Sheriff races are contested in 14 Wisconsin counties

By: - October 20, 2022 6:10 am
Waukesha Sheriff's deputies monitor a protest linked to Patriot Front, and other white supremacist groups. (Photo | Patriot Front leaks, Unicorn Riot)

Waukesha Sheriff’s deputies monitor a protest linked to Patriot Front, and other white supremacist groups. (Photo | Patriot Front leaks, Unicorn Riot)

Across Wisconsin, there are 14 contested races for sheriff in the November general election. In half of those races, an incumbent is facing a challenger for the seat. 

The races for sheriff, which occur every four years, come as Republicans have worked to turn Wisconsin’s statewide elections into a referendum on crime and public safety. 

While 58 of the state’s counties only have one candidate for sheriff on the ballot in November, that’s a massive increase over the number of challenges district attorneys faced in 2020, when that position was up for re-election across the state. 

In the November 2020 general election, only three district attorney races included two candidates while another three counties had contested primaries for DA. This year, in addition to the 14 contested races in November, there were 16 contested sheriff primaries. 

Those contested primaries included the Republican primary for Waupaca County sheriff, which incumbent Tim Wilz won by 16 percentage points despite being the subject of an ongoing investigation by a special prosecutor over allegations that his office altered reports in ways that could affect the outcome of court cases. The primary effectively decided the final outcome, as Wilz faces no challenger in November.

Brown County 

In Brown County, incumbent Republican Sheriff Todd Delain didn’t face a primary challenge and technically won’t have an opponent on the ballot in November. But former Brown County Sheriff’s Deputy David Van Vonderen is running a write-in campaign against Delain. 

Delain has held the position since 2019. 

Chippewa County 

Current Chippewa County Sheriff Jim Kowalczyk, a Democrat, is retiring after 16 years in the position, leaving an open seat. Kowalczyk’s brother, Chris, is running as a Democrat to replace him. Chris Kowalczyk has been with the office for more than 30 years and currently works as an investigator. 

His opponent is Travis Hakes, who is currently a patrol officer for the Cornell Police Department and previously served as the police chief in Elk Mound. Hakes narrowly won the Republican primary in August with 52% of the vote. 

This is the second time Hakes has run for the post. In 2018, he ran against Jim Kowalzcyk, losing by about 2,700 votes. 

In a candidate forum earlier this month, the two candidates took positions on cannabis legalization that are opposite from the platforms of their own party. In the forum, Hakes said he’d support legalizing cannabis because “chasing kids for dime bags of pot” is not a productive use of resources when meth and opioids are “destroying our communities.” Kowalczyk, meanwhile, said he had reservations about legalization because he believes it’s a “gateway drug.” 

Dane County 

In its first contested general election since 2010, the race to be the Dane County sheriff has become contentious.

Incumbent Democrat Kalvin Barrett is running to serve a full term as sheriff after he was appointed by Gov. Tony Evers to the position in 2021 to replace the retiring Sheriff David Mahoney. Barrett is running against Republican Anthony Hamilton, a detective at the sheriff’s office. 

In the largely Democratic-leaning county, Barrett has a massive fundraising advantage, bringing in more than $100,000 since July 2021. That far surpasses the amount raised in the most recent countywide election, when County Executive Joe Parisi raised $57,700 in his 2021 race against challenger Mary Ann Nicholson. 

Hamilton, who has been with the department for 14 years, has accused Barrett of “paying lip service to extreme ideologies” and allowing a severe staff shortage to fester. Hamilton has attacked Barrett for trying to recruit women and people of color to work in the office — which is far short of its ideal staff count. 

In September, Hamilton was placed on administrative leave. Hamilton has claimed he was told he was being placed on leave for sharing confidential information. The leave came just days after Hamilton had filed a civil lawsuit against Barrett. 

The lawsuit alleged that Hamilton was forced to participate in what he believed was an illegal search and that he was retaliated against for raising concerns. Barrett’s campaign and an attorney for Dane County have said Hamilton was punished for taking unauthorized video on equipment not provided by the department and then sharing it on the Signal messaging app. 

Eau Claire County 

The race for the open seat in the Eau Claire County Sheriff’s Office is between two current department employees. The candidates are running to replace longtime Sheriff Ron Cramer, who announced in February that he would be retiring at the end of his term but died in September. 

The election is between Republican Don Henning, a detective in the office, and Democrat Dave Riewestahl, currently a captain. 

With an increasing population in its jail, Eau Claire County is considering an expansion to the facility. 

Riewestahl said that efforts to decrease the jail population have to come from more than just the sheriff and that he’d be opposed to expansion but that it is “on the table.” Henning said he’d support the project but would want it to include spaces dedicated to education, alcohol and drug treatment, and to aid in securing housing when people are released.

Forest County 

The race for Forest County sheriff pits incumbent Ron Skallerud, an independent, against challenger Jeffrey Marvin, a Republican. 

