The trouble in Glendive began almost as soon as (now-former) Mayor Teresea Olson was sworn in.

This story also appeared in Glendive Ranger Review

All the ingredients were there: a multi-generational power structure with a long-established way of conducting business under next to no scrutiny; a collective amnesia about local civic history; a population (4,871, as counted in 2021) anxious about the economic future of their town, which, like many tiny towns across the prairie, had stagnated — even with its newly legal marijuana dispensaries and proximity to intersecting highways, the Yellowstone River, Montana’s largest state park, and the once-money-minting Bakken Formation. 

Then came Olson. She said she didn’t run for mayor as a revolutionary, just as an alternative to a two-decade incumbent. Powered by an earnest sense of municipal do-goodery, she wanted to revive local manufacturing, generate jobs, expand trail access and support a struggling and understaffed police department. The voters of Glendive were willing to trust her, electing Olson over her predecessor by a huge margin. The eight-member City Council, not so much.

“When I ran for mayor … it wasn’t for the big money,” Olson told the council and a crowd assembled at City Hall when she announced her resignation on Sept. 5, the climactic moment of an almost two-year period of governmental dysfunction and discord. “It was because we wanted to make Glendive better.”

That had proved harder than anyone could have imagined. When Olson left City Hall that day, she left Glendive with no mayor, no director of operations (a position akin to city manager) and no police chief. The city was a ship without a rudder or sail, adrift in a sea of anger and political confusion. In the weeks since, the city government has managed to tenuously stitch itself together with interim appointments. But the mutual trust and open communication that form the warp and weft of civic fabric are badly frayed. 

Ego, miscommunication, stubbornness and inexperience combined with the claustrophobia of small-town life generated acrimony that engulfed essentially all of Olson’s term, which began in January 2022 and ended, prematurely, with her resignation last month. She and the council fought over everything from nuisance petitions to the very form of city government. And in what proved to be the real beginning of the end, they fought over Olson’s controversial firing of Glendive’s new police chief. 

Along the way, Olson’s supporters began attending council meetings to defend their mayor. To them, the mistreatment they felt she faced from the council indicated deeper problems. At best, Team Olson thought, the council members were rude and dismissive, members of an insular good ol’ boys club. At worst, they alleged, council members were breaking the law. Olson supporters began circulating recall petitions, and two are now following their frustrations to the next logical step: running for council themselves. 

Insults and insinuations flew in both directions, a judge slapped a council member with a restraining order, and Olson’s attempt to clean up a derelict home led to an allegation of car theft. Olson, frustrated by what she perceived as unending disrespect from the council, used the occasion of one particularly heated email exchange to suggest the council president had dementia. 

As she put it in a Facebook post following her resignation, Olson felt “sabotaged” from the start. Her supporters agreed. 

“I had people that gave me a chance,” Rick Norby, the mayor of nearby Sidney and a friend of Olson’s, told Montana Free Press. “She didn’t get that. And now she’s the one that’s suffering for it.”

But in the eyes of the council, the political neophyte Olson was simply unwilling to learn. They contend that she left them in the dark on key decisions, that she preferred to seek advice from outsiders rather than the seasoned policymakers in front of her. 

“I had people that gave me a chance. She didn’t get that. And now she’s the one that’s suffering for it.”

Sidney mayor Rick Norby

“When [former mayor] Jerry Jimison swore her in as mayor, gave her the keys, and walked out the door, is when it went south,” Council President Leon Baker told MTFP. 

Even so, if she had stuck around, the council members swear, she could have charted a course forward. But she didn’t, and her abrupt resignation left the council to pick up the pieces. 


The story of this political moment in Glendive began almost 40 years ago.

It was 1974. Directed by the newly ratified Montana Constitution of 1972, Glendive and other cities were to register their preferred form of government with the state. The statute laid out a number of options, each featuring different configurations of executives, councils and city managers. Under each of those options were sub-options. Would the mayor, for example, have unilateral hiring and firing power? Or would they need to seek approval from their city council? 

Glendive defined itself as a commission-executive city with a strong mayor who needed council support to appoint department heads but could hire and fire anyone else at will. 

The Constitution says that voters may alter their city’s form of government every 10 years, beginning in 1976. If voters didn’t choose an alternative form of government that year, the city would default to a statutorily defined configuration beginning in 1977. 

A 1976 study commission in Glendive proposed reorganizing the city under the commission-manager system. The proposal failed by a wide margin. The city then retained its commission-executive status. It would have partisan elections. 

From that juncture forward, Glendivians passed on the option to propose alterations to their form of government every decade. Voters seemed content with a system in which the mayor has some executive authority but generally shares power with the council. In 1996, a member of a study commission wrote that Glendive’s existing form of city government had served the city well since 1881, and would continue to do so in the future. 

