IN THE TORY HOMESTRETCH
Liberals look on as race wraps
As the Conservative Party convenes in Toronto this weekend to choose its new leader, the person many thought the most likely to win will instead be where he is most comfortable: sitting on a media panel, performing for the cameras.
Kevin O’Leary was the frontrunner in the race to succeed Stephen Harper. Victory was within reach when, just weeks before the convention and with ballots with his name on them already arriving in voters’ mailboxes, he made the sudden decision to pull out of the race. As the person who chaired Kevin’s campaign, I’ve had more than a few questions about happened. It came down to one thing: he was never fully committed.
My journey with O’Leary began with a brief phone call at the end of November. I had never met the business man turned-reality-TV-star, but after months of rumours about his candidacy — rumours he happily fuelled — Kevin was now looking for someone to actually lead his campaign. A mutual friend had passed along my name. “Will you be my guy?” It made me laugh, because it sounded like he was asking for a date. I suggested we should meet first.
Having spent a lifetime in Tory politics, I was returning to Canada from New York after running the Americas region for the global public relations firm H+K Strategies. I had watched the Trump phenomenon unfold firsthand, and had met enough of the U.S. political establishment to wonder whether Canada was ripe for a similar change.
So I took the meeting. And liked the guy. Politically green, he was insightful about how to make an impact on public opinion, with a good strategic mind and a willingness to learn the political side of things. He also had some strong views on how he could leverage his media profile for the advantage of the party. “There has never been a candidate like me,” he’d say, and he was right.
The strange candidacy of Kevin O’Leary was rooted in the most basic Opposition responsibility — to present a true alternative to the party in power at a general election. Well, O’Leary was certainly different. A brilliant communicator who didn’t know the meaning of subtlety, he had both high name recognition and a successful business career in Canada and in the United States. Image is of course huge in politics. It had already worked in the U.S., why couldn’t it work in Canada?
Liberal elites are fond of saying that Canada is different from the United States, and in many ways it is. But that ignores the fact that the same forces working to undermine the status quo in the U.S. are also at work here.
Canadian labour force participation rates are at their lowest level in decades. Men in particular have seen participation rates fall off dramatically as blue-collar jobs in the manufacturing and natural resources sectors have declined since the 2008 recession. Meanwhile, falling birthrates mean Canada needs an increasing number of skilled immigrants, many of whom move to parts of the country where housing costs are already high, helping to keep housing out of reach for a growing number of Canadians.
Midway through the leadership campaign, new data published by Edelman, the world’s largest public relations agency showed that Canadians’ trust in government had eroded profoundly since Justin Trudeau became prime minister just 15 months earlier. Canada is now in the category of nations who distrust their institutions, the first time this has happened in 17 years.
The same cocktail of discontent that brought Donald Trump to power is brewing here in Canada, and it only needs a voice to give it the attention it deserves. O’Leary could have been that voice, even though he had only a superficial understanding of the forces that would have allowed it to happen.
From my first meeting with him on December 3, the campaign went from a standing start to a fully functioning operation by mid-February. He formally entered the race on January 17. We were able to recruit experienced and respected organizers — the likes of Chris Rougier, who became O’Leary’s campaign manager, and Andrew Boddington, our senior policy and communications strategist. O’Leary also attracted the support of longtime party stalwarts such as Mike Harris and Marjory LeBreton, giving him immediate party credibility. Money came in quickly.
Much of the Conservative rank-and-file remained skeptical, however. “I’m leery of O’Leary,” said longtime Conservative supporter Nancy McFadden, which pretty much summed up the view of half the party. According to the campaign’s independent research, 45 per cent of members initially ranked him at or near the bottom of the 14 candidates vying for the leadership. Once we toned down his bluster Conservatives became more comfortable with him. The number of party members for whom he ranked in the bottom tier dropped from 45 per cent to nearly 30. Though still high, every scenario that we modelled quantitatively suggested it was good enough for him to win the leadership, especially given the extent to which O’Leary was able to outstrip the other candidates in sales of new membership sales during the limited time he was in the race.
That success in selling memberships means he would have been even stronger had he entered the race sooner. Pundits have pointed to his late entry as a sign he wasn’t serious about winning. It’s a valid point.
But O’Leary understood that timing is everything and believed waiting until the last minute would have the maximum impact on a dull race. And when he officially entered the race, he rose to the top of the polls almost immediately.
Even O’Leary’s driest policies were delivered with his customary bluster, to ensure maximum media coverage. “All media is good,” he’d say — including the time he spent on U.S. television during the campaign, though it underscored the impression that he wasn’t all-in on a career in politics.
Those questions about his commitment were amplified by his failure to appear at many of the party’s debates. Contrary to what most believe, O’Leary’s spotty debate attendance had little to do with his lack of bilingualism. He was a quick study in French. He was never going to be able to carry out a conversation by the end of the campaign, but he was able to muster enough to satisfy most members he met that he was serious about learning the language. O’Leary real issue with the debates was that no one was watching them. It required a lot of preparation and travel and expense to participate in events the networks weren’t interested in and at which even the live audience struggled to stay awake. “I don’t do bad TV,” he’d say.
But if O’Leary made such an impact on the campaign, why did he pull out just before the moment of truth?
Something about politics clearly appealed to him. After a meeting with the Conservative caucus on Parliament Hill in early December, he told me he felt people were treating him differently — that he was no longer just a celebrity, but an emerging leader.
