With ​Toronto's popular — but polarizing — chief planner Jennifer Keesmaat leaving this month after five years in the role, her sudden announcement prompted questions: Why now? And what's next?

After arriving by bike to the CBC building on Thursday, Keesmaat opened up on Metro Morning about the timing of her departure.

"The tricky thing about city building is projects do go on and on and on," she said. "There's never a good moment."

But leaving the role now does make sense, she said, because the city is "putting a bow" on many projects, including a five-year strategic plan in the city planning department and the recently-approved King Street Pilot Project.

"The question I asked myself was, either I'm going to create another five-year strategic plan and stick around for another five years, or this was the moment to make a graceful exit," she said.

Not an exit from city building, she quickly added, but an exit from her current role — something Keesmaat said was her decision, which is prompting speculation about her next move.

Keesmaat with Dwight

Outgoing chief planner Jennifer Keesmaat during a sit-down interview with CBC Toronto's Dwight Drummond earlier this year. (CBC/Martin Trainor)

An outspoken voice

In Keesmaat's half-decade tenure as chief planner and executive director of the city planning division, she was praised for being a passionate champion for bike lanes, pedestrian-friendly streets, and improved transit. She was also known for being outspoken about issues she felt were in the city's long-term interest, which she said frequently bumps up against short-term politics.

In one instance, Keesmaat clashed with mayor John Tory on the so-called "hybrid" plan to leave much of the aging Gardiner East elevated expressway in place, when she advocated to have it torn down.

"The only thing, generally, I think public servants should not be doing is sort of debating politicians because they are public servants and there is a line to be drawn there," Tory told CBC's Metro Morning back in 2015.

In a recent Toronto Sun piece, deputy mayor Denzil Minnan-Wong slammed Keesmaat, saying he is "looking for someone who is interested in paying attention to the planning department and less interested in sending out tweets that have little to do with city planning."

Minnan-Wong also said he wants Toronto's next chief planner to "stick to the knitting" — as in, stick to planning the city.

Several councillors quickly jumped to Keesmaat's defense on Twitter, and she didn't mince words when asked about Minnan-Wong's comments on Thursday.

"He might as well have told me to go back to the kitchen," she said. "And just so you know, I've never been there; I've never been a very good cook. I think it's a deeply offensive comment."

As the Canadian Press later reported on Thursday, Minnan-Wong says his comments were taken out of context, but added he nonetheless believes the city's next chief planner should focus on planning.

In her interview, Keesmaat also praised the democratic process and said once council made a decision, even if she disagreed, she couldn't speak out against it. She admitted that did lead to being put in the "awkward" position of having to implement ideas she didn't always agree with, such as the controversial one-stop Scarborough subway.

"I went away and created a network plan that was really about making the best that I possibly could out of that decision from city council," she said.

While Keesmaat's clashes with council made her a polarizing figure, her many supporters are now hoping she'll now run for mayor, something that may not be in the cards any time soon.

Keesmaat said she's still figuring out her next move, which won't include running in the next municipal or provincial election.

After she leaves her post at the end of the month, Keesmaat hopes her replacement stays the course, focusing on community-oriented values.

"My one word of advice would be for them to stick to evidence-based planning and to stick to their values — and to think very long-term," she said.

"That's the great value a public servant can bring to this role."

With files from Metro Morning, Canadian Press