In 2002, Jerry Jimison, an All-Big Sky Conference defensive lineman for the Montana State University Bobcats in the 1960s, was elected to the first of five consecutive four-year terms as mayor of Glendive. 

And he was elected, along with the city council, on a nonpartisan ballot. It’s not clear, in fact, if Glendive has ever elected city officials on partisan ballots, despite that being the city’s choice back in the 1970s.

Over the years, Jimison and the council, which has had some of the same members since he took office, developed a strong, cooperative relationship, aided by long-serving Operations Director Kevin Dorwart, an accountant by trade, several long-time members of the council said. The council often voted as a bloc. And they also voted on personnel decisions that, again, were technically the sole purview of the mayor under the city’s organizing framework. 

To call the council a “good ol’ boys’ club” applies a normative judgment. But there’s an element of truth to the label. In the current council, Leon Baker, the council president, is the father of council member Doug Baker. Former Mayor Jimison is the father-in-law of council member Rhett Coon. The council has its own traditions and lore. Members regularly meet after meetings at the Beer Jug on Merrill Avenue. Part of this is the reality of small-town politics. Leon Baker, asked by MTFP whether the council ever reached a quorum at the Beer Jug — a potential violation of the state’s open meeting law, depending on what they discuss — replied that it’s just as easy to reach a quorum by happenstance in the hardware store or at a high school basketball game. 

Jeremy Swisher (left) signs official documents following his swearing-in as chief of police, as Mayor Teresea Olson observes. Credit: Brendan Heidner / Glendive Ranger Review

Meetings, historically, were sparsely attended by the citizens of Glendive, members of the council said.

“I can almost count on one hand the number of times we had any audience,” Gerald Reichert, who’s sat on the council since 2009, told MTFP. “Spending in excess of $20 million on a wastewater treatment facility, I think we had two different hearings. No one showed up.” 

Glendive still had problems. The city’s police department was chronically understaffed, according to Baker, the council president, who began serving on the council under the mayor before Jimison. There was an especially dire dearth of dispatchers — a recurring issue that would crop up again and again in the city’s future.

Over successive elections, Jimison began to face challengers, each chipping away at his margins of victory. 

In 2021, Teresea Olson, a nurse, physician assistant and medical massage therapist, decided to run. She’d made an unsuccessful bid for the county commission in 2020 and was involved in a number of local organizations, including a nonprofit that advocated connecting the badlands of eastern Montana and the badlands of North Dakota with a trail system, but otherwise had no political experience. 

She knew Jimison reasonably well. She’s friends with his daughter, and her kids went to a dance studio operated by Jimison’s late wife. Maybe 20 years ago, she recalled, the Jimisons invited her over for Christmas. She says she wasn’t running against Jimison in particular. 

“I just ran on making Glendive better,” she said. “I’m not a basher. I had just a little brochure and I put it in a little thing and just hung it on people’s doors. I put a lot of miles around town. I had pictures of my family and my kids. My identity for a long time in town was Rikki’s mom, Kasi’s mom, Lacey’s mom, Tate’s mom. I highlighted myself as a good, honest, hardworking person.”

Come election day, Olson trounced Jimison, 702 votes to 373. The voters, it turned out, were ready for something new. 


Teresea Olson pulled up to a Glendive coffee shop on a September afternoon in an old red Jeep with a sticker on the back that says “United States Terrorist Hunting Permit, Gun Owner, No Bag Limit” — it came with the car when she bought it, she said. As she walked in, she embraced supporters who greeted her by her first name, pronounced, despite the extra “e,” like “Theresa.” She had resigned about a week prior.

Approaching a reporter she’d never met before, she meted out another hug. Glendivians later said that this was standard. She’s a hugger. 

Olson has frizzy blond hair and wore turquoise reading glasses that framed squinting eyes set into a broad, angular face that has weathered single motherhood, long hospital shifts, and the general wear and tear of hard-won existence in rural America. 

Glendive abuts the badlands of Makoshika State Park, Montana’s largest state park by area. Credit: Clayton Ryerson / SOVRN Creative

As she sat down for what turned out to be a four-hour interview — she’s a talker as well as a hugger — she presented her resume, from which she began to read verbatim. 

“Fifty-six-year-old female. Grew up in eastern South Dakota, in Aberdeen. I did a lot of firsts in my life. I was one of the first girls in my high school to take auto mechanics, rebuilt a 250 Chevy engine. My dad was a truck driver, mom worked at a mobile home dealership. I have a total of four kids, they’re all married, and eight grandkids. My book is going to be titled ‘Bad Girl of the Badlands.’ I’ve been married a few times, dated a lot of people.”

She’s worked as a nurse in hospitals across the region, developing  expertise in sexual and domestic violence victims’ services. She helped develop the sexual assault nurse examiner program at the hospital in Glendive, she said. She has often testified as an expert witness in court. 

