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Toronto Mayor John Tory is greeted during an interview in Toronto on Oct. 10, 2018.Christopher Katsarov/The Globe and Mail

Sitting on a patio in a midtown Starbucks, Toronto’s incumbent mayor is relaxed, perching his elbow on the railing and greeting people who pass by. This stretch of Mount Pleasant Road, a mix of florists and cafés surrounded by upscale homes, is decidedly John Tory country.

A passing mom presents her two shy young daughters. With the temperament of a grade-school principal, Mr. Tory asks one whether she does her homework without being told. Minutes later he’s recognized by a young woman in ripped white jeans. She’s a blogger and wants to take their picture.

For Mr. Tory, 64, this is old hat. His campaign schedule has not been that different from his pre-election routine, which was packed with community festivals and events. And with the polls so far suggesting his main rival, former chief planner Jennifer Keesmaat, is trailing far behind, it’s perhaps no wonder he seems so at ease.

But this election, in many ways, is a warm-up fight. The harder battle will take place after the vote on Oct. 22, when Toronto’s mayor will have to negotiate the city’s delicate relationship with Ontario’s new Progressive Conservative Premier, Doug Ford. More than transit plans and promises about taxes, this mayoral election has become a contest about who can represent Toronto under the reign of Mr. Ford, who has shown he is more than willing to stick his fingers into the city’s affairs.

Mr. Tory’s key pitch to voters is simple: He is the even-tempered deal maker who can work with even the likes of Mr. Ford to secure the billions for public transit and housing the city needs. Ms. Keesmaat, on the other hand, has positioned herself as scrappier, quicker to condemn the Premier and vocal about what she calls Mr. Ford’s “not normal” government.

Whichever attitude prevails, Toronto’s next mayor had better be ready for a fight, says Councillor John Filion, who sat near Mr. Ford when he was a councillor and wrote a book about his brother Rob Ford’s scandal-plagued term as mayor.

“Anybody who thinks that it’s going to be anything other than him pounding whoever the mayor is, is naive,” Mr. Filion said. “And it doesn’t matter whether you try to be his friend or be his opponent. I think he will actually respect you more if you are fighting back fiercely. But he’ll punch you out either way.”

It was Mr. Tory’s response to Mr. Ford’s sudden move cut to city council almost in half this summer that inspired Ms. Keesmaat to jump into the race. Mr. Tory called for a referendum on the idea. But what he sees as diplomacy, she sees as weakness.

Toronto Mayor John Tory and his mother, Elizabeth Tory, walk together towards an advance polling station in Toronto on Oct. 10, 2018.Christopher Katsarov/The Globe and Mail

“You choked," she told him on stage at this week’s debate. "You didn’t do anything about it.”

The mayor, a lawyer, former CEO of Rogers Media and onetime Ontario PC leader, points to his record, arguing he knows how to do business with anyone. He boasts he has worked with both Liberal and Conservative governments, securing billions in funding from Ontario’s former Liberal premier Kathleen Wynne, the federal Conservative government of Stephen Harper, and the current Liberal crew under Prime Minister Justin Trudeau.

But he does concede that dealing with Mr. Ford, who ran against Mr. Tory for the mayor’s job 2014 and was poised for a rematch before his sudden move to Queen’s Park, is different.

“I realize he is much less predictable than other people I might have dealt with,” Mr. Tory acknowledged over his coffee this week.

Mr. Tory insists he and Mr. Ford have many common interests. The Premier is from Toronto and favours keeping taxes low, building public transit and ensuring that the city attracts people, jobs and new investment. He thinks they both see Toronto’s economy as a key driver for the province’s prosperity as a whole.

“If he wants to get himself re-elected, he should hope Toronto is just absolutely going gangbusters four years from today, as it is today,” Mr. Tory said.

Ever since Mr. Ford took to the provincial stage, Mr. Tory has mostly kept to a cautious, diplomatic script – at least until the Premier’s plan to reduce the number of council seats in Toronto from 47 to 25 leaked out in late July.

Ms. Keesmaat and some of her supporters on council’s left accused Mr. Tory of making an arrangement with Mr. Ford, pointing to the mayor’s acknowledgement that the Premier mentioned in an “offhand” remark that he wanted to cut council in a July 9 meeting. Mr. Tory says he did not think Mr. Ford was serious, and denies the accusation he made any deal. He says when he found Mr. Ford was going ahead in the middle of the election campaign, he told the Premier in a heated phone call it was not acceptable.

