Republican Darin Rice would keep the county's agreement with ICE. Democrat Jason Rippl would end it on day one. The Nov. 3 winner will be Winnebago County's first new sheriff in 16 years.
Winnebago County voters will pick their first new sheriff in 16 years on Nov. 3, and the choice comes down in part to whether the county keeps helping federal immigration agents.1,2 Republican Capt. Darin Rice says the sheriff's office should keep its 287(g) agreement with Immigration and Customs Enforcement. Democratic Patrol Officer Jason Rippl says he'd end it his first day in office.1
The race is one of two Wisconsin sheriff contests, along with Sauk County's, that Wisconsin Watch and WPR identified last week as tests of local ICE cooperation.1 Trump won both counties by less than 5 percentage points in 2024, and both Democrats have promised to quit the federal program.1
Sheriff John Matz, a Republican, entered the county's agreement with ICE in March 2025.1 It uses the warrant service officer model, which ICE says lets designated local officers serve and carry out immigration warrants on people already in their custody.1,3 The ACLU of Wisconsin condemned the agreement when it was finalized, which made Winnebago one of nine Wisconsin counties in the program at the time.4
The program has grown quickly since then. WPR reports 20 Wisconsin county law enforcement agencies now cooperate with ICE through 287(g) agreements.1 Brown, Calumet, Fond du Lac, Manitowoc, Outagamie and Sheboygan counties all have warrant service agreements, and Kewaunee County uses the jail enforcement model, according to ICE data reported by WISN.5 Nationally, ICE had signed 2,617 agreements with agencies in 39 states and two territories as of Oct. 2.3
Federal money is driving part of that growth. The budget law Congress passed last year set aside about $4 billion for state and local immigration enforcement, the Wisconsin Examiner reported, and the Florida Highway Patrol alone was eligible for $26 million in reimbursements for three months of arrests.6
In Winnebago County, the numbers are small. ICE has recorded roughly 25 arrests in the county since January, almost all of them inside the jail, according to WPR's analysis.1 Matz told a county committee in February that ICE detained 17 people from the Winnebago County Jail in 2025 and three in January 2026, all held on criminal charges.7 More than a dozen residents spoke at that meeting and urged the county to end the agreement.7
In Sauk County, which signed its agreement in November 2025, ICE recorded about 100 arrests. That county also rents jail beds to ICE at $106 per person per day and took in more than $150,000 that way between January and June.1
Darin Rice has worked for the Winnebago County Sheriff's Office since 2004 and is captain of field services.2 Matz endorsed him when he announced in March that he wouldn't seek a fifth term.8 Rice told a packed Oshkosh City Hall forum in September that the low arrest count isn't a reason to drop the agreement. "I do believe that it needs to continue," he said.1 He's also said he doesn't support street-level immigration enforcement or renting jail beds to ICE. "I don't support turning our jail into a holding facility for immigration," he told FOX 11.1,2
Jason Rippl has been with the office since 1998.2 He told FOX 11 that keeping the agreement isn't appropriate until ICE "figures itself out," and told Wisconsin Watch he'd rather spend deputies' time on the county's backlog of non-immigration warrants.1,2 Rippl said he'd still honor warrants signed by a judge but doesn't think local jails should hold people past their release date on a non-binding ICE request.1
Both candidates have said they have reservations about license plate reader cameras. The sheriff's office suspended its partnership with Flock Safety in early September, according to WPR.1 Rippl has called the cameras the biggest issue in the race, and Rice has said he supports a pause.2 In Menasha, which sits partly in Winnebago County, the mayor ordered the city's Flock cameras covered over privacy concerns, as Fox Watershed reported in September.
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Whoever wins may not have the final word. Voces de la Frontera, represented by the ACLU of Wisconsin, sued five sheriffs, including Brown County Sheriff Todd Delain, arguing that state law doesn't authorize jails to hold people past their release on ICE detainers.1,9 The Wisconsin Supreme Court paused the case in July while the sheriffs' appeal to move it to federal court is pending at the 7th Circuit, and the U.S. Justice Department has moved to intervene to defend federal detainers.9,10 Winnebago isn't a defendant, but WPR reported that a ruling could affect every county's ability to honor detainer requests.1
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