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Ryerson journalism alumnus and former Eyeopener editor-in-chief Robyn Doolittle is at the centre of one of the largest stories in Toronto’s history. Features editor Sean Wetselaar got the details of her life, Ford and the future

Over a decade ago, in rural Forest, Ont., Robyn Doolittle walked into her Grade 11 English class ready to pick a fight. She was wearing a winter hat – contrary to her school’s dress code – because she’d been told that women were allowed to wear hats indoors. Her teacher asked her to remove her hat, and jokingly told her that women could only wear them inside if they had matching gloves.

Doolittle showed up the next day, gloves in hand.

When her teacher once again asked her to take off her hat, she held up her gloves. “He was like, ‘Why are you doing that?’ And I didn’t really have a good answer,” Doolittle says. “I like to poke things, I guess.”

It’s been more than 10 years since the glove incident and Robyn Doolittle, now a reporter for the Toronto Star, is still poking things.

They’ve just gotten a little bit bigger.

Instead of her high school teachers, her sights are now on the leader of the largest city in the country.

Doolittle’s coverage of Toronto Mayor Rob Ford began in earnest when the Toronto Star moved her from the crime beat to cover city hall in January 2010, just before the mayoral elections. She was initially hesitant about the move, which she thought would be “the most boring transfer ever” and wondered if she was being punished despite her editor’s assurance that it would be an exciting experience.

“And this is exactly the kind of stuff you tell someone when you’re handing them a story about a food drive or, you know, a pet fashion show,” she says.

The first 10 months of her new position was focused on the mayoral election, which Doolittle says became fascinating after Ford entered the race.

“He had so many blunders on his record that would have disqualified so many other politicians from continuing to pursue higher office,” she says. “And he’s not only running, he’s winning.”

After Ford was elected in October 2010, Doolittle and the Star continued to press for stories about the strangely popular mayor who refused to be interviewed by the paper that he would later call out for having a “vendetta” against him. A number of gaffes including public drunkeness and domestic disputes would lead Doolittle to pen a story in December 2011 about a series of 911 calls made from the Ford home. By March 17, 2012, St. Patrick’s Day, she started to receive tips about an incident involving the mayor that had taken place at The Esplanade’s Bier Markt, a popular downtown bar.

Doolittle’s file on Ford grew bigger and bigger. By March this year, after Ford was asked to leave the Garrison Ball, a military ball featuring a number of prominent local figures, and Doolittle ran a story breaking down the mayor’s alleged substance abuse. “And then about a week later someone phoned and said, ‘I have a video that you should see,'” Doolittle says.

Doolittle and the Star’s investigations editor Kevin Donovan’s story about a video being shopped around the city of the mayor appearing to smoke crack cocaine while making homophobic and racial slurs divided the city and spawned truckloads of outrage.

Despite the firestorm of criticism that followed the story, Ford continued to deny the video’s existence, noting, “I cannot comment on a video that I have never seen or does not exist.” It was one of the largest stories in Toronto’s recent history, and Doolittle was right in the middle of it.

Journalism was a backup plan for Doolittle, who had never considered a career in reporting.

Instead her aspirations were on the stage. When the time came to consider prospective universities, she chose Ryerson for its theatre program but she decided to also look at journalism. Just in case.

In order to fulfill portfolio requirements, Doolittle had to get published examples of work. She turned to her local paper, and eventually to the Sarnia Observer, where she asked for a meeting with the editor-in-chief and got it – along with a column in the newly minted teen page.

“I wrote a lot of stupid things,” Doolittle says. “I think there was something like a take down of Britney Spears, which is kind of ridiculous because I love Britney Spears. I was just trying to be contrarian.”

Somehow, though, Doolittle found herself falling in love with journalism, a career she’d never envisioned for herself. She’d grown up questioning rules and authority and finally she’d found a career that would not just let her do it, but encouraged it. When she finally applied to schools, she didn’t apply to Ryerson’s theatre program – just journalism. She would go on to work at The Eyeopener for three years, including a year as editor-in-chief, and take a series of internships at the Star, which eventually led to a full-time job.

“Suddenly it was like it all clicked. This is what I want to do,” she says. “All the characteristics of wanting to poke things and wanting to challenge things.”

Thursday, Oct. 31, a throng of reporters were clustered in the Toronto Star newsroom, crowded around a television monitor tuned to CP24. Police chief Bill Blair had just announced that Toronto police were in possession of a video that matched the Star’s description Thursday.