More recently, she helped found a nonprofit fitness center catering to the elderly, the young and military veterans. She’s started making and selling superfood granola with hemp hearts. 

“If there’s a need for something, I wanna try to fix it,” Olson said during her interview with MTFP. “When I was working in pediatrics in Aberdeen, it was my first exposure to child abuse. That probably planted the seed.” 

She said she was motivated largely by the need for economic development, especially in what she referred to as small-scale manufacturing. In the 1960s, Glendive was home to about 7,000 people; now, fewer than 5,000 live there. The town has lost population every decade except the 2010s, which saw a 4.4% increase. The 2020 census marked a return to normal: a 1.3% decline. That year, BNSF Railway closed its Glendive maintenance facility, costing 86 jobs. The closure of a sugarbeet processing facility in nearby Sidney earlier this year also meant the loss of hundreds of regional jobs and millions of dollars in economic activity.

Some of the decline could be explained by Glendive residents moving to developments in West Glendive, a census-designated place across the river that now has a population of about 2,000.

“You look at pictures of all of our small towns from like the ’50s and ’60s, what is it?” Olson said. “The main street, the small businesses, they were the backbone. And then our big box companies came in and broke that backbone. Then online shopping came and broke their backbone, and look who just came back around — our small businesses.”

That’s the environment in which Olson beat a longtime mayor by an almost two-to-one margin. Montana has grown its population every year for more than a decade. Glendive has not. That fact helps explain some of the problems that have dogged the city for years, but became especially glaring during Olson’s tenure.


In her resignation speech, available on the city’s YouTube channel, Olson references a conversation she’d had with a council member who told her that everything that happened after she took office was her fault. They must have been right, she said. She then lists her supposed faults: 

“I underestimated the power of old habits, past practice, and ‘the way we’ve always done it.’ I overestimated others’ ability to adapt to new facts and information and change course accordingly. I assumed that referencing and supporting my decisions with legal opinion, risk management advice, and educational information would assure the council that I was making appropriate decisions. I just seemed to irritate them … I have a strong definition of right and wrong. There is very little gray in my life. That doesn’t mean I don’t make a lot of mistakes. But I try to identify them, apologize when needed, and change my path when I can. I cannot change the core of who I am. I will always do my best to stand up for what I think is right no matter what. I listened to our employees and the public. I have sought expert advice. 

“I don’t know what this ‘thing’ is that happened between me and the council, but it isn’t making Glendive better. I will step down as mayor.”

A crowd of her supporters shout in indignation, though it’s not clear who says what. 

“No! Goddammit! Please, no! Seriously!”

Olson says her electoral victory surprised her as much as anyone.

She faced one issue right up front, she said. She knew basically nothing of how to run a government meeting or of Robert’s Rules of Order, a commonly used manual of parliamentary procedure, and had to learn right away. 

Her inexperience would become a source of friction. Her learning curve, as she described it, was “vertical.” 

“As far as I understand, she had no previous relevant professional or academic training … that would have prepared her for the role of being the CEO of a multimillion-dollar company,” councilmember Jason Stuart, a former reporter with the Glendive Ranger-Review, told MTFP. “Consider this: You add all the enterprise funds, water funds, sewer funds, garbage funds together, you get a budget of millions of dollars. Would you hire a part-time gym teacher and physical therapist to be the CEO of that corporation?” 

While several people said Reichert initially helped Olson with Robert’s Rules, Olson came to rely on the counsel of those not serving on the city’s policymaking branch, she and council members said, such as Montana State University’s Local Government Center; the Montana Municipal Interlocal Authority, which offers risk management services to local governments; Norby, the Sidney mayor; and her director of operations, Kitty Schmid. To Olson, the crash courses were a means of getting up to speed and demonstrating the thought behind her decisions, especially when, in her view, the council wasn’t particularly interested in helping her. To the council, it looked like Olson was actively ignoring the help they were offering. 

“It’s a two-way street,” said council member Betsey Hedrick. “It’s just like communicating. You can give advice, and you can give direction, but if the person doesn’t want it, but if the person may feel it was done in an incorrect way or incorrect tone, or maybe not even acknowledging that you were giving advice, what can you do?”

It was in the context of studying up, early in her mayorship, that Olson learned in a training at the MSU Local Government Center that, for reasons lost to time, Glendive had for years been operating under a governmental configuration other than the one voters approved in 1976. 

Glendive, as far as anyone could remember, had never held partisan elections, despite that being a component of the city’s ratified form of government.

The council’s personnel committee had historically been heavily involved in the hiring and firing of not just department heads, but several levels of municipal employees. The city’s form of government said the mayor needed council approval only to hire department heads. 

The city’s self-designated form of government described the position of “operations director” as an assistant who reports directly to the mayor. The job description for Kitty Schmid, the operations director under Olson, said she reported to both the mayor and council.