Downtown Councillor Joe Cressy, who despite his NDP membership card has worked with Mr. Tory on a range of issues over his term, says Mr. Tory let the city down when it was under attack by failing to organize broader opposition to Mr. Ford’s plan.

“I think that John Tory is a fundamentally decent man. … But I think when it came to what was the most egregious legislative attack on the city of Toronto since the megacity [amalgamation], John Tory did not stand up when it mattered,” said Mr. Cressy, who is supporting Ms. Keesmaat. “He tried to walk a line, while voicing his displeasure without organizing to stop it.”

Mr. Tory warned at this week’s mayoral debate that electing Ms. Keesmaat would mean “constant warfare” with Mr. Ford, and would burn bridges for the city.

But Mr. Tory himself entered into his own skirmishes, even with with Ms. Wynne, who led the most city-friendly government at Queen’s Park in recent memory. When Ms. Wynne withdrew her support for Mr. Tory’s announced plan to use tolls on the city’s two main expressways to raise cash for transit, he complained of being treated like a boy in “short pants” forced to beg for permission from the Premier.

He now points to the consolation prize Ms. Wynne offered instead as a success: a pledge of an additional share of the gas tax worth $170-million a year that Mr. Ford said he would honour.

Mr. Tory also mounted a campaign, complete with pamphlets targeting a west-end MPP, aimed at shaming Ms. Wynne’s government into coughing up hundreds of millions in funding for repairs to the city’s crumbling social-housing stock. Steven Del Duca, then Ms. Wynne’s transportation minister, complained that Mr. Tory had gone “over the line.” But their government would later come up with some of the needed cash – a cheque Mr. Ford has since cancelled.

Mr. Tory says he thinks he can convince Mr. Ford that fixing public housing now with retrofits aimed at energy efficiency will save money in the long run. Mr. Ford has already committed new money to the police. But other issues, the mayor acknowledges, will likely be more challenging. Among them is the city’s plans for light-rail lines, such as the Waterfront LRT, which needs cash from the Premier, who is well-known for preferring subways.

Mr. Ford is also poised to make a decision on the future of the supervised drug-use sites that have opened up across the province in hopes of preventing opioid-overdose deaths. Mr. Tory, who had to be convinced himself on this issue early in his mandate, says he has not had a chance to make the case to Mr. Ford that he believes the sites should stay open.

Then there is the question of the city’s financial sustainability. The previous city manager, Peter Wallace, repeatedly called the city’s reliance on the land-transfer tax risky and unsustainable. He said new revenue sources were needed to maintain even the city’s current service levels. However, Mr. Tory has repeated his pledge not to raise property taxes above inflation, a position his rival Ms. Keesmaat echoed this week.

The campaign itself has been lopsided from the start. Not only has Mr. Tory enjoyed the built-in advantages of an incumbent, his main opponent had to scramble to assemble a campaign team after jumping in at the last minute. Then the drama over Mr. Ford’s intervention preoccupied the city for weeks, denying Ms. Keesmaat crucial airtime. Mr. Tory had at least $1-million raised by July, weeks before Ms. Keesmaat even signed up, and he now boasts close to 2,000 volunteers. Plus, he has refused to debate Ms. Keesmaat one-on-one, in the name of allowing other lower-profile candidates a voice. Critics say this is a classic front-runner strategy meant to deny his main challenger a platform.

While the limited powers of Toronto’s mayor have always made getting what the city needs from other governments a key part of the job, this campaign is unusual in its focus on Mr. Ford, says Myer Siemiatycki, a professor of politics at Ryerson University. He says the question of who offers the best approach for taking on the Premier is easier for voters to grasp than debates about competing transit plans or how many thousands of affordable housing units can be built.

“It’s kind of the congenial, make-a-deal option in Mr. Tory or the stand-up-for-Toronto option of Jennifer Keesmaat,” Prof. Siemiatycki said. “I think Torontonians will make their decision in part on … which of those options do they think is best for the city.”

Editor’s note: (Oct. 12, 2018) A photo in an earlier version of this story incorrectly identified Elizabeth Tory's last name as Bacon.