The race to be Toronto’s mayor is finally set: Here are the six leading contenders

So, as of 2 p.m. Friday when nominations finally closed, we can stop asking “Who’s gonna run for mayor?” Between now and election day on June 26, the question is, “Who’s gonna run this town?”

A whopping 102 candidates on the ballot are hoping that they are the answer.

Most of us, frankly, don’t have time to sort through all of those.

There might be a dozen candidates who you could even conceive, based on their resumes and public profile, of being on anyone’s shortlist, and about half of those — I’d include Anthony Furey, Chloe Brown, Anthony Perruzza, Rob Davis, Giorgio Mammoliti and Celina Caesar-Chavannes — need something significant to happen to get close to the podium. It could come, but it hasn’t yet.

There are six I’d consider as having an obviously real shot: Ana Bailão, Brad Bradford, Olivia Chow, Mitzie Hunter, Josh Matlow and Mark Saunders.

In some ways, it’s an encouraging list. That’s more than the usual number of obviously qualified candidates and it reflects the conventional political spectrum. Maybe more notably, it’s a shortlist that reflects some of the diversity of the city: half of those heavy hitters are women, two of them are Black and one is Asian, four of them are immigrants to Canada.

That variety of perspectives will be helpful debating a pivotal moment for the city: there’s a crisis of housing affordability, and an affordability crunch in general. Much of the city’s infrastructure is falling apart, there are real concerns about public safety, TTC service is being made actively worse to try to save money and there’s a billion-dollar budget shortfall. And then there’s traffic (surprise, surprise, we all still hate it).

But the new mayor will have access to unprecedented power over the city’s government, thanks to “strong mayor” laws Doug Ford delivered last year.

Previous mayors have had to be wranglers and persuaders to attempt to lead council. The new boss will have the option of — well, of being a boss.

So, who are these candidates and where are they positioned as we enter the heart of the race?

We can start with Olivia Chow, who has a substantial but not overwhelming lead in every poll so far. She has recently been retired from politics serving on city council during the preamalgamation era and through most of Mel Lastman’s terms, and then as an NDP MP in Ottawa where she worked beside her late husband, the one-time Leader of the Opposition Jack Layton.

She has led polls for Toronto mayor before: In 2014, when she ran against Rob Ford (eventually replaced by his brother Doug on the ballot) and John Tory, she initially led before being overtaken and coming third. My own sense of that campaign is she lost in part by playing safe, afraid of taking any bold stances that might alienate suburbanites while she took the downtown progressive vote for granted — which wasn’t a safe bet in a race where many such voters just wanted someone they thought could beat Ford.

Chow says she learned from that campaign — that she was reading from a script a lot because she was afraid of how her accented English would come across, and now she’s more comfortable just being who she is — and will take a different approach this time. We’ll see.

Chow and her NDP supporters are claiming the mantle of progressive champion, but she’s faced an early challenge for that title from current midtown councillor Josh Matlow.

At city hall, he often served as among the most vocal and exasperated opponents of former mayor Tory — and Ford before him — and developed a reputation for not letting go of issues he believes in, like his opposition to the Scarborough subway extension (which he has since conceded is a lost cause) and the Gardiner Expressway eastern rebuild (which he still promises to halt if elected). He also developed a reputation for being blunt in his accusations of wrongdoing against colleagues and members of city staff — he spend 10 days this month forgoing his paycheque after being disciplined for accusing a senior bureaucrat of being dishonest.

Matlow put out waves of detailed policy earliest in the campaign, cementing his status as a top-tier candidate. His challenge is to move up from there as he becomes a target of opponents.

Mitzie Hunter, who served as a Liberal MPP representing a Scarborough riding until this week, is also looking to pick up votes from progressive voters. She has an MBA and a background as an executive at Goodwill and the Toronto Community Housing Corporation, then served as CEO of the civil-sector non-profit group CivicAction (where John Tory served as chair before becoming mayor). As an MPP, she served in the cabinet of Kathleen Wynne, then ran for leader of the provincial Liberals in 2020 (finishing fourth), and served as deputy leader of that party after last year’s election.

