It was July 27 when Premier Doug Ford introduced legislation to cut the size of Toronto city council from a planned 47 seats to 25, and many of those opposed to the move felt Mayor John Tory was not doing enough to get in his way.

Perhaps it was because he had few, if any, legal means to do so, but the whole affair rattled the city’s former chief planner, Jennifer Keesmaat.

“When the news started to leak out that city council was going to be reduced in size and that Mayor Tory had known about it in advance and had a really tepid response, what became clear to me is that we needed a mayor who was going to stand up for the city, and she would put the interests of the city first, because that’s what really what the job is to do.”

As the news of Ford’s plan continued to trickle out, Keesmaat tweeted out one word which drew a negative public response to her bid for the city’s top job: “Secession.”

Speaking to CP24.com she defended her choice of the word but said it is not something she wishes to pursue.

“That was very much a response to this frustration — this recognition that we’d been let down. Our city is something that we make together and local democracy in a city of 2.8 million people is a big deal.”

“We’re the sixth largest government in Canada. We are much larger and more complex government than many provinces are.”

But the Tory camp pounced on her use of the word.

“I heard this week about this idea of Toronto seceding from Ontario, and I thought to myself, well, it just sounded like a ridiculous idea,” Tory told The Globe and Mail on Aug. 1.

She said that running for office was a way to turn the perhaps ill-expressed frustration into something positive.

“That is why I engaged in what is an incredibly hopeful act and say look, there’s a different vision of the city, it’s one where we protect public transit, where we protect the public interest, where we protect and stand up for the residents of the city every day, not just when it is politically convenient, which is what happened (with Premier Ford).”

After feeling “let-down” by Tory’s response to the move to cut the city council in half, Keesmaat got in line at City Hall with the $200 filing fee in hand and did what friends and acquaintances had been urging her to do for months.

“Many of us know this is just the beginning of what will be a tumultuous time for our city, and we need someone who will do the mayor’s job,” Keesmaat said.

She dismissed Tory’s claim that although Ford did tell him of his idea to cut council in half during meetings, he said it in passing and Tory thought the suggestion wasn’t serious.

“I have likened that to your spouse walking up and saying ‘oh by the way I want a divorce,’ and you just kind of say oh that’s interesting and you walk away,” Keesmaat said. “No you don’t, you stop and you say this is very serious and we need to have aconversation. And the mayor obviously didn’t do that.”

“From Mr. Tory, (Ford) got a lot of head-bobbing,” she said.

In September, the city won an initial superior court ruling halting Ford’s council cut decision, saying it violated Torontonian’s rights under the Charter of Rights and Freedoms. The province appealed the decision.

In the meantime, Ford threatened to invoke the Notwithstanding Clause, a move lawyer Rocco Achampong, who argued in court against the council cut, called the “nuclear option,” for the first time since it was introduced in 1982.

With overnight sittings in the legislature, along with a morning session that became so disruptive that two elderly members in the public gallery had to be frog-marched out in handcuffs and charged with trespassing, the Ford government passed its law to cut council.

The province then sought an emergency injunction at the Ontario Court of Appeal, and won, meaning the Notwithstanding Clause was no longer necessary and the lower court’s ruling was put on hold.

As the former chief planner for the city, joining during the Rob Ford administration in 2012, Keesmaat has spoken out a few times since leaving the post. She says she did so when she felt the city had ruled against the best practices for a growing urban centre.

When council, at Tory’s urging, deferred a decision on the reconstruction of Yonge Street in North York, which would also move long-suggested bike lanes off of Yonge and onto parallel side streets, Keesmaat slammed the move.

“Platitudes about making our city greener. Platitudes about #VisionZero + eliminating pedestrian deaths. Platitudes about creating a more equitable city. A real plan with a real design to move our suburbs towards becoming all of this? Inaction,” she wrote on Twitter.

In the last two and a half months, Keesmaat has promised to tear down the eastern Gardiner, which the Tory-led council voted to rebuild at a cost of up to $2.3 billion, enact gender parity on all city boards and the senior ranks of the civil service, and start construction on the downtown relief line three years earlier than Tory is pledging. 

