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John Tory's second bid to be mayor of Toronto is a high-stakes personal gamble for the 59-year-old.

If he wins, what a vindication. All the critics who called him a four-time loser with a tin ear for politics would be silenced. After decades in and out of political life – nearly mayor, nearly premier, always a bridesmaid and never a bride – he would at last hold the reins of office, assuming leadership of Canada's biggest city and sixth-largest government.

If he loses, what a humiliation. His political hopes would be dashed for good. Another bid for any level of elected office would be unthinkable after so many flubs. He would go down in history as the best mayor Toronto never had, a perpetual also-ran who seemed to have all the attributes of a leader – intelligence, integrity, experience – yet somehow could never seize the throne.

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Now, after months of waiting, he has rolled the dice. How they will turn up, who can say? Contests for mayor can be wildly unpredictable. It is a long, gruelling campaign that often has many twists on the way to October.

There is no doubt Mr. Tory enters the race with some big advantages. He is a well-known figure in a competition where name recognition matters. He has a high-powered campaign team with links to both Liberal and Conservative parties. His Bay Street connections should make it easy to raise money and build a campaign war chest.

He has a killer résumé. As a former business executive with Rogers, he can claim to know about how to create prosperity and jobs. As a leader of the volunteer group CivicAction, he has worked on urban issues from transit to youth unemployment. As a talk-show host till he quit to run, he is well-read and articulate on all the issues.

He ran a good campaign for mayor in 2003 and came a close second to David Miller. He calls himself a fiscal conservative and yet acknowledges the need for public investment in a growing city.

In a series of media interviews after registering to vote at City Hall Monday morning, he painted himself as someone who can move beyond all the wrangling at city council and bring people together to produce results. He would get city councillors "working with each other, not against each other" and use his skills and experience to strike deals with other levels of government. He would work for a "livable, affordable and functional city."

And yet …

Even with all his strengths, Mr. Tory is far from a sure bet for mayor. No one from outside elected city politics has become mayor of Toronto in recent history. The leading outsider in 2010, George Smitherman, came into the race, like Mr. Tory, as a heavyweight but fizzled and lost to Rob Ford.

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This time around, Mr. Tory faces serious competition. Olivia Chow is at least as well-known, a Toronto MP and former city councillor with a long history in the city that would profit her if she came into the race. In a multicultural city, she might strike some voters as a more fitting mayor for the times. Karen Stintz and David Soknacki, on the other flank, are selling the same brand as Mr. Tory – moderate non-Ford conservative. Mr. Ford's camp, meanwhile, is portraying Mr. Tory as a blue blood out of touch with the ordinary folk, an image that, even if a caricature, could stick.

But Mr. Tory's worst potential enemy is himself. He is so fair-minded, so willing to see the other side, that he often seems all over the place. He talks a mile a minute, not always to his own advantage. His time in provincial politics revealed a man of weak political instincts who lost a general election, the seat he was contesting and a by-election before resigning as Conservative leader.

This is his last chance to prove himself on the political stage that he has hovered around for most of his adult years. A gamble indeed.

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