A Rocky day on the campaign trail ‘It matters how hard you get hit and keep getting up,’ mayoral candidate Kevin Klein says, referencing famous film’s fighter in wake of opponent’s allegations, apology-triggering column in his newspaper By: Malak Abas Posted: 12:00 PM CDT Friday, Oct. 9, 2026

Kevin Klein acknowledges it’s hard to foresee what he’ll wake up to each morning in the final weeks of a mayoral campaign.

But the seasoned politician, who has served as both a city councillor and a provincial cabinet minister, couldn’t have predicted the events — what he describes as “drama” — that unfolded last Sunday.

Fellow mayoral candidate Mike Vogiatzakis accused Klein’s campaign team of offering him a job to drop out of the race, while a guest writer’s column in the Winnipeg Sun that questioned the deaths of Indigenous children at residential schools, just days after the National Day for Truth and Reconciliation, sparked condemnation from a prominent Indigenous organization. (Klein is the CEO of the Klein Group, the company that owns the Sun. He has maintained he is not involved in its operations while running for mayor.)

The Free Press had already been scheduled to join Klein on the campaign trail Monday, intending to document a day in the life of the front-running candidate to unseat incumbent Scott Gillingham, before the controversies hit.

The allegations and criticisms were weighing heavily on Klein when the Free Press arrived at his campaign office and he spent much of the day addressing them. He denied Vogiatzakis’s allegations and said his rival’s team had offered him a similar bribe.

He vowed the controversial column would never have been published if he was still holding a position at the Sun, placing the responsibility on his wife, Sun editor-in-chief Heather Klein, and later apologizing to the Southern Chiefs’ Organization.

Periods of time when he wasn’t on the defensive were the parts of campaigning that Klein says are the most important to him — finding support from voters, be it through honks from drivers or handshakes at a local diner.

“All this kind of stuff coming up, it’s not me or my platform, and I think we have developed a platform that is strong,” he said Monday morning. “I believe that Winnipeg can be better.”

8:04 a.m. The day begins at Klein’s campaign office on St. Mary’s Road, where seven staff members and volunteers are enjoying Timbits and coffee. As campaign manager Keith Poulson puts it, “we tend to be very relaxed here… but we’re doing some serious stuff.”

Klein is in a suit, and his supporters, all decked out in blue shirts emblazoned with his name, gather around a table. The team remains quiet as he details the back-and-forth accusations and expresses regret over the column.

He refers to a previous Sun column, written Sept. 28 by former MP Robert-Falcon Ouellette — who is Indigenous — calling on groups to “treat residential school issues more seriously,” and describes Vogiatzakis’s claims as “without merit.”

Klein speaks candidly, saying it feels like being “picked on,” and that he doesn’t want his supporters to get caught up in the fray.

“The entire thing is unfortunate, because for whatever reason, I have two candidates, in Gillingham and now Voigitzakis, acting like Donald Trump — it’s like an American-style election, just attack, attack, attack, with no merit,” he says.

“And I want to apologize to you guys, because you have been very good to me. You’ve been great supporters to me. I don’t want to let you down.”

Klein finishes speaking and Poulson places a supportive hand on his shoulder.

“Now we’re five minutes behind schedule,” he says, and everyone laughs, the tension breaking.

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8:21 a.m. Klein’s morning routine includes hot coffee in a massive white Yeti tumbler with a straw — half-decaf, with a bit of sugar-free creamer — and a handful of vitamins, including fish oil, glucosamine, turmeric and magnesium; good for the joints, he says, after years of practising Taekwondo and walking the two family dogs, a German shepherd named George and a Maltese called Indy.

Klein and his team set up on a stretch of road near the office, waving campaign signs and pumping fists. Lots of supportive honks, including some from Winnipeg Transit bus drivers.

8:48 a.m. Back in the office. Klein has a campaign announcement scheduled for 10:30 a.m. at the Granite Curling Club on transparency at city hall. He calls it a “big one.”

Still, the allegations and criticisms of the last 24 hours loom. Klein knows reporters will have questions and he plans to address them ahead of his transparency announcement, hoping they switch their focus to that.

When asked how he approaches media scrutiny, especially on a day like this one, the words tumble out.

He spoke with Poulson about the allegations early this morning, and then with a friend he describes as a mentor figure. He consoled his family — he and his wife have six adult children and seven grandchildren — who were worried about him. He prayed.

Barbs from other candidates often touch a sensitive nerve, he says. He describes his upbringing as “dysfunctional:” he constantly moved between schools, his family was often evicted from homes and his life was shattered after his mother was murdered by her partner.

“That is a big part of it. It’s a big part of it because it does bring back a lot of childhood stuff,” he says. “It’s like — again? I’m not new to the school this time.”

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9:09 a.m. Klein reads his talking points for the upcoming announcement softly to himself. Campaign staffers fiddle with a printer that isn’t co-operating.

Klein announced his intention to run for mayor on Sept. 1, leaving him with less than two months to campaign before voting day on Oct. 28. It’s not a lot of time, he acknowledges.

His announcements typically come after several weeks of research, he says. Some, like his homelessness strategy, started with research that began before he announced his intention to run.

“One of the most difficult things (about) running as not (an) incumbent is you don’t have the same access to city information… so we have to dig a little deeper,” he says.

For Poulson, a former nurse who has worked on more than two dozen campaigns in the last 40 years, the last month has been non-stop. He swears this one is his last. If it isn’t, he jokingly suggests, his wife might kill him.

