Kevin O'Leary hasn't made an official announcement as to whether or not he’ll run for the Conservative Party leadership.
However, this is a step closer to a commitment:
In late February, he’ll be speaking at the Manning Centre's "Recharging the Right" conference.
According to the program, O’Leary (among other CPC leadership hopefuls) is speaking on the topic, “If I Run, Here's How I'd Do It.”
Well, I have some ideas for how he should do it.
First, I’d suggest that his how-to plan should begin with a formal bid for the leadership. He can only go so long playing it coy and cool with various media outlets before the momentum dies and leaves him looking apathetic or stunted by a case of cold feet.
Granted, the leadership election isn’t until May 2017, but like any self-respecting conservative, I want a leader who’s eager.
Then, once O’Leary replaces “if I run” with “when I run” he needs to work on his conservatism.
Shortly after O’Leary flirted with running for the CPC leadership, Brian Lilley exhumed O’Leary’s lefty history, including his donations to American Democrats, and his naïve belief that Canada can negotiate with ISIS. Most troublesome, and even amusingly, O’Leary described himself as a “political agnostic,” and said to journalist Evan Solomon, “I’m not a conservative.”
So far, I would say, this is a good how-not-to do it.
Like everyone else, I find it impossible to mention O’Leary’s interest in the Conservatives without drawing the comparison to Donald Trump. But never mind their TV reality roles or their killer business instincts. The key similarity now is if they’re true conservatives. This analysis has nagged Trump and it will similarly badger O’Leary.
The difference, however, is that Trump claims to have had a change of heart. He’s seen the light emanating from the right and he’s converted. If anything, his sincerity is the prime question, not his positions.
Whereas, with O’Leary, he seems sincere but it’s his positions that might hinder him. If he’s not a conservative, and proudly says as much, why apply for the job? Is he an unusually honest opportunist?
Maybe as a lifelong entrepreneur and never a needy applicant, he hasn't learned the art of the job interview, such as not plugging one’s nose at the mention of the company name.
On a more positive note, "Mr. Wonderful’s" reputation as a go-getter and straight shooter make him a worthy candidate.
On Dragon’s Den, contestants often favoured and sought O’Leary’s approval first because of his unflinching honesty. He wasn’t swayed by tears or desperation; if he liked your idea, it was good one.
I never found him callous, as some have said, and in fact, being unemotional can be an asset when making big decisions.
I’d go even further and say that of all the current Conservative Party prospects, O’Leary’s demeanour would be the best opposition to the soft, hesitant nature of Justin Trudeau.
But if O'Leary is planning on denouncing conservativism and campaigning from the centre or left he'll be wasting his time. Trudeau’s supporters would have no reason to change camps. It’s up to O’Leary to be the alternative, and to sell conservatism with the same enthusiasm he uses to sell his Cabernet Merlot.
I’m not a political insider, but I know this much—“recharging the right” will be impossible if you’re aiming from deep in centre field.
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