Kevin O’Leary Can Learn a Lot From Canadian History

Kevin O'Leary, future leader of the Conservative Party of Canada?

Kevin O’Leary, future leader of the Conservative Party of Canada?

A few days after offering to buy Rachel Notley’s resignation, former CBC Host and Dragon from Dragon’s Den Kevin O’Leary announced that he may run for the leadership of the Conservative Party of Canada. The immediate response from many media establishments was to label him as Canada’s own Donald Trump, with the Toronto Sun even going so far as putting Trump’s hair on O’Leary’s head on the front page of their newspaper. Overlooking what is apparently Canada’s bizarre desire to have our very own egomaniacal  celebrity businessman turned politician, Canadian history should provide O’Leary with plenty of cautionary tales should he decide to run for the leadership of the CPC and ultimately, seek a place at 24 Sussex.

While frequently making excellent cabinet ministers, wealthy businesspeople have often failed fairly spectacularly as political leaders in Canada; when they even manage to win party leadership in the first place. Belinda Stronach’s failed leadership bid in 2003 was simply the most recent example of a rich, high-profile business leader seeking to jump directly from corporate to political leadership and failing. Future Prime Ministers Paul Martin and Bryan  Mulroney both also failed in their first bids for party leadership in 1990 and 1976 respectively. Particularly with strict financing laws regarding leadership races, the advantages of personal wealth are greatly diminished in a way that they aren’t in American campaigns. Unlike in earlier days, a prospective candidate cannot simply finance their entire campaign and are instead forced to rely on donors to fund their campaign.

Even if they manage to win party leadership and later the general election, in many cases the leadership attributes that allowed someone to succeed in private industry are often problematic in politics. Since I’m a historian I’ll leave Paul Martin’s failed tenure as Prime Minister to others to dissect. Or I’ll do it in a blog post when I retire and the Martin years’ have truly become the province of history. Rather, I wish to focus on Canada’s 11th Prime Minister, one Richard Bedford (R.B.) Bennett. While Bennett was a lawyer by training, he was a savvy investor and managed to become the owner of E.B. Eddy Match Company. According to Bruce Hutchinson, taking inflation into account, Bennett may well have been the wealthiest prime minister in history. Yet, despite his success in private industry, Bennett’s single term in office is widely – but not unanimously – considered a failure.

R.B. Bennett all dressed up. Why did people think he was rich and out of touch again?

R.B. Bennett all dressed up. Why did people think he was rich and out of touch again?

Bennett is not solely to blame for his disastrous legacy, as he had the misfortune of coming to power right when the effects of the Great Depression truly began to hit Canadians. While initially denying the problem and then implementing half-measures, Bennett and the Conservatives did finally react with a “New Deal” style program in 1934 and, despite his slow response, many of the institutions Bennett created have continued to shape Canada to the present day; the CBC, Bank of Canada and the Wheat Board being the most prominent examples.  However, by then it was much too late to either revive Canada’s sagging economic prospects or recapture voters’ good will and the Conservatives were defeated by Mackenzie King’s Liberals in 1935.

Bennett’s problems though went beyond economic management. Rather, in a time of extreme suffering, his public displays of affluence were held against him. The most widely known example was his residency at the Chateau Laurier throughout his five years in office. In the 1930s Prime Ministers – or their party – were responsible for securing their own accommodations in Ottawa and Bennett chose Ottawa’s fanciest hotel for his. While it was his personal money paying for his residency, living in luxury while hundreds of thousands were homeless didn’t play well to the voting public. Similarly, Bennett was always exceptionally well dressed, frequently being seen in public wearing  a tuxedo. The final straw was a protracted illness throughout 1934 that forced Bennett to retire from the public eye for most of the year, furthering the impression that he was living in an insulated bubble and not experiencing the hardships of his constituents. Combined with his extreme reluctance to discuss his private life and extensive philanthropy, Bennett’s seemingly ostentatious displays of wealth gave the impression that he was out of touch with “real” Canada.  Adding in his government’s slow policy response to the Great Depression and Bennett  created a damaging  impression that was impossible to overcome during the 1935 election.

Beyond public perception, Bennett’s approach towards governing alienated many possible allies. In a fascinating profile of the Conservative Party by Graham Spry of The New Commonwealth, Spry documents how Bennett used his personal fortune to fund both his leadership bid for the party in 1927 and the Conservative Party’s successful election campaign in 1930. Doing so freed Bennett, a Calgarian, from the Tory’s powerful Toronto fundraisers who traditionally financed the party. However, Bennett believed that he could then run the party the way he saw fit, without taking into account other, powerful and entrenched interests. The result was disastrous. He ultimately fell out with powerful Vancouver Tory H.H. Stevens, who subsequently ran his own slate of candidates in the 1935 election under the Reconstructionist Party banner and split the right-wing vote across most of the west. Internally, Bennett also appointed loyalists to cabinet, whom many in the media and voting public simply saw as “yes-men” and Bennett lackeys. This perception is best demonstrated by this editorial cartoon in the Winnipeg Free Press from 1931. While other Prime Ministers have been undone by internal power struggles and accusations of autocracy, for Bennett I would argue, these problems stemmed in part from his background as a successful investor and business owner. He saw himself as the boss, an approach that alienated many key party supporters.

Much as one can do in business, Bennett tried to buy his independence. While being the sole (or majority) shareholder can free oneself from shareholder pressure, money can’t buy political independence. Particularly in the 1930s, party leaders needed the buy-in of powerful regional lieutenants such as H.H Stevens on the West Coast. While funding the 1930 campaign limited the pull of Toronto financiers, it didn’t negate the need for a national network of party sympathizers, many of whom expected some form of payment, either through jobs, influence or favours in return for their loyalty. Bennett’s unwillingness to engage in these “tit for tat” backroom deals ultimately sunk his re-election campaign in 1935. When reading through the letters failed candidates sent him in the aftermath of the 1935 vote one theme dominates; the Conservatives suffered from a lack of organization and rank and file participation in many ridings. Simply put, Bennett’s leadership style alienated many potential Conservative supporters just when the party needed them the most.

From Larry O’Brien as the Mayor of Ottawa to R.B. as Prime Minister of Canada to Kevin O’Leary, the problem for many business people entering politics is that they assume that the same people management skills that allowed them to be widely successful in business will also work in politics. However, as history has shown, that is almost never true. Rather, political leadership requires compromise and deal making of a very different kind. Bennett found this out the hard way, alienating so many party supporters and voters that he only lasted one term in office. Ultimately, at their convention in 1938, the Conservative Party even voted to abandon Bennett’s New Deal style programs, thus marking a total repudiation of his legacy. Bennett also left Canada for good in 1938, moving to Britain where he ultimately died in the 1940s, tired of living in a country that had quickly tired of him.

Will O’Leary become the next Conservative leader? It is possible according to recent polls. If he does win though will he be able to return the Conservatives to power? Again, it certainly is possible, and his reputation as a savvy investor will bolster his and his party’s reputation on key files relating to the economy, which will help attract voters back to the CPC. However, if O’Leary is smart he will pay attention to the experience of previous Conservative leaders who have come before him. Money often makes gaining political power easier, it is, however, is no guarantee of keeping it.



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