Keesmaat says she’s not a politician, but this race has turned her into one
FORMER PLANNER HAS PROVED A QUICK STUDY
In the likely event that Jennifer Keesmaat fails to win Toronto’s mayoral election on Monday, the circumstances of her entry into the race may look even more peculiar in hindsight than they did in the moment. Had Christine Elliott barely defeated Doug Ford for the PC leadership instead of vice versa, and had incumbent Mayor John Tory given a more rousing press conference one Friday morning in July, Keesmaat would almost certainly still be CEO of the Creative Housing Society, working on innovative affordable housing ideas for Canadian cities.
It was her first major gig since a high-profile fiveyear stint as Toronto’s chief planner. She was only five months into the job. And despite much discussion about the possibility of her entering politics, for the time being she had decided firmly against.
But on Thursday, July 26, in the midst of what was supposed to be the summer’s last City Council meeting, media confirmed rumours that new Ontario premier Doug Ford would unilaterally cut Toronto’s governing body from 47 councillors to 25 — just three months before election day, and with dozens of registered candidates already having campaigned for weeks. It sent many councillors into apoplexy — especially those on the progressive side of the spectrum, who, having misgivings about Tory’s fight-back against the province, decided someone with a name would have to run against him — and that someone would only have until 2 p.m. that day to register.
Emerging from a meeting Friday morning, her phone having “blown up,” Keesmaat says she called back some councillors who urged her to run; then her husband, Tom Freeman, who was out of town on vacation with their 13-year-old son, Luis; and then real estate developer Ian Gillespie, founder of the Creative Housing Society.
“Ian was the first person to say to me … ‘Sometimes you don’t choose the timing; sometimes the timing chooses you,’” Keesmaat recalls. She says Gillespie argued Mayor Jennifer Keesmaat would be in a position to accomplish much of what they were trying to do at Creative Housing — namely, “to create a city for everyone.”
She arranged a family teleconference. Freeman, son Luis and 18-year-old daughter Alexandra all said go for it.
Cleared for takeoff, Keesmaat suddenly needed a team — for a campaign that would kick off three months after Tory’s, supporting a candidate who had never so much as run for student council or been in a debate club. But when she got home Friday, she says her house was packed with supporters. “(There were) business leaders, NDP leaders, Liberal leaders, there were some community activists. There were lots of planners,” she says.
On social media, you could watch Toronto progressives begin to project their fondest hopes on to Keesmaat, the progressive downtown city-builder: She would cancel the Scarborough subway, nuke the eastern portion of the Gardiner Expressway from orbit, and hike property taxes to take better care of the city’s most vulnerable and build desperately needed infrastructure.
Less than a month later her perfectly slick and professional campaign, led by NDP backroom veteran Brian Topp, launched at a café in Regent Park. Keesmaat told the crowd she wasn’t a politician. But just a few weeks into her career, she’s already a lot better at politics than many lifers. Having given scores of speeches and talks over her years as city planner, she’s articulate and forceful in front of the camera and on stage. In debates, she attacks Tory’s record with brio, never mind whether she’s really answering the question at hand — just as you’re supposed to.
After the first mayoral debate, nominally focused on Toronto’s arts-and-culture industry (and subsidies for them), a reporter asked Keesmaat a very simple question three separate times: Has John Tory refused to debate you one-on-one?
She found three different ways not to answer it, each more maddening than the last.
At the time Keesmaat was recruited for the Toronto planner job, in 2012, she claims to have been reluctant: “I’m an entrepreneur, not a bureaucrat,” was the recollection she offered in a Toronto Life interview. She had co-founded the planning firm Office of Urbanism, which after a merger became Dialog. She worked on city-planning projects across the country, including the gigantic Union Station revamp in Toronto, and was making more coin than she ever would at City Hall.
She didn’t head in blind, though. Twenty years earlier, she had gamed out everything that goes on under the clamshell while working for councillor Joe Mihevc — an experience she described in her Master’s thesis (technically a “major paper”) in environmental studies at York University. Observing the interactions of constituents, lobbyists, bureaucrats, council staff and councillors, she sorted them into various categories: B1-type bureaucrats are “professionals … caught between the wishes of their managers and the demands of councillors,” for example, while CST2-type constituents “(call) continuously to seek assistance, at times with matters that are beyond the jurisdiction of the city.”
Her goal was to figure out how a bold and progressive city planner might get things done under such a complex system, and in hindsight, she says, those insights helped a lot. “What matters less in municipal politics is where you sit on the political spectrum, and instead what type of a player you are, because of the way decisions get made,” Keesmaat says she learned. “I was … able to use that to my advantage as chief planner.”