She also wants residential speed limits lowered to 30 kilometres per hour and proposed converting three city-owned golf courses into parks or spaces with other uses since they operate at a loss every year.

But when it comes to transit, the same man who prompted her entry into the race, Ford, may prove to be her greatest foe should she win.

Ford has pledged and is already working on a plan to upload costs and responsibility for building and operating Toronto’s subways. He has tapped a special advisor to take on the task.

Keesmaat’s transit plan accepts this possibility in part, including Ford’s preference for a three-stop Scarborough subway instead of the current one-stop plan, but she has placed conditions on accepting Ford’s help.

She says the entire transit network, including subways, must remain in public hands, meaning no public-private partnerships. She says the TTC must continue to operate any trains and any decisions on where to locate subways must be made by city council.

There’s no guarantee Ford will respect these conditions, so in the case of a dispute, Keesmaat says she’d look to how things are done elsewhere, such as trade negotiations with the United States.

“There’s a smart little woman who has been negotiating with one of the biggest bullies in the world. His name is Mr. Trump and her name is Chrystia Freeland. And no one thought she would get her way because he was such a big bully, but what she did was she very clearly identified the Canadian interest and the public interest and she went to the negotiating table with that interest in mind and that is what leaders do.”

Throughout the campaign, Keesmaat has criticized Tory’s surface rail plan, dubbed SmartTrack, which now consists of six additional stops along existing GO Train lines.

Keesmaat says SmartTrack was “sketched up by political strategists on the back of a napkin,” and distracts from more important transit projects that need to be built first, like the downtown relief line.

On taxes, Keesmaat told the Toronto Star editorial board she wouldn’t raise property taxes above the rate of inflation, mirroring Tory’s continuing pledge.

But fiscally,she differs from Tory, she says, because one of her key housing promises relies on a new 0.4 per cent property surtax paid by owners of homes worth $4 million or more.

“What I have introduced is a progressive tax, and saying that on the .001 per cent I will bring in a luxury home tax in order to fund the rent-to-own program,” Keesmaat said.

The rent-to-own program would see $80 million raised over four years to help renters purchase the home they are renting over a period of one to four years, with the city or a non-profit partner possibly sharing in the ownership of a unit for a period of time to help the buyer manage making their payments.

Apart from housing, which is always on most Torontonians’ minds, the rising rate of gun violence in the city, combined with two seemingly out-of-the-blue mass casualty incidents this year — has many people on edge.

There have been 85 homicides in Toronto so far this, up from 51 at this point, last year.

Keesmaat blames Tory in part for this, saying the police modernization plan was put in motion, it froze the size of the force at a time when they needed to respond to rising rates ofviolent crime.

“Mr. Tory had four years, and the first thing he did was freeze resources, and then we saw all sorts of stalling and problems. This yo-yo-ing approach that he has is hurting our city,” Keesmaat said.

Council has voted to ask the federal government to consider banning the sale of handguns inside city limits. The federal government has replied that it is considering some sort of ban and will consult the public over the next year.

But Keesmaat wants more.

“I could not use stronger terms to express how much I support both a handgun ban but also assault weapons (ban) and also ammunition sales in our city.”

Assault weapons, as defined by most police and firearms experts, are already prohibited in Canada.

Keesmaat says her ammunition ban would extend to any round that can be fired in a handgun or assault weapon, meaning she is in favour banning the sale of most types of ammunition within the city.

In addition, Keesmaat says the city should enact community safety plans, currently in place only in five of the city’s neighbourhoods, to extend to every neighbourhood in the city.

Keesmaat wants the city to take a more active role in solving the perceived problems the community faces.

She wants more plans put in place, more bike lanes, lower speed limits, a new tax and a new intervention in the housing market to help renters become home owners, even if it means seeing the city serve in an unfamiliar role a bank in some circumstances.

At various times, she described Tory’s leadership over the past four years as “lackadaisical” and “tepid,” and says her style of leadership would challenge the status quo and conventional wisdom.