Why Kevin O’Leary is wrong for Conservatives

Former Harper advisers say business tycoon needs less Ayn Rand and more Edmund Burke

Kevin O'Leary attends the Disney ABC Winter TCA Tour in Pasadena, Calif., in this Jan. 10, 2013 file photo. (Photo by Richard Shotwell/Invision/AP)

Kevin O’Leary attends the Disney ABC Winter TCA Tour in Pasadena, Calif., in this Jan. 10, 2013 file photo. (Photo by Richard Shotwell/Invision/AP)

The next year-and-a-half could be one of the most ‎important in the contemporary history of the Canadian conservative movement.

It might compare only to the period between the Conservative Party of Canada’s creation in December 2003, Stephen Harper’s selection as party leader in March 2004, and the founding policy convention roughly six months later. This initial period was historic not only because it brought an end to the vote-splitting that had bedevilled Can‎ada’s political right for more than a decade, but it is when Harper began to realize his vision of a political party underpinned by a clear, coherent, and positive conservative philosophy. This philosophy—a commitment to economic and personal freedom along with a traditionally conservative conception of key institutions such as the family and one’s local community— formed the backbone of the Conservative party’s ‎political coalition as well as the intellectual foundation of its governing agenda.

The next 18 months will determine whether the Conservative party continues to subscribe to Harper’s successful vision and holds together its robust political coalition or goes in another direction. Which brings us to recent speculation about Kevin O’Leary’s prospective interest in the party’s leadership.

O’Leary is a successful businessman who has transformed himself into a television personality and one of the country’s most famous proponents of capitalism. There is no question he is good at what he does. He is the talking head that people like to hate and whose weekly appearances invariably become the subject of water-cooler fodder. His breakthrough into the U.S. market is a validation of his carefully designed persona.

Related: Kevin O’Leary doesn’t speak French but says he could still be PM

The problem is his presentation of markets and entrepreneurialism more ‎resembles a left-wing caricature of what constitutes conservatism than it represents the proper balance between freedom and tradition and liberty and order. His assertions like “greed is good,” “money is my military,” and “you have to be willing to sacrifice everything to be successful, including your personal life, your family life, maybe more” reflect a one-dimensional understanding of what motivates people and what sustains strong and dynamic communities.

If O’Leary wants to position himself as a thoughtful and compassionate conservative, he needs less Ayn Rand and more Edmund Burke.

The true conservative vision is about much more than “go[ing] to bed richer,” to quote another O’Leary-ism. ‎Conservatives subscribe to the principles of classical liberalism and thus place an emphasis on personal freedom and understand that the market is the most efficient means of allocating scarce resources and that private property is a bulwark against state coercion. But they do not give primacy to individualism or market economics at the expense of all other considerations. Instead, conservatives also adhere to the Burkean values of subsidiarity and attachment to one’s family, community, and civil society as highly as markets.

Related: Rachel Notley to Kevin O’Leary: ‘Bring it on’ 

Harper shared this broader conservative conception of society and saw its potential as the basis of a “coalition of ideas.” He called on Canadian conservatives to “rediscover the virtues of Burkean conservatism” to serve as the guideposts of a new intellectual and political movement that brought together classical liberalism and traditional conservative values. As we have argued elsewhere, this fusionist vision is the basis for the success of the Conservative party for the past 12 years.

O’Leary’s narrow, materialistic vision has more in common with modern liberalism than it does with conservatism to the extent that it is preoccupied with ‎material needs unrooted from any moral or transcendental foundation. Such a narrow vision would fracture the Conservative party’s successful political coalition. It would also diminish conservatism’s contribution to Canada’s intellectual life.

Related: Kevin O’Leary has another passion: Photography

An appreciation of free enterprise ought to be a necessary but insufficient condition for the next leader of the Conservative party. ‎O’Leary is a successful businessman and impressive showman. But his narrow conception of conservatism is not enough to make him a successful modern Canadian conservative leader.

Ken Boessenkool and Sean Speer are former senior advisers to the Rt. Hon. Stephen Harper. 


Why Kevin O’Leary is wrong for Conservatives

  1. Ok..so two harperites conclude that O’Leary is not a real conservative as he doesn’t understand the philosophical underpinnings. In other words he’s too dumb and a randian to boot. Do you think that matters to the readers of the Sun papers? The Rob Ford fans? The people who think Donald drumpf is a good man for president? Not!

    He already has a following just for being a loud mouth jerk and a proud greedy prick. Just think what a little media hype can do.

  2. The Conservative talent pool is a s shallow as their gene pool.

  3. The problem is that Harper groomed his base to love the messages of the O’Leary’s and the Trump’s.

    • My, my what ridiculous generalizations are being spewed regarding Canadians who voted conservative. Calgarians for the most part voted conservative federally and yet they have a Muslim mayor who enjoys the one of the highest approval ratings of any mayor in the country. Brad Wall is the only provincial conservative premier and he enjoys the highest approval ratings in the country amongst premiers. If Harper groomed his base to love Trump’s message or O’Leary’s then he failed because most federal conservatives would like to see Brad Wall lead the federal party.