The council members, some of whom had been on the job since even before Jimison’s term, were incredulous. Here was a newcomer mayor who had never worked in government and who, after consulting with MSU’s Local Government Center, was raising the possibility that the city had been out of compliance with the law for decades, with all the potential legal liability that includes.

“[Jimison] felt the council should be involved in things,” Leon Baker, the council president, told MTFP. “So maybe we did have a lot more decision-making authority than what the law required.” 

Schmid proposed rewriting city code to bring Glendive in alignment with the law. 

The long-time councilmembers said in meetings that they detested the concept of partisan elections, believing that party labels would inject vitriol into otherwise mundane council business. 

“The issues we deal with are not red and blue, they are just sewer pipes,” Reichert, the council member, said at one meeting, as reported by the Ranger-Review. “It doesn’t make a difference what your political spectrum is, you are faced with the same thing and we just have to get this work done.”

And they had become accustomed to being involved in personnel management. The mayor might have the authority to fire people without consulting the council, they said, but it’s better for everyone to be on the same page.

“The issues we deal with are not red and blue, they are just sewer pipes. It doesn’t make a difference what your political spectrum is, you are faced with the same thing and we just have to get this work done.”

Gerald Reichert, Glendive CITY council member

“At the end of the day, I believe that Glendive has been functioning correctly this whole time, but in that correctness, a way was made that was functioning in a way that looked a little different than it looked on paper,” Hedrick said. “But through the study commissions that were done, they didn’t recommend any changes. They saw everything functioning well. Then when we were told everything was wrong, that was hard.” 

The council ultimately voted down a resolution, proposed by Schmid, to provide for partisan elections. Other proposals to bring the city into alignment with its organizing documents failed. Municipal elections in November, as in years past, will be held without party labels. Reichert and Baker said that the best time to consider such a radical change, if at all, would be in 2024, when voters would have another chance to study the city’s form of government and propose changes.

Olson felt that she had no choice but to support changes to the city’s form of government and to follow the law and the Constitution, she said, whatever the old ways may have been. Moreover, she was concerned about legal liability for the city. She’d sworn an oath, after all. 

“That means something to me,” she said. 

The form-of-government disagreement would have profound downstream consequences. The two sides developed into what seemed like competing governments with contradictory understandings of their proper roles in relation to each other and the community. Olson said she wasn’t trying to strong-arm the council, just wield the power that the city’s mayor should have had the whole time. That was all fine and good with Baker and other members of the council, they said, but they didn’t think they should be left in the dark as a result.

“It’s a politically charged environment,” Clark, with the Local Government Center, told MTFP,  “because the City Council had been used to doing it like that for a long time as a standing tradition.” 

On one side, there was Olson, Schmid, city attorney Scott Herring — not a newcomer to Glendive city government, but someone that several council members said they didn’t think highly of — and a cadre of citizen supporters. On the other, the council, which found itself increasingly in the dark on what they felt were important decisions, members said.

In one relatively minor early example, Olson wanted to move City Council meetings to a multipurpose room in the ambulance building adjacent to City Hall, where the council held meetings during the heat of the COVID-19 pandemic, as it could accommodate more people and had better disability access. Her supporters argued that the relatively small size of the council chamber was restricting citizens’ ability to participate in their government. The council members, for their part, felt that Olson couldn’t just unilaterally move the body’s meetings out of City Hall — after all, it’s the City Council chamber, not the mayor’s personal office. Baker proposed and passed a resolution stating that only the council could move its meeting space. 

But the growing gulf between the council and the mayor was widest when it came to repairing the city’s police department. 

The city, as Baker and others attested, had long struggled to retain staff in the police department, whether chiefs, officers or dispatchers. Glendive has a long-standing contract with Dawson County to assist its police department for that reason. Olson described sometimes going out on “civil calls” herself to deal with issues like animal control. 

In April of 2022, Chief John Hickman resigned, taking a job in Nebraska shortly thereafter. The exact circumstances of his resignation are unclear — both Baker and Olson mentioned unspecified privacy concerns — but both sides gave the impression that the resignation helped highlight some of the department’s systemic issues, and both sides rushed to fill the vacancy. 

The council and the mayor got in each other’s way at almost every step. In one instance, both sides wanted to hire a local sheriff’s deputy for the job. Both sides vetted him separately. Olson held a meeting with the candidate and several other advisers from the local law enforcement community, but no members of the council. The council was set to make a motion to hire the candidate but, at least in the opinion of the city attorney, planned to do so under an inappropriate order of business. Chaos broke loose in a meeting with the candidate present. He subsequently backed out. 

Then a sheriff’s deputy from Larimer County, Colorado, named Jay Harrison applied for the job. Olson, her advisers and a few members of the council vetted him. He had dinner with the county sheriff and drafted a course of corrective action for the department. Olson indicated to him that he just needed to make it past the personnel committee and he’d likely have the job, she said. 

