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For 26 years, Wisconsin’s Driftless Area was represented in Congress by a moderate Democrat. Through multiple presidencies, including President Donald Trump’s first administration, Ron Kind was considered to be one of the most bipartisan House members and was easily reelected.

Now the 3rd Congressional District is one of the biggest battlegrounds in the nation. 

Republican U.S. Rep. Derrick Van Orden was first elected in 2022 after Kind retired and has held the seat since. He’s now seeking a third term. 

Van Orden has shown a fiery reputation in Congress, faced some controversies and been an ardent Trump supporter. But this will be his first election as an incumbent where the odds aren’t in the GOP’s favor, particularly with Trump’s approval rating polling at a historic low. Despite that, Van Orden has continued to align with the president throughout his reelection campaign. 

Democrats, after losing the House in 2022, are heavily targeting the district. In a rematch, Democrat Rebecca Cooke is challenging Van Orden for the seat after losing by 3 points last election. 

The Democratic Congressional Campaign Committee has put the 3rd District, along with the 1st in southeastern Wisconsin, on its “Red to Blue” list. The program provides candidates with organizational and fundraising support.

Kind, who has endorsed Cooke, told Wisconsin Watch he believes Van Orden “can’t afford to have any degree of separation” from Trump because the president is a large part of his political success. But in the current political climate, that could also be a liability for the 26-year Navy veteran.

“People are beginning to realize what this guy is all about back home and the fact that he’s not making their lives any easier by supporting the president’s policies,” Kind said.

Kind won some of his last few elections by substantial margins, winning by 13 points in 2014, unopposed in 2016 and almost 20 percentage points in 2018. In 2020, though, Kind defeated Van Orden by less than 3 points. In 2022, national Democrats weren’t targeting the open seat and canceled its ad spending for the district, according to WPR. That year, Van Orden defeated state Sen. Brad Pfaff by just under 4 percentage points.

Democratic polls show Cooke ahead of Van Orden by up to 4 points. A Republican poll in September showed Van Orden leading by 5 points. 

University of Wisconsin-La Crosse political science professor Anthony Chergosky said GOP candidates faced a strategic choice with their campaigns this year.

“Are they going to double down on Trumpism in a bid to motivate the president’s supporters, or are they going to try to open up some daylight between them and the president?” Chergosky said. 

Van Orden’s strategy of sticking with Trump, Chergosky said, is likely a move to lean into the president’s heavy supporters to carry him to reelection. He said many voters were highly motivated in 2016, 2020 and 2024 simply because Trump’s name was on the ballot, but those same voters didn’t turn out as much when Trump wasn’t on the ballot. Over 95,000 more votes were cast in the race for the 3rd Congressional District in the 2024 presidential election than in the 2022 midterm.

The district voted for Trump all three times he ran, even when Kind won in 2016 and 2020, so Van Orden’s presidential ties might help bring out those voters again.

“There’s something that’s sorely lacking in this political business and it’s loyalty,” Van Orden told The Associated Press before the GOP midterm convention in August. “I think we’d be a lot better off if we were more loyal to our fellow Americans to begin with.”

Van Orden’s campaign spokesperson did not respond to requests for an interview for this story.

U.S. Sen. Bernie Sanders, I-Vermont, one of the most liberal members of the Senate who won Wisconsin’s Democratic presidential primary in 2016, joined Cooke at a rally in Eau Claire on Sunday.

“In my view, this is the most important midterm election in the modern history of our country,” Sanders said. “What Rebecca’s race is about and the reason that I am here is that the time is long overdue for us to hold the most dangerous president in the history of the United States accountable.”

He applauded Cooke for her working class background as a waitress and emphasized the importance of that representation in Congress.

Candidates take starkly different positions on issues

Van Orden and Cooke overlap on few issues that have been part of Trump’s first term. Those differences were clear when they met Oct. 20 for their first and only debate and sparred over the economy, immigration, health care and the war in Iran.

Cooke said she would not have supported Trump’s One Big Beautiful Bill Act and criticized it for giving “billionaires tax breaks and tax credits.” The tax incentives on average benefited higher earners rather than lower earners, according to the Tax Policy Center. 

