Just days after Jennifer Keesmaat cycled to city hall and dramatically signed up at the last minute to challenge John Tory in Toronto’s mayoral race, she was surrounded by advisers in her midtown kitchen.

The ad hoc group assembled around her, according to two people who were there, were comprised of a collection of NDPers, including Councillor Joe Cressy, a smattering of Liberals, including MP Adam Vaughan, now re-elected councillor Shelley Carroll and several of former premier Kathleen Wynne’s staff members who would later be visible on Keesmaat’s campaign.

A “kitchen cabinet” of sorts, they came to one conclusion: the ballot question had to be about Premier Doug Ford slashing council nearly in half without warning. It had to be about which candidate could better stand up to a bully.

In the end, sources say, the campaign team that later assembled all but abandoned that narrative. Several agreed that, overall, it was Keesmaat’s team that let down Toronto’s former chief planner.

The Star is not naming sources who requested anonymity because their positions do not allow them to speak freely about confidential campaign information.

In the wake of a commanding victory by a still-popular Tory in Monday night’s election, those both on the periphery and inside the campaign say the lack of time Keesmaat had to make her pitch made the gap nearly impossible to close. But attacking Tory more than focusing on a fight with Ford, and failing to lay out her vision for the city, hurt her case.

Since 2017, Toronto progressives had calls and meetings trying to identify a progressive standard-bearer. Those who said no included Vaughan, former Toronto deputy police chief Peter Sloly, Councillor Mike Layton, retired sports executive Richard Peddie and Keesmaat, confirmed multiple sources who spoke to the Star on condition of anonymity.

Until the morning of July 27, when Ford confirmed his plan to slash the size of city council and Tory responded with what many saw as a meek response, Keesmaat was firmly against running, say all those who spoke to the Star. Tory, a conservative first elected in 2014, had no serious challenger.

The candidate search instantly restarted with a flurry of phone calls. Layton and Vaughan seemed to have considered the question but again said no, said a source on the calls. Keesmaat, after a conference call with family members, said yes, triggering her trip to city hall and answering the prayers of progressives who feared Ford’s toll on Toronto if Tory insisted on playing nice with the premier.

Her supporters — she walked into the race with no team — hoped they could catch lightning in a bottle.

“In the end this was not Jennifer’s race to win,” Cressy said in an interview. “The biggest lesson is that mayoralty campaigns require exceptional organization and preparation, that launching a campaign before the wings are on the plane is extremely difficult.”

A seasoned team was quickly assembled, eventually moving out of her Chaplin Estates home — a mix of former Liberal premier Dalton McGuinty staffers, Wynne staffers and seasoned NDPers. Her campaign manager was Brian Topp, the former chief of staff to Alberta NDP Premier Rachel Notley. Most did not know Keesmaat and were less familiar with city hall politics than Tory’s mix of Liberals and Conservatives.

Keesmaat herself drove the policy that was released, with the team at first slow on the uptake to distil her detailed ideas into platform planks that were palatable to the public, one insider said. It included a rent-to-own housing program, turning city-run golf courses into more accessible public spaces and a push for gender equity on city boards and commissions.

The initial rollout was slow. Over the course of just over 60 days, she made about a dozen major announcements. After the first announcement on Aug. 7 about her affordable housing plan, she did not return with another pitch to voters until Aug. 30, 23 days later, rolling out her transit plan.

In the first announcement on affordable housing, the successful businesswoman and former chief planner, who is in demand for speeches worldwide, relied on notes and speaking points in front of her — something insiders say was a repeated mistake.

One political observer said the voters who don’t remember her from her city hall days never got to see the real Keesmaat — a planner obsessed with evidence and details, who talks easily and inspirationally about transit-oriented development and complete communities.

“All that was missing,” said one source who observed the campaign from the periphery, noting the campaign got Keesmaat speaking on an NDP message track instead of Keesmaat finding a team to rally around her own confident, unique vision.

Another tactical error, sources said, was the focus on attacking Tory.

Three to four weeks into the campaign, a team meeting to regroup on messaging happened in a boardroom at DIALOG — the planning consultancy that encompassed the firm started by Keesmaat before she became chief planner. Keesmaat rehearsed a new stump speech slagging Tory, which some in the room said was too off-brand.

Those in attendance were divided over whether attacking Tory as a primary campaign tactic was the right move.

The team also failed, one source said, to slap Tory for his refusal to debate Keesmaat one-on-one. A chicken suit was ordered to shame him but its arrival, the source said, was delayed by customs. It was eventually used briefly to no effect.

Keesmaat’s team, the same source said, also failed to capitalize on Ford’s decision to invoke the notwithstanding clause to overrule a court judgement that blocked his legislation cutting the size of council to 25 wards.

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Another source said: “Jennifer’s not an attack dog . . . I feel like she was limited to really transmitting who she was as a leader.” One insider noted Keesmaat was struggling in the limelight to transform from urbanist speaker and ex-bureaucrat to hard-hitting politician.

“She was trying to find her own voice as a politician too,” one source told the Star, acknowledging Keesmaat frequently stuck to talking points in the beginning. “It was an entirely new thing for her.”

Meanwhile, the campaign only ever really mounted an “air war” — messaging — without any serious efforts to mobilize a ground game to get signs in yards and identify voters to get to the polls.

Keesmaat did not agree to an interview for this story.

Chris Ball, a former Ontario NDP communications staffer and principal at Earnscliffe Strategy Group, who ran Keesmaat’s war room, told the Star he feels good about the campaign they ran.

“It started on the last day for registration and we did build a bit of a movement behind us,” he said. “I think getting around 25 per cent of the vote is actually a good showing for a campaign that had less time than the incumbent. We took on a popular incumbent and Doug Ford dominated the race for about two-and-a-half weeks.”

Keesmaat also had advice on key policy from the likes of Sloly, and those with business acumen like former MLSE boss Peddie.

“We had a mayor who has never really stopped campaigning since the day he got elected four years ago. He’s a photo-op waiting to happen,” said Peddie. Tory was, he said, the safe candidate in an uncertain time for the city under Premier Ford.

“Time was not an ally for her. When she started she didn’t have an office, she didn’t have a (campaign) phone. She was starting from nothing and that had to hurt. Would a couple of more months made a difference? Sure it would have. Would it have been enough to beat a safe-looking incumbent? Probably not.”

Throughout, one insider said Keesmaat remained “upbeat” as volunteers and residents said they were compelled to get involved for the first time because of her candidacy. Peddie said she was “very happy with the team around her.”

The source who was critical of the campaign’s tactics made clear Keesmaat herself was a “solid candidate” full of confidence and poise.

“In some ways, what she did from a dead start was pretty remarkable,” that source said.

Another source with outside knowledge of the campaign said Keesmaat never really had a fighting chance — that there was likely no progressive candidate who could have bested Tory.

“In this city, unless you’re a crack-smoking mayor you’re pretty safe for two terms, and I’m not convinced Rob (Ford) couldn’t have been re-elected.”

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

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