Skallerud was appointed to the position last November by Evers. He’d previously been a deputy in the department and served as the public safety director of the Sokaogon Chippewa Community Police Department. Marvin is currently a captain in the sheriff’s department. 

Iowa County 

Iowa County is set to have a new sheriff for the first time since 2003, when current Sheriff Steve Michek took office. The race is between Republican Michael Peterson, who is currently the county’s jail administrator, and independent Kim Alan, the first woman to run for the position and a Madison Police officer for the past 11 years. 

Alan told NBC15 that her experience as a patrol officer will help her understand the needs of her staff when in a leadership position. 

“I’ve gotten so many reps on tough calls, on people that need high amounts of resources, a person in a leadership position that’s already seen that over and over, it’s much easier,” she said.

Peterson, who was born in the county and has spent 18 years working for the Iowa County jail and emergency dispatch, told the TV station he believes his approachability as a community member will help him in the job. 

“Open door policy, if you need anything, stop by and see me; I’ve had a lot of people stop by the office, just knowing that there’s someone at the sheriff’s office that cares, that will try to help their family member,” said Peterson.

Kenosha County 

Kenosha County is set to have a new sheriff for the first time in two decades with the retirement of Sheriff David Beth. Beth’s departure will mark a complete turnover of law enforcement leadership in Kenosha County and the City of Kenosha since the unrest that took place in the city in 2020. Former Kenosha Police Chief Daniel Miskinis retired last year. 

Since the unrest, the community has seen a number of debates over public safety, crime and guns. The county board, which has had Republican-aligned candidates gain a majority, has taken a number of actions that reduce gun restrictions in the county. 

The race for sheriff pits Republican David Zoerner, a sergeant in the office, against Democrat James Simmons, a deputy in the nearby Lake County, Illinois Sheriff’s Office.

In 2018, Zoerner ran for sheriff as a Democrat, but this year he won a three-way Republican primary. Simmons was unopposed in the Democratic primary. 

La Crosse County 

Current La Crosse County Sheriff Jeff Wolf is retiring after one term in the position. Vying to replace him are two longtime members of the office. Investigative captain John Siegel, who is running as a Democrat, has worked in the office since 2003. Running against him is Fritz Leinfelder, who has spent all 29 years of his law enforcement career with the La Crosse County Sheriff’s Office — the last 21 as an investigator. 

Siegel drew attention earlier this year when the senate campaign of Lt. Gov. Mandela Barnes listed him as a law enforcement endorsement. Siegel had not endorsed Barnes and he was removed from the list. 

Both candidates recently told La Crosse-area TV station WXOW that they plan to address mental health issues in the county and improve outreach to its more rural communities. 

“Some of our visions we have within the department is to try to address some of the mental health aspects that we have,” Leinfelder said. “The substance abuse problems we have and the large scale drug trafficking. We can’t solve them alone in law enforcement.”

Leinfelder said he would offer “some of the connections with the different corporations within the community to make those things maybe work a little bit better.”

Siegel told the station he hopes to improve the county jail while better connecting with the community. 

“Building relationships in the community is very important to me,” Siegel said. “I think we have people in the community who have been underserved who, when it comes to law enforcement, are still not comfortable to come in and have a conversation. I really want to work on that.”

Siegel also said he would reach out to rural communities in the county — “Places where the Sheriff’s Department serves and we take calls, but maybe we haven’t been as present as we could be. I’d like to figure out ways for us to be more visible within those parts of the county.”

Lincoln County 

Incumbent Lincoln County Sheriff Ken Schneider is facing a challenger who doesn’t work in law enforcement. Independent candidate Garett Dinges, who currently works for the county’s social services department, told the Tomahawk Leader he’s running against Schneider because he believes the county needs a new direction. 

“The definition of insanity is to do the same thing over and over again and expect different results,” Dinges, who previously worked as a correctional officer, said. “That is what Lincoln County has done for decades.”

Schneider has worked in the sheriff’s office for 32 years. 

“I believe the people in Lincoln County should have the most experienced person for this position,” Schneider told the Wausau Daily Herald. “I believe I am that person.”

Portage County 

Incumbent Democratic Sheriff Mike Lukas is facing a challenge from Republican Scott Kenneth Noble, a teacher. 

Lukas told the Stevens Point Journal that his eight years of experience as sheriff, in addition to his relationships with county leaders, make him the best candidate. 

“I am running for office because I love the community in which I live and serve, and I want to keep moving Portage County forward,” he said. “There are still many things I want to accomplish and numerous projects I am in the middle of completing, such as new body and car cameras for the entire office.”

Noble said he’s running to protect Portage County residents’ constitutional rights and that he’d make sure the department would defend the constitution. 

“I am the best candidate because I will be a representative of the will of the people in Portage County,” he said. “I am a fierce advocate for constitutional rights and civil liberties. I will work very diligently and swiftly to implement constitutional peace deputies in Portage County.”

