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John Tory: Toronto's next mayor, or once again the loser?The Globe and Mail

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.

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.

To his credit, though, his campaign message is concise, catchy and you know what it's about. It fits into his wider vision of transportation not just as set of vehicles, but as part of an economic tide that lifts under-serviced, under-privileged areas such as Jane-Finch out of their geographic and professional isolation, connecting them to far-flung parts of city to work or pleasure and then carries them back to shore.

Mr. Tory believes that there is no contradiction between careful spending on social programs and transportation and fiscal conservatism. To him, the philosophy is a means to an end: the wider creation of wealth across classes. "I think one of the reasons you are a fiscal conservative is that you want to preserve and conserve and create the resources to help people who need help. That's not hand outs. That's hand ups. And that's something we prize as citizens: that we're going to be there with a little bit of help."

"You want to talk about something I'm against? I'm against the notion that you can't be fiscally conservative and have a social conscience," he said.

His former opponent and current friend, David Peterson, says too much is made of Mr. Tory's past failures. Losing comes with the political territory. "Who the hell hasn't lost an election? The only ones who haven't lost haven't run," says the former Liberal Ontario Premier. "You gotta want to win and John does. He has the bug."

The people who are paid to look into the minds of their foes – including Mr. Tory's – say he lacks the killer instinct, and this week has been proven to be a surprise test. The October 27 contest is shaping up to be as vicious a contest as Toronto has ever seen, and so far, Mr. Tory has not been as restrained as one might imagine. The occasional flash of aggression likely comes from the flinty mind of Nick Kouvalis, the former Ford campaign manager who has joined Mr. Tory's team.

On Monday, Mr. Tory dramatically preempted the entry of conservative rival Karen Stintz with his own announcement.

"It was cheeky to rain on Karen's parade, and because of who he is, he didn't come out looking like he was mean," said Mark Towhey, Mr. Ford's former chief of staff.

For the earlier part of the week, Mr. Tory made a careful effort not to criticize the Fords by name. But after the Fords alleged that conspiracy between him, Mr. Pringle (a Ford appointee who sits on the police services board) and the police chief, the Tory campaign quickly issued a statement, calling the accusation "a disgrace" and said that "Torontonians deserve better."

(Sources close to the relationship say that in the interest of not looking partial to any potential candidate, Mr. Blair has been keeping a careful distance from Mr. Tory – he has stopped appearing on Mr. Tory's radio show – since the TPS investigation of Mr. Ford, Project Traveller, accelerated.)

Political operatives say Toronto remains an angry, disaffected city that demands a steel-toed Greb boot be applied to city council. "They want someone to go to city hall, kick ass and get things done," says Mark Towhey, who knows a thing about capitalizing on civic disaffection. Mr. Towhey, along with several other political operatives, suggested Mr. Tory still has to work hard to shake off his image as someone who isn't tough enough to make hard decisions.

It's a contention that Mr. Tory takes great issue with. Talking over the tinny whine of a Top 40 song, his sentences speed up, his even tone unusually exercised. "I don't think you can do the things in life that I've done and not be tough. Be the CEO of two large companies for nine years and produce successful results and, by the way, work for Ted Rogers? He was a great friend and mentor, but very difficult to work for," he said. "If you say being a gentleman means being respectful to other people, no matter who they are and no matter what their point of view is, yeah I'll take that."

Selling the idea to his wife, Barbara Hackett, took some toughness as well. Friends say Ms. Hackett was averse to his third trip to the plate. "Wary," he said, correcting me. "People used to bump into us on the street and say you must be mayor and she'd pull me by the arm and say, 'I'm not sure that's happening but nice to see you!' She even said something in The Star that it's okay if he runs as long as he promises to lose."

So how did lawyer Mr. Tory present his case to his family – his wife and his four children? "I presented in a fatherly way. I said that I could really make a positive difference in in turning around the situation," he said. "That it's at a turning point and we have to make sure it remains a great city."

While that recounting doesn't exactly ring with intimacy, age seems to have played a part. Almost 60, Mr. Tory talked about the wonders of having grandchildren, how it makes you feel like a parent again. He also mentioned that it offers you a make-over of sorts. "When you get to be a grandfather, you get to start all over again," he said. He says he feels wiser, more energetic, more vigorous than ever. Though sometimes mocked about his stolidness, Mr. Tory seems able to laugh at himself.

He also recounted a recent time when he took one of his granddaughters, Isabelle, to Riverdale Park, one of his favourite destinations, and took out the stroller. "I'm very happy with myself because I've got it all set up and then some nice woman recognizes me and says, 'So nice to be here, and by chance, did you know you happen to be pushing that stroller backwards?'"

The conversation wrapping up, Mr. Tory offers to drive to visit a friend, Dennis Keshinro, a high school teacher who spends most of his extra time and a lot of his personal money running after-care programs, called Belka, for children of double-income parents who work double shifts. Many of them take computer literacy classes in old TTC buses that Mr. Keshinro retrofitted with the help of Mr. Tory and former CFL great Pinball Clemons.

Nosing his Lexus SUV out of the Jane-Finch Mall to head over to Mr. Keshiro's space, Mr. Tory said that no particular event pushed him to run. It was simply what was happening to the city. "Did I have a dramatic moment when I made that decision? I'm not that kind of person."

But we suddenly confront a more mundane drama: in order to get to the left-hand-turn lane, which is already lined up, he has to cut across two lanes of moving northbound traffic. Should he be one of those elbows-out drivers who makes everyone wait so he can get where he needs to go? Or take the more honourable route of turning right and then U-turning all the way back down south?

If you bet he took the more gentlemanly route, you bet wrong.

Note to readers: An earlier online version of this story incorrectly stated  Mr. Tory lost  his seat in the 2007 election. It already belonged to Kathleen Wynne. This online version has been corrected.

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