The video was reconstructed from a hard drive seized in connection with Project Traveller, a massive string of police raids in drug-related crimes in June. Alexander “Sandro” Lisi, a friend of Ford’s and occasional driver, was also charged with extortion for allegedly attempting to recover the video. Lisi had been previously arrested on alleged drug dealing.

“I think that Blair coming forward and saying he has the video was a victory for journalism,” Doolittle says. “The Fords, to defend themselves, have put reporters on trial, put journalists on trial … and so now that it’s been proven that we’re not making this stuff up, I hope that people will take a step back and consider how important this kind of reporting is.”

Sunday, Nov. 3, Rob and Doug Ford settle into their chairs in the Newstalk 1010 studio at the set of their regular radio show The City. The mayor was expected to make an announcement following the announcement by Blair. Rob wastes no time.

“I’m the first one to admit I’m not perfect,” he says, following a brief opening in which he calls for the release of the video – though the police have said the evidence is before the courts. “I have made mistakes. I have made mistakes and all I can do right now is apologize for the mistakes. I sincerely, sincerely apologize.”

Huddled outside the studio, in the throng of reporters waiting to speak to the Fords after the show, Doolittle continues to doggedly follow the story she helped to break. She, like many other reporters in the city, hopes to get a response out of the Ford brothers after they exit the studio. But despite promises to arrange meetings with the media if asked, the Fords buzz past the media, making no further statements.

It’s an iconic moment for the Ford scandal, though. For the first time since the story broke, Ford did not outright deny substance abuse, instead apologizing frequently throughout the show for his “mistakes.” Doolittle says she does not feel vindicated, but it’s hard to miss a hint of pride in her voice.

“Kevin and I have always known we were right all along,” she says. “So it’s not so much vindication. But it was obviously a really good day when we learned that the people in Toronto might get a chance to see this video.”

Though Ford’s approval rating actually went up five points after Blair’s announcement, Doolittle says her sources on the mayor’s team have confided in the past that it would be very difficult to re-elect the mayor if the video does become public.

“I think certainly his chances at re-election, it would stand to reason, [are lower],” Doolittle says. “Certainly there is a vulnerability now.”

Around noon Tuesday, Rob Ford finds himself facing a now all-to familiar spectacle – a scrum of frantic reporters outside his office. Ford looks and sounds troubled, more than usual.

Then, he asks reporters to ask him the question they’d first asked him in May.

“Yes, I have smoked crack cocaine,” Ford says. He stresses that he is not an addict, but, “Have I tried it? Probably in one of my drunken stupours, probably about a year ago … Yes, I’ve made mistakes. All I can do now is apologize and move on.”

There’s a frenzy of questions, of flashes, but Ford doesn’t have much else to say. Soon, he retreats back into his office, amid shouts from the shellshocked media.

It hasn’t been an easy road to get to this point for Doolittle. Following enormous backlash from the crack scandal, she was placed under immense pressure by swarms of supporters from Ford Nation.

“I think it’s safe to say that over the last six months, it’s been challenging for sure,” she says. “And I’m not complaining because a big part of it comes with the job. I guess it would be accurate to say I’ve received hundreds and hundreds of letters of hate mail.”

One such letter, artfully crafted on a small note adorned with a red cardinal in carefully-printed cursive has, in an ironic twist of fate, been framed by Doolittle. She thought it was beautiful despite its message, which included the words, “How do you sleep at night?” The criticism Doolittle takes the most to heart, she says, are attacks based on her gender and appearance.

A column in the Huffington Post by Mark Hasiuk published shortly after the crack story broke made careful note of Doolittle’s “alabaster skin” and, she says, it strived to discredit her based on her appearance rather than her work. It also made no mention of Donovan’s role in the story.

“The one thing that really bothers me [are these attacks],” Doolittle says. “And that is when it gets very challenging to; that’s when it’s difficult to not get angry … It’s not like it’s hurting my feelings. I just, I get angry. I get angry that that opinion is so prevalent.”

Doolittle has spent four and a-half years at city hall, and though she plans to stay there through the October 2014 elections, she admits that she wouldn’t be opposed to a change of scenery.

“I have no idea [what’s next], to be honest,” she says. “I think it’s good to not start being there as long as the wallpaper.”

Doolittle, a woman who initially did not even want to pursue journalism, continues to live without concrete plans. But given her track record, it’s safe to say that she’ll continue to poke things for the foreseeable future.