Gillingham on the go Winnipeg’s mayor, seeking a second term in the upcoming election, does double duty while hitting the campaign trail By: Malak Abas Posted: 4:54 PM CDT Friday, Oct. 2, 2026 Last Modified: 5:56 PM CDT Friday, Oct. 2, 2026 Updates

In the weeks leading up to the civic election, Scott Gillingham has been performing a juggling act: he’s running to be Winnipeg’s 45th mayor, while still serving as its 44th.

“If someone asks me about the campaign, I’m going to answer them. But I think for most people, I’m the mayor of Winnipeg, even if I’m showing up as a candidate,” Gillingham, 58, says. “I try to do all I can to maintain that distinction.”

The Free Press joined Gillingham on a recent rainy September Saturday on the campaign trail, where he served in both roles during an event-laden day. City council’s final meeting before the Oct. 28 election was days earlier.

In Winnipeg, it’s rare for an incumbent to be defeated. But Gillingham knows his win in 2022 wasn’t exactly a landslide — he won with 27.5 per cent of the vote — and he’s been thinking about his second term ever since.

“I’ve treated this term of office as a long campaign to try to, obviously, increase Winnipeggers’ confidence in me and trust in me,” he says. “In part because knowing that I wanted to run for a second term, I wanted to have a stronger foundation and a stronger base. I have run hard these last four years.”

About this time four years ago, Gillingham, the former councillor for St. James, was trailing the front-runner at the time, Glen Murray. Gillingham knows better than most how fast things can change.

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9:10 a.m. The day begins at Gillingham’s home, where he lives with his wife, Marla. Louie, an excitable 10-year-old Shih Tzu and Yorkshire Terrier mix, is the first to greet the Free Press at the door. They’re just wrapping up breakfast — for Marla, a leftover croissant from Le Croissant, for Scott, egg whites, toast and black coffee. Louie will get a little bit of egg and a Greenie, a Saturday treat.

“Now that the kids are older and out of the house, he’s the centre of attention here,” Gillingham says.

Gillingham has already finished breakfast, having gotten up hours ago. He describes himself as “a big breakfast eater,” but lunch is more slapdash — he’s known to walk out of the house with a can of tuna and an apple, Marla says.

Conversation shifts to the 12-hour day ahead. A day this long, Gillingham says, is a regular facet of campaign life.

He pulls up his calendar on his phone, packed solid with blocks of green and grey — the former for campaign duties, the latter for mayoral ones.

9:44 a.m. The Gillinghams, Caitlin MacGregor, a communications officer for the mayor’s office, and a Free Press reporter and photographer pile into Marla’s Honda CRV. It is a tight fit.

While Premier Wab Kinew regularly travels with a bodyguard and security detail, Gillingham doesn’t normally have an entourage. He says there’s only one time where he had to hire a security detail, but asks that the incident that caused it remain off the record.

He said his office has had to deal with threats and has had to contact police.

“I don’t live concerned, really, but it’s an unfortunate reality of the way our world seems to be going,” he says. “The vitriol and the venom and the number of people who are unwell and just think that they can say anything and threaten politicians is really concerning.”

9:54 a.m. First stop is the mayor’s St. James campaign office. The child lock on the vehicle is broken, briefly trapping the Free Press reporter in the back seat. This will happen five more times during the day. It’s a post-election issue to fix, Gillingham jokes.

9:55 a.m. The space is bustling with campaign staff and volunteers putting together signs and hunched over laptops. Among them is Gillingham’s 94-year-old grandfather, Gordon Alder, who is smoothing stickers that say “re-elect” onto campaign signs in the back office.

“He didn’t get the brains from me, but that’s OK,” Alder says, chuckling.

10:08 a.m. Gillingham sits down with Colin Fast, his director of communications, and Brian Kelcey, who works on policy in the mayor’s office. They’re discussing a press release that will come out the next day promising a committee tasked with preparing Winnipeg for a wide range of “disruptive tech,” ranging from artificial intelligence to e-scooters.

Gillingham is mostly quiet, listening intently as Kelcey goes over the latest draft of the press release. It has gone through a few edits, focused on creating a positive tone about the ability to control rapidly growing tech if the work starts now.

They go back and forth on a line stating the city would be “surveying” the public on the issue. Gillingham suggests that, in light of “managing people’s expectations clearly,” the wording be changed.

They settle on “consultation,” and the final release describes them as public hearings.

The re-election campaign is slightly behind schedule, Kelcey says. Every promise requires consultation and research, be it with business owners, community groups or other levels of government.

“Even for this simple piece where we’re kind of saying, ‘We’ll legislate on something someday,’ there’ve been 10 different conversations before, and there’ll probably be another 30,” Kelcey says.

Kelcey describes much of the current campaign work as forward-focused, whereas the last four years involved a lot of picking up long-running issues that previously had gone unaddressed. Gillingham’s promises this time are centred on how Winnipeg’s council can have a proactive hand in how the city’s future might take shape.

10:40 a.m. MacGregor films a social media video for the mayor’s Instagram account. Right after, it’s back to the car. The next stop is the community studio space 618 ARTlington for its “Works in Progress” open house. Gillingham runs into Wolseley MLA and Transportation and Infrastructure minister Lisa Naylor. They fiddle with Naylor’s phone, trying a few different selfie methods, before sharing a high-five.

11:02 a.m. The mayor was invited to the space for what will presumably be his tiniest ribbon-cutting of the campaign trail: the public launch of an ornate diorama, nestled in the crook of a wall. Gillingham is handed a small pair of scissors and gives a short speech.

