Memorable moments in Manitoba
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Three years before Justin Trudeau beat down the incumbent Conservatives in the 2015 general election -- launching a more than nine-year period as prime minister -- Dan Vandal stepped into the ring with the Liberal leader to trade blows in downtown Winnipeg.
Vandal, then a Winnipeg city councillor, had just met Trudeau, who attended an event at Université de Saint-Boniface while seeking party leadership. That evening, they went to the Pan Am-Boxing Club in the Exchange District to get to know each other and work out with trainer and club president Harry Black.
It's a moment that has stuck with the Liberal MP in the years since and one he returned to Monday, as he and others reflected on their relationship with the prime minister, who tendered his resignation.
"I held the hand pads for him for a couple of rounds. I gave him some pointers on his technique," Vandal said.
"(He) and Harry then went through a gruelling 12-minute round where Harry showed him the ropes. The prime minister certainly was very fit. Harry put him through an excellent workout that day."
Afterward, Vandal showed Trudeau -- who was elected leader of the federal Liberals about two months later -- some of the sights in downtown Winnipeg.
Vandal joined him in the House of Commons two years later, when he won the seat of Saint Boniface -- Saint Vital, and Trudeau won his first term as prime minister in the 2015 general election.
Trudeau enjoyed a surge in popularity in Manitoba ahead of that first election, according to data from Free Press-Probe Research polls. At the time, the Liberals had the support of 45 per cent of decided and leaning Manitobans who were surveyed, compared with 35 per cent for the Stephen Harper-led Conservatives.
MP Kevin Lamoureux witnessed that rise first-hand, becoming fast friends with Trudeau when he was still a fledgling politician.
The pair first met in 2010, when Trudeau joined Lamoureux at a campaign rally. Lamoureux was running for the Liberals in a Winnipeg North byelection that he went on to win.
About 300 people were in attendance at a banquet hall on Mandalay Drive in The Maples. Many were focused on Trudeau, who was already a political rock star, and many people were queuing to speak to or pose for a photo with him, Lamoureux said.
"It was a like a love-in atmosphere, where all the attention was on (Trudeau)," he said.
From there, Lamoureux said he and Trudeau formed a close relationship in which they discussed family and other things outside of politics. Over the years, Trudeau has joined Lamoureux at events in Winnipeg North, including some of his weekly visits to a McDonald's restaurant on Keewatin Street, where he invites constituents to chat or express concerns.
"He didn't have to do these types of things," Lamoureux said.
The day after Scott Gillingham became Winnipeg's 44th mayor in 2022, he was having dinner with his wife at The Keg Steakhouse and Bar on Portage Avenue when his phone rang and he stepped out on the patio.
"I was told I was going to get a phone call from the prime minister's office," he said. "That will always be memorable because it was a bit of a surreal moment to receive a call from a prime minister congratulating me."
It was the beginning of a "good working relationship" with the federal government, Gillingham said.
Trudeau has been a political stalwart for young Canadians such as Victoria Romero, 22, who has known no other prime minister during their adult life.
The University of Manitoba student, who uses gender-neutral pronouns, has met Trudeau on several occasions.
Romero first spoke to him at 14, when he hosted a town hall event at the University of Winnipeg.
"It was a very exciting time to be a young person opening their eyes to politics," Romero said.
"At that time, the outlook was very different in terms of what the Liberal party was pushing for, as opposed to now. It signified a lot of great change for our country. There was a lot of interest from young people, from women."
Romero said one of the prime minister's best qualities as leader has been his ability to defend party values off the cuff, referencing an impromptu debate Trudeau had with a student regarding abortion in 2023. Video clips of the interaction went viral online, showing Trudeau defending a woman's right to access such medical care.
"That was a great moment that shows while the policy of the Liberal party has been lacklustre at times... it is reassuring to at least have someone who is willing to say those things," Romero said.
Romero said they hope the PM's departure will open the door for voters to think "outside the box" and consider parties other than the Liberals and Conservatives.