Kevin O’Leary’s increasingly-less-exploratory Conservative leadership committee released a report last week effectively telling the outsider businessman to run for the top job. The report suggests that potential support from millennials could play a big role in O’Leary’s path to victory.

It might be on to something. Data suggest that O’Leary’s candidacy could open a door to this hard-to-woo voter group, but it will take more than lip service to motivate young people to vote Conservative in 2019.

It’s no secret that Canada’s Conservatives have a brand problem with young people. Only 20 per cent of voters aged 18-29 voted for Stephen Harper in the last election, and public opinion data credit young voters with giving Prime Minister Justin Trudeau his majority win.

It’s also no secret that, historically, young people tend to vote for left-of-centre candidates. A silent majority of conservative millennials waiting to be mobilized by the right leader and message remains a pipe dream for the centre-right in Canada.

But while no research suggests the millennial vote is eager to abandon the left, it does suggest Kevin O’Leary may have the best shot at turning their attention toward the Conservative party. Abacus Data conducted a survey assessing the likability of Tory leadership candidates and came to some interesting conclusions. Among all Conservative voters surveyed, O’Leary’s likability was strongest among all age groups, including those aged 18 to 35.

But given how few millennials voted Conservative in 2015, it’s less important for Tories to find a candidate that speaks to current young Conservatives than it is to find one who can grow support in this key voter group.

This is where the data start looking better for O’Leary. Among the 391 millennials surveyed who said they would consider voting Conservative today, support for O’Leary is high, at 30 per cent — double that of their number two choice, Lisa Raitt.

The factors making O’Leary more appealing to millennials than his rivals probably aren’t all that different from those that drew millennials to Justin Trudeau initially; name recognition and a bit of star power go a long way in getting the attention of any voter. But it would be a mistake to suggest that millennials are only wooed by charm and nice hair (that latter point should come as a relief to Mr. O’Leary).

For young people, Trudeau’s appeal was rooted in his optimism for Canada’s future — difficult to channel when you’re also suggesting the country is on the brink of fiscal disaster. For young people, Trudeau’s appeal was rooted in his optimism for Canada’s future — difficult to channel when you’re also suggesting the country is on the brink of fiscal disaster.

While it’s true that millennials are more likely to vote on the basis of feelings rather than policies, Team Trudeau will tell you that you have to connect with millennials to get their support.

There, O’Leary has a few advantages. He has more access to young people than any other candidate in the race through his teaching gigs at various universities in Canada and the U.S. While he’s not bilingual, he does speak the language of jobs — something top-of-mind for nearly every young person (and their parents) given the high youth unemployment rate. O’Leary also has championed the sharing economy — universally embraced by young people — and has knowledge and experience of mortgages and housing, another core concern for many Canadian millennials.

The challenge for O’Leary will be in turning his knowledge of millennials into meaningful connections with them. For young people, Trudeau’s appeal was rooted in his optimism for Canada’s future — difficult to channel when you’re also suggesting the country is on the brink of fiscal disaster. Despite an upbringing at 24 Sussex, Trudeau was viewed as relatable and genuine — qualities that are tough to project when your brand is that of a ruthless, wealthy executive.

As the election of Trudeau and Donald Trump showed, you can live a life of extreme privilege and wealth and still win the support of the average voter. And as we learned from Bernie Sanders’ bid for the Democratic nomination in the U.S., you don’t have to be young to connect with millennials if you have a message that reaches them — especially online.

But while this may sound favourable for O’Leary’s leadership ambitions, there’s no suggestion voters have any desire to emulate Trump’s politics in Canada. Here’s where O’Leary’s challenge lies — in distancing himself from the comparisons to Donald Trump. Both are outsider TV personalities who’ve reached the highest rungs on the corporate ladder. Should O’Leary win the leadership, he’ll have done so by using moves from the Trump playbook — a high-profile candidate with no party history emerging victorious from a crowded field, leaving the establishment scratching their heads.

At the end of the day, though, American millennials rejected Trump’s presidential bid; 55 per cent of them voted for Clinton, while only 37 per cent voted for Trump. Even more troubling for O’Leary is the fact that three-fourths of Canadians disapprove of Trump’s presidency.

O’Leary seems to see the threat in the comparison and has been attacking the Trump image head-on. As Trump was winning the Republican nomination, O’Leary was asserting his Lebanese-Irish heritage and telling people, “I don’t build walls. I am very proud of the society we’re building in Canada”. But that was a year ago, and the comparisons persist. Tories are right to question whether this may still be the case in 2019.

Even if O’Leary shakes the Trump image, and can passably imitate Trudeau’s charm, that won’t mean the millennial vote going blue in the next election. But if O’Leary can even make the Tories competitive among young voters, that would be a compelling reason for Conservatives to line up behind him. We can’t let another election go by without making headway with Canada’s largest voter cohort.

Which is why he’s still an option for my leadership ballot.

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