As John Tory made his way out of a Bloor West Village press conference one recent Saturday morning, his spokeswoman Amanda Galbraith pulled him aside to deliver some bad news.
Like every weekend since he entered the mayoral race eight months ago, Mr. Tory's day was packed with appearances, and until that point, everything had gone smoothly.
But standing a few feet from the crowd, they spoke in hushed tones. The night before, he'd wrongly claimed that he hadn't donated money to the campaign of rival Doug Ford four years ago. Now, another rival, Olivia Chow, was calling him on it
"I was wrong – that I donated to Doug's campaign?" Mr. Tory said, irritation creeping into his voice. "I mean, who gives a shit?"
He remained annoyed even after speaking again with reporters. "I mean, so what?" he said as he walked away toward the car. "So what?" he repeated again a few minutes later, on the phone with strategist Nick Kouvalis. "Is that the best she can come up with?"
It's understandable if Mr. Tory is tenser than usual. With just a few weeks left in what has already been a gruelling campaign, he has managed to maintain a comfortable lead in the majority of recent polls – and increasingly under attack by his rivals.
And, after a string of political defeats – losing the mayoral race in 2003, a provincial by-election win in 2005 quickly followed by losses in 2007 and 2009 – Mr. Tory is poised, for the first time in almost a decade, for victory on election night.
The Globe spoke with more than 20 people who have worked with him throughout his career at Rogers Communications Inc., the Canadian Football League, and Queen's Park for insight on what kind of a mayor Mr. Tory might make. Some paint a picture of a leader ideally suited for City Hall: an executive with experience in turning around tough situations and a talent for bringing people together – like he did in keeping the CFL afloat. But at a time when City Hall remains deeply divided and under extreme scrutiny, others speak of a man who has trouble dealing with criticism, who lacks experience and has a tendency to micro-manage.
But in the car that Saturday, Mr. Tory said he was confident he could do the job.
"I know how to be a leader, and the job is to be a leader," he said that Saturday in the car.
He paused for just a second. "Do I know how to be a leader? The answer is yes."
Despite describing his upbringing as "normal," Mr. Tory also happens to come from one of the most well-connected families in the city, with ties to some of Canada's most powerful institutions.
His late father, lawyer John A. Tory, was a trusted adviser to the late Kenneth Thomson, whose Woodbridge Co. Ltd. is majority owner of The Globe and Mail. And the senior Mr. Tory's father founded prominent law firm Torys LLP.
But his family instilled in him the importance of public service from an early age, Mr. Tory said, with Christmases spent delivering meals to the needy, and other regular volunteer work. "We were told that we were fortunate to be in a fortunate kind of upbringing."
By 14, Mr. Tory was a card-carrying member of the provincial Progressive Conservative party working on political campaigns – a job he would continue through Osgoode Hall Law School.
After rising to managing partner at Torys, and politically, as principal secretary to former premier Bill Davis, Mr. Tory was asked in 1995 by family friend Ted Rogers to run Rogers Media. The ties between the two families run deep. Mr. Tory's father was a long-time friend and adviser of Mr. Rogers, who himself articled at the Torys law firm before launching into the broadcasting business.
Mr. Tory's arrival at Rogers was timed the year after the company executed a hostile takeover of Maclean-Hunter. "I was sent in to bring these companies together and to cause them to sort of form one united team," he said.
Several of his colleagues at Rogers say he was well-liked by employees, and adept at dealing with the hard-driving Ted Rogers, who died in 2008.
"So he gets everybody onside. He's not a polarizer. He doesn't go out of his way to make you mad. He doesn't go out of his way to prove he's smarter," said David Peterson, the former Ontario premier who sits on the Rogers board. Mr. Tory acted as "peacemaker" between the Rogers family, the company's other shareholders and its directors, he said.
By 1999, Mr. Tory was promoted to CEO of Rogers' cable division, the heart of the business.
But at least one former senior insider says that Mr. Tory was distracted during his time, and that many of the big decisions were being made by Mr. Rogers and his long-time right-hand man, Phil Lind. The former insider, who would only speak to The Globe on the condition of anonymity, also said Mr. Tory had designs on Mr. Rogers' position at the helm of the parent company.
"He sort of kept the ship going," the source said of Mr. Tory. He said Mr. Tory was busy at the same time with charity work and an eye on politics: "He was never 100 per cent committed to being in there, rolling up his sleeves and running the business."
Mr. Tory denied this, pointing out that revenue rose steadily during his tenure, with new products, such as video-on-demand, introduced in that time. He added that much of his charity and political work was done outside office hours.
He acknowledges that he would have liked the top job at Rogers, but said the real reason he left in 2003 was to pursue politics.
"He was never going to give up the reins," Mr. Tory said of Mr. Rogers. "So in that sense, you might have said 'you'd take his job if it was offered,' but it was fairly clear to me that it wasn't going to be available."
At the same time he was running Rogers, Mr. Tory was also cleaning up a mess at the CFL.
"I had to keep it alive. It was bankrupt," he said of his role as chair, then volunteer commissioner of the league. After years of declining revenues, and a failed expansion in the United States, several teams found themselves on the verge of bankruptcy.
