by J. Maureen Henderson CONTRIBUTOR (FORBES.COM)
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.
In addition to tweaking his public character like the veteran TV performer that he is, O’Leary is also able to show chinks in his armor. Can you imagine Donald Trump getting choked up remembering being fired from his first job at an ice cream parlor? Scratch that, can you imagine a teenage Trump scooping ice cream at all? Or dabbing away tears when hearing a story about a young entrepreneur trying to find business success so that he can finally bring his fiancee to America? Whether calculated or spontaneous, what keeps O’Leary’s bombast from becoming tedious are these tiny moments of seemingly genuine humanity in the midst of hubris.
Despite living in a golden tower bearing his name, Trump was somehow able to position himself as anti-elitist outsider who spoke up for the disenfranchised “average American” voter. By contrast, O’Leary’s sneering elitism is a core element of his character. The opening credits of Shark Tank show him swirling a glass of wine, of which he is a great connoisseur, as he never fails to mention on the show when the opportunity arises, frequently getting in a plug for his own winery. He does interviews wearing a fur-trimmed overcoat. He collects luxury watches, vintage guitars and art. His own photography has been the subject of professional shows. His is a performance of cultured, aristocratic wealth, while Trump’s performance is the ostentation of a hustling populist who made it big, despite their respective backgrounds being the opposite. While relatability and the the capacity to connect with voters as a person of the people is fundamental in the American political process, Canada repeatedly elected a prime minister who was roundly mocked for dropping his kids off at school with a firm handshake in lieu of a hug, so O’Leary’s lack of the common touch may not be a deal-breaker for voters. His inability to speak one of Canada’s two official languages, however, could be.
When it comes to a policy platform, O’Leary has Trump’s penchant for floating ludicrous trial balloons, but, in customarily Canadian fashion, doesn’t embrace the latter’s focus on law and order and/or building the country’s global reputation as a heavyweight not to be messed with. At present, he’s content to offer up “business knows best” platitudes and when asked about comparisons to Trump, he’s quick to tout his own background as the son of immigrants and dissociate himself from the idea of building walls and cracking down on who enters the country.
While Trump’s ascendance may have paved the way for Kevin O’Leary to take his own run at politics and while both boast pop cultural pedigrees that far dwarf their political experience, the two men aren’t necessarily cut from the same (very expensive) cloth. O’Leary’s sly self-awareness and more polished showmanship aside, there’s another reason he’s not Canada’s answer to Donald Trump — that role has already been filled by one of his leadership competitors, Kellie Leitch. Her attempt to latch on to the rhetoric that launched Trump to victory might have seemed like a smart move at the time, but, to date, has garnered nothing but mocking from the media and her political rivals. Kevin O’Leary, one suspects, is much too savvy and conscious of the merits of own brand to try peddling a cheap knock-off of someone else’s.
