Pierre Poilievre has a likability challenge. Here’s what Conservative insiders say he should do about it — and where he’s going wrong

OTTAWA—Glasses or no glasses?

Federal Conservative Leader Pierre Poilievre has hit the road for his first full summer as party boss, having shaken off the shackles of the House of Commons after a sitting that insiders say saw him finally settling into the job.

But top of mind for Conservatives is how Poilievre is faring as he prepares for the job he wants — being prime minister.

That’s where the Great Glasses Debate comes into the mix.

A persistent problem confronting Conservatives since Justin Trudeau became Liberal leader in 2013 is how to run against a guy who is a de facto celebrity?

The Tories say the narrative they’re building about the Trudeau Liberals is resonating with an increasing number of voters; polls do place their party ahead of the Liberals on most counts.

But what about Poilievre himself?

What’s known as his “negatives” — how many people have a negative impression of him — remain stubbornly high.

As a recent poll by Abacus Data suggested, while Canadians would like a change in government, they’re not sure he’s the one they want.

The Conservatives, the Star has learned, will begin making the case he is in fact the best choice in a series of digital and broadcast ads starting later this summer and into the fall.

The goal is to twin Poilievre’s political narrative with his personal one to broaden people’s awareness of him — not just as the Conservative leader, but as an individual.

In the meantime, he’s test-running a few things: ditching the glasses and tie where he can in an early bid to bring home the message he’s relatable to voters and can be trusted to run the country.

Still, based on how he’s run things the last several months, insiders say, the jury is out over whether that’s going to be possible.

The challenges he faced upon becoming leader — running caucus, the party and preparing both to face voters in the next election — remain that: challenges.

The Star spoke to MPs, strategists, party members and others to get the insider assessment of how it is all going, and where things need to go next.

Caucus support — for now

With the majority of Conservative MPs in his corner for the leadership, Poilievre has the backing to instil a measure of caucus discipline past leaders never enjoyed, and that in turn has created a public-facing show of unwavering support in his decisions.

That’s not to say there is no tension behind closed doors. MPs are chafing at the discipline, but as he warned them earlier this year when details of a caucus meeting leaked to the press, if internal gripes end up in the media, punishment will be meted out.

Poilievre has also had to find ways to balance the competing social ideologies in his team.

A recent private member’s bill by MP Cathay Wagantall to impose tougher sentences on those who attack pregnant women was an example.

Detractors saw it as a way to reopen the abortion debate.

Poilievre — who has said he supports a woman’s right to access abortion — insisted nothing in the bill itself would restrict access to abortion. He voted for it, and caucus was told to do the same, in part to quell any appearance of internal party conflict.

Still, MPs say it’s not always a top-down edict. Poilievre does listen to their ideas and feedback.

Some cited a decision by the Tories last year to take on the issue of a children’s medication shortage as an example of being responsive to ideas from inside.

He’s also made more of a concerted effort to showcase his own team; at a campaign-style swing in New Brunswick this week, he made a point of introducing local MPs and thanking them for their work.

The party gets reorganized

Poilievre raised $9.3 million for his leadership bid, so much that there was a surplus he kicked over to party coffers. Since then, the party has continually out-fundraised its rivals.

Poilievre has also reorganized the senior-most ranks of the party, bringing in new leadership for its fundraising arm and many of its staff positions.

There’s some degree of unease around those choices.

A major driver of Poilievre’s support during the leadership race was his prowess on social media, work done with a firm called MASH, which he had on retainer throughout the campaign and is expected to work with him on the next general election.

The firm’s founder, Derek Robinson, ran digital strategy for former Conservative premier Brad Wall, and was behind a third-party campaign to get long-time Liberal MP Ralph Goodale booted out of his seat in that province in the 2019 election.

The firm is also working with beleaguered New Brunswick Premier Blaine Higgs, facing a caucus mutiny over his governance style, and whose recent social media attacks on Trudeau were seen as being the handiwork of MASH.

“Lots of Conservatives are worried about the decisions Pierre had made in building his team — and the Higgs fiasco has justified that concern,” said one long-time insider, granted anonymity over fear of reprisals from Poilievre’s team.

That concern has also been expressed widely following recent byelections.

The Tories should have had an easy win in Oxford, a rural Ontario riding, but ended up needing to deploy the full weight of caucus to help campaign for their candidate after a divisive nomination battle soured some of the grassroots against Poilievre’s pick.

The byelections aren’t the only thing frustrating some party members.

Last week, Poilievre was observed on video not bowing his head during a moment of silence in the Commons for National Indigenous Peoples Day.

Many MPs often look around the Chamber during moments of silence.

But a clip of Poilievre doing it was soon turned into a critical online video, circulated by Liberals and others.

Among those turned off by it was Andrew Puglas, who quit his role with the Conservative riding association in North Island-Powell River as a result.

He told the Star he’s been active in Conservative politics for years, and felt he was making steady inroads convincing Indigenous voters in particular they should give the party a look.

Poilievre managed to undercut that in a single video clip, he said, by showing he wasn’t serious about reconciliation.

The party said that Poilievre did issue statements to mark National Indigenous Peoples Day, but Puglas said if that was the case, he never saw them.

“I liked his approach to becoming leader, but he is taking steps back here,” he told the Star.

“I did lose respect for the guy.”

Getting ready for the next election

The argument that for every step Poilievre takes forward it appears he takes two back isn’t only been made by Puglas.

Former and current MPs, party stalwarts and others all used similar language when asked to assess how things were going under the new boss.

What’s winning universal support is his focus on the economy, and in particular housing.

But there are numerous examples of what’s seen as muddling those efforts. Among them: a flyer circulated during the byelections that seemed to attack People’s Party of Canada Leader Maxime Bernier for being pro-LGBTQ rights, his support of controversial academic Jordan Peterson and his willingness to opine on local politics — he said it would be “bonkers” to elect Olivia Chow as mayor of Toronto. She won on Monday.

They are fights he shouldn’t have bothered picking, insiders argued.

“Why does he have to swing at everything?” one bemoaned.

The recent byelections, however, have most Tories convinced there is time yet for Poilievre to more fully flesh out his arguments, and his personal approach.

They point to the across-the-board decline in the NDP vote as the reason. Absent strong support for their party, why would they pull out of the supply-and-confidence deal that keeps the Liberals in power?

“The biggest story of the night was that the NDP was nowhere to be seen,” said former Conservative party staffer Jonathan Ingraham.

“I think this is further proof that this Parliament will go the distance to 2025, even if it is dysfunctional and accomplished little.”

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