But while a lot of party members got what O’Leary represented, he never quite got the party. As the campaign moved from membership sales into the persuasion phase, we expected him to focus his efforts on the small list of 200,000-plus paid-up party members who would be eligible to vote for the leadership. O’Leary, though, grew increasingly frustrated at the inefficiency of meeting those members after spending months communicating with the entire country via social and traditional media.
At the end of March, tired and worn down with the flu, facing a brutal schedule in which he tried to continue his business commitments and accommodate an aggressive campaign tour, O’Leary’s mood boiled over. “I’m not going to the Maritimes again!” he told his team. “Let’s focus on social media.”
Social media was effective for some things, but it couldn’t replace retail politics when we were trying to influence the party members who were used to having a relationship with their leadership. In any event, half the voting members weren’t even on Facebook, and O’Leary’s late entry had made it more difficult to establish the relationships other candidates had been building for years.
As the campaign wore on, O’Leary grew increasingly nervous about the outcome. He started raising myriad concerns about what would happen if we won, including the polarizing effect he’d had on the party or his weakness in Québec. “You know,” he would say, “the party really doesn’t like me.” Or “The caucus is really going to be a problem.” Or ”I’m never going to win in Quebec in the general election.” Our answer was that he would build a relationship with the party and the caucus over time, and we reminded him that when Stephen Harper was first elected he barely spoke French.
But these arguments held little sway for an entrepreneur used to getting his own way. Early in the campaign, after I chewed him out for an embarrassing tweet showing him firing an automatic weapon at a U.S. gun range, he told me that he wasn’t used to someone “managing my brand” and that he didn’t like it.
The idea of spending the next two years building relationships in communities across Canada frustrated him. He envisioned himself using his celebrity status to promote the party while also keeping his business interests going, selling them or putting them in an arm’s-length trust once he was elected to office.
He lacked focus in part because he was keeping his options open.
Reality struck home for O’Leary towards the end of April when he and his wife Linda were the subject of abuse at an event in Toronto. “You’re the f----- who’s going to destroy Canada,” someone yelled from the crowd. Being a celebrity is easy. Being a politician can bring fame, but it also brings abuse. O’Leary didn’t like that.
His true feelings came to a head less than a week before he pulled the plug on his candidacy. Over a couple of beers, he expressed concern about how his life would change if he won how his family unity would be tested, and about the business opportunities he would lose. He mused aloud as to whether there was a way he could stay in the race but find a way to avoid winning, and to come a close second.
Those of us leading his campaign were stunned.
By now it was clear to us that he was going to win. We gave him two options: either he would commit to being all-in through to the general election in 2019, or he should exit the race and throw his weight behind another candidate. The nightmare scenario, which seemed all too plausible: if O’Leary didn’t pull out while he still could, he might succeed in winning the leadership but then bolt back to his business and TV career, badly embarrassing the party before we even got the chance to fight an election against Trudeau.
We held our breath over the weekend as O’Leary consulted with Linda. Then he returned to us with his answer. I thought I had seen it all in politics, but this was a first: the leading candidate deciding to drop out of the race.
Having made the difficult choice to withdraw, opting to support Maxime Bernier was easy. The truth is, he had toyed with supporting Bernier last year when he hosted the Quebec MP at his Muskoka cottage. The two are aligned on most policies, but O’Leary was bolder in the way he communicated. While O’Leary gave voice to the 83 per cent of Canadians who are not bilingual, and who resent being told by the media and political elites that this disqualifies them from high office, reality also hit home on the importance of speaking more than just the language of jobs to French Canada. And all of our voter identification and political research indicated that more than half of our supporters preferred Bernier on a second ballot. And if O’Leary couldn’t be prime minister, he at least wanted to be kingmaker.
So was our frantic five months with O’Leary a waste of time? Was his candidacy a distraction from the race? I don’t think so.
An Ipsos poll in January had shown that O’Leary had the best chance of beating Trudeau. And while his organizers always knew there was risk in an O’Leary candidacy, with risk goes reward.
Indeed, O’Leary made the leadership race. He disrupted the campaign and forced all the other candidates to be bolder in their policy and communications. Candidates began adopting more effective social media as a tool for raising money and recruiting supporters, and they began to open the door on unconventional policy options about how we should govern this country.
Going public with concerns about fake membership helped ensure the party’s next leader would be chosen in a clear, untainted process.
But most of all, O’Leary showed the party what it would take to win over millennials, women, new Canadians and the LGBTQ community. Maybe some in the party didn’t like him for it, but activists know that the path to the victory in a general election won’t lead through a narrow definition of conservatism.
I hope O’Leary stays involved along the way to that general election. He has talked about running in the Toronto riding of Rosedale, but I’m not banking on it. Much of what O’Leary says is for effect.
Whatever his choice, a singleminded focus on defeating Trudeau must be front and centre for the Conservative Party, which could benefit from using O’Leary’s communication skills to promote policy, raise funds and recruit new members, and learn from his willingness to abandon the party’s disdain for the media and accept it as an important vehicle to get out our message.
It’s often said that being the Leader of the Opposition is the worst job in Ottawa. You have to commit to the rubber-chicken circuit as you crisscross the country, all while placating a lot of very high-maintenance MPs. O’Leary would dismiss that as doing politics the old school way, arguing that a focus on traditional and social media is the modern way of winning.
The truth is, you need both. O’Leary was unwilling to do both.
I’m sure we haven’t seen the last of Kevin O’Leary, but now we need a Conservative leader who is committed to putting in the hard work required to give a voice to the millions of Canadians who feel they are not being represented in government. That is the big missed opportunity in Kevin O’Leary’s aborted candidacy. It is up to Maxime Bernier, or whoever wins tonight, to pick up the mantle and be the voice for so many of these Canadians.