She clearly relished the public-facing aspects of the job: there were blog posts, podcasts, TED talks and speeches, all designed to educate Torontonians as to how the nuts and bolts of city planning affect their daily lives. But especially at first, it often seemed she might be more comfortable driving the boat rather than toiling down in the engine room.
Indeed, sometimes she seemed rather like a type-B1 bureaucrat: “powerful supervisors of city staff (who) generally hold councillors in contempt.” It did not go over well when she authored one of history’s truest tweets: “Now that half of council is considering running for mayor, the speeches at council are … insufferable.”
This boundary-testing came to a head in the debate over the fate of the Gardiner East, which Keesmaat made no secret of wanting to level. Pugnacious conservative strategist and John Tory campaign guru Nick Kouvalis accused her of being “unprofessional” and “insubordinate,” and effectively of campaigning for office from the planning department. “I look forward to her name on the ballot (which I believe has been driving her public campaign to brand herself ) in 2018,” he tweeted, prophetically.
Many expected Tory would give Keesmaat the boot. But after a private meeting in his office, they managed to maintain cordial relations — publicly at least — until her departure last year. “I admire her a great deal because she pushes the leadership of the city to think forward about the city,” Tory told The Globe and Mail upon her departure.
And while many on council disagree with her basic view of the city’s future — transit, bikes and pedestrians yes; cars, not so much — she has few virulent public detractors. Even Kouvalis kicked off his Twitter tirade by calling her “an extremely competent planner.”
Keesmaat’s record navigating City Hall’s greasy jungle, combined with her quick-study skills as a politician, certainly makes for a compelling package. But there’s something undeniably awkward about her running against a mayor whose city-building record is so intertwined her own. Upon her departure from the city planning job she went miles beyond what was necessary in praising her boss.
She said she would “always treasure the working relationship that we had.” She lauded his leadership on the Rail Deck Park and King Street projects.
In fact, before Ford threw everything into disarray, she outright endorsed Tory for Mayor: “I believe he really deserves a mandate to continue … the work that he’s already begun,” she told CTV.
After years of putting a positive face on the city’s trajectory and prospects, her whiplash-inducing pitch now is that we’ve “gone backward” for four years: on congestion, on affordability (housing especially), and on safe streets — both when it comes to cars and when it comes to gun-toting criminals.
“I think Toronto is a great city with great potential,” she says, “(but) cities fall into decline very quickly. Look at Detroit.”
Detroit? Really?
“The more that children are encouraged to walk to school, the safer — and healthier — our city will become,” she wrote in a 2014 op-ed. At her campaign launch she announced that she and her husband had taken their son’s bike away for safety reasons. It’s true, she insists, but for a selfstyled non-politician, it sure sounds like she’s rapidly turning into one.
Keesmaat’s campaign is grounded in speed: where Tory has pledged to build 40,000 affordable housing units in 12 years, she says 100,000 in 10 years is realistic — because the city owns so much land, and she knows from experience how to unlock it. She attacks Tory’s SmartTrack plan as an unnecessary diversion, and supports accelerating construction of the $50-billion city-wide transit network plan approved by council.
Her transit plan is admirably free of brand new, backof-a-napkin ideas. But the elephant in the Keesmaat campaign office is money. Even as she predicts Ford will target Toronto in evermore vindictive and damaging ways, she has not fulfilled many of her supporters’ wishes on the revenue file. Her “property tax surtax” on homes worth more than $4 million would raise $80 million a year to subsidize a rent-to-own housing program — assuming Ford’s provincial government agreed to it, and there is no reason to believe it would.
But that’s at the pointy end of the stick. Not long ago it seemed perfectly clear Keesmaat believed the city needed vastly more money to fulfil its ambitions: “Really, I don’t care how we do it, as long as we do it,” she said in 2013. Now her “affordability crisis” pitch extends to homeowners sitting on $3.5 million in real estate
Asked about her apparent change of heart, Keesmaat points to her long-standing advocacy for a fiscal realignment between municipal, provincial and federal governments. “In the past 20 years we have seen a significant downloading onto the municipality, but we have not realigned how our tax dollars are in fact distributed between three levels of government,” she says. “(That) creates an incredibly burden on cities like Toronto that need to deliver significant infrastructure like transit (and) housing.”
That is indeed the case. But that realignment is not immediately in the offing — and as many Keesmaat supporters will tell you, Torontonians pay the lowest property tax rates in the GTHA. So barring a stunning outcome on Oct. 22, it will be intriguing to see how Keesmaat’s political brand evolves. Most who know her describe her as a natural centrist rather than a natural leftist. But having taken to politics like a duck to water, it seems safe to assume more winnable campaigns will soon present themselves.