She put him up for the job, and the committee voted for him on her recommendation. But Stuart, a former reporter, was doing research of his own. He announced his findings during a subsequent meeting: In 2010, Harrison had run for sheriff of Larimer County. In March 2011, he was fired. He sued the sheriff — the man who beat him for the position — for wrongful discharge. A judge eventually tossed the suit. 

Olson told MTFP that Assistant Chief Katie Mills had already spoken with Harrison about the issue and cleared everything up, and that she didn’t feel the need to look into the matter further. In one dramatic meeting, Harrison brought his wife to Glendive, prepared to explain himself to the council. The meeting ended with the council tanking his nomination and Harrison’s wife in tears, Olson recalled. 

“It didn’t take me more than five minutes behind my computer and a Google search to start finding things about Mr. Harrison from Colorado that start to give you pause, especially when you’re trying to rebuild a department,” Stuart told MTFP. 

Assistant chief of police Katie Mills sits during a Glendive City Council meeting in September. Credit: Clayton Ryerson / SOVRN Creative

A full seven months after Hickman resigned, the council and the mayor landed on Jeremy Swisher, then a criminal detective for a parish sheriff’s office in Louisiana. His early tenure seemed like a huge success. He fully staffed the dispatch center, importing staff from Louisiana. His top priority was to stabilize the department, he said. 

“The department was severely understaffed when I took over,” Swisher told MTFP in an email. “There were concerns about reports not being completed and officers simply not responding to calls. Public opinion was horrible. The evidence storage was an absolute mess. The communications center was one step away from losing its state license. The highest-ranking officer on staff was a senior patrolman. There was simply no supervision or guidance.”

He said he was aware of conflict between the council and the mayor before he was hired, with both sides warning him about the other. It did seem, he noted, that Olson went out of her way to keep the council in the dark. 

“I can only assume she had her reasons,” he said. 

Then, in August of this year, without involving the council, Olson fired Swisher, who was still in his probationary period.

Swisher said that he was headed to a meeting of the city police commission with his assistant chief when he got the news.

“When we arrived, the former mayor [Olson] asked my assistant chief to step outside,” he said. “The former mayor then read me a termination letter out loud and demanded my badge and gun. I asked if I could get an explanation and her response was, ‘Everything you need to know is in that letter.’”

The letter said Swisher wasn’t “meeting the performance and conduct expectations for the position.”

Leon Baker is the Glendive City Council president. He says that things started going south as soon as Olson was sworn in. Credit: Arren Kimbel-Sannit / Montana Free Press

Then, he said, Shannon Kadrmas, a member of the police commission and an ally of Olson’s, attempted to clean out Swisher’s office, “which shocked me and my assistant chief considering a police commission has three primary roles, one of which would have been to review the conditions of my termination had I opted to grieve them.” 

Swisher told Kadrmas he couldn’t access the office, just as he would have done with “any civilian without a justified reason.” 

Swisher sought a copy of his personnel file, which contained no complaints, he said.

But after probing by the council, Olson eventually revealed during a council meeting that members of the department had approached her “regarding the working conditions at the police department and dispatch.” 

“The employees met with me several times and contacted me multiple times regarding their concern for retaliation in the workplace, anti-union sentiments [and] surveillance at work,” she said. 

No official grievance had been filed by the police union or an employee of the department regarding the allegations. 

“If they object to something, shouldn’t they file a grievance and then it’s handled through the process?” councilmember Mike Dryden asked Olson. “There would be a record … It either happened or it didn’t.”

At a September meeting, Vaughn Jenkins, now a city council candidate and an Olson supporter, also raised the fact that Swisher was the subject of a Montana Fish, Wildlife and Parks investigation. The Ranger-Review confirmed that a judge had issued a search warrant as part of a civil investigation in July. Swisher later confirmed that it was a fish and game matter. The case is currently under seal. 

“Our reactions to [Swisher’s firing] … were based on complete and utter shock,” Stuart said. “This was like somebody basically dropping a nuclear bomb in our City Hall at a time when things were already fractured and heated.”

It seemed, he said, that there was a pattern “​​where [Olson] protected or even hired people of dubious employability while on the other hand generally having issues with people who from the council’s perspective were good, solid, hardworking employees of the city.” 

When Olson resigned, she told the council to hire Swisher back if they felt so strongly about him. Several members of the council clapped. Olson’s supporters, already sensitive to what they saw as endless eye-rolling and pen-clicking directed their mayor’s way, saw this as the council clapping at Olson’s resignation.

“This was like somebody basically dropping a nuclear bomb in our City Hall at a time when things were already fractured and heated.”

Jason Stuart, Glendive city council member

Indeed, in late September, just weeks after his termination, the council re-hired Swisher as a temporary consultant. Some of Olson’s supporters, Kadrmas among them, questioned whether the move was either legal or proper. The council responded that they had the support of the town’s recently hired attorney, John Hrubes — it had voted not to renew the contract of his predecessor, Herring.

