Two Wisconsin sheriff races test the future of local ICE cooperation

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This article was produced in partnership with the nonprofit journalism publication Bolts, which covers criminal justice and voting rights in local governments.

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• Voters in Sauk and Winnebago counties will choose sheriffs who hold different views on local cooperation with ICE.
• Both Democratic candidates pledge to end their counties’ 287(g) agreements while their Republican opponents support continuing them in some form.
• In Sauk County, both candidates would maintain a contract allowing ICE to house detainees in the county jail, despite disagreeing over the financial and humanitarian implications.
• In Winnebago County, residents have also raised concerns about the law enforcement use of Flock license plate cameras.

Half an hour into a packed June candidate forum in Baraboo, the moderator turned to the issue looming over the race for Sauk County sheriff: immigration enforcement. 

“As chief law enforcement officer of Sauk County, how will you separate the demands of ICE from your duty to uphold the law and protect the residents of Sauk County?” Baraboo Optimist Club President Joseph Viney asked.  

The six candidates at the front of the public library conference room offered well-rehearsed responses.

Three months and a primary later, one Republican and one Democrat remain, with the question still central to the race ahead of the Nov. 3 election.

“People are fired up and they’re frustrated with ICE in general from a national perspective, and it does have local consequences,” Ryan Jesberger, the Democratic nominee, told Wisconsin Watch and Bolts.

ICE agents haven’t turned up in large numbers in the largely rural south-central Wisconsin county to check homes, jobsites and cars for undocumented immigrants. Unlike in neighboring Illinois and Minnesota, U.S. Immigration and Customs Enforcement has relied on jails and prisons to make most of its arrests in Wisconsin since President Donald Trump returned to office in January 2025. 

Sauk County is no exception. ICE has recorded about 100 arrests in the county during that period, almost all through custody transfers at the local jail. An agreement between the sheriff’s office and federal authorities makes a small portion of those arrests possible by allowing county jail supervisors to play a limited role in immigration enforcement.
The Sauk County Sheriff’s Office is one of 20 county law enforcement agencies in Wisconsin that cooperate with ICE through 287(g) agreements: voluntary partnerships allowing designated local officers to carry out some immigration enforcement tasks. Voters in two of those counties — Sauk and Winnebago counties, 90 miles apart — will have a say in the future of their sheriffs’ ICE partnerships this fall. Trump won both counties by less than 5 percentage points in 2024.

The Trump administration has tapped local law enforcement agencies across the country for help in its immigration enforcement push, often in the form of 287(g) agreements. Those arrangements are drawing pushback from immigrant rights organizations and, in some cases, shaking up local elections.
Sheriffs are “the most important state(-level) race for immigration purposes,” said Hannah Schwarz, a staff attorney with the ACLU of Wisconsin. The civil liberties organization opposes local law enforcement cooperation with ICE. 

Sauk and Winnebago county voters will now choose between Republicans promising to stay the course and Democrats campaigning to dial back cooperation with immigration authorities. Both Democrats promise to quit the 287(g) program as soon as they take office.

But the partisan split conceals a more complicated policy landscape in Sauk County, where both candidates in the race favor keeping in place a contract that allows ICE to rent out space in the local jail to detain immigrants.

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In Sauk, ICE cooperation takes multiple forms

Sauk County sits on the edge of Wisconsin’s Driftless Area, a region of sandstone bluffs and organic farms that has veered toward Republicans over the past three presidential elections after more than a decade of favoring Democrats. 

Baraboo, the county seat, peters out into cornfields within city limits. Wisconsin Dells, the Midwest’s waterpark capital, spills across the county’s northern boundary. The city’s resorts hire foreign workers on temporary visas ahead of the summer rush; other immigrants, many without visas, milk cows on the county’s dairy farms. 

Signed by Sheriff Richard “Chip” Meister in November 2025, Sauk County’s 287(g) agreement enables the county’s six jail supervisors to execute immigration warrants on people in county custody — a task ICE officers would otherwise perform. Executing an immigration warrant transfers them to ICE custody. 

The Sauk arrangement “streamline(s) our existing relationship with ICE,” Meister wrote in an email to Wisconsin Watch and Bolts.

But Meister is set to retire this year after 16 years, leaving the future of this arrangement uncertain. He endorsed Capt. Matt Burch, a Republican, ahead of the August primary; Burch won the primary by a wide margin. 