“Big corporations and the ultra wealthy should be paying their fair share of taxes,” Cooke said. 

Van Orden touted the act and how its changes led to an influx of revenue for BadgerCare, the state’s form of Medicaid. The act, however, made $1 trillion in cuts to Medicaid overall through mandatory work requirements for able-bodied adults and tighter caps on provider taxes.

He also criticized Cooke for not condemning unauthorized immigrants who commit violent crimes. She said they should be deported and the border should be secure. She also said she does not support sanctuary cities, but affirmed that there should be a “clear pathway to citizenship” and acknowledged immigrant contributions to the workforce.

According to an April 2023 study by the University of Wisconsin-Madison School for Workers, unauthorized immigrants alone make up an estimated 46% to 70% of the dairy farmers in the state. Van Orden has emphasized in his campaign his support for Trump’s immigration policies, which have emphasized large-scale deportations and rolling back authorized immigration.

Campaign signs reading "Marklein State Senate," "Van Orden U.S. Congress" and "Tom Tiffany Governor" stand on a grassy roadside bordered by trees.
Political campaign signs for Republican state Sen. Howard Marklein, Republican U.S. Rep. Derrick Van Orden and Republican U.S. Rep. Tom Tiffany, who is running for governor, are displayed along a stretch of U.S. 18 in Bridgeport, Wis., on Sept. 30, 2026. (Brittany Carloni / Wisconsin Watch)
Stacks of political yard signs for John Rindy, Jenna Jacobson and Rebecca Cooke stand along a wall next to a sign reading "Had Enough? Vote4Dems," beneath a bulletin board.
Political campaign signs for candidates including 3rd Congressional District candidate Rebecca Cooke sit in the Crawford County Democratic Party office in Prairie du Chien, Wis., on Sept. 30, 2026. (Brittany Carloni / Wisconsin Watch)

Cooke said one of the first things she would like to see in Congress is ending the war in Iran, which Van Orden has voted against ending. While he said he does not inherently want to be at war, he said it’s the only way “radical Muslim mullahs” will listen.

“I know about war. I spent my entire adult life either training for war, training others for war or a war myself. I do not want our country to be involved in war,” Van Orden said. “We tried diplomacy. We tried sanctions, upped them again and again and again, and these radical muslim mullahs don’t respond to that … they only respond to this horrible thing that is war.”

Van Orden currently sits on the Agriculture, Armed Services and Veterans’ Affairs committees. Since his election to Congress, he has introduced and passed veteran-forward legislation, like aiming to help veterans avoid foreclosure. He has also co-sponsored passed laws like providing whole milk in schools, expanding autism and developmental disability programs and allowing for hunting programs in schools.

Cooke, a waitress and former political consultant, wants to increase the federal minimum wage to $15 an hour, address teacher shortages with pay increases and signing bonuses, change the school funding formula to give more funding to low-income districts and double Pell college grants for low- to moderate-income families. She also advocates for expanding Medicare to dental, hearing and vision coverage and protecting abortion rights.

A person wearing a pink sleeveless blouse and a clip-on microphone gestures while standing near a video camera outside a building where people gather around tables.
Rebecca Cooke, the Democratic nominee for Wisconsin’s 3rd Congressional District, speaks to reporters outside of Sen. Brad Pfaff’s annual corn roast at the La Crosse Fairgrounds Speedway in West Salem, Wis., on Sept. 2, 2026. (Brittany Carloni / Wisconsin Watch)

One of the few issues that Van Orden and Cooke seem to agree on is supporting agriculture and dairy farms. Wisconsin’s 3rd Congressional District ranked 17th in the nation in 2022 for most farm producers at 31,470. Both Van Orden and Cooke have promised to support the state’s agriculture system and dairy farms. Cooke wants to ensure tax incentives and subsidies for small farms, expand export markets and fight big agriculture to support small farmers. 

As for data centers, Van Orden wants local communities to decide on new developments and to protect farmland and water resources. He has co-sponsored the bipartisan Ratepayer Protection Act, which would ensure ratepayers aren’t forced to pay new energy bills required by large data centers. Cooke wants a moratorium on new developments and to end the tax breaks given to data centers, but data center laws are largely up to state and local governments.