The firing of Swisher in particular marked a breaking point for Stuart, already one of Olson’s harshest critics and one of the biggest targets of her supporters’ ire. 

At a small protest outside the council chamber in August, Stuart told MTFP he heard an attendee say, “We should keep the mayor and kill the council.”

It was with this fractured relationship — and what he describes as fear — in mind that he made the comments that led Olson to obtain a restraining order against him. 

Someone with an office at Dawson Community College, where Stuart taught a class, overheard Stuart’s part of a late-August phone conversation about Olson and Swisher’s firing. The witness heard Stuart say something to the effect of “We’re going to stomp this bitch into the ground.”

The individual sent their recollection of the conversation to Kadrmas, who sent it to Olson (and later shared it with MTFP). Court records show that a city court judge granted a temporary protective order in September and a full order the next month. The order is in effect until 2025, barring another ruling. Stuart lost his job with the college, he said. 

“I should have been more discreet, that’s obvious,” Stuart told MTFP. 

“I will apologize for using a gendered slur to describe the former mayor,” he said. “I shouldn’t have used that specific word. There’s a lot of things that I can call the former mayor.”

He claimed that the “stomp” comment was a form of “political speech.” He wanted, he said, to “stomp her ass politically,” to “make it untenable for her to serve and to have another term.” 

He said the restraining order isn’t necessary. He’ll be happy to never see her again. 


Scott Herring had been under contract as Glendive’s attorney for years, long before Olson’s tenure began. Schmid, a former employee of the town of Ekalaka, was hired to replace longtime operations director Kevin Dorwart a few months before Olson was elected.

Both individuals became allies of Olson. Schmid did not return multiple requests for comment regarding this story; Herring directed all questions about the city to his replacement, Hrubes, and did not respond to a further email clarifying that MTFP was seeking answers to questions about his tenure in particular.

Schmid, like Olson, was new to Glendive city government. Herring was an old hand, but not popular with the council.

“The whole time I had been on the council, I had never seen Scott [Herring] at a meeting,” Hedrick said. 

The two worked in tandem to advise Olson and affirm her decisions at a time when her relationship with the council was essentially nonexistent. In particular, Herring’s legal opinions became a sort of weapon in the conflict between the two sides. For example, he issued a legal opinion in 2022 that said the council should not have an agenda item entitled “Other Business” during its meetings because of public notice concerns, much to the chagrin of the council, which argued that the interpretation was erroneous, and that it was common practice to discuss items not on the agenda so they could be placed on the agenda for future meetings. 

The lack of coordination between the two sides again led to conflict, especially when it came to enforcing the town’s nuisance ordinance. Take the David Steiner case.

Steiner’s Glendive property was declared a nuisance by the City Council. He successfully obtained continuances from the city, which expired in September of 2022. The council directed the city attorney to enforce the city’s petition, which would involve city staff cleaning up the property and billing Steiner. But Herring, who multiple people said had helped write the nuisance ordinance, declined to enforce it, arguing that the house posed no safety risk and that it was unconstitutional for the city to punish someone because of their property’s aesthetic faults. The city’s code defines nuisance as “anything which is injurious to health, or is indecent or offensive to the senses, or is an obstruction to the free use of another’s property, so as to interfere with the comfortable enjoyment of life or property of another.” 

Steiner’s neighbor filed a lawsuit in June 2023, suing the city for failing to enforce its own ordinance. In the lawsuit, which is ongoing, the neighbor describes the Steiner house as having broken windows and shingles that fall off the roof. 

Later in the summer, the city took the opposite approach with a different property on Pearson Avenue. 

In June, a local resident emailed Olson and the council alleging that the city had cleaned up his late mother-in-law’s property without any notice to him, the executor of her estate, and had given him a landfill bill to boot. The person who came onto the property, he said, was Olson. 

The house had been subject to a nuisance complaint in 2022, but the city was apparently unable to find anyone to speak for the deceased owner. The council never took up the issue again. 

The next year, a neighbor frustrated by the city’s inaction told Olson about the house. She drove by and saw the condition it was in: overgrown and broken down with cars and other debris in the yard. But, she said, the city’s maintenance staff was already stretched thin dealing with the impacts of summer rains. 

So she asked Herring if she could clean up the property herself, and got his sign-off. She mowed the lawn, then returned with a truck to remove some garbage. City records show a $29.70 landfill ticket signed by Olson, the Ranger-Review reported. 

Someone — Olson isn’t sure who — got in touch with the deceased homeowner’s son-in-law, Nicholas Heinrich. Heinrich was incensed and accused the mayor of trespassing to enforce a nuisance complaint he knew nothing about. He also discovered that some cars on the lot he had intended to sell were missing, leading to a brief moment where it seemed that Olson might have moved the cars herself. It was later discovered that neighbors had moved the cars, which they said had become home to a variety of vermin. 

