Jennifer Keesmaat jumps right in. “This is not cool.”

She’s recounting the moment she “hit the threshold” and decided to get into the mayor’s race. It was after Doug Ford announced his plan to cut council in half and John Tory’s “tepid” response was to call for a referendum instead.

“It became abundantly clear to me that Doug Ford was going to continue to interfere with the city of Toronto,” says Keesmaat, who registered to run hours before the deadline. “And that you can’t really fight conservative cuts with a conservative mayor who was the leader of the conservative party for five years.”

And so begins my 30-minute sit-down with Keesmaat.

Values. Passion. Tenacity. Those are the words used to describe her on her campaign literature. Troublemaker. Fighter. Straight shooter are others. They all fit.

Less clear is if running for mayor is a dry run for something else. It bears repeating. I mean, it’s not everyone who can decide to go at the drop of a hat and raise the seven figures necessary to make it happen. Political observers have pointed out that the Ontario Liberal Party, for example, happens to be looking for a new leader.

“For many months people had been approaching me,” Keesmaat insists. “For me it was something that built and built and built.” Until, boom.

The trajectory has been a steep one for Keesmaat. Before she took the job of the city’s chief planner in 2012 (she was asked three times to apply before finally agreeing), she was principal of her own international design firm. But planning wasn’t always in the cards either.

Born and raised in Hamilton, she majored in philosophy and English at Western before earning her master’s in environmental studies, planning and politics at York. It was Jane Jacobs’s The Death And Life Of Great American Cities that inspired her conversion.

Keesmaat doesn’t want to bore me with the details before she tells me the story of Bud Osbourne, the homeless man she met while working in the non-profit sector in Vancouver. Woodward’s, the famous department store in the city’s Downtown Eastside, had gone out of business, and plans to put a condo in its place were met with widespread resistance from residents concerned the proposal would drive poor people out of the neighbourhood. Keesmaat helped organize a speakers’ series around the issue. The city eventually decided to buy the property from the province and build affordable housing in the form of single and family units, along with market-value units.

It’s a model Keesmaat would like to see repeated in Toronto, where the luxury condo boom is eating up what affordable pockets we have left and pushing those who can’t afford skyrocketing rents to suburbs that are becoming increasingly defined by race and eroding social-economic status.

Keesmaat says the city could be leveraging land it owns to build more affordable housing at 80 per cent of market value. Her plan also includes a rent-to-own program. She says the latter idea is resonating for people in the burbs who are either renting and can’t afford to own or have children who they know are going to struggle to achieve housing in an increasingly expensive city.

“It doesn’t have to be that way,” says Keesmaat. “We’ve got luxury housing. We’ve got social housing. What we’re missing is the middle.”

Keesmaat puts affordability right up there with transit, an issue she says she became personally acquainted with when she first moved here and had to spend an hour each way on the TTC to make it from her basement apartment in Etobicoke to her classes at York.

“I was young and didn’t have kids. But imagine a mother spending three hours on the bus. That’s a deal-breaker [in terms of] whether you can get to your job or not. Transit has been so politicized that we have really significant gaps in our network.”

Keesmaat has proposed closing some of those gaps by fast-tracking the Finch LRT (whose future is now uncertain under Ford) to connect the Jane and Finch, Rexdale and north Etobicoke neighbourhoods to the overall transit system. For Keesmaat it all relates back to social justice.

“This city has always been about newcomers, about opportunity and about young people being able to stay and see their dreams come true. And that has been continually eroding. As the city has gotten wealthier, it’s also gotten more and more divided. How we change that is a choice, and that’s the leadership piece. We need a leader who’s not afraid to do bold things to get things done.”

It’s here that Keesmaat draws a line connecting the summer’s upswing in gun violence to the erosion of opportunities for people in priority neighbourhoods.

“There is no reason that youth end up in crime other than that they really don’t feel they have other options. People are feeling shut out and like they don’t have access to the greater prosperity we see.” She takes her theory a step further to say that the “incredible violence” we’re seeing is not cyclical, but a direct consequence of cancelling after-school programs.

“We need to take a completely different approach to policing based on prevention,” she says. “It’s not rocket science. There are international best practices to show the approach works. There just needs to be accountability.” And Keesmaat includes a yearly review of the chief in that.

“Policing isn’t an end in and of itself,” she says. “It’s one tool. We also have local school boards. We have local health networks. We have grassroots organizations. We need programs working with at-risk youth to get them off the street.”

Members of minority communities who don’t see Keesmaat as all that different from Tory on policing issues will be happy to hear that. Accountability is also an issue that comes up in relation to Tory, who has been ducking debates, including a number of one-on-ones with Keesmaat, as polls show him well ahead with a week to go.

Tory is coasting, which is a word that could also be used to describe his first term in office. Tory has turned out to be more small-fry than city-builder (see SmartTrack). A little like Olivia Chow, who ran against him in 2014 and is supporting Keesmaat, said Tory would be: good on the small stuff, not so good on the vision thing.

Tory shows up to Pride. And talks a good game when it comes to the importance of diversity. He seems nice enough. But having a nice guy for mayor hasn’t made the lives of many Torontonians any better over the last four years.

“I want to have a conversation about the future of the city,” Keesmaat says, before adding that Tory “may be a bit more worried than you think.” She leans back and smiles. It’s the troublemaker in her coming out. The papers say she doesn’t stand a chance. But Toronto could do with an unexpected surprise right about now. The city’s destiny may depend on it.

enzom@nowtoronto.com | @enzodimatteo