Jennifer Keesmaat's mayoral bid already a small win for Toronto's progressive voters

Toronto's former chief planner announced just before the nomination deadline on Friday that she will run for mayor. In filing to run, she upturned what most assumed would be a dull mayoral election, with Mayor John Tory coasting to a second term without a high-profile challenger.

Keesmaat has a history of shaking things up like this. When she came to Toronto City Hall as chief planner in 2012 under the tumultuous reign of former mayor Rob Ford, hers was an unlikely and surprising hire.

Ford opposed bike lanes. She rode her bike to work.

He fought against light rail — you'll remember the "Subways! Subways! Subways!" line — over concerns about its impact on automobile traffic. She held a city-wide consultative study on transit that ultimately recommended the city build a whole lot of light rail. After the Ford era ended, she shook things up with Tory too.

When Tory backed a plan to maintain the elevated eastern part of the Gardiner Expressway, Keesmaat publicly announced that she disagreed with the mayor. Tory later told her she should not debate him publicly, and there was brief speculation that he would ask for her resignation.

Keesmaat's outspokenness, coupled with her use of social media, made her one of the highest profile bureaucrats in the city's history. But can that profile translate to political success?

There's reason to be skeptical.

In 2017, pollster Main Street Research tested a hypothetical mayoral race pitting Tory against Keesmaat and Doug Ford. In that match-up, Keesmaat drew support from just six per cent of those polled.

The results suggested that her name recognition may not extend far beyond the population of Toronto urbanists who can tell you what a "woonerf" is. (It's a Dutch "living street" where drivers are restricted to walking pace.)

Keesmaat may position herself as a 'Ford fighter'

Keesmaat has time on her side. Before the Oct. 22 election, Keesmaat will need to outline a series of platform policies that set her apart from Tory. The election of Doug Ford as Premier of Ontario may boost her fortunes. The premier's unprecedented move to slash the size of Toronto City Council is likely to have a lot of voters hungry for a mayoral candidate who will fight back hard against the provincial government.

Keesmaat, who responded to the early news reports about the provincially-mandated council cut by tweeting about Toronto secession from the province of Ontario, seems ready to fill that role as a Ford fighter.

Still, the smart money in this mayoral race remains on Tory. There's good reason why, until Keesmaat's self-described "impromptu decision" to register to run, no high-profile challenger had stepped up to challenge Tory. Incumbent mayors are hard to beat.

But even if she starts with long odds, Keesmaat's entry into the race changes a lot for Tory.

It won't be enough now to just promise more of the same. Keesmaat is likely to push him to take strong positions on issues — particularly urbanist issues that tend to rank highly with progressive voters.

If she lays out an ambitious vision for the city's transit system or a plan to greatly increase funding for affordable housing developments, Tory will be pressed to answer with plans of his own.

Regardless of outcome, by changing the race candidate Keesmaat already represents a small victory for progressive-minded voters in Toronto. She's shaken things up again. Her next, and more difficult, task: figuring out how to win.