“One of the things I’ve learned in four years of being the mayor is that we have a deeper, richer, more wonderful arts community than I think the average Winnipegger understands,” Gillingham tells the crowd. “We ooze talent, we just ooze talent in this town.”

11:52 a.m. After traversing all five floors of the building, meeting with designers and taking selfies, the next stop is just a few minutes away — a visit with artist Kal Barteski at her home to pick up lawn signs she designed for him.

The signs feature Barteski’s signature thick, inky brushstrokes, previously used by business giants such as Lululemon and Starbucks.

“I love it, that’s so great,” Gillingham says, looking at the signs. “Thank you so much for doing this.”

“Any time,” Barteski replies. “Thanks for looking after our city.”

12:10 p.m. They return to the Gillinghams’ residence for a change of clothes and to regroup before the next event.

“My team always tells me, ‘don’t wear a hat,’ because people don’t recognize you if you wear a hat,” Gillingham says.

“I always tell him he has the typical middle-aged white-guy look — balding, glasses, right?” Marla notes, while Gillingham laughs, chiming in with, “I’m a man of the people.”

1:04 p.m. A St. Paul’s High School football game is the next stop. Despite the rain, the bleachers are packed. There are more selfies with the mayor.

1:29 p.m. A handshake and hug with community advocate and St. Paul’s alumni Mitch Bourbonniere turns into a serious conversation about Winnipeg’s drug crisis. Bourbonniere strongly encourages a focus on drug treatment options in the city and targeting punitive measures on those selling drugs.

1:55 p.m. A parent asks Gillingham what he thinks is Winnipeg’s most pressing issue. They discuss safety.

2:03 p.m. Leaving the game, Gillingham stops to say hi to a baby and his mother, and waves to more moms and their young children in the bleachers.

“Shaking hands and kissing babies,” one of the mothers jokes.

2:21 p.m. Another rain-drenched youth sports event — the Charleswood Bronco Family Day, where the “Crunchers” football team, composed of eight- and nine-year-olds, are playing.

Gillingham grabs a late lunch — a cheeseburger, with pickles and banana peppers — from a barbecue set up for the event. Mid-burger, he is approached by one of the leaders of the volunteer-run football club.

“I’m gonna petition you for a turf field right now … we’re flooded out,” he says, gesturing to the sopping wet grass.

It’s a chance for the mayor to reiterate one of his campaign pledges. Earlier this month, he promised two heavily used sports fields will get a makeover from grass to artificial turf yearly if he is re-elected.

2:59 p.m. Gillingham catches the rest of the first half from the bleachers. A couple of East Side Eagles players boast to the mayor that they’ve been killing it this season, and they like winning.

“Right on,” Gillingham says, and the kids nod solemnly.

3:15 p.m. The Gillinghams return home while everyone takes a break before the mayor’s evening itinerary gets underway.

6:21 p.m. Yet another football-focused event, The Blue Bombers Hall of Fame Celebration at the RBC Convention Centre. MacGregor moves swiftly, making sure the mayor has water in between handshakes. There’s a lot of talking involved as Gillingham mingles with the crowd.

A conversation between the mayor and Bombers running back Brady Oliveira goes well. “He just (told the mayor), ‘You got my vote,’” MacGregor says cheerfully. “You can quote that.”

7:05 p.m. Gillingham grabs a few slices of salami and cheese from a charcuterie board as he heads out. Based on how the night’s going, this will be dinner.

“You eat when you can in this job,” he says.

7:46 p.m. The day’s final stop is Nuit Blanche, where Gillingham will give opening remarks at the St. Boniface Cathedral. In the midst of touring the art installations, Gillingham is confronted by an attendee, a long-time bus user who accuses the mayor of ruining the transit system when the city overhauled the network in 2025.

“You’ve over-convoluted the bus system. It’s much worse,” Annachie Baskier-Pasternak says. “Trust me, I’ve taken the bus for 20 years. I don’t know how long you’ve been taking the bus for.”

Baskier-Pasternak disagrees with the mayor’s responses, and the conversation gets heated. At one point, MacGregor steps in, asking the man to give the mayor a chance to respond.

The conversation lasts a few terse minutes, but ends with a handshake. The man says he appreciates Gillingham for listening, but departs with a declarative “F—- Transit.”

Later, Gillingham says those kinds of confrontations are a part of the job.

“I put the facts on the table, but I can’t get too defensive,” he says. “I do have to listen because it’s a system that he depends upon.”

8:24 p.m. Addressing the crowd, Gillingham says the work that goes into putting together Nuit Blanche is “indicative of the kind of unity that we want to move towards.”

8:42 p.m. After a long day, the Gillinghams settle onto a water bus tasked with taking Nuit Blanche attendees across the Red River from the cathedral to Stephen Juba Park.

The conversation becomes introspective. Gillingham notes that while some days are fun-filled like today, other are much harder.

As an example, he cites the day he received a call from the Winnipeg Police Service informing him that they were arresting Jeremy Skibicki, a serial killer charged with the murders of four Indigenous women.

Gillingham spent more than 20 years as a Pentecostal pastor before entering politics. Those years, and his continuing Christian faith, inform all of his days, whether they are easy or difficult, he says. He describes his work in acts of interconnecting service — to the City, to his family, to his faith.

“I go back to service,” he says. “Try to serve the community with a blend of compassion and wisdom.”

The Gillinghams then meet up with their daughter, Hannah, and head off into the night to take in the rest of Nuit Blanche’s offerings.

malak.abas@freepress.mb.ca

(The Free Press will be documenting a day on the campaign trail with Kevin Klein, Gillingham’s leading challenger, next week.)