Jennifer Keesmaat, the city’s outspoken former chief planner, is running for mayor of Toronto, hoping to prevent John Tory from winning a second term in office.

“There are times when we need to stand up for our city,” Keesmaat told reporters after signing up at city hall Friday afternoon shortly before the 2 p.m. registration deadline.

“We need bold leadership and this is an opportunity, this is a unique moment in history when, I believe, bold ideas can make our city even more livable. Even more open. Even more equitable. And even more prosperous.

“I am running for mayor because I believe we need bold ideas in this city.”

Read more: Toronto Star’s election coverage

Her emergence as a progressive challenger to Tory is the second big jolt to city hall since Thursday night when the Star’s Robert Benzie revealed that Premier Doug Ford plans to slash the number of Toronto council seats from 47 to 25.

After Ford’s plan was revealed, Keesmaat unleashed a critical string of tweets that included the suggestion Canada’s biggest city and its economic engine should secede from the province of Ontario.

Share your thoughts

“This changes everything,” she tweeted after the news broke, followed by a deconstruction of Ford’s argument that city council needs to shrink to be more efficient, and then one word: “Secession.”

That was followed by: “FunFact: if #Toronto were to secede from Ontario, it would be the *fifth* largest Province/Territory in Canada. This is not a crazy idea. Why should Provinces be delineated based on geographic boundaries alone?” and “Even if you believe that Toronto City Council should be reduced in size (but remember, city councillors already represent a population the size of a small town — this is a city of 2.8 million) — the *way* this is being done is something that needs to be questioned.”

On Friday morning she tweeted, “Now I have had a chance to sleep on it. Secession. Why should a city of 2.8 million not have self governance?” and, shortly before she appeared at city all, “Good governance is the goal. Whatever should be done should be done. Laws change.”

At city hall, where she arrived by bicycle, as she did many days when her whiteboard-covered office was in the east tower, she noted that she hadn’t had time to tell her parents she’d decided to run, calling it an “impromptu” decision “but one that comes deeply from my heart and passion for this city.”

Keesmaat, an internationally known champion of cities and urban design, had for months resisted enormous pressure to challenge the conservative Tory who has primarily courted suburban support since his 2014 election.

Councillor Kristyn Wong-Tam said she and other progressive councillors have been encouraging a number of people, including Keesmaat, to challenge Tory for a while.

Keesmaat’s decision to run “didn’t happen overnight,” Wong-Tam said.

“Conversations were being had (with Keesmaat) leading up to this day for some time,” she said. “People see her as confident, a natural leader, a visionary, and she’s bold and she's bright.”

Keesmaat will also ensure Tory “does not get a cakewalk” to his second term.

“I think he needs to be tested on the policies he’s put forward,” Wong-Tam said. “There’s nothing but goodness for democracy, when we have healthy civic debates about the fate of our city and the direction we are headed in. I know Jennifer can bring all of that and more. We need big ideas.”

After her appointment from the private sector in 2012, Keesmaat and Tory worked together, sometimes in conflict but often in harmony. Keesmaat left city hall last fall and took up teaching duties at the University of Toronto. Since leaving that post, she teamed up with the private sector to work on addressing the affordable housing crisis in cities like Toronto.

Her leadership style sparked praise from those who valued her vision and sharp rebukes from those opposed.

A battle over the future of the Gardiner Expressway saw Keesmaat pushing to tear down the eastern section and create a “grand boulevard.” In 2015, that led to a prolonged, public spat with Tory who successfully pushed to keep the elevated expressway up.

Loading... Loading... Loading... Loading... Loading... Loading...

A year later, she presented a revised plan that saw the controversial Scarborough subway, reduced to a single stop, approved at council and Tory clear another hurdle in moving forward with a campaign promise.

In the back-half of the term, Tory and Keesmaat were said to be on good terms. Sources confirmed at the time that Tory personally asked Keesmaat not to leave. Another source said Keesmaat told Tory she wouldn’t challenge him in this election as progressives searched for a candidate to go toe-to-toe with the mayor.

In a statement at the time, Tory thanked Keesmaat for her “tremendous passion,” adding she “used her platform and voice as chief planner to help guide council’s efforts to build a better city for all Torontonians.”

On Friday, she noted how lucky the city is to see job increases and a booming economy, but said “there are times when the wonderful things, many of which we use every day — like transit or parks or access to public spaces” — are “potentially compromised.”

“In changing times, we need changing leadership,” she said. “My commitment to this city is to work incredibly hard to be incredibly collaborative and to not be afraid to make the hard choices and decisions when bold leadership is, in fact, required.”

With files from Samantha Beattie

David Rider is the Star's City Hall bureau chief and a reporter covering Toronto politics. Follow him on Twitter: @dmrider

Jennifer Pagliaro is a Toronto-based reporter covering city politics. Follow her on Twitter: @jpags

Read more about: