John Tory may run for mayor again. The question on everyone’s minds: Why?

Is former Toronto mayor John Tory planning a political comeback in next year’s municipal election? In a new report from the Toronto Star, various unnamed sources say Tory is currently “on the fence” about running and put his chances at “more likely than not”—but also “50/50,” “90 per cent” and “changing by the day,” so the situation is obviously super clear.

Tory himself has not commented on the rumours, but one of the Star’s sources notes that he is “very cognizant of legacy” and would move forward with the plan only if he felt confident he could win. Candidates do tend to send up a trial balloon before launching a campaign, which could very well be what this is.

It’s been more than two years since Toronto’s steadfast mayor famously fled office following revelations of an inappropriate sexual relationship with a 31-year-old office aide (Tory is 71). The shock was seismic. Granted, the bar for outrageous mayoral behaviour will forever be weighed down by Tory’s predecessor, Rob Ford, but this was John Tory—a man whose version of cray-cray was letting his hair grow out (and even that took a global pandemic).

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By October, the integrity commissioner had concluded that his conduct was officially naughty, but Tory was long gone by then. Insiders speculated that his swift exit was a strategic move to shield his personal life: when he stopped being mayor, whatever workplace canoodling he was up to ceased to be a matter of public interest. The Canadian media is fairly serious about respecting the privacy of private citizens, even recently retired mayors. But all of that goes away if Tory throws his hat back in the ring—any dirty details from his office affair would once again be fair game.

Could he win against Olivia Chow? He’s beaten her before, when both ran for mayor in 2014. That was before her approval ratings settled at an iffy 48 per cent. If the recent federal election taught us anything, it’s that in polarizing times, Canadians love nothing more than a safe centrist (read: a white male boomer with name recognition and a robust collection of navy blazers).

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But the question remains: Why would he want to? He’s already done the job, which is taxing and thankless and more challenging than ever. Doesn’t he have golf courses to frequent? Boards to get paid an exorbitant amount of money to sit on?

The deadline to enter the race is almost a year away, which means there’s plenty of time for water-testing, discreet polling, leaks to local media from well-placed anonymous sources to gauge public reaction and so forth. So, while we can’t be sure how he’s feeling, he obviously wants to know how we’re feeling—and that’s revealing in itself.