He takes a position similar to Meister’s. 

“Our focus remains strictly on removing individuals who commit serious crimes rather than targeting members of our community solely based on their immigration status,” Burch wrote in an email. He does not, however, plan to extend the office’s partnership with ICE beyond the county jail. “Our authority applies exclusively to individuals who are already in our custody for violating local or state laws.” 

About half of people transferred from the Sauk County Jail to ICE during Trump’s second term had prior criminal convictions, a Wisconsin Watch and Bolts analysis shows; the other half had pending criminal charges. At least 8% of those transferred to ICE custody inside the jail had a prior conviction for driving while intoxicated — by far the most common conviction among Sauk County arrestees.

Jesberger, the Democratic candidate running against Burch and a former University of Wisconsin-Madison police lieutenant, promises to end the county’s 287(g) agreement “on day one.”

“It’s not an anti-ICE or pro-ICE view,” he said. “We’re not talking (about) not doing any interaction,” he added, but instead about scaling back the county’s role. Jesberger also argues the 287(g) agreement sidesteps a contentious and unresolved question about the limits of local law enforcement’s arrest powers.

Law enforcement agencies with or without 287(g) agreements can choose to honor ICE “detainer” requests, which can entail holding people in jail up to 48 hours past their scheduled release to give immigration agents time to take them into custody.
The ACLU of Wisconsin petitioned the state Supreme Court in September 2025 to take up a lawsuit claiming five Wisconsin sheriffs’ offices — including Sauk County’s — violate state law by honoring the requests. The lawsuit argues that jailing someone beyond the person’s scheduled release date on an ICE detainer qualifies as an arrest and that state law does not authorize law enforcement to make arrests solely on the agency’s administrative warrants. 

The lawsuit is currently caught in a jurisdictional tug-of-war.

Jesberger shares the ACLU’s view on detainers, which he called “request(s) to take an action we are not authorized to take.” 

“It’s easy to say we should just hold onto someone,” he wrote in an email. “The problem is that under Wisconsin Law, there is no legal authority to conduct an arrest on this civil detainer.”

Jesberger would, however, honor warrants signed by a judge.

A 287(g) agreement enabling jail supervisors to serve immigration warrants is not the same as honoring ICE detainers, he added, but it still blurs jurisdictional lines. “Entering into the agreement to act as federal agents,” he said, “is going around state law.”

Jesberger also argues that even the county’s current agreement can strain sheriff’s office resources.

“Our deputies are busy enough doing things for the citizens of Sauk County,” he said, “so adding roles and responsibilities and, frankly, liability on top of all that is a concern of mine.”

Alongside its participation in the 287(g) program, Sauk County built on its partnership with ICE last year when it extended a long-standing agreement to hold federal detainees to include people held on immigration grounds. 

The county’s original agreement with the U.S. Marshals Service dates back more than two decades. The sheriff’s office modified that agreement in April 2025 to also include ICE. More than 200 ICE detainees have since passed through Sauk County, most of whom entered ICE custody either at the jail or in other Wisconsin correctional facilities.

ICE reimburses the county $106 per day for housing a person in removal proceedings, plus $38.45 per hour for staff time spent transporting ICE detainees. That contract yielded more than $150,000 for the Sauk County Sheriff’s Office between January and June – less than 1% of the office’s annual budget, and about 15% of what Burch calls its “flexible” budget, or the portion not already devoted to wages and benefits. 

“That money is important to us,” Burch said at the June forum.

Jesberger also promises to maintain the county’s contract to provide jail space for ICE detainees, though he pushes back on Burch’s focus on the revenue it yields, calling on law enforcement to “stop talking about human beings as numbers or revenue generation.” 

Instead, he sees the housing contract as a way to protect immigrants’ due process rights while they await rulings in their removal cases. 

Aside from offering Wisconsin-based attorneys easier access to their clients, Jesberger argues that a responsibly managed contract can ensure people in custody “are treated with respect and dignity, are not laying on a concrete floor with a foil blanket in overcrowded cells (and) are not being shipped out of state to detention facilities with inhumane conditions.”

Some Wisconsin immigration attorneys and immigrant rights advocates aren’t sold on that pitch. “Any amount of custody is an incentive for ICE to continue” its crackdown, said Aissa Olivarez of the Community Immigration Law Center in Madison.