Rock County 

In Rock County, Democrat Curtis Fell is facing Independent Craig Keller for the open seat. Fell has worked in the sheriff’s office for 28 years. His father also worked for the office and his son currently serves as a patrol deputy. Keller worked in the sheriff’s office from 2001 until he retired in 2019.

With the county moving forward on a $96 million project to build a new jail, both candidates said in a candidate forum earlier this month they support the decision and hope it can provide better opportunities for jail inmates to get mental health services and addiction counseling.

Keller said in the forum that he wants to form a citizen’s committee to help the office better work with community members. 

“We have got to get back to being community oriented,” he said.

Fell said he believes the department does a good job reaching out to communities but it does need to diversify its staff. 

“We need to do a better job of recruiting people of color,” Fell said.

Sauk County 

Sauk County Sheriff Chip Meister, a Republican, is facing two challengers in November. Becky Blackman, an independent, and Paul Hefty, a Democrat, are both trying to unseat Meister, who has held the position since 2011. 

“I believe that experience is the best teacher because the lessons are from first-hand knowledge,” Meister said on his campaign website. “I am an effective Sheriff because I have acquired the technical knowledge of the business and leadership skills during my 38-year law enforcement career, I have a clear vision of the future for the Sauk County Sheriff’s Department, along with what it will take to continue moving forward.”

Blackman has been with the department since 2003, and her campaign website states she wants to increase positive interactions between department staff and the community through cultural diversity training. 

Hefty retired as a detective with the department in 2006. He previously ran for sheriff in 2010, 2014 and 2018. In his 2018 campaign, he told the Baraboo News Republic he wanted to put an end to an “old boys club” at the sheriff’s office. 

Sheboygan County 

Sheboygan County Sheriff Cory Roeseler, a Republican, is facing a challenge from Jarrod Fenner, an independent. Roeseler was appointed to the position in 2018 and is running to serve a second term. 

Fenner has been with the department for 30 years and is running on a platform of “keeping politics out of policing.” He resigned from the department in July after an internal investigation found he had lied on minor reports, the Sheboygan Press reported

Fenner told the Sheboygan Press he wanted to be sheriff to improve the department’s relationship with the community and better represent its employees. 

“First, the sheriff needs a stronger connection with the community. Sheboygan County’s citizens, along with its visitors, is a diverse group. These groups can offer vast information, knowledge, and ideas so law enforcement can better serve those we are sworn to serve and protect,” he said. “Second, the department’s administration needs to be more in touch with their employees. I want to encourage the employees, empower them and build the best public safety team.” 

Roeseler told the outlet he was running again to keep making progress on unfinished work. 

“I am running for another term as sheriff because I have a lot of work to finish yet,” he said. “My administration has done so much over the past five years, but there is still so much to do yet. I still love coming to work every day and working hard for the citizens of Sheboygan County. We have a proven track record and I want to keep working hard for Sheboygan County. We have a great county and I want to continue to make it a great place to live and work.”

Vernon County 

In Vernon County, there’s a four-way race for the open seat as sheriff. Republican Roy Torgerson is facing off against independents Janice Turben, Philip Welch and Joe Keenan in a race to replace the retiring John Spears. 

Torgerson, a longtime deputy with the department, told the Vernon County Times he’s running for the position because he loves the community. 

“As a lifelong resident of Vernon County with thirty years of experience with the Sheriff’s Office, I am running for the Office of Sheriff to truly help people, make a positive impact on the community, and keep Vernon County a safe place to live, work, and enjoy recreation,” Torgerson, who said addressing mental health issues and holding drug dealers accountable would be his biggest priorities. 

Turben, a correctional officer with the sheriff’s office, told the paper she wants to fight against drugs, theft, mental health issues and sexual assaults if she’s elected and that she’s concerned about low morale within the department. 

“We are facing challenges such as low morale and employee recruitment,” she said. “Low morale is often seen when administrations continue to use outdated management practices that no longer serve the people in their charge. Times have changed, and we need to change with them.”

Welch, who is currently the chief of the Coon Valley Police Department, told the paper his experience as a law enforcement leader makes him best qualified to run the sheriff’s office. 

“I’m the only candidate who has spent 7 years as the head of two different law enforcement agencies,” he told the paper, with experience “from traffic stops to personnel to policy writing,” he said. “I am passionate about serving the public, and this is an opportunity to bring my leadership to a larger, county-wide community.”

While he’s on the ballot, Keenan does not have a campaign website and did not return the Vernon County Times’ candidate questionnaire.


Our stories may be republished online or in print under Creative Commons license CC BY-NC-ND 4.0. We ask that you edit only for style or to shorten, provide proper attribution and link to our web site. Please see our republishing guidelines for use of photos and graphics.

Henry Redman
Henry Redman

Henry Redman is a staff reporter for the Wisconsin Examiner who focuses on covering Wisconsin's towns and rural areas. He previously covered crime and courts at the Daily Jefferson County Union. A lifelong Midwesterner, he was born in Cleveland, Ohio and graduated from Loyola University Chicago with a degree in journalism in May 2019.