10:30 a.m. Outside of the Granite Curling Club, Klein takes to a podium in front of reporters, photographers and camera operators. He acknowledges “some interesting developments and false claims,” and takes questions.

Later, he pivots to his announcement; he promises to bring back the city’s independent ombudsman, tasked with investigating cost overruns on projects.

On the drive back to the campaign office, he says it’s difficult to gauge news conferences in terms of successes or failures.

“I just have to tell my truth, and it’ll be reported the way it’s reported. I give up trying to guess, you know?” he says, pausing before glancing at the Free Press reporter.

“How did you think it went?”

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11:26 a.m. An interview with francophone weekly newspaper La Liberté.

12:01 p.m. Lunch at Red Top Drive Inn, a staple for Klein and the team. Despite a burger on the menu named “The Mayor,” Klein goes for the classic breakfast, which features eggs, sausage, rye toast and coffee with milk. He doesn’t do a lot of sit-down meals, he explains, but he’ll eat breakfast foods any time of day.

The conversation is light and casual, a break from campaigning. Klein and his staff chat about favourite foods, an upcoming film about the production of the 1976 Oscar-winning underdog boxing movie Rocky and Thanksgiving plans.

Klein notes he’s been hinting to his kids via texts that it should be hosted at one of their homes.

“We have kids, make it their job,” he says with a laugh. “I’m working on that.”

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1:15 p.m. “Good luck, buddy,” a diner says, shaking Klein’s hand before leaving the restaurant. Minutes later, another supporter — a friend and local business owner, Klein explains — also stops to wish him well and introduce him to his dining companion.

“I’m sorry you had to have lunch with this guy,” Klein says with a smile.

“Be nice now, you’re supposed to be nice to me,” his friend counters.

“Oh, right, it’s a political season… I forgot,” Klein says, inspiring some laughs.

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1:39 p.m. Another media interview, this time with Citytv, focused on transit safety.

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1:47 p.m. Heather Klein arrives at the campaign office. She has served as the Sun’s editor-in-chief for the past year or so, and has taken full responsibility for the column that appeared in Sunday’s paper.

Her eyes well up and her voice catches when describing the backlash.

“I feel sick,” she says. “I never thought it would be me that would hurt him.”

Her workload has doubled since her husband stepped away, she says, adding it’s been a lot to juggle.

“I’m going to blame it on being absolutely overwhelmed with what’s going on in this moment, and it was the wrong decision, absolutely, to put it out,” she says as Klein pats her arm supportively.

She says the column’s comments don’t reflect the couple’s views, but notes that she believes people “have a right to share their opinions.” After it was published, she defended it in a column of her own titled “Disagreement is not denial.”

Regardless, she says, its publication was “very poor timing.”

She already wasn’t sure about her husband running for mayor a second time — he finished third behind Gillingham and Glen Murray in 2022 — but became convinced after hearing from voters “who seemed desperate for change.”

She describes the race as stressful and hard on their family.

“I prefer to have him at the Sun because it’s a hard job without him. But I also believe Winnipeg desperately needs help, and that’s where we’re at,” she says.

She pushes back on the question of whether her husband has a special advantage during the campaign because she’s the the editor of the Sun. Even if the paper comes with an inherent “perk,” the incumbent has the advantages of being in office, she says.

“It is an advantage, for sure. I would never discount that,” she says. “But Scott (Gillingham) has an advantage, too.”

“I don’t think we’ve ever used that advantage,” Klein replies.

She acknowledges that it’s hard to say for sure.

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2:29 p.m. Time to put out requested lawn signs at supporters’ homes. The editor sees the candidate off, teasing him not to play too much ’80s music — his favourite — while driving.

While Klein places one lawn sign, a woman walking by stops to speak with him about his homelessness strategy.

“I’ll be voting, I vote every election,” she says.

3:07 p.m. Klein spends some time connecting with constituents over the phone. On one call, it appears he’s speaking with someone sympathetic to what he endured over the past day.

“Ever the Rocky figure, taking the hits, you know me,” he says with a laugh.

“I’m just gonna start telling Keith (Poulson) to, ‘Cut me, Mickey, cut me,’” he adds, referencing a classic mid-fight line from the movie between Rocky and his trainer.

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5:33 p.m. The day ends with a bingo game at the Belgian Club Legion 107. It’s a packed house filled with experienced players and their good-luck trinkets and bedazzled dabbers lining the tables.

Klein, meanwhile, is explaining to some of his younger staff members why the Canadian sci-fi comedy Resident Alien is one of his favourite shows.

“My wife hates it, because I watch the same TV series to go to sleep, every night, for years,” he says.

5:54 p.m. A bingo veteran has questions for Klein after overhearing he’s a mayoral candidate. After some small talk, he’s sold.

“You’ve already got my vote,” the man says, sipping his drink.

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6:33 p.m. Klein doesn’t gamble, but says it’s a nice chance just to be around voters without being imposing or obtrusive.

There have been several mentions of Rocky — which embraces the theme of perseverance through struggle — during the day.

Klein says he understands that struggle all too well.

“It doesn’t matter how hard you get hit, it matters how hard you get hit and keep getting up. And I really felt that today,” he says over noise inside the bingo hall.

“I really felt that I took a lot of hits today, but I’ve got to get back up because… I believe in what I’m doing. I believe that I can help our city.”

malak.abas@winnipegfreepress.com