​Here’s a very simple question which, I suspect, has a very complicated answer: Who does the mayor of Ontario’s capital city want to win the next provincial election?

On the surface, the answer seems obvious. John Tory has been a loyal Progressive Conservative supporter since he was a teenager. And he actually has many things in common with Doug Ford, the PC party’s newly minted leader.

In 2004, Tory won the same job Ford now has at a leadership election that used essentially the same rules by which Ford emerged victorious. Like Ford, Tory didn’t have a seat in the legislature when he won the leadership, and, like Ford, Tory was offering himself to PC voters as a successful businessman (CEO of Rogers Cable) who’d run once for mayor and lost (to David Miller in 2003). Both men were urged to seek the PC leadership on the strength of exceeding expectations during their mayoralty defeats.

Tory started his campaign for mayor in single digits in public-opinion polling but ended up north of 38 per cent, losing to Miller by only five points. He surely over-performed. Ford was thrust into the 2014 mayor’s race literally with an hour to spare before the nomination deadline because his brother Rob, elected in 2010 as mayor, was fighting a life-threatening illness. Despite having only a month to campaign, Doug Ford achieved 34 per cent of the vote, trailing Tory, the eventual winner, by just six points.

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Now consider all the reasons why Tory and the current premier, Katheen Wynne, might not get along, starting with election night in 2007. As PC leader, Tory had hoped to lead an urban renaissance for a party which had precisely zero seats in the city of Toronto after the 2003 election, by challenging the then-popular cabinet minister Wynne in her Don Valley West riding (where he grew up). But Wynne beat him badly, by almost 5,000 votes. And under Tory’s leadership, the PCs again were shut out of the 416 seat count. (That would happen again in the 2011 and 2014 provincial general elections; that’s 0 for 92 if you’re keeping score.)

But by 2014, the two had become friends. Wynne, now premier, was on an overseas trip when she learned the news that Tory had bested Doug Ford for Toronto mayor. “Hallelujah!” she was quoted as saying. And for a while, the relationship between Queen’s Park and city hall was much improved from the days when Wynne actually refused to take a meeting with Mayor Rob Ford, so upset was she with his behaviour.

But then came road tolls. Tory and Toronto wanted them put on the two highways the city controls (the Gardiner Expressway and the Don Valley Parkway), and after giving every indication that that would be fine with her, Wynne buckled when the Liberal caucus threatened mutiny. The tolls, which required provincial permission, were out.

Tory was furious, and he offered up one of his most famous quotes (“It’s time we stop being treated, and I stop being treated, as a little boy going up to Queen's Park in short pants” begging for dollars). The relationship soured significantly. Tory started having press conferences with the two opposition leaders, refused to have joint press conferences with the premier, and once provoked Liberal cabinet minister Stephen Del Duca to rail against the mayor after Tory encouraged residents of a public-housing complex to complain to their Liberal MPP about the state of their buildings.

By all accounts, the premier and the mayor have patched up their differences. They like each other personally, even if their political ideologies are rather different (Wynne is too left-wing even for Tory, a notorious progressive among conservatives in the PC party). They disagree on some things that confound both of their supporters (road tolls), and they agree on other things that also confound their supporters — such as a $3.4 billion-and-counting one-stop subway in Scarborough, which neither of them supports by marshalling evidence-based arguments, but rather by essentially saying, “Council has decided, so let’s just get on with it.”

Despite all the similarities with Ford and the differences with Wynne, I’m betting Mayor Tory won’t shed a tear if the Liberal government is re-elected on June 7. Above all else, Tory has brought a civility to the mayor’s office that simply wasn’t there when the current PC party leader’s brother was in power. Tory has (mostly) lets the facts lead him to the decisions he’s made, and he respects the premier’s intellect and commitment to public service.

I have not talked to the mayor or any of his people for this column, figuring I’d simply get an echo of what he will no doubt repeat a thousand times between now and election day — that he will not endorse any political party at Queen’s Park, but will merely offer cherry-picked endorsements of the policies all of them offer, that are best for the capital city. And that’s fair enough.

Politics is filled with irony most days, and if you live in Toronto, you’ve just been confronted with one of the most unusual ones ever. Doug Ford, in part, dropped out of a rematch with Tory for Toronto mayor in October because he likely knew he couldn’t beat him.

Tory now finds himself a virtual lock to repeat as mayor. But it’s entirely possible that, rather than getting rid of Doug Ford from politics, he’ll be making the trip to Queen’s Park to see him in the premier’s office — an office he had once very much hoped to sit in.