Eleven days before the election to determine who will be Toronto’s mayor for the next four years, candidate Jennifer Keesmaat visited a boardroom in the Toronto Star offices to begin her closing argument.

“There is an incredible appetite in this city for us to be a forward-looking city,” she said, describing the time after she left her job as chief planner of the city and before she decided to run for mayor. “People kept coming up to me, on a daily basis, coming up to me and saying, ‘We need someone who believes in the future of this city and is prepared to advance a future vision of this city, who is focused on taking Toronto into the 21st century as opposed to keeping it the same,’” she said.

This was about an hour into her 65-minute chat with a group of editors, reporters and columnists from the Star — a closing argument to her visit and the start of one to the electorate. During the hour she had performed well; the format suited her better, it seemed, than the prickly back-and-forth of debates, allowing her to make apparent how deeply she understands most of the policy areas she is discussing, and to outline a bit how her planner-style thinking ties a lot of overlapping issues together in ways that don’t always add up to stand-alone sound bites.

She still seemed to struggle to give a straight answer to a simple question at times — her plans to keep the base property tax rate stable with inflation and to leave the Vehicle Registration Tax in its grave had to be virtually dragged out of her after long explanations about the decision-making “framework” she brings to the topics — but what she thinks are her points of differentiation from Mayor John Tory, her primary opponent, became clear enough.

Some who will likely vote for her — or would like to — surely wish those differences were greater or more apparent. In a city where property taxes are, on average, lowest in the region and where the previous city managers frequently warned of a looming revenue crisis, for instance, why promise to hold the line, as her opponent has?

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In response she spoke of making things more progressive — charging more from wealthier people — and about not wanting to feed into the city’s unaffordability.

Whatever the reasons, polls (ones she claimed not to be concerning herself with) show her message hasn’t yet connected with enough voters to make her an obvious threat to Tory. More than a week left, lots can change, but a 25-point-plus lead is a lot to overcome.

In my mind, one of the hurdles for her has been making the case for why a change is needed, in a city where people seem generally content, more or less, with the city government. That’s why the most interesting point, for me, was the uninterrupted story she began telling.

“We saw at Christmas time, in very cold conditions, people were left out on the street. What that put into focus for me is that we’ve become a really prosperous city, we’ve become really, really prosperous. But as we know from the research of David Hulchanski, as we’ve become more and more prosperous, we’ve become more exclusive,” she said, referencing the University of Toronto researcher who has documented the disappearance of middle-income neighbourhoods in Toronto and the polarization of the city into areas of great wealth and great poverty.

“There are neighbourhoods that have been completely left out of that prosperity, and a mayor of Toronto needs to acknowledge that and needs to be willing to address that. Because the vast majority of Torontonians in every single corner of this city, North York, Scarborough, Etobicoke, East York, the Beach, Mimico: everywhere I go in this city, no one thinks that’s acceptable. And for some reason our current mayor is not doing anything about it. He has a status quo plan.”

Mayor Tory, of course, points when he talks to incremental progress on lots of fronts — his anti-poverty plan, his affordable housing plan, his free fares for children on the TTC. But his campaign certainly has not launched much that is new, instead promising more of the same, the evolution of those incremental plans — a status quo pitch. And Keesmaat claims that isn’t good enough.

“There has been this building recognition that our city is becoming something fundamentally different from what it was,” she said. “This used to be a place where you could come with 200 bucks and your suitcase and make a life. And that, increasingly, is not the case. The Toronto Real Estate Board released data last week saying 94 per cent of youth between the ages of 18 and 30 are thinking of leaving because they can’t see their future here. And that is heartbreaking. That’s not who we are as city. We’ve always been about welcoming newcomers, but we’ve become something fundamentally different. We’ve always been a place where young people can see and imagine their dreams come true. And that’s no longer the case today.”

She retold an anecdote she used in the speech she delivered to launch the campaign.

“This hit me very personally several months ago when my daughter said to me — she had a part-time job teaching kids. I said, ‘Oh Alex, maybe you want to be a teacher.’ And she looked at me, dead in the eye, and said, ‘Are you kidding? I could never afford to live in Toronto if I was a teacher.’”

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Keesmaat herself may recognize how this will sound to many in Toronto in a position to think of teachers as among the fairly affluent in Ontario. That may be part of the point.

“That’s a kid who’s white, has every privilege and every opportunity, and she can’t see her future in this city,” Keesmaat said of her daughter. “Now let’s take that to kids who are in low-income neighbourhoods, who are not white, and multiply that by 100.

“C’mon, that’s not who we are. That’s never been who we are. How can we let that happen and not be outraged?”

That is the question she poses to the city as it prepares to vote. One to which she puts herself forward as an answer. It is her best, most straightforward pitch. One she’ll continue taking to voters between now and election day. One it is up to Torontonians to decide if they will swing at.

“Torontonians have been approaching me over the past six months and saying, ‘We can do so much better,’” she summed up. “‘We can do so much better as a city. The status quo? The status quo is not acceptable.’”

She was Toronto’s chief planner for five years, known for being outspoken on what she felt was best for the city. Now, Jennifer Keesmaat is taking on John Tory to be mayor. Is she ready to serve as a politician instead of a bureaucrat?

Correction — Oct. 15, 2018: This article was edited from a previous version that misquoted Jennifer Keesmaat as stating her daughter's name as Alice. In fact, Keesmaat referred to her daughter as Alex.

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