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John Tory celebrates at the Liberty Grand after winning the election on Oct 27 2014 to become Toronto's next mayor. Heading into today's vote, Tory was leading Olivia Chow and Doug Ford.

Fred Lum/The Globe and Mail

Nick Kouvalis, the pollster who helped put both John Tory and Rob Ford in the mayor's office, draws three lines on a napkin – the trajectory of Toronto's 2014 race for mayor.

The place where the bottom and top lines cross – July 14 – was the turning point for the Tory campaign, and the moment when Toronto's next mayor did something he had never done before: take the lead in a general election campaign.

But the back-of-the-napkin graph hardly tells the whole story. In a series of exclusive interviews, some conducted in the final days of the race, Tory operatives revealed to The Globe and Mail how they navigated a path to victory that was anything but a straight line. It was littered with twists and turns: Rob Ford's initially strong performance, which gave way to his drug controversy, his trip to rehab, his stunning hospitalization and the last-minute entry into the race of his brother Doug Ford. There was the collapse of Olivia Chow's support. And to cap it off, a sprint to the finish with the come-from-behind Doug Ford campaign on election night that left him just six points behind.

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"There is no precedent for what happened in this campaign," says Tom Allison, the Liberal strategist who managed Mr. Tory's bid for mayor and who has worked on more campaigns than he cares to count. "I can't think of anything like it."

And it almost didn't happen.

Mr. Tory, a former Rogers executive, had seen more than his share of defeat. After his first failed run for mayor in 2003, he lost provincial bids in 2007 and 2009. When advisers began calling him about the 2010 mayoral election, he considered, but ultimately decided against it. "The wounds were too fresh," a close adviser says.

In summer of 2013, those same political organizers began calling again. By then, the first series of Rob Ford scandals – including details of the first crack video – had begun to rock City Hall, triggering a chain of events that would ultimately lead Mr. Ford to be stripped of most of his mayoral powers.

One of those people was Bob Richardson, who would go on to co-chair his campaign. He went to see Mr. Tory at his cottage; others, too, called him on the phone. They all wanted to know the same thing: Would Mr. Tory run against Mr. Ford?

He discussed it with his family. His wife of 37 years, Barbara Hackett, had reservations, given past experience. "It was sort of going into it with our eyes wide open," she said in an interview in October. "We sort of know too much, so I think it causes you to really think about it a little bit longer."

What Mr. Tory wanted to know, most importantly, was whether they'd be able to put together a team with a "broad base of support – Conservatives, Liberals and civic activists."

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That team would include Mr. Kouvalis, best known for his "message discipline" and steering Rob Ford's 2010 campaign. A Tory victory would give both the candidate and Mr. Kouvalis a chance to redeem themselves.

Publicly, Mr. Tory has said he didn't finally decide to run until mid-February, but it appears to have happened earlier than that. In mid-December, the team held a "pub night" with Mr. Tory to discuss "Toronto's bright future," and by February they were meeting regularly and putting together a detailed launch plan.

"It was never that iffy, I don't think," said a senior campaign source. "I think it was more publicly iffy because the guy was a radio show host, so you couldn't be running around saying 'yes, I'm running for mayor,' and then stay on the air."

When Mr. Tory finally jumped into the race on the morning of Feb. 24, it was just hours before Karen Stintz was scheduled to register. As a result, the popular talk show host captured most of the attention.

Tory organizers turned most of their initial focus on then-front-runner Ms. Chow. They promised to run a "positive" campaign, but did not hesitate to paint their rival as the tax-and-spend candidate. "We immediately branded her as NDP candidate Olivia Chow," said Tory war-room director John Mraz. "We made no qualms about that."

But for all the planning, it turned out to be Rob Ford for whom Tory organizers were not really prepared. At the first debate, televised on March 26, the mayor performed better than anyone expected. Mr. Kouvalis, Mr. Ford's former chief of staff, had played the mayor in debate rehearsals, but he hadn't prepped Mr. Tory for what unfolded that night. During a commercial break, the team tried to give their candidate pointers and Mr. Tory expressed his dissatisfaction to a floor director over camera angles.

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"It was a tougher evening for us than we would have liked," Mr. Richardson said.

At the following night's debate, Mr. Tory had some freshly written lines about the mayor's behaviour in his opening remarks.

On April 30, Mr. Ford surprised them for a second time.

That night, The Globe and Mail reported the existence of a second video allegedly showing the mayor smoking crack cocaine. Around the same time, the Toronto Sun reported that Mr. Ford had been recorded ranting and swearing in a bar. Just hours later, the mayor issued a statement: He was going to rehab.

The Tory campaign was stunned. They had expected the mayor's behaviour might continue through the race, but not this.