All of a sudden, Olson was being accused of breaking the law for doing what she felt was the right and legal thing for her town.

“The council had a fit about me doing this,” she said. “No one said anything when I was going on police calls last year, right? No one had a complaint when I was going out, doing animal control and an animal surrender, which was dangerous.”

The Olson administration’s approach to nuisance complaints contributed to a particularly bizarre exchange between Olson and Baker. In a letter to the council president, Olson recommended that he “seek medical care for evaluation of a cognitive impairment disorder such as early dementia.”

The letter followed a council committee meeting in May about Schmid’s job description. As part of the revelation of the city’s form of government problem, Olson and Schmid learned that the job description authored by her predecessor, Dorwart, made her accountable to both the mayor and the City Council. But the state statute governing Glendive’s chosen form of government states that she should really be Olson’s assistant.

Schmid rewrote her job description, dramatically reducing the number of her responsibilities. Baker, upset by that action, referenced during the meeting another statute he believed the city wasn’t following. 

Olson, he said, had neglected her duties by not enforcing the nuisance ordinance in the Steiner case. 

The next day, Olson, believing she had been accused of violating the law, wrote to Baker.

Glendive’s City Council meetings are abuzz with activity — and acrimony. Credit: Clayton Ryerson / SOVRN Creative

His comments, she wrote, “were not only insulting and defaming to my professional character, but damaging to my future professional success.” 

She also wrote that Baker regularly seemed confused, and alleged that he had insulted public employees during pay negotiations.

“As a healthcare professional,” she wrote, “I highly recommend you seek medical care for evaluation of a cognitive impairment disorder such as early dementia. If you do not have such a disorder then there is no excuse for your inappropriate behavior and your fellow Council Members need to intervene.” 

She signed the letter as mayor and as a certified physician assistant and registered nurse.

A day later, Schmid supported Olson in her own letter addressed to the council and said city business could not continue unless Baker was removed as chairman of the council’s ordinance committee. The city’s codebook was badly in need of updating, Schmid said, and Baker stood in the way. 

“To accomplish that goal, Mr. Leon Baker would have to be removed as chair by the city council, and a council member not harboring a personal vendetta against the current administration would have to take his place,” Schmid wrote.

Schmid’s relationship with the council had long been in a state of disrepair. Hedrick and others remember one argument Schmid had with Baker at the Beer Jug. 

“She said, ‘You guys are doing it all wrong, you’ve been doing it wrong for so long, everything’s wrong,’” Hedrick recalled. “Leon, being the proud council person that he is, and the host of the party, took great offense.”

In October of 2022, Schmid filed a letter of intent to sue the city, the council and “specific individuals to be named.” She did not make any specific allegations, writing only that she planned to seek relief from the U.S. Department of Labor, the Equal Opportunity Employment Commission and “other federal and state agencies” that can address claims of harassment, age discrimination, gender discrimination, slander, defamation and a hostile work environment.

The council heard nothing further from Schmid or an attorney. 

Dryden said the council always tried to walk on eggshells around Schmid, not harass her. He also fervently denied her allegation of gender discrimination — a claim that Olson’s supporters have also repeated against the “good ol’ boys’ club.” 

“I tell you what, I don’t know why we don’t have a woman president,” Dryden said. “I always thought, I had a mom and a dad, and my mom is the one who got everything going. I worked with a lot of women teachers, and they were very confident and successful.” 

Even with the history of conflict, Schmid surprised both the council and Olson when she resigned, effectively immediately, on July 13, 2023. 

“Please accept this letter as my official resignation as the director of operations/administrative assistant for the City of Glendive due to council’s persistent harassment and unwillingness to let me do my job in the full capacity for which I was hired,” she wrote.

Her resignation came as the city was in the middle of crafting its budget for the next fiscal year. Olson was open about the fact that she knew little about municipal budgeting. Schmid had been leading that charge. 

The council’s personnel committee held an emergency meeting and tapped the city clerk and treasurer to take over. The clerk, treasurer and council found, Reichert reported in a September council meeting, “that numerous things hadn’t been done.” 

Reichert then contacted an outside accounting firm that the city hired to help finish the budget. At that September meeting, the council voted to extend the agreement.

Reichert, emphasizing to an angsty crowd that he had no intention of pointing fingers, did just that, as MTFP witnessed. 

“The former mayor and the former director of operations had no hand in [the budget],” he said. “We did it as a council.”


Olson. Swisher. Stuart. Schmid. Harrison. Herring. 

These are all people who, through the course of a tumultuous, almost two-year period of discord and disarray, lost something. Some lost jobs; others, just their tempers. 

Olson’s supporters are especially aggrieved.

