The far-right People's Party of Canada leader lost his Quebec seat in the 2019 federal vote and lost again in the 2021 election.
The riding of Portage—Lisgar came up for grabs after longtime Conservative MP Candice Bergen, who served as the party's interim leader before Poilievre took over, decided to resign. Bernier will test his luck in the rural Manitoba riding that delivered his fledging party its best result in 2021, with slightly more than 20 per cent of the vote.
Numbers like that spooked Conservative MPs, especially those in the West who saw their typically rock-solid support slipping to a more populist party.
Bernier stood vehemently against COVID-19 health restrictions, while then-Tory leader Erin O'Toole struggled to strike a position on vaccine mandates that satisfied anyone the party's base.
Now with Poilievre at the helm, the federal Conservatives are facing a rematch and supporters are looking for a victory that quashes the idea that the PPC poses a real threat.
Poilievre plans to host a "special meet and greet" rally Friday evening in Winkler, a city roughly an hour and a half south of Winnipeg. MPs have also visited the area, including House leader Andrew Scheer, whose razor-thin defeat of Bernier in the Conservatives' 2017 leadership race paved the way for the former Quebec MP to strike out on his own.
But the People's Party's candidate from the 2021 race attributes his support in that vote to momentum driven by strong feelings about the pandemic.
And Solomon Wiebe thinks the political climate has shifted.
@PierrePoilievre tries to head off #PPC vote as @MaximeBernier bets on social conservatives. #CDNPoli
"(Bernier) would be very lucky to get half of what I got last time," he said in an interview on Thursday.
"This is just what my expectations are, and I like to keep my expectations real."
As far as Bernier is concerned, his biggest challenge is operational, given that his party lacks the strength of the Conservatives. "We didn't have that team in the beginning of the campaign." Money is another matter, as the Tories raised $8.3 million in the first three months of the year, compared to the People's Party, which hauled in just under $300,000.
Bernier believes people across the acres of farmland and Mennonite communities that dot the sprawling rural riding remember the pandemic.
It's a reality the Conservative candidate knows, too.
Branden Leslie — who managed Bergen's election campaign in 2019 — won the party's nomination over three others, including the former provincial health minister, by highlighting that he stood as "pro-freedom" while his opponent locked down churches.
It was in the region where Bernier was also arrested for violating COVID-19 restrictions in 2021.
His strategy for attracting support for the June 19 byelection has so far involved making anti-trans statements targeting youth and children — characterizing it as a position on "gender ideology" — and vowing to reopen the abortion debate. Both are issues he views as weaknesses for the federal Conservatives.
"It's important for people here," he said in an interview. "People want to have a real debate about (these) issues."
He also hopes to tap into frustration over what he calls "climate hysteria."
Poilievre also rails against what he calls "destructive woke policies," releasing a recent video showing the toppling of statues, vandalized Christian churches and a decision by one Quebec school to replace Mother's Day events with a celebration of parents — a move that was made to acknowledge that some students were living in foster care, or had lost a parent.
Poilievre earned the support of social conservatives during last year's leadership race for his vocal opposition to vaccine and mask mandates, but there remain some who believe he should put a greater focus on cultural issues.
He has said a future Conservative government would not pass a law restricting abortion. And after ousting a social conservative candidate during a nomination race in rural Ontario back in March, some supporters of Campaign Life Coalition say they are "very cautiously observing" what Poilievre does next.
"We're not ready to abandon the Conservative party by any means," said Jack Fonseca, director of political operations for the anti-abortion group, adding he hopes that situation was a "one-off" and not indicative of the way social conservatives can expect to be treated.
At the time, a party spokeswoman said the candidate, Gerrit Van Dorland, was barred for failing to comply with a request to provide all previous comments made online or in other publications. His campaign disputed that.
Fonseca, who said his group has support in almost 900 households across Portage—Lisgar, likes at least some of what Bernier is proposing.
RightNow, another anti-abortion group that spoke out after Van Dorland's disqualification, is providing its supporters with information on where Bernier and Leslie stand on certain matters in the upcoming byelection, rather than endorsing anyone outright. That's because both espouse certain "pro-life" stances, according to co-founder Alissa Golob.
In a written statement, Leslie said he is "pro-life" and attacked Bernier as a parachute candidate.
"Maxime Bernier will say and do whatever he thinks people want to hear in order to get attention. He is pretending to be a social conservative, even though his entire record as an MP was to support woke policies," Leslie said.
Bernier, meanwhile, continues to blast the federal Tories as "fake conservatives." His message to prospective supporters is to "give Maxime a chance."
"'If you don't like what I'm doing, if I'm not keeping my word, then just vote me out in 2025."
This report by The Canadian Press was first published June 2, 2023.