I Got Drunk on Kevin O’Leary’s Wine and Watched ‘Dragon’s Den’ to Figure out his Politics

Illustration by Ben Ruby

Will Kevin O'Leary be Canada's Donald Trump? There are certainly troubling similarities between the mole-rat resembling O'Leary and the chapped-lip demagogue down south. There are their respective reputations as successful businessmen as well as a trail of lawsuits hinting that that reputation is more a result of bluster and ego than business acumen. There is the unwillingness to play by the traditional rules of decorum and procedures of each of their country's electoral process and how this disregard only bolsters their appeal and claim to being outsiders. A shared belligerence and cruelty all point to O'Leary being the President's Choice knock off of America's TV dinner fascist.

Can he pull it off though? Does he have the madness, the narcissism, and the vindictiveness to rally the resentful masses of Canada behind a cult of his awful personality? To figure it out I decided to do a little research, a dive into O'Leary's cultural output to see if I could figure out if I should be worried about this bird-dicked loser. So I bought myself two bottles of Cabernet Merlot from Kevin O'Leary Fine Wines and settled in for a four episode binge of CBC's hagiography to the wisdom of the investment class, Dragon's Den, to see if I couldn't peer into the appeal/mind of this human embodiment of overpriced douchey leather gloves.

First some tasting notes on O'Leary's wine. The blurb on the back of the bottle states the wine's raison d'etre:

"I love great wine! I hate paying crazy prices for it. That's why I created O'Leary wine. If you like your reds big, bold and brimming with flavour like I do, look no further. If I put my name on it, it's spectacular. That's why they call me Mr. Wonderful - the only Shark you can trust about wine."

Now it is true that the price for the wine was reasonable. I bought two bottles for just under thirty bucks. Also the flavour is big and bold like drinking a cup of melted crayons would be big and bold. You know when you have a massive hangover that causes you to throw up all day, leaving your throat raw and burning, that's what this wine tastes like. The legs on it look like a professional bowler's legs. The mouth feel is the feel of when you accidently drink from a bottle of beer that everyone at the party was using as the ashtray. O'Leary estate wines: the only wine you can get just as fucked up on huffing it as drinking it!

Confession time, Part 1: I really don't know much about wine and I couldn't help but conflate his personality with what I was drinking. Online reviews suggest it is "not bad for a celebrity wine" and "precocious yet petulant!" Also, apparently it's good with "hearty stews or roasted meats from the oven."

Confession time, Part 2: I meant to drink two bottles of wine of this stuff but I had to tap out after one. Instead of the warm glow that I expect from alcohol it immediately made me feel agitated and nauseous. Drinking this bottle of voodoo economics made me feel like my head was shrinking.

The wine though is a solid pairing for a four episode run of CBC's Dragon's Den, the battery acid merlot complements perfectly scenes of Canadians who have sacrificed everything for a bad business idea having their dreams smashed by the pitilis Dragons. If you're not familiar with the concept of the show, entrepreneurs of all sizes, successes and entertaining ill preparedness present their business ideas to a panel of titans of Canadian business  (like the owner of Boston Pizza, Canada's premier location for parking lot fights) in the hopes that they will invest in them. It's like American Idol meets Thomas Friedman's hairy taint.

To be clear: this show is not great. A shoddy, cheap looking reality show that raises dramatic tension with what seems like a thousand dramatic zoom shots per episode. (If I would have drank every time the camera zoomed there is a 100 percent chance I would have died choking on sleep vomit.) And despite the zooms, the show is boring. So boring. Like I thought this was going to be fun to write, drink some wine, watch some TV, but halfway through the second episode all I could think was: Holy shit another invention. There's five an episode why does it feel like 40? How many entrepreneurs are there in this stupid country? Goddamnit I hate your ingenuity, I hate your pluckiness and I hate people your dreams. Why can't you all be jaded service industry workers like the rest of us?

As a seething socialist, it was impossible to ignore the stench of propaganda coming out of "the Den." The show, so badly, wants you to realize that these Dragons are impressive beasts. Watch them and be in the awe of the way they solemnly write figures down on their leather notepads and the way they sit in grave dignity as they crunch those numbers in there head. Oh look at sultry Canadian investment banker Brett Wilson. He's touching his lips again in a serious manner. I can only imagine his thoughts, divining deals and percentages in his luscious cranium that would make a regular schlub's eyeballs melt. Witness the gravitas of the investor, of the job-creator, those who giants can fathom the depths of trends and markets and triumph over uncertainty. Only they, as they stare incredulously at another dumb plebe with another dumb idea, can hear and understand the whisper of the literal stacks of cash that are placed everywhere around the set. They deserve our adulation, our viewership, and certainly they deserve to be able to take full advantage of all tax loopholes.