In conversations with Olson’s supporters, hope for improvements to Glendive’s economic vitality — or frustration with the disappearance of what it once was — came up often. They expressed a variety of grievances that could seem plausibly like the city’s fault: It wasn’t doing enough about stray animals, it wasn’t doing enough to fix broken asphalt where a tree had been uprooted, the town’s economic developers were courting the wrong kinds of businesses. Olson helped awaken some citizens to problems they’d previously ignored, her supporters said, serving as a kind of avatar for frustration they didn’t know they had. 

“But the good ol’ boy club consistently kept fighting her, fighting her and fighting her, and said, ‘We don’t like change, We don’t need to change. It’s been working the way we’ve been doing it.’ Well, no, it hasn’t,” said Kari Keller, a longtime City Council critic who started attending meetings in 2012 to advocate for a firework ordinance. “And the thing about people just voting [for] the same people over and over is that nobody knew the problem. Nobody came to address the problem.”

Keller, who briefly campaigned for City Council this year before deciding instead to focus on recall petitions against several members of the council, is among Olson’s most vocal supporters. When the council refused to move the chamber to a building that could accommodate more people, Keller began live-streaming the meetings. At one council meeting witnessed by MTFP, she brought her own PA system, passing a microphone around as people laid into members of the council while simultaneously claiming they weren’t being allowed to speak.

Keller and others — business owner and council candidate Vaughn Jenkins, candidate Carrie Skartved, local police commission member Shannon Kadrmas, and West Glendive resident Gary Francis, to name a few — met MTFP for an interview in September. Asked whether they were blaming the City Council for things outside of its control, or for things that many cities like Glendive are enduring, the answer was a resounding and unified “No.” 

People who haven’t been as intimately involved in the conflict, who aren’t regulars on the now-multiple “Dawson Discussion” Facebook pages where much of it has played out, see it all as a bit strange, even embarrassing. Could people not just work it out?

Among that contingent is Deb Dion, the interim mayor of Glendive appointed by the council this month. Dion, one of five candidates for the position, was the administrator for a felony DUI treatment program run in cooperation with the state Department of Corrections until her retirement in 2014.

Earlier in the 2000s, she served as secretary of a study committee assembled to hear community concerns about the possibility of a new treatment facility in town. As such, she’s no stranger to the occasional vitriol of public meetings, she said.

Deb Dion, right, is sworn in as the mayor of Glendive by Glendive City Council President Leon Baker. Credit: Jamie Crisafulli / Glendive Ranger Review

Dion, a retired, lifelong Glendivian, had not paid much attention to the contemporary political upheaval. But she began to notice the various controversies as they accumulated. The council, she felt, was probably not running meetings correctly. The crowd of public commenters, she said, had no idea how to be heard at a public meeting. People accused the council of suppressing public comment, but to Dion, it just looked like council members were trying — and failing — to keep order. 

“I thought we were looking like a bunch of idiots, the way this was going on,” she said. “It was embarrassing to me.”

Some friends asked her to volunteer to carry out the rest of Olson’s term, which lasts until the beginning of 2026. She was hesitant, but when she stopped by City Hall only a few days before the deadline, nobody else had applied. Though others ultimately put their names forward, the council selected Dion. 

She said she likely won’t run for re-election.

“I’ll be in my 70s by then, when my term is up,” she said. “I really hope I can encourage younger people to get involved in city government. We need people to step up who are younger.”

She said one of her top priorities is to educate the public. She’ll also take another look at the circumstances of Swisher’s firing and re-hiring, she said. She read through and understands the budget, she said.

“She was very diplomatic and composed and calm,” Hedrick said of Dion. “I felt so good after the interview.”

Baker, who insists he does not have dementia, intends to stick around as long as he can. 

“The reason why I keep running, you know, is I’m not a quitter,” he said. “I don’t like to see people quit things. I’m from the old school. Until I get unelected, I’m going to keep doing what I can.”

Olson had thought about submitting her name for the interim mayorship, but didn’t want to subject herself to an inquisition by the council, she said. For now, she will rest, take care of her family and her business. Throughout it all, she said, she started drinking and cursing more. 

Editor’s note: This story was produced through MTFP’s summer reporting residency program, which places Montana Free Press reporters in small newsrooms statewide to help us better understand the ins and outs of different corners of Montana. Arren Kimbel-Sannit reported this article while spending a week in September 2023 in the Glendive Ranger Review newsroom. 


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Raised in Arizona, Arren is no stranger to the issues impacting Western states, having a keen interest in the politics of land, transportation and housing. Prior to moving to Montana, Arren was a statehouse reporter for the Arizona Capitol Times and covered agricultural and trade policy for Politico in Washington, D.C. In Montana, he has carved out a niche in shoe-leather heavy muckraking based on public documents and deep sourcing that keeps elected officials uncomfortable and the public better informed.