Who will replace John Tory in four years? A look at the insiders, the outsiders -- and a surprising longshot

Thestar.com
Nov. 14, 2022

John Tory will officially begin his third and final term as mayor on Tuesday. Speculation about who will replace him won’t be far behind.

Tory has pledged he won’t run in the next municipal election, which would open the 2026 race to a competitive field of new candidates.

With the dust still settling from Tory’s victory in the Oct. 24 vote, so far no one has announced their intention to run for his job four years from now.

But Myer Siemiatycki, professor emeritus of political science at Toronto Metropolitan University, said serious candidates are likely already plotting their campaigns.

“You can’t start planning for a mayoral race too early, given the fundraising that’s required, the wide network of volunteer support, endorsements, etc. that are necessary,” he said, noting that a successful mayoral campaign in Toronto can require raising more than $2 million.

A lot can happen in four years, but based on interviews with experts and city hall sources, here are some potential contenders for Toronto’s top job when Tory steps down.

The insiders

Some sitting council members will likely try to make the jump to the mayor’s chair. Chief among them is Josh Matlow (Ward 12 Toronto--St. Paul’s), who’s widely expected to run in 2026.

In his three terms on council Matlow has been a vocal critic of Tory’s, and has garnered media attention for advocacy on hot button issues like legalizing drinking in city parks, reducing the police budget and cancelling the Scarborough subway.

Lorne Bozinoff, president of the Forum Research polling firm, said Matlow’s engagement on citywide issues has boosted his name recognition outside his ward, a critical factor in mayoral campaigns.

“I think he in particular does have a leg up,” said Bozinoff.

Coun. Michael Thompson has privately told colleagues he harbours mayoral ambitions, according to sources.

The veteran Scarborough Centre representative has spent years building up his profile by serving as chair of the economic and community development committee and as one of Tory’s deputy mayors.

But he was forced to resign those positions in September after he was charged with two counts of sexual assault. The allegations haven’t been tested in court. Although he won re-election last month, his political future is under a cloud.

Matlow’s chief of staff Andrew Athanasiu said the councillor has no current plans to run.

“Josh is focused on serving the people of Toronto--St. Paul’s, the job he was just elected to do,” Athanasiu said.

Thompson also told the Star he’s focused on working for his constituents and isn’t yet thinking about the 2026 race.

Former insiders

A handful of councillors who didn’t run for re-election this year could come back to be viable mayoral candidates in 2026.

They include Ana Bailão, the well-liked former Davenport representative who was the mayor’s point person on the housing file.

There’s also Mike Layton, whose political family and work on inequality and climate change while councillor for University-Rosedale made him one of the most well-known figures in local politics.

Fellow progressive and former Spadina--Fort York councillor Joe Cressy has also been considered a potential successor to Tory. While chair of the board of health this past term, he was praised for working with the mayor to guide Toronto through the pandemic.

Bailão told the Star she doesn’t know if she’ll run for mayor, and for the moment she’s looking for work in affordable housing.

“If I find that I can give something back to the city at a certain point in time, I have all intention of (doing so). But there’s many different ways that you can give back,” she said.

Layton has left politics but hasn’t closed the door on a future mayoral run.

“I’m not sure what I will be doing next month, let alone in four years,” he told the Star.

“While I’m not planning on it, I wouldn’t rule it out entirely.”

By contrast, Cressy is unequivocal that he won’t be returning to city hall. He’s spoken openly about how mentally taxing council can be, and called working in politics “toxic.” He recently started a position as senior vice president at George Brown College.

However, Cressy is likely to continue to be linked to the mayor’s job among those in the city who consider him a gifted politician uniquely qualified to carry the torch for Toronto’s left.

“He’s smart, he’s hard working, he’s incredibly articulate, he’s very strategic,” said John Filion, who is the outgoing councillor for Willowdale.

“It’s hard for me to imagine Joe Cressy wanting to be mayor and not getting elected.”

Bozinoff said that any former councillor hoping to win the mayor’s race 2026 will have to keep themselves in the public eye for the next four years, as Tory did before his successful mayoral run in 2014 by hosting a radio show and chairing CivicAction.

Once a politician is out of office, “people start to forget pretty quickly,” Bozinoff said.

Parachuting MPPs and MPs

The successful mayoral runs last month of former Ontario party leaders Andrea Horwath, Steven Del Duca and Patrick Brown are an indication of how easily figures from senior levels of government can transition to city hall when their political fortunes change.

The next provincial election is scheduled for June 4, 2026 about four months before the Toronto municipal vote. Depending on how their parties do, some current Toronto MPPs might find a mayoral run appealing. One name that’s been rumoured is the NDP’s Kristyn Wong-Tam (Toronto Centre), who is a former city councillor. But she told the Star she has no plans to run, and will endorse another candidate. Ontario PC MPP and Associate Minister of Transportation Stan Cho (Willowdale) is also seen as someone who could launch a viable campaign.

Siemiatycki also predicted a Liberal loss in the next federal election could convince someone like Deputy Prime Minister Chrystia Freeland, who represents University-Rosedale, to turn their attention to city hall.

“(If) the Liberals are defeated and she wasn’t particularly enamoured of four or more years in opposition, could the mayor’s chair in the city of Toronto interest her? Quite possibly,” he said.

The premier

It would be a shocking political twist, but Filion predicted that Doug Ford could attempt a surprise return to municipal politics in 2026.

The premier served one term on council while his late brother Rob was mayor.

Filion, who wrote a book about the Fords, said Doug isn’t suited to being opposition leader and won’t stick around at Queen’s Park if the Conservatives lose the next provincial election.

He believes Ford is still stinging from his loss to Tory in the 2014 mayoral race, and his controversial moves to cut the size of council and impose a strong-mayor system on Toronto indicate he feels he has scores to settle at city hall.

“He would see it as unfinished business, a game that he started to play and didn’t win,” Filion said of a potential 2026 run for Ford.

“I’m not saying it’s an even money bet. But I’d certainly take good odds on it.”