The inside story of how Pierre Poilievre captured the hearts of Canada’s Conservatives

OTTAWA - Pierre Poilievre began his Conservative leadership campaign with a video featuring him alone, dressed in a dark suit and crisp white shirt, seated at a heavy wooden desk, shelves crammed with books and photos behind him.

His campaign's final video showed him on a stage in a rumpled blue shirt, sleeves rolled above his wrist, surrounded by thousands of cheering fans.

What took him from one to the other is the story of a politician who had long thought about what he'd do if he became prime minister, and finally decided to give it a try.

It's also about a campaign that subsequently unfolded beyond his or anyone else's wildest imagination.

Poilievre, first elected as an MP in 2004, steadily amassed political credibility and support in the years of Stephen Harper's Conservative government - and the reputation of a fierce partisan attack dog who delighted in digging into policy and ideas.

In the post-Harper era, he began to come into his own in the high-profile position of finance critic, a job he would leverage all the way to his landslide win on Sept. 10.

How he handled that job bore hallmarks of the leadership campaign to come.

As an Ottawa MP, he would often be asked to hold news conferences on the issues of the day because he was almost always in town.

He'd agree, but insist they be on Sundays. It was a slow news day and he knew it might help set that week's agenda.

This was well before social media was the force for Poilievre it is now, but a sense of timing and marketing was a skill set he'd continue to hone.

What his message would be in this leadership race, and who he'd need it to reach to win, also wasn't that different from what he'd been advocating his entire political career.

In the 2019 general election, Poilievre faced two challenges: the Liberals were gunning for his seat, and his riding boundaries had changed.

There were thousands of people who didn't know him and he needed to get them onside.

In an interview that year with The Canadian Press, he spoke about his doorstop pitch to voters as a fighter who wants to make their lives economically better.

He made that the central issue of his leadership campaign.

When it came to the role he felt government ought to play in people's lives, he used an expression in the 2019 interview he would go on to repeat in dozens of campaign rallies this year: Government is the servant, not the master."

His time on the opposition front benches, and the spotlight he earned there, had made Poilievre a revered figure in the party.

He was constantly in demand at local fundraisers, through which he built a network he'd leverage throughout the leadership campaign.

Free from the communications constraints of being in government, he began to experiment with social media, and videos talking about everything from coffee to taxes. He found footing in the online world and kept on walking.

Poilievre held onto his seat in the 2019 election, but the campaign ultimately cost Andrew Scheer - a longtime friend and political kindred spirit - his job as party leader. That left Poilievre with a choice: should he run to replace him?

He decided to make the jump, booking a room in an Ottawa recreation complex for a Sunday afternoon announcement. His popularity with the grassroots and strong beliefs in bedrock conservative principles - and ability to articulate them - were going to fuel his campaign.

Then, the night before, he got cold feet, deciding it wasn't the right time for him to place the burden of a leadership campaign on his young family. He sat the race out.

The subsequent months saw Poilievre express regret he hadn't taken the plunge, Conservative sources told the Star.

Some insist that, had he run that year, he would have won.

But it was the months after that leadership race - and then the 2021 general election - which cemented how he won this campaign.

When Erin O'Toole became the party's leader in 2020, he kept Poilievre on as finance critic. But O'Toole's team had a problem: it wanted to reshape the party's narrative and Poilievre was proving hard to corral.

By then, he had a YouTube channel and various social media accounts that had hundreds of thousands of followers and continued to draw more people into his orbit using petitions on various causes.

The petitions weren't the kind that formally go to the House of Commons for a government response, but online sign-ups that allowed Poilievre to build a massive database of names that were his alone and not fed into the data sets of the Conservative party.

One in particular, Stop the Great Reset," frustrated O'Toole's office as it was seen as edging too close to a conspiracy theory about the World Economic Forum.

O'Toole decided to shuffle Poilievre out of the finance critic's role - a move that triggered an unprecedented onslaught of complaints into party headquarters, sources told the Star. Although Poilievre was eventually reinstated, the demotion was one of many decisions that ultimately cost O'Toole his leadership.

Another contributing factor in O'Toole's demise: a Jan. 27, 2022 interaction Poilievre had with reporters.

That day, opponents of COVID-19 vaccination mandates who called themselves the Freedom Convoy" were on their way to the nation's capital.

O'Toole struggled to articulate a response to the protest - and the fact it included viewpoints and messages more extreme than just calls for an end to vaccination mandates.

Asked about the issue, Poilievre rounded on what he called the Liberal media" for singling out the radical elements and tainting thousands of others who were just trying to have their voices heard.

In that moment, several MPs told the Star - at a time when they felt O'Toole had lost his way - they saw a fighter.

O'Toole was toppled as party leader by a vote of his own caucus less than a week later.

That Poilievre was going to seek the leadership this time may have seemed inevitable, but it wasn't an automatic yes, according to Conservative sources interviewed by the Star who were not authorized to speak publicly.