Schwarz of the ACLU of Wisconsin agrees, saying that housing contracts like Sauk County’s make it easier — and cheaper — for the agency to scale up its operations.

Cooperating with ICE in any capacity has a “chilling effect” on immigrant communities, Milwaukee-based immigration attorney Marc Christopher said, and can make immigrants less likely to contact law enforcement in an emergency.

But Christopher also noted that Sauk County is far easier to reach than the larger detention facilities in Indiana, Kentucky, Louisiana and Texas where many Wisconsin arrestees land while awaiting outcomes in their removal cases. “I can meet with them in person,” he said. “Their families know where they are, and their families can meet with them.”

Jesberger and Burch have no debates scheduled ahead of Election Day, but a local coalition that opposes all cooperation with federal immigration authorities is planning an Oct. 3 event featuring the ACLU of Wisconsin and immigrant rights group Voces de la Frontera. 

In Winnebago, sheriff candidates diverge amid a broader debate on surveillance

Eastern Wisconsin’s Winnebago County is more than twice as populous as Sauk County. Sheriff John Matz entered its 287(g) agreement — also a warrant service model — in March 2025. 

ICE has recorded roughly 25 arrests in the county since last January, almost all inside its jail. Capt. Darin Rice, the Republican running to replace the retiring Matz, says that low number is no reason to end the agreement. 

“I do believe that it needs to continue,” he told a packed audience in an Oshkosh City Hall conference room in September. Still, he underscored that he isn’t interested in “street-level enforcement” or renting jail beds to ICE.

Rice is running against his colleague, Patrol Officer Jason Rippl.

Rippl, the Democratic candidate, has broader 287(g) qualms than Jesberger. 

“I feel like the 287(g) agreement may open the door for additional involvement with (ICE),” he told Wisconsin Watch and Bolts, “and I think that by any modern law enforcement standards, we’ve seen pretty clearly that their tactics are sloppy.”
He promises to void the county’s 287(g) agreement on his first day in office, which he argues would free up time to “clean up our own backyard” by digging out of a backlog of warrants unrelated to immigration.

Rippl said he would honor warrants signed by a judge, but he doesn’t “feel it is the responsibility of local jails” to hold inmates beyond their release date based solely on a non-binding ICE request. 

Though Winnebago County isn’t named in the ACLU lawsuit, a ruling could affect any Wisconsin county’s ability to honor ICE detainer requests. Sheriffs could also refuse to honor detainers absent a court ruling, as some have done elsewhere.
The early attention on Winnebago County’s relationship with ICE may be shifting to law enforcement’s use of surveillance technology. Both Rice and Rippl said they had reservations about the handling of sensitive data from the license plate cameras, citing the well-documented recent history of the technology’s misuse.

The Winnebago County sheriff’s office decided in early September to suspend its partnership with Flock, the embattled tech company that has built up an extensive camera network nationwide and has drawn increasingly bipartisan backlash this year. 

Sauk County’s sheriff’s office continues to operate Flock cameras, introduced as part of a pilot project last year. Burch, the GOP nominee for sheriff, called the program a  “pet project” and credits the cameras for solving several high-stakes cases. Other law enforcement agencies in Wisconsin have, like Winnebago County, ended their contracts with Flock.

“We had a lot of pushback early on to the 287(g) program,” Rice told Wisconsin Watch and Bolts. “That’s now taken a back seat to Flock cameras.”

Rippl agreed that Flock is “certainly the more prevalent conversation topic” in his conversations with constituents, though he does not believe it has “overshadowed” the 287(g) debate.

Ongoing controversies over ICE’s use of Flock camera data link the two issues.

404 Media revealed last year that local law enforcement agencies across the country have queried data from Flock cameras on ICE’s behalf, including some in states with strict restrictions on local cooperation with ICE. Wisconsin has no such restrictions. 

The Sauk and Winnebago County sheriffs did not reply to a request for comment on how often their Flock cameras have been used for immigration enforcement. In Verona, a Madison suburb with a population roughly one tenth of Winnebago County’s, public records revealed hundreds of searches tied to ICE last year.

Two Wisconsin sheriff races test the future of local ICE cooperation is a post from Wisconsin Watch, a non-profit investigative news site covering Wisconsin since 2009. Please consider making a contribution to support our journalism.