Kevin O'Leary's campaign got rolling over lunch

How the reality TV star shifted from flirting with a Tory leadership bid to organizing the real deal

When Kevin O’Leary popped up on Facebook late last week to nearly, almost, not quite declare his bid for the federal Conservative leadership, close watchers of Canadian politics must have been thinking, “Get on with it, Mr. Wonderful!” After all, O’Leary, celebrity investor and TV personality, has been flirting shamelessly with Tories for about a year, going back at least to his appearance last February at the Manning Centre Conference, an annual Ottawa gathering of right-wingers, where he headlined a session bluntly billed as, “If I run, here’s how I’d do it.”

Despite O’Leary’s undisguised interest in the job, though, he appears to have been seriously assembling a campaign organization for only a few weeks. The key meeting to start that process in earnest happened on Dec. 5 at Toronto’s Nota Bene restaurant. O’Leary met at the noted Queen Street business power-lunch venue with Mike Coates, a longstanding party insider, whose past roles ranged from raising money for Brian Mulroney to helping Stephen Harper prepare for election debates.

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Coates was returning to Canada after three years in New York, where he had been working as Hill and Knowlton Strategies’ Americas president and chief executive. Retiring to a less demanding vice-chairman’s role at the global consulting company, Coates was ready for a new Canadian political project. So when O’Leary called him in late November, Coates was primed to hear him out. Over lunch at Nota Bene, he agreed to chair a campaign “exploratory committee.”

In short order, partly on Coates’s advice, O’Leary signed up two key young operatives, sending a signal to party insiders that he wasn’t fooling around. Chris Rougier, a former federal Conservative staffer, viewed as among the party’s top Harper-era experts on data and voter-contact techniques, came aboard as campaign manager, assuming O’Leary takes the plunge. Andrew Boddington, who has worked in both the federal and Ontario Tory wings, including managing the failed provincial leadership bid of Christine Elliott, signed up to help craft O’Leary’s message.

In an interview, however, Coates admitted that O’Leary, who is expected to formally announce his candidacy any day now, has left it late. To be eligible to cast a ballot for Harper’s successor in May, voters must be signed up as Conservative party members by March 28. “Nobody else could do it,” Coates said when asked about the timing. “Only somebody with a brand like Kevin’s, with as much presence in social media as he has, and in traditional media, could do it this late in the day.”

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Along with betting on O’Leary’s ability to run a social-media-fuelled sprint to the leadership finish line, his backers see him tapping into the moment’s yearning for unconventional politicians. He is, of course, a former star of CBC’s Dragons’ Den and ABC’s Shark Tank, both shows on which real investors vet the business ideas of aspiring entrepreneurs. As a real-world venture capitalist, he heads O’Leary Financial Group.

He lacks any real political experience, though. Still, former senator Marjory LeBreton, a mainstream Tory stretching back to John Diefenbaker’s leadership in the 1960s, joined his exploratory committee. LeBreton met with O’Leary for about an hour in early December, on Coates’s urging, and says he impressed her as a moderate with a firm focus on economic policy, especially spending discipline. As well, he promised not to disparage other leadership candidates—a strict condition for LeBreton, who views in-fighting as a cardinal political sin.

And then there’s the Donald Trump factor. O’Leary’s credentials as a reality-TV star coming as an outsider to politics inevitably invites the Trump comparison. But LeBreton said he assured her he would not be unleashing Trumpian attacks on particular segments of Canadian society. “I don’t think you’ll ever see Kevin O’Leary personally insulting people or saying things that are very unkind about certain groups of people,” she said. “I just don’t believe you’ll ever hear that.”

Listen to John Geddes in conversation with Marjory LeBreton

Coates also addressed the Trump parallels. He said he sees a similarity in the appeal of a newcomer who talks like a TV star, not a traditional politician. “I think people are tired of the same old blah-blah, and they’re looking for something different, something out of the box, and they’re looking for someone that’s not a career politician,” he said. But he added that O’Leary’s core policy prescription bears no resemblance to Trump’s winning presidential positioning. “Kevin is pro-trade, he’s written in his books that globalization is the way of the future. He’s definitely not a protectionist,” Coates said. “He’s not going to be engaging in identity politics.”

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All that still leaves at least one big nagging question: Can O’Leary seriously contend without being able to speak French? Supporters of his leadership rivals suspect he has left his launch so late largely to avoid having to take part in this week’s French-language debate in Quebec City. Both Coates and LeBreton said O’Leary has assured them he is serious about learning French. Indeed, he has recently switched from saying speaking French isn’t essential to promising to be proficient by the time of the 2019 federal election.

It seems at least some traditional qualifications for becoming prime minister—even in era of politics that assigns enormous value to reality-TV skills and social-media reach—can’t entirely be brushed aside.

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