But ultimately, the case was made - if he didn't run now, he'd lose the momentum he'd been building for years.

His launch video was shot in a matter of hours, and dropped on a Saturday night like a political bomb.

Poilievre's team felt it already had solid support among the party's existing members, and could broaden that out the usual way - by selling more memberships.

But unlike in previous leadership races, the team wasn't going to do that by targeting factions like firearms enthusiasts, or anti-abortion groups and specifically address their issues. Rather, the central plank of his campaign would be a unifying message about economic freedom for all.

That's not to say he wasn't alive to niche - and sometimes conspiratorial - concerns within the base and his new members. Persistent calls for him to disavow any connection with the World Economic Forum eventually led him to film a video denouncing the organization, and he also ended up walking alongside a popular figure in the anti-vaccine movement in a march to Ottawa earlier this summer.

The list of rivals solidified. Poilievre would face off against MP Scott Aitchison, Brampton Mayor Patrick Brown, former Quebec premier Jean Charest, former MPP Roman Baber and MP (and former leadership contestant) Leslyn Lewis.

Attacks against Charest and Brown were vicious from the get-go, with a tone that some insiders felt risked ripping apart the party.

But every time Poilievre was attacked for his tone or attitude, it actually worked in his favour, numerous sources told the Star. The surest way to position himself as a fighter for the everyman was to make it look like the establishment was against him.

Behind the scenes, that was hardly the case: a who's who of Conservative politicians and operatives were on Team Poilievre, including former cabinet minister John Baird, Sen. Leo Housakos, and strategic powerhouse Jenni Byrne.

Their tough-as-nails reputations complemented Poilievre's and as a group, they'd routinely clash with the race organizers over everything from the length of the campaign to the rules around the debates.

And although it would take months of negotiations before it was public, Poilievre landed the endorsement of the biggest establishment conservative of all - Stephen Harper, who publicly supported him in July.

By the end of the campaign, he'd also had the majority of MPs on side, even poaching a few from Brown as that campaign sputtered and ultimately ended.

The everyman pitch included another tactic - an emphasis on online fundraising over ticketed fundraisers.

Although establishment Conservatives vied for a chance to introduce Poilievre at fundraising events, the campaign didn't want to set ticket prices because of the optics of charging for access.

Rallies started off small - a coffee shop here, a bar there, publicized on social media and through direct emails to the list of supporters he'd amassed already, as well as through local MPs.

Then, in late February, the campaign began to notice the handfuls of people were turning into dozens. Then into hundreds.

At first, organizers figured it was lapsed party members just returning to the fold.

But when they received the first membership list in mid-March, they were startled: it contained hundreds of new names.

Then the hundreds of people at the rallies turned into thousands.

Something is happening here," was a common refrain among campaign organizers in the wake of rallies that were spilling onto sidewalks or turning into parking-lot jamborees.

The campaign moved to turn that momentum into memberships. It set up a system that gave everyone a chance to wait in line for a photo with Poilievre - and, while they waited, volunteers ran up and down the line, making sure people had memberships. If they didn't, they were sold one on the spot.

The team ultimately sold upwards of 311,000 memberships - more than the party's entire membership list for the 2020 race.

With Poilievre's members came the dollars.

At the end of the first major fundraising period, Poilievre's campaign officially reported raising more than $4 million. By the time the dusts settles, it's expected the number could be twice that.

The money propelled his machine forward - he could do more rallies, run more phone banks, do regional polls to see where his support was hard or soft.

It also meant he had the funds for an all-hands, get-out-the-vote effort.

As it ran through its supporter list, Team Poilievre would call them personally and invite them to private get-out-the-vote events, sometimes with him in attendance, sometimes just with the local MP.

We got a lot of people between the ages of early 20s and mid 30s that gravitated to Mr. Poilievre's message, and most of that particular demographic are people that have only voted Liberal in 2015, 2019, 2021," Housakos told reporters this week.

Not everything went smoothly.

As part of his economic message early on, Poilievre spent a few days campaigning on his support for cryptocurrency, even visiting a shawarma shop where he bought a sandwich with digital money.

It's not a new area of interest - he confessed to having spent late nights watching videos on the subject - but the campaign saw in the crypto community like-minded people interested in breaking down old institutions.

But when the crypto market crashed in mid-May, so too did Poilievre's public focus on the subject - deliberately.

It was an instance, insiders say, of Poilievre listening to advice when he needed to redirect.

Another: the team was sensitive to attacks that his support wasn't reflective of the diversity of Canada's population, so they switched up his social media videos to start featuring a much broader swath of supporters.

There was a lot more I' at the beginning and a lot more you' at the end," said one longtime Conservative.

The breadth of that support became evident on the night the results of the leadership race were announced: he'd swept 330 of 338 ridings.

And as he told his supporters that night - he's just getting started.

Stephanie Levitz is an Ottawa-based reporter covering federal politics for the Star. Follow her on Twitter: @StephanieLevitz