He’s best know for his blunt opinion and razor tongue on the popular reality TV shows Dragon’s Den and the Shark Tank.
But that could soon change. Last week, after months of buzz, businessman and TV personality Kevin O’Leary launched a new committee and website that he says will help “identify a path to victory for his potential Conservative Leadership.”
So could the brash and outspoken businessman truly rise to the top of Canadian politics? For insight guest host Jody Vance reached out to former Conservative strategist and Vice-Chairman of Summa Strategies Tim Powers.
LISTEN: Could O’Leary be Canada’s Trump?
First off, Powers says, it’s important to note despite his latest move, O’Leary has not officially joined the race, and in fact has until the end of February to make up his mind.
“He is enjoying toying with many people and getting the attention that that toying provides. He’s obviously the biggest personality in the field of people who are in or not in right now and seems to be riding that.”
That said, Powers says there are certainly similarities in style and approach, including the way O’Leary makes use of both traditional and social media to connect with the public – just as Trump did.
“It’s also the power of his brand, and I think that’s what Kevin O’leary is trying to do,” he says. “He’s trying to be the Don Cherry of politics.”
He says Trump was known as the blunt talking face of The Apperentice, and was able to take that message as “the one who shakes things up” to a cranky electorate.
“And the Americans, those who voted for Trump seemed to say that’s what they wanted at the moment.”
Same game, different rules
But while there may be similarities to the way the two reality TV businessmen have approached politics, Powers says O’Leary faces different challenges based on the way politics is fought in Canada.
To begin with, he’ll be barred from pressing his personal fortune into his quest for political power: Candidates for Conservative leader may only spend $25,000 of their own money.
“Arguably Trump says he didn’t spend much money, but he spent a hell of a lot more than 25 grand.”
On top of that – the leadership race process is different than the state-by-state popular vote marathon that characterized the Republican Primary.
Instead, the Conservative race is about trying to win some 16,000 “points,” in a competition where each of Canada’s ridings is worth 100.
“What you try and do is sign up the most members in each of those ridings, so that you get the bigger portion of those 100 points.”
On that front, Powers says O’Leary is at a clear disadvantage by delaying his entry to the race.
“He’s a little behind the eight ball because he isn’t officially a candidate, so he isn’t officially signing up members that he could then point to and say ‘hey, look, I’ve got this magic number they’re spread across all of these ridings in the country, I’m going to win.'”
In full Trumpian style, Powers says O’Leary may be stirring controversy in order to win the “air war,” attracting attention to himself in order to be best positioned as many people’s second choice and able to rack up supporters as other leadership candidates withdraw.
However, he says it won’t necessarily be smooth sailing.
“The Challenge O’Leary is going to have among Conservatives is, is he really committed to this? Some see a comparison between O’Leary and the old Liberal Party leader Michael Ignatieff, both were tagged with being in it for themselves, as opposed to being in it for the people.”