Within 10 minutes, they had convened a meeting. "There was a debate, and some people said we should be cautious here – this is a guy with a health issue," Mr. Mraz said. "But the majority of us believed that we needed to call on him to resign." That same night, the campaign issued a press release doing just that.

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Ms. Chow's support continued to dwindle throughout the summer, but in mid-August came a major misstep: a tweet from war-room director Warren Kinsella asking: "Is John Tory's Smart Track, you know, Segregationist Track?"

"I thought to myself, 'that's outrageous,'" said Mr. Mraz. He pointed the tweet out to Mr. Allison, and shortly after, to Mr. Kouvalis. "It was clear to everybody that if we let it stand, it would always stand," he said.

"We needed John to respond to this with someone who's got credibility in the community, who could never be accused of supporting a racist," he said. So he called former boxer Spider Jones. The next day, Mr. Jones appeared at Mr. Tory's side at a news conference. "If John Tory's a racist then I'm the grand wizard of the Ku Klux Klan," Mr. Jones said.

Although Ms. Chow later denounced the comment and tried to paint Mr. Kinsella as a rogue volunteer, the incident had a lasting effect, Mr. Mraz said.

"I think it demonstrated to people that Olivia Chow's campaign was prepared to drag Toronto into a conversation about race and gender and class warfare that would've been no different than the conversation we'd been having about elites and suburbs and downtown," he said. "Torontonians were sick of being divided."

While the mayor was away in rehab, and all eyes were on the provincial election, Mr. Tory took a gamble, introducing the centre piece of the campaign, the SmartTrack plan. The "surface subway" proposal hinged on a Liberal victory because it required the electrification of GO rail lines. If Kathleen Wynne had lost power, the campaign's main plank would have been on the ropes. "It was, without a doubt, a critical moment in the campaign," Mr. Richardson said.

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Then on Sept. 10, as polls showed Mr. Tory with a commanding lead, came the biggest turn of events. On that rainy Wednesday, the mayor was nowhere to be found at City Hall. At 6:18 p.m., a press release was issued: Rob Ford had been hospitalized with a suspected tumour.

Unlike Ms. Chow, who held a hastily-arranged news conference from her home, Mr. Tory hung back, opting instead for a short statement offering the mayor his best wishes.

But two days later, when the Fords followed up with more stunning news – the mayor was dropping out of the race and brother Doug running in his place – Mr. Tory expressed his condolences to the Ford family, but came out swinging against Doug.

"I don't think Doug Ford offers four more years of the same," he told reporters. "In fact, he may offer Toronto something that is worse."

Advisers say it took some convincing to get Mr. Tory to deliver that line, including a call from Mr. Kouvalis, who was in Windsor for the weekend to see his family. Mr. Tory watched Ms. Chow express only sympathy for the Ford family and he wanted to do the same. Advisers told him to act quickly to present himself as the alternative to the new rival.

"Much was made of that – should we not give the grieving brother Doug some space and room?" said Mr. Mraz. But "the minute you pick up a sword, you're on the field."

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Publicly, the Tory campaign called the bombastic Doug Ford the easier brother to beat. But quietly, there were some concerns. Their internal polling had always showed Doug as less popular, but none of that polling accommodated for Rob being diagnosed with cancer and Doug carrying the torch.

They also worried about spending. They had held back the majority of their spending for the end, but still, they worried about Doug's ability to spend up to the full $1.3-million limit with just six weeks left in the race.

Going into election day, there were also fears that Tory voters might not show up at the polls if they felt the race was a foregone conclusion. There were also worries that polls had inflated Mr. Tory's support because of voters embarrassed to admit they were voting for a Ford.

That night, Mr. Tory took in the results with his family in a private room at the Liberty Grand, one flight of stairs up from the ballroom where his supporters were gathered.

At 8:14 p.m., the first results began trickling in on the news broadcasts. Mr. Tory was leading – but just barely. Five minutes later, Mr. Tory was still leading with more than 200,000 votes – but Mr. Ford was right at his heels, with 180,000.

"It was a lot closer in the very beginning than most of us thought," said Chris Eby, the campaign's director of communications who has since been named the mayor-elect's chief of staff.

Mr. Tory was reassured by his brother Michael, who told him that the polls that hadn't yet reported would likely turn up strong numbers for him. "That'll open up a significant gap," Michael said.

At about 8:25 p.m., most networks declared Mr. Tory the winner. He took about 40 per cent of the vote, falling short of his team's 50 per cent target and he did not win all four parts of the city, as the campaign had hoped. But it was enough.

Mr. Tory had tears in his eyes, Mr. Eby said.

His expression? "Incredible happiness. And relief."

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