National polarization and negativity

Similar to their first matchup two years ago, Van Orden and Cooke continue their heated rivalry in the high-stakes election. Van Orden has posted AI-generated fake videos of Cooke on social media, making it seem like she was saying she was the “anointed one” and that voters will “comply” and vote for her. She sent him a cease-and-desist letter in September and boosted a citizen complaint filed Oct. 22 with the Wisconsin Ethics Commission.

Cooke told Wisconsin Watch the district is looking for a “representative that’s rooted in reality” and focused on issues rather than making these deepfakes. She called for more AI regulation for campaigns in the future.

Chergosky said it’s unclear how the AI deepfake issue will play out and what voters think about this new territory.

Van Orden and Cooke also have been trying to undercut each other’s authenticity in their campaigns. Van Orden has slammed Cooke for portraying herself as a political outsider while working as a Democratic fundraiser and political consultant for controversy-courting Minocqua Brewing Company owner Kirk Bangstad. She also has worked with the center-left think tank Third Way. 

Van Orden also has found himself in controversies throughout the years, including inflammatory social media posts and his presence in Washington during the Jan. 6, 2021, Capitol riots. In 2023 he scolded teenage Senate pages and in 2021 accosted a Prairie du Chien library worker over an LGBTQ+ book display.

A person wearing a green hat reading "Make Agriculture Great Again" and a blue plaid shirt stands facing two people in white shirts.
Republican U.S. Rep. Derrick Van Orden, who represents western Wisconsin, speaks with attendees during the World Dairy Expo, Oct. 2, 2025, at the Alliant Energy Center in Madison, Wis. (Joe Timmerman / Wisconsin Watch)

Cooke blasted how Van Orden has never held an in-person town hall throughout his time in Congress, as well as his support for Trump’s tariffs and the war in Iran. 

“His devotion to this administration is greater than his devotion to people in this district,” Cooke said. “I think it’s a mistake on his part, but it’s like a blind loyalty that he has to the president.”

Kind said Van Orden has “insulated” himself from his constituents, and Pfaff told Wisconsin Watch that Van Orden has been at the “beck and call” of the White House and has “never had any original thought.”

“I do not believe he has a vision,” Pfaff said. “I don’t believe, deep down, he has a fundamental understanding of what this district is, who the people are in this district and what it would take in order to work the public, private effort in order to continue to move this area forward.”

Kind was noted for being one of the more bipartisan members of Congress, ranking 17th most bipartisan in the House in his last congressional session, according to The Lugar Center’s bipartisanship index.

Van Orden ranked 138th most bipartisan in his first year in office and the second-most bipartisan House member representing Wisconsin, behind former Republican U.S. Rep. Mike Gallagher at 33rd. The least bipartisan from Wisconsin was Republican U.S. Rep. Tom Tiffany, who is now running for governor, in 379th place.

What’s different this year?

Given the rematch, 2024 and 2026 look very similar. Both years, the district was heavily targeted and categorized a toss-up, but one thing remains largely different: It’s not a “Trump year.”

This is the first year since 2020, when Van Orden lost and Joe Biden narrowly won the state, when he is running in a likely poor year for Republicans. In 2022, Democrats controlled the White House — historically the president’s party has fared worse in midterms. In 2024, Trump narrowly won Wisconsin. Now, with a Republican president, Democrats are favored to flip some seats and take back Congress.

Whichever party comes out of November with control of Congress will “profoundly influence the final two years of Trump’s presidency,” Chergosky said.

“In 2022, it was about Republicans trying to gain control of Congress. In 2024, Republicans were trying to retain control,” Chergosky said, “and now, Democrats are trying to get it back … this could be one of the decisive seats in a high-stakes race for Congress.”

Wisconsin Watch is a nonprofit, nonpartisan newsroom. Subscribe to our newsletters for original stories and our Friday news roundup.

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Audrey Lopez-Stane joined Wisconsin Watch as a statehouse reporting intern in June 2026. She currently studies journalism and political science with a certificate in history at UW-Madison. Audrey serves as the state news editor at The Daily Cardinal and previously interned at WisPolitics.