It’s a resume that, combined with her being from Scarborough, and a youngish (GenX) Black woman, would seem to make her a campaign manager’s dream — an experienced hand and a breath of fresh air at the same time. In her campaign this month, she’s been releasing eye-grabbing, detailed policy proposals on transit and housing. But early on, she has seemed to be getting only a little traction in polls, and also seems to have less of a heavy-hitting backroom team working on her campaign than most of the other candidates.

Ana Bailão, positioning herself as John Tory’s heir as the consummate centrist moderate, has that backroom organizational muscle to a steroidal degree. A former deputy mayor who oversaw the housing portfolio, she has inherited much of Tory’s team. She’s already drawn endorsements from many of the councillors who served on Tory’s executive committee, and notably, she’s got endorsements from some of the city workers’ biggest labour unions.

So she’s got the pros, and she’s going to be able to raise whole trainloads of money.

But what she hasn’t got so far is a clear identity among members of the public. I watched her at city hall over her three terms as a councillor and saw her at first as a nominal progressive who could often be bullied or cajoled into supporting Rob Ford, and then as a loyal right-hand woman to John Tory. But I would have a hard time telling you — beyond strong support for unions and a focus on housing policy — much about what she stands for or believes in, in her own right.

Some early campaign statements that anticipated announcements that were coming from others (on subway cell service, and moving the Science Centre) seemed more odd than bold, and her housing and traffic policies often sound like modest tweaks of Tory’s ideas.

She has the money and political smarts on her team to try to grab voters by the lapels, if it turns out she has the personality for it to work.

Depending on which month of his previous term as a city councillor you looked at Brad Bradford’s speeches and public stances, you might have expected him to be jostling for position as a progressive. But he’s got a Conservative campaign guru and an Ontario Proud meme-lord on his team, so now suddenly he’s accusing others of trying to defund the police, all tough on crime and promising to be the authoritarian “strong mayor of action” to stop all the talking and get to the doing.

What Bradford has is energy — his many social media videos are kinetic adventures, with him speedwalking and quick-talking like a shaved-headed Rick Mercer without the jokes, drinking beer with Leafs fans and eating beef patties in Scarborough and borrowing Tik Tok users’ complaints to scaremonger about transit.

What he doesn’t have so far, is much detail in his policy promises.

And as his ideological elasticity mentioned above would indicate, he may lack a certain authenticity to pull off the tough-guy shtick he’s peddling.

If there’s someone who would have tough-guy cred as the conservative law-and-order candidate, it would be a former police chief. And Mark Saunders has been playing to type, with a platform aimed heavily at fighting crime — and stoking fears of it — peppered with bashing of bike lanes on the side.

The thing is that the soft-spoken former chief, whose rhetorical style is more meek than commanding, was not a particularly well-liked or successful police chief.

He is nonetheless the choice of team Doug Ford in the election, with the potential to be a loyal henchman to the premier who loves nothing more than running Toronto from Queen’s Park. And in that, he is the default conservative voting option, so far. As a man who rose through the ranks to become the city’s first Black police chief, the one under whom the discriminatory carding policy was officially (if reluctantly) ended, and who said to me on the first day of his campaign that part of what he’d learned as police chief is that the solutions to crime aren’t all about arrests but also about community and mental health support, it’s possible to imagine a more nuanced kind of campaign from Saunders.

But so far, he seems to be making announcements with an eye to fending off a possible populist challenge from Anthony Furey on his right, who could conceivably emerge to take the mantle of Fordian outrage — the specialty of the Toronto Sun where Furey used to work — from him (if not the pseudo-endorsements of the premier himself).

As much as any policy positions — though ones that resonate with people are table stakes here — over the next month and a half these candidates are going to give us a look at who they are, how they handle the spotlight, how they speak to us and about us and for us. I am on the record wishing for a candidate with an expansive vision backed by smart policies. But we don’t vote for visions or policies, we vote for a person.

So their job is to convince us that we know them and can trust their judgment. Most polls still show massive numbers of undecided voters. Many of us are still waiting for all of them to properly introduce themselves.

We’re about to hand a mayor more authority over the government than we ever have before. We’ve got a lot of options. And roughly six weeks to make our choice.

Correction — May 18, 2023: The story referred to John Tory as having been CEO of Civic Action before Mitzie Hunter, when in fact he was chair of that organization while she was CEO.

Edward Keenan is a Toronto-based city columnist for the Star. Reach him via email: ekeenan@thestar.ca