Not too long ago, Jennifer Keesmaat, a 42-year-old city planner at Dialog, tweeted "Political meddling=bad planning."
 
Keesmaat, who headed the new official plans for both Moncton and Regina, was responding to Toronto Mayor Rob Ford's pushing for a Sheppard subway extension despite opposition from TTC staff. Not much later, after having been hired as the city's chief planner, she was quoted saying this: "As a bureaucracy you can't get too far ahead of those elected officials. I have great respect for elected office. At the end of the day, these are the leaders who were elected in this city."
 
If you wanted to be cynical, as I initially was, you might see the distance between those two public utterances as evidence that the lady's been tamed. But if you were to talk to her yourself, as I did recently on the School restaurant patio in Liberty Village, you would most likely come away seeing it as evidence the city may just have hired the ideal chief planner. Keesmaat's views on planning—at least as close as you can get to them in face of her careful avoidance of almost any particulars that might offend pretty much anyone—are the stuff Torontophiles' dreams are made of.
 
The first woman to hold the chief planner position, and the first non-bureaucrat (at least in recent memory) is pro-transit, but against investing too much in very low density areas. She is pro-bike, but even more enthusiastically pro-pedestrian, while remaining anti-anti-car by favouring what she calls multimodal transit arteries. She thinks St. Jamestown is a failure, but that CityPlace and Concord Park Place have enough room for adaptability that the jury on their success as a communities will be out for at least another decade. She thinks the greatest planning disasters of the last century were the Robert Moses-esque freeways that bulldozed neighbourhoods across the continent.
 
The city took a while hiring Keesmaat. Gary Wright retired in March with several months' notice. Not much was said before the Keesmaat announcement, so folks reasonably assumed it would be an inside hire, and someone no one but insiders had heard of. As the Toronto Star pointed out, her three immediate predecessors each spent more than 20 years in city government prior to their appointments.
 
What they perhaps hadn't factored in was that councillor Peter Milczyn was one of the three people who made the hiring decision. Those who figure the Fords administration is unrelentingly evil and/or incompetent often forget that Milczyn, a Ford ally and appointee to the chair of the planning and growth management committee, is a former architect and a current architecture enthusiast who takes planning and aesthetics very seriously, and has similar tolerances and intolerances to many of his bosses' critics. (Milczyn says by email that the mayor also met with her before she was hired.)
 
So what they got was Keesmaat and her track record. When the request for proposals went out almost a decade ago for a new city plan for Moncton, it stated that whatever the plan was, one thing was certain: there needed to be more parking downtown. To which Keesmaat—who was then in her mid-30s and at a point in her professional life where snagging this level of gig would be the sort of thing that could make her career—replied, "You don't need more parking, you need more downtown."
 
She got the job, and downtown Moncton today is an different, more vibrant, attractive, enjoyable place. But that was Moncton. This is Toronto.
 
"There's huge cultural differences in terms of what we're prepared to live with, and those differences exist within the city," she says. "I think that diversity in housing typologies is our strength and ought to be our strength going forward in the future. You can appeal to a whole variety of demographics and a whole variety of income levels when you have diversity in built form in the city."
 
Talking about how the variation in housing form affects Toronto's culture, Keesmaat reaches further into her past. "My family's from Holland and my mother grew up on a street in a row house, a very, very modest row house." On her street, there was a tremendous amount of diversity. Her father was a barber, a few doors down was a doctor, a few doors down from that was a butcher, and there was a cultural expectation that everyone lived in a similar housing form. "We traditionally haven't had that in Canada, we tend to say something with the size of our house."
 
But she's aware that traditions are being made and remade all the time, especially in a city as tumultuous as Toronto. That it can result in unexpected evolutions. She points out as an example that she used to live in High Park, but found the neighbourhood too busy and filled with traffic. So she moved to Yonge and Eglinton. She now lives on what she describes as "one of those miraculous streets where our six-year-old son can run out into the street and play." She talks about Jarvis, once a street of stately mansions, that's evolved into a low-rise, high-density, low-rent neighbourhood, and Regent Park, which went from slum to housing project to something she now thinks is quite remarkable.
 
"Ensuring that the city remains affordable for people to raise their family is a really significant issue," she says. "I've heard this from my employees at Dialog—these are very urban people, well-paid professionals—and they don't know how they're going to afford a house. To me, there's something fundamentally wrong there."
 
When I ask her about her five favourite neighbourhoods in the world, she starts to list off Amsterdam's Haarlem, San Francisco's Mission and New York's Meatpacking District, before telling me that really, if she were to be honest, all five of her favourite neighbourhoods would actually be in Toronto. When I press her to name them, though, she demurs.
 
"The problem with the question is that I'm bringing my own sensibilities," she says, which I point out is the point of the question. "It means there's all kinds of people living in neighbourhoods that I'm leaving out and I don't want to leave anybody out." So she refuses to name any.
 
When I ask her to name her top five planning disasters, she once again goes vague, talking about expressways, but not naming any particular one. She also says she's not a fan of the so-called power centres. She does get specific about why: "The problem with them from my perspective is that they only cater to one kind of user and the user gets there and discovers they don't work very well. If they're successful and meet their objectives, they create a transportation crisis, a car crisis, and if they're unsuccessful, they're a waste of land." But when I mention the power centre at Eglinton and Laird as an example so we can talk about particulars, she refuses to engage. This is very frustrating for an interview, but, given the nature of the job that's before her, probably a good instinct.
 
Being named chief planner for a city that's in the middle not only of its own biggest growth spurt, but the biggest growth spurt of any city in North America—and, by the number of towers going up now (196) and by the end of next year (300), probably anywhere in the world—means there's an awful lot that's already out of her control. With so much already done, with the skyline already so utterly changed from what it was just five years ago, does she feel she may have arrived a little late to the party?
 
"Well, it depends on when the party ends. If it's 10 o'clock and the party ends at 3am, I don't think so. If it's over at 11, I might be. And what's the great thing about our industry is that you never know."
 
Bert Archer is Yonge Street's development editor.