Some owners' spending – including on player salaries – was "just outrageous and ridiculous," said former league president Jeff Giles, and Mr. Tory helped convince them that those types of decisions disrupted the salary structure for the entire league. "They were all seeing the challenge through their own lenses. What I remember was John's ability to focus on the common goal," Mr. Giles said.
Later, as leader of the Progressive Conservatives at Queen's Park, he exercised those same skills working with a party deep in debt, and caucus members who owed little to the new leader.
"It's a group of caucus members that will win their seats almost no matter what they do," said Brendan Howe, Mr. Tory's press secretary at the time. "There was no pull that you have to try and get them to fall in line."
To counter this, Mr. Tory spent much of his time travelling to members' ridings, listening to their concerns, and became known for personally calling every member of caucus every Christmas Eve to wish them a Merry Christmas.
But Bill Murdoch, who was kicked out of caucus by Mr. Tory after speaking out against Mr. Tory's promise in 2007 to extend public funding to all Ontario faith-based schools, attributes the "bone-headed decision" to his political inexperience – and warned it could be his downfall this time, too.
Mr. Tory's faith-based schools decision was widely unpopular among the public, and a misstep that would ultimately lose him the election. He also made the gamble to run in the Toronto riding of Don Valley West against then-popular minister Kathleen Wynne – a decision he defends as based on principle, but left him without a seat after he lost.
Two years later, Mr. Tory lost another by-election, after Laurie Scott stepped aside in Haliburton-Kawartha Lakes-Brock, and he resigned as party leader.
"I think it really helps an MPP or an MP to be in municipal politics and stuff like that to work your way up," Mr. Murdoch said. With the decision to stick to the faith-based funding issue despite it being unpopular – and then to kick him out of caucus – Mr. Murdoch said, "he was trying to prove a point, that he was a boss."
Others say Mr. Tory was simply sticking to previously-made promises. "I think John has a kind of commitment to principle that outweighs in some respect political consideration," said former MPP and now-senator Bob Runciman.
Still, Mr. Murdoch believes Mr. Tory would do a good job as mayor.
By 10:30 a.m., Mr. Tory is headed to his third event of the day, a giant Eid Festival celebration at the Direct Energy Centre.
On his way in, he shakes hands and greets people – many of them he knows by name through his work in the community. "I'm not showing any disrespect by walking around while they're praying?" he asks a volunteer, who shakes his head no.
He makes his way into a reception area where he was set to give a speech, and standing inside was Premier Kathleen Wynne – also there to speak.
Ms. Wynne was careful to say that she's not endorsing any candidate, but described Mr. Tory as a "friend."
"He ran against me," she says, chuckling, when asked about running against Mr. Tory in 2007. She says she has since used the race as an example to show staffers "how I believe people need to relate to each other. We had a respectful campaign and we came out friends at the end."
But others said that Mr. Tory might face a tough transition at City Hall.
He wakes up at 5 a.m. every morning, and has been known to arrive at work as early as 6 a.m., leaving staffers scrambling to unlock the doors. He described himself as a "demanding" boss – "but at the same time, very encouraging." And the bureaucracy at City Hall could prove frustrating for him, given a leadership style that several staffers – at least when it comes to campaigning – describe as micro-managing.
"A normal candidate might not necessarily want to know how many signs have been ordered, are they at the stations, did we get this length of the wood of the stick, how are we pounding them into the ground, and all that sort of stuff," said a member of his campaign team – one of several members to speak with The Globe on the condition that their names be withheld.
Mr. Tory acknowledged that he can be a micro-manager, but said it's only because he has worked on so many campaigns in the past. "I've done it, and that unfortunately creates a history in your head."
And if elected, Mr. Tory's every move will be dissected, and subject to fierce criticism – something that two members of his campaign say he can be prickly about. "I think he's developed more alligator skin – tougher skin than he had before, but I think it's a fair point that he can take some of these things too personally," said the member of his campaign team.
Onstage in debates, he does his best to show he has the stomach for the rough and tumble exchanges – fending off the boisterous Doug Ford, who charges him with being an out-of-touch elite, with quips of his own. But he clearly does not relish it.
"It's very different from 2003," he says of the tenor of this race. "David Miller and I … we had disagreements on issues, but it was entirely respectful. Entirely respectful."
His mother, meanwhile, has stopped watching the debates. "She'd call me – she's 82 – and ask 'why is he saying that? If your father saw that, he'd be upset.'"
Mr. Tory himself acknowledged that he doesn't like criticism, but said he wasn't alone on this.
"I just think oftentimes politicians aren't honest when they say 'none of that stuff bothers me,'" he said. "What human being would wake up to the newspaper in the morning, read some column containing some stuff that is diminishing your career personally, and not be concerned by that?"
The solution, he said, is "much of the time, I just don't bother to read it."
Later, he was asked about a recent article describing his past political defeats. "I think they described it as having gone through the 'valley of hell?'" a reporter asked him.
Without missing a beat, he corrected her: "The valley of defeat."