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Quick: name an urban planner. People in most cities would have trouble answering that. Not so in Toronto. Jennifer Keesmaat, the city's chief planner for the past five years, is one of the most visible people at City Hall, a powerful voice in the civic discourse.

With her tenure about to end – she announced this week that she would step down in September to pursue "other interests" – Ms. Keesmaat could only go so far in renovating Toronto. And the place still needs a lot of work.

Ms. Keesmaat is an extraordinarily good communicator and she used her position as a bully pulpit for progressive urbanism. In an interview this week, she expressed confidence about her work over the past five years. "There's a trajectory that we have been able to set that was very different from the one the city was on when I started," she said. "I think we've been able to shift the public discourse about the city in significant ways."

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That is true. Ms. Keesmaat championed bike lanes; walkable development oriented to transit; the importance of parks and the public realm. Her department passed zoning changes that could radically improve life in thousands of apartment towers.

And there's much more. Ms. Keesmaat significantly increased the places and forums through which planners engage with community members, a change that was sorely needed. She also pushed for her role to be expanded, giving her a voice in transportation planning. The King Street pilot, giving more room downtown to the majority of commuters sardined into streetcars, was driven by her office.

All of that took backbone. In a city hall where top civic officials have gotten fired for telling the truth, Ms. Keesmaat at times stood up to Mayor John Tory. Unfortunately, she couldn't stop Mr. Tory from making disastrous decisions. After a public skirmish, she failed to sway him on rebuilding the eastern stretch of the Gardiner Expressway. That will proceed, sinking about $1-billion (and counting) into one useless and destructive megaproject. Then there is the Scarborough subway extension, whose costs are now north of $3-billion (and counting). On that file, Ms. Keesmaat wound up having to defer to council as they pursued that terrible, expensive idea.

Now she will be free to speak her mind. She wouldn't confirm or deny a run for office: "I'll talk about that in more detail in the upcoming weeks and months," she said. But in many ways her agenda of the past few years reflects what 21st-century Toronto is going to need. More housing, including social housing, with room for more people. More transit, in the right places. More emphasis on public places and public life. A recognition that cities are for people, not cars.

It's not an easy agenda to move forward. The Gardiner East and Scarborough subway decisions each demonstrate how a house-owning, car-driving elite is shaping today's Toronto for the worse. So did this week's Margaret Atwood affair, in which the author came out against an eight-storey building near her house in the Annex. It illustrated very well how Toronto's growth is being constrained by opaque policies – centred on the experience of house owners and protecting "stable residential neighbourhoods."

The subject of land-use planning has been the very heart of Ms. Keesmaat's job, and here she hasn't made much change. Development remains tightly restricted. If you doubt that, ask why the city is putting thousands of people into the old industrial wasteland of Liberty Village and almost none on the Bloor-Danforth subway line. Ms. Keesmaat's planning department has introduced some smart policies, but even these can be conservative. The new TOCore plan for downtown looks at the city's core in a deep and intelligent way, but it refuses to touch the sacred cows of house neighbourhoods, such as Ms. Atwood's.

And the planning department under Ms. Keesmaat has been very conservative when developers try to get creative; the Westbank King West project, for instance, has been stalled in negotiations over its form for many months. Toronto these days is building very few places that are genuinely interesting. That's a shame.

Ms. Keesmaat adamantly rejects criticisms that her department is overreaching – "We are not a slow-growth city," she said. "We are experiencing explosive growth" – and this is understandable. She didn't even write most of the rules. Shaking up Toronto's planning culture is a lot to ask of one person.

After all, the city's main planning principles are 50 years old – stemming from the progressivism of the 1960s and 70s, which saved old Toronto from much of the urban renewal's craziness. And Toronto is a temperamentally conservative city, as it always has been.

But if the city's cautious, bottom-up approach has served it well for the past half-century, it won't any more. The town is poised to grow by about a quarter in the next 25 years, a massive change, and this will demand vision that comes from the top. Ms. Keesmaat has shown that, if she can't remake the city alone, she isn't short on ideas. For now, "I'm very happy with where Toronto is going," she said, "but the job is never done." Spoken like an urban planner with more work to do.

Take a fast stroll through the streets of Cityplace in Toronto near Front St and Spadina Ave. The area previously criticized for being a glass condo jungle has grown into a true neighbourhood.