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John Tory: Toronto's next mayor, or once again the loser? (PETER POWER/THE GLOBE AND MAIL)

John Tory: Toronto's next mayor, or once again the loser?

(PETER POWER/THE GLOBE AND MAIL)

POLITICS

Can John Tory win this time? Add to ...

Three strikes and most players would have walked away from the plate. But not John Tory.

When the former Rogers CEO and CFL chairman ran for the job in 2003, he lost to milquetoast David Miller in a squeaker. Four years later, Mr. Tory lost to Premier Dad McGuinty for the Ontario premiership, even though as leader of the Progressive Conservatives he had polled higher in personal popularity. Having failed to win a seat in a 2009 by-election, he resigned.

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Though he has worn many professional hats – lawyer, radio host, CivicAction chair – Mr. Tory’s critics would rather him wear another hat, one with a permanent scarlet ‘L’ on his forehead. But he’s arguably the most threatening kind of loser, a political Tantalus who has almost eaten the fruits of major victory too many times and won’t give up. Mayor Rob Ford and brother Doug may depict him as a pampered toff, but one could also argue that his losses make him an empathetic underdog, the tireless city champion who could be make a great mayor if he could only mount a more punchy campaign.

If the petty, paranoid and vituperative tone of the race’s first week is any indication, it will be far from gentlemanly. Mr. Ford’s brother Doug is already taking shots at Mr. Tory as a Manchurian candidate of the blue-blooded elites and a tax-and-spender who gets his advice from former aides of defeated mayoral candidate, Liberal George Smitherman. They also allege that Mr. Tory, his supporter Andy Pringle and Police Chief Bill Blair are working in cahoots.

Mr. Tory already has his work cut out for him: If he takes the high road in this brawl, few will notice him.

Sitting at a Tim Hortons in the Jane Finch Mall, Mr. Tory warned against attaching too much significance to losing. “This is assuming that there is a dishonour in losing. Is there a dishonour in losing a soccer game? Is there a dishonour in losing a business deal? Or a law case? If I tried my hardest, if I functioned as a matter of principle and represented my client’s interest to the best of my ability is there a dishonour in that?” he said, his voice slightly irascible.

The Globe and Mail asked Mr. Tory to pick a location that had personal significance, which brought us to the famously troubled intersection. It is the crossroads for some of the city’s most impoverished families, an area that lifts him out of the gilded boardroom and into the community he has spent countless hours as an organizer and mentor. It’s also a path to victory: we’re in a little hamlet of Ford Nation, a swath of terrain that will also be sympathetic to his likely left-wing rival candidate Olivia Chow.

Wearing biker boots and vintage-style Maple Leafs jacket, the politician who is sometimes derided as being too much of a gentleman to be in the game says that he’s learned a few things from his failures. “You know the old expression, You learn more from your bad days than your good days. But I’ve also learned a lot from my good days.”

Trying to extract those lessons, however, is a small failure unto itself. Mention his controversial campaign to extend public education funding beyond Catholic schools and he’ll say it was a matter of principle, so disregard that. Nor can we include the personal attacks on his character. Those he couldn’t help. If anything, he says that he learned to hone the message.

“I’ve learned that less is more when it comes to saying, ‘look, I’m just for these five things.’ I learned as an executive you can’t have more than four or five priorities because if you have 27, you have none. That’s why you hear me talk about livable, affordable functional,” he says, one of the many times he uttered his new campaign slogan during our discussion, a frequency that could inspire one to bristle or name a drinking game after it.

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