewalk patio program dogged by complaints from business owners.

"Those are just the beginning. There's so much more to do," she said.

But on two of her most important files, affordable housing and the city's finances, the real tests of her leadership are still ahead, said Myer Siemiatycki, professor emeritus of politics at Toronto Metropolitan University.

Chow will head into the 2024 budget process with an estimated $1.5 billion shortfall and no immediate clarity on how it will be filled. And her banner campaign promise to get the city back into building affordable rental housing will require time and political will, he said.

"Has she made a significant dent into municipal finances and housing files? ... The jury is still out on that," said Siemiatycki, who applauded her early tenure.

"It's a crisis that none of her predecessors were able to crack."

Chow has already looked to make advances. She fast-tracked discussions about, and then secured council's approval for, a long-term financial plan that came alongside new graduated tax rates on the sale of luxury homes and mulls a number of possible revenue-generating tools, from a parking levy to a multi-year property tax policy.

But asked what she sees as a defining moment since she took office on July 12, she points to council's support for her committee appointments.

"That was really important for me," she said. "Some of them really know how this place functions inside out, so having their experience is really important."

Those appointments also caught the attention of city hall watchers who see it as a savvy attempt at coalition building.

Shelley Carroll, one of the council's most vocal backers of Chow's main mayoral campaign challengers, secured the high-profile budget chief position. Jamaal Myers, a rookie progressive and transit advocate for the city's east end, is heading up the Toronto Transit Commission board. Even Stephen Holyday, a fiscal conservative and one of Chow's least reliable votes, is in on the action, chairing the audit committee.

Siemiatycki said it cuts a contrast with former mayor John Tory's more tightly managed inner circle.

"I think in terms of the culture, the dynamic, the vibe at city hall, that has been perhaps her foundational, greatest achievement, because that will enable everything else to come," he said, speaking about Chow's first 100 days.

And to others, that culture shift extends beyond council appointments.

Diana Chan McNally, an outspoken harm reduction worker, said she and other front-line housing advocates have been invited into city hall conversations and directly consulted by the mayor.

"Instead of having a stranglehold on the conversation ... what we're seeing now is that we're actually willing to have, if not a balanced conversation, then a conversation about what needs to be done. That's the thing that really stands out," she said.

McNally advised on the city's winter homelessness plan, which she said is still "deficient," but includes some important gains. Among them, the plan includes a 24-7 respite centre, something advocates had pushed the city to include in last year's plan, as well as additional sites at warming centres.

"We'll never agree on everything, but at least the conversation can happen," said McNally.

Chow lamented the slow pace of the city's discussions with the federal government, but said she was encouraged by the working group she struck with Premier Doug Ford on stabilizing the city's finances. That group is set to report back with a proposed deal by the end of next month.

Her approach garnered recognition from a former Tory confidant. Chris Eby, chief of staff during former mayor Tory's first term, praised the way Chow has made the case for financial support to the other levels of government.

"Having been there, I know how difficult it is, and I know how difficult it is to get things done. But to me, she's doing all the right things," said Eby, who noted he was not speaking on behalf of Northcrest Developments where he now works as an executive. The company is lobbying at city hall as it steers the redevelopment of the Downsview airport lands.

"She's reached to other governments, she's tried to find common ground, and she's doing exactly what you'd hope a mayor would do."

This report by The Canadian Press was first published Oct. 20, 2023.