  4. The regular Maclean’s Harper clones may have a point.
    Interestingly, although the media went ga ga over the possibility of an O’Leary candidacy they never reported on downsides. As PM, because of his endless steam of outlawing Union comments on TV, he would have to do that as a top priority. That would mean a national strike.
    O’Leary would slash taxes, and distribute the reduced expenditures in a different way. More to business and individuals who are so called job creators.
    O’Leary hates unproductive people.
    So if you’re a senior living in government subsidized care, or a disabled child or adult, or even retiree living on a exhorbitant public sector union pension, Mr Wonderful will be coming after you. That nursing home gruel will get a bit thinner, care givers hard to find, and forget about that new wheel chair, or that special Ed teacher.
    Of course he’ll never make PM. So no need to worry about implications.

  5. These two birds continue to spew their delusional lies. They keep repeating the word “successful in relation to Haper’s tenure and yet the only success that he had in my view was to fool the Canadian public early on with his lies about openness and transparency and we all know how that worked out.

    Harper’s “successful vision” included pitting Canadians against one another.
    Harper’s “intellectual” movement appealed to and brought into the political limelight such luminaries as the Ford brothers and their followers and a wonderful assortment of racists, religious extremists and other assorted fringe players.

    So, is O’leary the main threat to the Canadian Conservative party?


    The threat lies within from people such as Boessenkool and Speer who still do not acknowledge that Harper’s tenure was an abysmal failure that did more harm to our country than in any previous government in its history.

  6. We need a Conservative in the mold of Brad Wall of Saskatchewan. Sensible, able to manage the books, and respectful of the indivudual.

    that’s all that is required. Leave the showboating and show-business to folks like Trudeau and O’Leary.

    • I agree Brad Wall would be a fine Conservative leader and next P.M. But even O’Leary with his understanding of how to get results along with his warts would be far superior to the selfie focused fluff currently running the country. When is the man child going to get to work on his 367 and growing “promises” as well as learn to speak without saying “ah” every fourth word??

  7. He is perfect for the party: He makes up facts, He lies. He talks about things that he has no idea about.

    • Sounds like a much better fit for the Liberal party, to be honest with you…

  8. The Libs and Dippers all think O’Leary would be a fine Con leader.

  9. And so we have a left wing rag telling conservatives that to be acceptable we have to be more like Liberals. And of course the leftists amongst us in the comments are gleefully spouting out with brainless comments. Same-o same-o, nothing has changed. But as time is proving, having a leader that has no intelligence or qualifications but has a pretty face, will be bad news for Canada.

    • I love when people call Macleans left wing. It always always says more about the commenter than the magazine. Now then, where is a comment calling Macleans a right-wing Conservatice lickspittle? Usually you get both on an article like this.

      I’ll just say that if these authors think modern liberalism is purely “materialistic” and “preoccupied with ‎material needs unrooted from any moral or transcendental foundation,” they must live in a precious little bubble. That kind of simple-minded misunderstanding of small-l liberalism is why they kept dismissing Trudeau this past election and then were surprised to lose to large-L Liberals. Keep drinking the kool-aid boys.

  10. He’s just a loud mouth. He would be the perfect Conservative leader.

  11. O’Leary, according to the Ottawa Sun, has never donated a penny to the Conservative Party, but has been a big donor to various US Democratic candidates.

    And since we know money is the only unit of measure important to O’Leary…

    So a conservative he is not!

  12. Kevin O’Leary priority in any venture is really only motivated by $$$.
    He could care less about Canada as a whole as his investing advice over the last 5 years is any country such as China rather than Canada.He is so one dementional that he in fact is very boring.
    No his god and government is money. So be it.
    As PM his morality factor is 0 on a scale of 10.

  13. 15) Focusing your life solely on making a buck shows a certain poverty of ambition. It asks too little of yourself. Because it’s only when you hitch your wagon to something larger than yourself that you realize your true potential.”
    Barak Obama

  14. I care not one wit about politics, however, Kevin is one of, if not, the most hilarious examples of what a society based on an economy instead of love spawns. I have shuddered with laughter to the point of passing wind watching him on “Dragon’s Den” and that other show where “big business types” are on display ….I truly believe most completely miss Kevin’s true value……just mention his name to people I know and they immediately burst how laughing and showering his name with expressions of..well you know

    • An economy of love? That’s not a thing. I’m no O’Leary advocate, but suggesting a “love based economy” is pure nonsense.

      • ARK2…..

        DP must be speaking of Trudeau, who wanted to “grow the economy from the heart outward”


        yes, that idiot really said that. And people really voted for him.

        when the shitz hits the fan and folks start losing their jobs…AND THEY VOTED LIBERAL OR NDP………I’ll just laugh in their face.

        Reap. Meet. Sow.

        This will apply to some folks who were expecting to build ships in the maritimes; but voted for a party that has a history of mistreating and shortchanging the military.

  15. Pardon me, just one more thing, I’m all for Kevin getting the attention he craves and love that sneering face of his but he really is a terrible guitar player so as long as he stay’s out of that I’m happy to phart myself laughing in my big boy diapers when he’s on TV….

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