If Kevin O’Leary has his way, Donald Trump won’t be the only public official who won power as a businessman-turned-reality TV star. 
From the set of ABC’s Shark Tank — produced by Mark Burnett, who also brought Trump to the small screen with The Apprentice — O’Leary hopes to wage a campaign to bring his brusque ‘shark tank’ mindset to Canadian politics, first to the Conservative Party, then by bringing the fight to current prime minister Justin Trudeau’s Liberal government.
Unlike Trump, however, O’Leary will at least be able to say that he’s won an Emmy.
After months of consideration, O’Leary three weeks ago entered the crowded race to lead the Tories. So far, he’s a shark who is making a splash.
O’Leary, the son of an Irish father and small businessman, got his big break in business as the founder of Softkey, a Canadian software producer, riding the wave of growth in the personal computer industry that began in the late 1980s and exploded in the 1990s. O’Leary’s financial empire, over the years, grew to include everything from investment management to physical storage services. But his real claim to fame lies as one of the stars of Dragon’s Den, a reality TV show that launched on CBC in 2006. On the show, O’Leary portrayed a no-nonsense venture capitalist judging the projects of various contestants. (Sound familiar?)
Wildly popular in Canada and, indeed, one of the most popular television programs in Canadian history, Burnett picked up the concept for American television in 2009 and turned the series into Shark Tank, where O’Leary continued to hold a leading role and quickly assumed the nickname ‘Mr. Wonderful.’
Conservative Party members increasingly believe that Mr. Wonderful may also be Mr. Right, insofar as they think O’Leary can lead them out of the Trudeau-era wilderness and back into power. They will vote in May to crown the party’s first permanent leader since prime minister Stephen Harper’s defeat in the October 2015 general election.
An Ipsos poll from January 23-25 gave O’Leary a staggering lead of 60% among Conservative supporters and a Forum Research poll from January 22 gave him 27% support among Conservative Party members and 50% among Conservative supporters. At either 30%, 50% or 60%, that makes O’Leary the first clear frontrunner in the leadership race to date. His splashy entrance follows a year during which many Conservative heavyweights, including former defence and justice minister Peter MacKay, former foreign minister John Baird and former defence minister Jason Kenney, and rising right-wing stars, such as Alberta’s Michelle Rempel and three-term Saskatchewan premier Brad Wall, all ruled out leadership bids.
O’Leary promises to run a campaign, by Canadian standards, just as disruptive as Trump’s campaign in the United States. He has ruled out running for a seat in the House of Commons, he currently doesn’t speak French (though he was born and grew up in Montreal) and says he may continue to appear on Shark Tank even during the campaign — and even if he wins the Tory leadership race in May and becomes the official opposition leader. Unlike Trump, however, he shies away from social issues that have long been settled by the standards of Canadian society, law and policy, including abortion, marijuana use and same-sex marriage.
Nor does O’Leary seem particularly troubled that he’s not the loudest voice opposing Canada’s legendarily generous immigration laws. Instead, it’s Kellie Leitch, a 46-year-old MP from northern Ontario and former labour minister, who has embraced Trump’s anti-elite and hardline approach to refugees, pledging that she will introduce new vetting procedures for all immigrants, including screening for ‘anti-Canadian values,’ though Leitch has struggled to define what exactly that means.
Both Leitch and O’Leary are a test run of whether Trump-style politics can work in Canada, where Trudeau now remains one of the last stridently pro-trade, pro-immigrant defenders of liberal democracy across North America and Europe.
Nevertheless, O’Leary shares with Trump an outsider sensibility and the notion that his background in business will allow him to make better deals with countries across the world, all to Canada’s benefit. He’s already savaging Trudeau as a poor manager, and polls show that O’Leary’s bellicose attitude could give the Tories the best shot to unseat the now-dominant Liberal majority at the next election, which must take place before October 2019.Though Trudeau remains wildly popular over 15 months after his landslide victory, his approval ratings are starting to slip for the first time below 50%. Within days of entering the race, O’Leary targeted Ontario’s unpopular Liberal premier Kathleen Wynne as ‘incompetent,’ tangling with Wynne over everything from the level of investment for Ontario’s auto industry to oil prices.
The path to October 2019 is a long time by any reckoning. O’Leary is today emptier as a political vessel than even Trudeau was when he won the Liberal leadership in 2012; if the best O’Leary can manage now is simply a draw with Trudeau’s Liberals, the Conservatives might easily falter by the time 2019 comes around, when O’Leary is no longer a novelty. By that time, Canadians will have had nearly three years to assess Trump’s legacy in the United States, which is likely to include a prickly renegotiation of the North American Free Trade Agreement, and the populist Trump/O’Leary bluster may lose its shine in three years’ time. On the other hand, if Canada’s economy fails to improve (or if it worsens) during the course of the Trudeau government, any Conservative challenger would have a decent shot at winning the next election.
O’Leary entered the race in late January, joining 13 candidates for the leadership and one day after a French-language debate in which he would have struggled to communicate his message. But he will now spend the next four months with a glaring target on his back. That was clear enough in his first debate performance last weekend, with all 13 challengers ganging up to mock O’Leary’s inexperience, lack of policy specificity and, above all, that O’Leary currently lives in Boston and not in Canada. (Former Liberal leader Michael Ignatieff, a former Harvard professor, took all sorts of hell from voters for living outside Canada for decades).
Since entering the race, O’Leary has already suffered from his lack of political acumen. On the same day that a far-right gunman killed six people in a Quebec City mosque, O’Leary posted a photo to Twitter of himself shooting various automatic weapons in Miami. While he removed the photo, it was a reminder that O’Leary is still just a political neophyte. Moreover, his lacking French language skills could make him a skeptical choice for Quebec’s contrarian voters.
Indeed, O’Leary’s top opponent for the leadership might be Quebecois MP Maxime Bernier, a 54-year-old veteran of Conservative government, serving alternatively as foreign minister, industry minister and small business minister in various Harper cabinets. Bernier, who is waging a campaign with a distinctly libertarian message, led the 14-person field in fundraising, at least by the end of 2016, both in terms of absolute dollars and number of donors.
Rona Ambrose, a 47-year old MP from Edmonton, Alberta, and a longtime minister in Harper’s prior governments, has served as interim Conservative leader since November 2015. The party’s members will vote on May 27 to elect Harper’s successor. It marks just the second time that the party will choose a permanent leader since its formation in 2003, the merger of the eastern-based Progressive Conservative Party and the western-based Canadian Alliance. Though only members in good standing can vote (and membership fees raised from $15 to $25), the contest features a ranked ballot system. This favors candidates with relatively broad appeal, as no one will win the leadership without the support of a majority of voters (even if that candidate wasn’t the first choice of all voters).
If by the end of May, O’Leary has a ceiling under 50% of the Conservative Party membership, he might lose the leadership to a consensus candidate that gains support as other candidates drop out. That includes someone like Bernier, who is amenable to many party members, and probably doesn’t include Leitch, whose immigration views fall outside even the Tory mainstream. But it might also include any number of candidates in the race, including a troika of up-and-rising Ontario MPs: Chris Alexander, the 48-year-old former immigration and citizenship minister; Michael Chong, a 45-year-old iconoclast who resigned from the Harper cabinet in 2006 over Quebec’s recognition as a nation within Canada and who embraces a nationwide carbon pricing scheme; and Lisa Raitt, another Ontario MP and the 48-year-old former transport minister, labour minister and natural resources minister.