Jennifer Keesmaat’s harshest critics often complained about how directly she shared her opinion on what she saw as best for the city, even when it was in conflict with the mayor’s vision — a light-rail line to serve more people when a subway was promised, razing the Gardiner Expressway instead of rebuilding it.

That kind of talk was for politicians, not for a senior city bureaucrat, they said.

Now here she is — running for mayor, and putting forth her own vision of Toronto’s future. Keesmaat is calling for stronger autonomy for the city, committing to building “excellent” transit and giving Mayor John Tory a failing grade on making Toronto more affordable.

It was Tory’s comments on Friday morning — calling for a referendum in the face of Premier Doug Ford’s move to slash city council to 25 wards, which some called a “meek” response — that pushed Keesmaat, the former chief city planner, into the mayor’s race.

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“I think like a lot of Torontonians who woke up that morning, I was feeling that Toronto needed to stand up tall and needed to stand up together,” Keesmaat said in an interview with the Star just five days after putting her name on the ballot. She’d biked down to city hall on Friday, with the needed identification in her backpack, to register just moments before a 2 p.m. deadline.

“I was pretty preoccupied with those thoughts that, OK, this is a moment where leadership is required in our city. This is it,” she said.

For months, Keesmaat had been pressured to run — by actors across the political spectrum, community leaders and residents, she said. The number of calls escalated in the weeks leading up to the deadline, with no big-name challengers yet signed up to take on Tory.

“And then Friday morning happened,” she said.

Her calls for Toronto’s “secession” in the wake of Ford’s move and ahead of her entering the race have caused a stir among people in Tory’s camp and beyond. Though she told CP24 earlier that it was a response to the news and not a policy plank, she said she believes the largest cities in Canada need “more autonomy.”

“They need self-governance,” she said. “They need stronger tools from the government in order to be able to do more. I believe that strongly. Those tweets were really an expression of that.”

Tory himself has chastised the provincial government, under former premier Kathleen Wynne, for interfering in council’s plans, such as a scuttled attempt to toll its own expressways, and has opposed the need to go to Queen’s Park in “short pants” to ask permission to drive the city’s own destiny.

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Serving as chief planner for five years gave Keesmaat a “front-row” seat to the decisions being made in the council chamber and meeting rooms, she said. It fed her desire to run.

“On many of the issues that matter most, we have to ask the questions: Have things gotten better?” she said.

“Has the commute gotten better? Because that was a pretty big promise … Has transit gotten better or have we just continued doing it the way we were doing it before, still spinning our wheels?”

And on building affordable housing, on which Tory staked the early part of his re-election campaign, she said many still feel squeezed out.

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“When we ask, are things getting better on the affordability front, I think the report card doesn’t look so great.”

As for Tory’s campaign promise Wednesday to keep property taxes at or below inflation, Keesmaat said a bolder vision is needed.

“A slogan isn’t a fiscal plan,” she said. “This city needs a fiscal plan. It needs a strategy.”

She promised her own in the days to come, with her policy platform not yet defined.

It’s not clear what to expect on several fronts from Keesmaat, a progressive, urban voice once considered a viable candidate for the Liberal party at the provincial and federal levels, surrounded now by several NDP strategists. She’s never run for political office anywhere.

Her stance on some issues is clearly known from her time at city hall.

She was unapologetic about her views on a boulevard option, rather than constructing a new elevated eastern stretch of the Gardiner Expressway, which drew sharp remarks from Tory in 2015.

Her position on controversial issues like the Scarborough subway is more complicated.

In 2013, she worked behind the scenes to try, unsuccessfully, to stop council under then mayor Rob Ford from scrapping a fully funded, seven-stop light-rail line to replace the aging Scarborough RT. They approved a three-stop subway instead. In 2016, it was Keesmaat who introduced what became known as a “peace-in-the-land” plan that, she claimed, could use the savings from deleting two subway stops to fund an extension of the Eglinton Crosstown LRT to the University of Toronto’s Scarborough campus.

“I believe in excellent transit for Scarborough. I also believe in excellent transit for this entire city,” she said Wednesday, promising an approach to transit that is not “project-based” but about the entire system. She noted studies showed a large number of people who use transit in the suburb take trips that begin and end in Scarborough.

“It will be driven by what is in the best interests of Scarborough and what is in the best interest of this city.”

On issues like transit and housing, she said there are solutions Tory and council haven’t pursued yet and ideas that she couldn’t explore within her limits as chief planner.

“I’ve been on the other side of the glass saying, ‘Hey, if I was over there, there’s all these other tools that I would have at my disposal that I could use to really move the dial on the commute, on transit, on affordable housing,” she said.

“I’m aspirational, and I don’t believe the way the city has been run is aspirational. I think it’s been about messaging. It’s been about politicking. I believe it’s in our DNA to be aspirational as a city and that we can have aspirational leadership once again.”

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