Rewind 2014: Losing & listening teach John Tory how to win

When John Tory hung up his headphones on a Friday after hosting his daily radio show, he knew by Monday he would officially be in the running to be Toronto’s next mayor.

His wife, having seen the polling numbers, wasn’t so sure about the decision.

And the brain trust of political heavyweights that had selected Tory as their candidate and pledged to get him elected hadn’t heard for certain if he would run.

Since leaving politics following a crushing loss at Queen’s Park, Tory had spent more than four years hosting the afternoon drive call-in show, Live Drive with John Tory, on Toronto radio station Newstalk 1010.

It was this experience he credits with convincing him he could win the race for mayor.

During his time on-air Toronto had been thrust into the international spotlight while then-mayor Rob Ford battled scandal after scandal.

Gridlock on city streets was matched by gridlock in the city council chamber as the obstinate mayor and his brother councillor Doug Ford struggled to maintain support in the face of a growing tide of resentment from fellow councillors frustrated with the distractions at city hall.

But among the admissions of drug use and damning videos of intolerant behaviour and the council’s decision to strip Ford of most of his powers, the polls suggested Rob Ford could win them back in the next election.

Tory spent the weekend discussing his plans with his wife, Barbara Hackett.

On Monday, he was in.

‘I took the gamble’

Tory commissioned polls to gauge his chances, but his internal polls were showing the same thing the public polls turned up: He was third behind a powerless mayor and an imaginary candidate, Olivia Chow, who hadn’t officially entered the race yet.

The bleak numbers combined with Tory’s personal history of running — and losing — over his political career was never far from anyone’s mind.

Even the man who ran who would eventually serve as a chief strategist on Tory’s successful mayoral campaign had actively campaigned against him in the past.

Nick Kouvalis, a PC activist at the time, launched the Draft a Leader campaign in 2008 after Tory lost his seat at Queen’s Park and led the PC party to defeat at the hands of Dalton McGuinty’s Liberals.

When Kouvalis went on to run Rob Ford’s 2010 campaign, he targetted Tory again.

Though Tory was adamant he wouldn’t be running, Kouvalis endeavoured to ensure he would not change his mind by enlisting a a goofy YouTube video depicting Tory as a Ford foe unworthy of stopping the gravy train and planting a caller to Tory’s radio show who questioned his integrity.

But even after losing the last three elections he’d ran in, Tory took a chance on this one.

“These things are a gamble in politics as they are in life … I took the gamble,” Tory told 680News political affairs specialist John Stall in a recent interview.

After four years spent listening to people talk about their frustrations on his talk show, Tory believed people wanted something different from their municipal government, and he could be the guy to give it to them. Running wasn’t about vindication for past losses.

“I didn’t have some particular point to prove in running. I’d run before and lost. And won,” said Tory.

He is a man who maintains his calm.

After losing the mayor’s race to David Miller in 2003, he joked in his concession speech that he couldn’t reach Miller on the phone to congratulate him because the new mayor was busy chatting with the prime minister.

“I was speaking to an employment agency on the other line, Tory quipped.

That cool demeanour served him well during the campaign, when Rob and later Doug Ford would lay on strong attacks.

Before debates, Tory said, Rob would challenge him, look him in the eye and warn him the next hour wasn’t going to be pretty.

“He’d point to his binder and he’d say ‘What’s on this paper is going to lay you out cold on the floor.’ And he’d say, ‘Buddy,’ that’s how he talks, ‘Buddy, you won’t even be able to get up when I’m finished with you,'” Tory said.

“It took some discipline to stand there when Doug Ford would impugn my character in every way he thought he could, and just say, ‘Well that’s very interesting. Is that the best you’ve got?’ As opposed to, ‘Let’s talk about you for a minute, and your mother wears army boots,'” Tory said.

“It’s not in my nature to want to engage in that. But I just didn’t because it wasn’t going to advance the aims of my campaign.”

The aims of Tory’s campaign were calculated and succinct.

From his very first town hall meeting, held over the telephone on the Monday he entered the race, Tory talked touted his campaign buzzwords: livable, affordable, functional.

He appealed for more calm, more action on files, such as transit, that he thought were being neglected as chaos unfolded at city hall under the Ford administration.

“I had a faith that the kind of skill set I would bring to the job spoke to a kind of calmer, less polarized, more professional management of the city’s affairs that would appeal to people after all the chaos,” Tory said.

And though other candidates, like Olivia Chow or David Soknacki, could also trade on their distance from the last four years at city hall, he believed more left-leaning candidates could have led to the same kind of polarization seen under ultra-conservative Ford.

“I think I can win. I think there is an opening,” Tory said to himself before running.

‘Over to you’

Tory’s subway ride to work used to be a calm and solitary experience.

That all stopped on Oct. 27 when Tory won the mayor’s race with 40 per cent of the vote.

Days before taking office on Dec. 2, his train stopped in the tunnel.

“And the people were all kind of looking at me going, ‘Well, I guess you’re going to have to deal with this in a couple of days,” Tory said.

“Now when I go on the subway… they’re gonna say, Over to you.”