Chuck Winn in Bozeman May 8, 2024
Bozeman’s Interim City Manager Chuck Winn poses in front of city hall on Wednesday, May 8. Credit: Matt Standal / MTFP

For Bozeman’s Chuck Winn, taking on the city’s top executive role is a culmination of more than 40 years of work for the city.

In fact, he’s the longest-serving city employee on the books.

Winn was promoted from assistant city manager to interim city manager in April by commissioners who had voted unanimously to sever ties with his predecessor, Jeff Mihelich.

The transition was predicated by a leaked video showing the former city manager belittling commissioners, discussing his salary and uttering the phrase “small-town shit,” during a frustrated gossip session that went viral online.

Describing the incident as an “unfortunate distraction,” Winn said those kinds of comments are not the prevailing attitude at city hall and never have been. 

“We need to put that behind us,” Winn told Montana Free Press. “We need to learn the lessons from that, and we need to move forward.”

“Bozeman is so much bigger than one person,” said Winn, adding that a priority for the city is to convince citizens that their government is working for them and not the other way around.

“We’re still picking up the garbage. We’re still patrolling the streets. We’re still putting out the fires. We’re still providing water and sewer services. All of that continues regardless of who the city manager is,” Winn said.

An approachable, affable 60-year-old, Winn has an office decorated with firefighter memorabilia and a view that includes his “favorite tree” growing in a little wooded area outside city hall. He points to a framed photo of him encircled by shooting flames while standing on top of a burning building. 

“It got so hot the paint was peeling off the truck, and we had to shut the engine down,” Winn said.

Which is to say Chuck Winn is no stranger to putting out fires in the city.

Among the many unique pieces of decor in Winn’s office is the official badge of Bozeman’s city manager.
Among the many unique pieces of decor in Winn’s office is the official badge of Bozeman’s city manager. Credit: Matt Standal / MTFP

Winn worked his way up from volunteer fireman in the early 1980s and retired from the Bozeman Fire Department in 2008. Along the way, he served in every department role, including captain, fire inspector, fire marshall and eventually fire chief. 

Tapped to lead Bozeman’s public safety services, including police, fire and parks departments, Winn started his second career with Bozeman in 2008, becoming assistant city manager under then-manager Chris Kukulski. 

Along the way, Winn briefly stepped into the city manager role when Kukulski resigned in 2017 and has worked under three other city managers who have filled the position since.

Citing the limited shelf life of Bozeman’s recent spate of city managers — three in less than seven years — Winn admits that he never set his sights on the permanent job because he’s always wanted to stay in Bozeman.

“City managers move around a lot,” Winn said. “It’s the nature of the business, and when you get into that business, you understand it.”

However, Winn’s latest move into the executive hot seat comes as the city government is battling ongoing trust issues in the fallout of the Mihelich incident. According to Winn, co-assistant city manager Kira Peters’s departure for personal reasons, which she posted on the day Mihelich was put on leave by the city commission, compounds the matter.

“So where there were three, now it’s just me,” Winn said.

There’s also a laundry list of important issues the city is poised to address this summer, including the ongoing struggle over urban camping, a municipal judge suing the city over gender discrimination, a slew of controversial housing developments and the looming specter of a changing development code that will guide the burgeoning city’s growth.

Add to that a newly elected majority of city commissions, a new mayor, deputy mayor and an unfilled commission seat, and Winn said he’s already busier than ever before, studying up on issues like wastewater, affordable housing incentives and public works projects. 

“I’ll never complain about, or never talk about how many hours I work,” Winn said. “I don’t clock in and I don’t clock out. I never have.”

Shoring up trust in city hall is just one reason the city commission again appointed Winn as the acting city manager, according to Bozeman Mayor Terry Cunningham, who described him as a “known factor to the community.”

“Chuck has an even keel,” Cunningham said. “He’s had almost every single department reporting to him during his tenure.”

The other reason for Winn’s appointment, according to Cunningham, is due to the local government study commission that voters could approve. Ballots were mailed this week. 

Held once every 10 years, the election offers voters in cities and counties statewide a chance to fund a group of officials to study the effectiveness of the local government and recommend changes.

Cunningham said that means voters could reject Bozeman’s current council-manager government in favor of a mayor-council system, where the elected mayor assumes the role of the city manager, effectively putting that person out of a job.

“If we were to go out at this time and do a national recruiting effort, one of the things we’d have to disclose is that there’s a chance that the form of government may change,” Cunningham said.

This is just fine with Winn, who still hasn’t moved into the city manager’s “official” corner office. He said he made a deal with the commission to stay as long as they need him but requested his old position be put on hold.

“Over the 40 years that I’ve been here, the one constant is we have really great people who care about Bozeman,” Winn said. “They care, and they invest in this community, and that’s what I’m most proud of, is that I get to work with these people.”

The city of Bozeman is recruiting for an assistant city manager to replace Peters. The annual salary range is $184,000 to $202,000.

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Matt Standal is a Montana-based multimedia journalist with a background in filmmaking and outdoor education. While he's produced stories for local news broadcasters in Minnesota and Idaho, Matt's favorite job is leading backcountry ski tours in Yellowstone National Park. He's also a former PADI scuba instructor, emergency medical technician and devoted book nerd. You can find Matt teaching avalanche safety classes when he's not working with film crews or digging into stories.