J. Maureen Henderson’s argument at Forbes that Kevin O’Leary is not Canada’s answer to Donald Trump, but rather that he’s more flexible and personable, can be read as reassuring and cause for concern all at once.
When you think of an ego-driven business mogul turned reality TV star with designs on the highest office in the land, it used to be only a single name came to mind. Not anymore. Following in the footsteps of Donald Trump, Shark Tank’s Kevin O’Leary has decided to leverage his small screen fame for political gain, throwing his hat in the ring in the leadership contest of Canada’s Conservative Party earlier this week. In Canada’s parliamentary system, this means he’s competing to be the guy who acts as a thorn in Prime Minister Justin Trudeau’s side for the next several years. While this sounds like a thankless job, the self-proclaimed Mr. Wonderful has plenty of competition for the role.
It’s easy to draw parallels between O’Leary and Donald Trump. Both are tonsorially-challenged businessmen with a taste for self-aggrandizing who gained pop cultural prominence through star-making turns on reality TV hits (The Apprentice for Trump and Shark Tank for O’Leary) where they gleefully crush(ed) the dreams of ambitious contestants. While Trump is fond of calling perceived foes “haters” and “losers,” O’Leary has no qualms about dismissing entrepreneurs with untenable business ideas as “cockroaches” among other colorful terms. Both men claim to be killer deal-makers, but O’Leary, like Trump, has lowlights on his resume that are bound to come under renewed scrutiny now that he’s entering the political fray.
To dismiss Kevin O’Leary as Canada’s answer to Trump, however, is to do his carefully-cultivated persona a disservice. O’Leary knows he’s on Shark Tank to play the intimidating alpha with a cutting one-liner for every occasion and he relishes the role. He’ll claim to be a vampire. He’ll announce he’s wearing $900 underwear hand-sewn by Italian virgins. He’ll offer predatory deals that no one in their right mind would accept just to test the savviness of inexperienced entrepreneurs. The other Sharks defer to him and mock him in equal measure.
And while O’Leary isn’t shy about shouting down his fellow investors, he takes their ribbing of him in stride. Not an episode goes by where someone doesn’t call out his ego or bombast and he simply smiles or offers a chuckle. Unlike Trump and his Twitter tirades about critics, he doesn’t push back against shade, he embraces its ratings potential. It’s clear that O’Leary knows that his persona, however much it hews to or deviates from who he is off-screen, is good for business and you can see him frequently winking at this understanding.
Pro wrestling became one of the de facto metaphors for understanding the 2016 election season, with writers who likely hadn’t watched a match since childhood trying to paint Trump as a heel (wrestling parlance for the bad guy), without acknowledging that the era of pure heels and faces (the good guys) is largely over. The WWE roster is currently packed with characters who can’t easily be slotted into either camp, but who manage to blend a fairly complex (or complex for sports entertainment, anyway) combination of arrogance, athletic aptitude, sharp mic skills and occasional flashes of vulnerability to put themselves over with audiences — think of Seth Rollins, Kevin Owens, Chris Jericho, etc. WCW’s NWO faction of the mid-to-late 90s deserves a lion’s share of the credit for creating the archetype of these neo-heels and their ability to bring smirking self-awareness and wit to the idea of stock bad guys and treat the crowd’s boos as if they were oxygen. If we’re sticking to pro wrestling as a political metaphor, O’Leary with his obvious glee in manipulating his Mr. Wonderful persona is much more of a modern heel than Donald Trump. When he films a Facebook video in which he brandishes a spatula and talks about scraping the “crap” out of Ottawa, he might as well be cutting an in-ring promo.