Skip to main content

Kevin O’Leary is not Donald Trump – but their paths to politics could be similar

Kevin O'Leary speaks during a session entitled "If I run here's how I'd do it" during a conservative conference in Ottawa Friday, February 26, 2016. Celebrity businessman Kevin O'Leary says he's amassed a team of advisers on whether he should run for leadership of the federal Conservatives and now wants advice from Canadians.

Adrian Wyld/THE CANADIAN PRESS

Kevin O'Leary is not an immigrant-basher and displays no interest in pretending to be one.

There are no evident signs of him tapping into anti-establishment populism, and after spending much of his time outside Canada, it's unclear he would know where to look for such a thing here.

Based on his unappetizing vow to bring a spatula to Ottawa to "scrape all that crap out," and his clunker of an attempt to label Justin Trudeau a "surfer dude," he is not necessarily even all that adept at coming up with catchy political slogans or nasty names for political opponents.

Story continues below advertisement

Read more: Kevin O'Leary asks Canadians to weigh in on possible Conservative leadership bid

Read more: There are early hints of where the Conservative Party's leadership campaign is going

Read more: Kevin O'Leary considering campaign staff for possible Tory leadership bid

In short, despite inevitable comparisons as he gets closer to launching a Conservative leadership bid – unveiling on Friday both a new website and an advisory committee that included former Ontario premier Mike Harris – Kevin O'Leary is not Donald Trump.

But there is one way in which, to have any chance of actually winning the race, the businessman and television personality would need to mirror the president-elect: He would have to rely on his celebrity to circumvent the unwritten rules for how to compete for his party's top prize.

Ordinarily, leadership contests in this country are all about organizational grunt work, with media exposure not counting for much. To win, candidates have to spend just about every waking moment out pressing the flesh – speaking to any audience that will have them, slowly winning over existing party members and, most pivotally, signing up new ones they can coax and cajole to cast ballots on voting day. If not quite winning over each voter separately, it requires painstaking effort to attract local organizers who will do that for them.

Mr. O'Leary does not have enough remaining time to do any of that properly. There is a common view among Conservative organizers that even candidates such as Lisa Raitt, who officially jumped into the race almost seven months before the May 27 vote, gave too much of a head start to earlier entrants, including Maxime Bernier, Kellie Leitch and Andrew Scheer. If Mr. O'Leary takes the plunge in January or February, he would have to attract an army of organizers and clone himself several times over to have any chance of winning the traditional way.

Story continues below advertisement

But then, Mr. Trump didn't do the things candidates for the Republican nomination were supposed to have to do, either – declining to join rivals glad-handing Iowa farmers or trudging through snow in New Hampshire. Instead, he demonstrated that traditional ways can, under just the right set of circumstances, be upended by a particular mix of celebrity and social media.

Until recently, high name recognition alone wouldn't be enough to make a candidate competitive, because there was no easy way to identify and mobilize supporters. But when millions of them are willing to self-identify through Twitter or Facebook, that can change things – enabling messages to be directly targeted, and valuable personal information to be collected.

Mr. Trump in one sense had a considerably easier task than would Mr. O'Leary. Republican primaries are much more wide-open affairs than Conservative leadership campaigns. Many millions of people, with limited affiliation or loyalty to any of the more mainstream candidates, were going to vote anyway; he had a fair chance of turning a good share into supporters, and non-habitual voters he was able to recruit had few hurdles to jump.

Mr. O'Leary, by contrast, is trying to become head of a relatively closed club in which he himself is barely a member in good standing. There are currently fewer than 100,000 Conservative Party members, and most won't gravitate toward an interloper. So he needs to focus primarily on getting people who have never before bought memberships to do so before a deadline in late March, and to pay $15 for that privilege.

But then, Mr. Trump had to convert his celebrity into more than 13 million votes to win the GOP's nomination. Mr. O'Leary would stand a pretty good chance if he could sign up anywhere near 100,000 members of his own – a not completely inconceivable sum for someone with a current Twitter following of almost 600,000.

What Mr. O'Leary will need from his advisers in the weeks ahead – the veteran backroom types on his committee, more so than the likes of Mr. Harris – is an honest assessment of just how much his profile is actually worth, in terms of sign-up potential. And they need to figure out whether it could translate into support with enough geographic balance to give him a chance in a leadership system in which all ridings are weighted equally.

Story continues below advertisement

They should also let him know that he would probably need to spend all his time between the membership cutoff and the voting date personally reaching out to opponents' supporters to try to make himself acceptable to them – necessary with a preferential-ballot system in which no candidate is likely to top 50 per cent of first-choice votes.

That's something Mr. Trump never had to do. But the path to competitiveness, despite all the differences between the two men, could look a bit familiar.

Report an error Editorial code of conduct
Comments

Welcome to The Globe and Mail’s comment community. This is a space where subscribers can engage with each other and Globe staff. Non-subscribers can read and sort comments but will not be able to engage with them in any way. Click here to subscribe.

If you would like to write a letter to the editor, please forward it to letters@globeandmail.com. Readers can also interact with The Globe on Facebook and Twitter .

Welcome to The Globe and Mail’s comment community. This is a space where subscribers can engage with each other and Globe staff. Non-subscribers can read and sort comments but will not be able to engage with them in any way. Click here to subscribe.

If you would like to write a letter to the editor, please forward it to letters@globeandmail.com. Readers can also interact with The Globe on Facebook and Twitter .

Welcome to The Globe and Mail’s comment community. This is a space where subscribers can engage with each other and Globe staff.

We aim to create a safe and valuable space for discussion and debate. That means:

  • All comments will be reviewed by one or more moderators before being posted to the site. This should only take a few moments.
  • Treat others as you wish to be treated
  • Criticize ideas, not people
  • Stay on topic
  • Avoid the use of toxic and offensive language
  • Flag bad behaviour

Comments that violate our community guidelines will be removed. Commenters who repeatedly violate community guidelines may be suspended, causing them to temporarily lose their ability to engage with comments.

Read our community guidelines here

Discussion loading ...

Due to technical reasons, we have temporarily removed commenting from our articles. We hope to have this fixed soon. Thank you for your patience. If you are looking to give feedback on our new site, please send it along to feedback@globeandmail.com. If you want to write a letter to the editor, please forward to letters@globeandmail.com.
Cannabis pro newsletter