But lo they are also humans these Dragons. Titter as they make bad scrotum puns about a powder product meant to soothe jock itch. Swoon as they support one another, acting friendly  praising each other's accomplishments. Squirm as the Dragons hop over themselves to compliment the asses of women modelling jeans with lifts in the posterior. Squirm even harder as one asks of the jeans (and the models wearing them), "Can I touch the technology?" And proceeds to do so. For these Dragons, they are horny, oh so horny. (Seriously, there are so many moments of old man lechery whenever the products involve women and are a smidge sexy that the show could be called Locker Room Talk.)

And the one who asked to touch the technology? The one who loves money more than the rest? The one who is the horniest of all, that's Kevin O'Leary.  While the other Dragons are likeable enough in a passably human kind of way, "O'Leary" is unrepentantly despicable. He spends the episodes mocking and bullying, laughing his villainous weasel in an animated film laugh. His whole vibe is "guy who answers his cell phone in the middle of a funeral." In the scene with Colombian lady selling her butt-lift jeans there is this exchange:

So shudder inducing. More like Kevin O'Leering Through Your Bedroom Window.

He also already acts like a petulant dictator in his constant bullying. In another episode, O'Leary is berating this biker dude Mike from Brantford about how much his presentation sucked (O'Leary is a straight talker, he won't be afraid to yell 'It Sucks!' over and over again at trade representatives from other nations). He asks the guy, "Be honest, have you ever been to the slammer? A heinous crime has begotten you. You've wasted my time, there are two officers waiting outside to take you to jail." Not only is that sentence nonsensical but I see it as a terrible foretelling of what will happen to dissent when O'Leary has triumphed and turned Canada into Mr. Wonderful's Wonderous Wonderland.

The other main characteristic of O'Leary on the show beside his sleazy meanness is how much he loves money. In the four episodes I watched, O'Leary repeatedly says things like: "That's all well and good but how do I make money," "I'm missing the part where I make money. That's the only thing that matters," and "You know what makes me feel positive? When I make a lot of money."

The defining money exchange I saw was when this sweet lady from Sudbury was telling a story about her father creating these sturdy lunch pails that miners could sit on when they ate. O'Leary asked "Did he charge them anything?"

She replied, "He did. He charged them $2.50 because at the time miners made $1.25 an hour."

"Did he make money?"

"He certainly did."

"That's important," he replies, his head bobbing with self-pleasure as if what he said was this glorious truth, "Because I love the story but I wanted to hear that he made some money."

Oh goddammit!  We get it! You love money Kevin O'Leary. For you there is nothing else in society that has any values. Money is your philosophy, your belief, and your morals, but give it a rest you one-note supervillain. Why don't you just dig up Milton Friedman's coffin and slide in there with him you free market sycophant.

O'Leary argues we shouldn't consider his TV appearances when we weigh whether he would be a good candidate. It was just great television he says not actual policy.  But he's mistaken because the character O'Leary plays, this sexist and cruel asshole, is also his credential as a good businessmen. His history is not actually that impressive. There is a trail of lawsuits and failure behind this guy. Instead it is his cruelty, his willingness if not eagerness to play the bad guy that is the evidence that this guy gets money.

As shown with every dismissal of a non-profitable idea brought into The Den, money is cruel. It doesn't care that you had to sell your farm, or take on debt or that you have sick family members, money is here to exploit you, to demand its debts and seize its profits or as O'Leary describes it on the show, "To squeeze your head."

Kevin O'Leary acts the way people think money acts. That's why he could pull this whole thing off. Trump's victory was one big angry, racist fuck you. In Canada, you can feel that same fuck you building. The forces that O'Leary personifies are tightening the screws around the country. Rents keep going up. Hydro bills get more shocking. Employment gets more tenuous and unsatisfying. The cowardly liberalism of Trudeau, with its big statements and promises of a harmonious society followed up with broken promises, unspent millions, and the continued catering to Canada's wealthy will be the perfect target for this resentment. Vengeance will be demanded by all those who trusted in the system, who prostrated themselves in front of the Dragons and were given nothing and who will just want to smash something pretty. And if there isn't a proper leftist alternative to the malicious forces of capital, O'Leary, in all of his rude, bullying, money-embodying glory will be set up as the perfect vehicle for the masses irrational, self defeating "Fuck You."

Though that could all just be the wine talking. I can state now with authority that Kevin O'Leary Fine Wine is evidence that the Conservative party is going to wake up with a massive, fuck-my life hangover.

Follow Jordan Foisy on Twitter.