Dems could get shot at seat once thought 'impossible to lose' after GOP lawmaker's gamble

Two Waukesha County Republicans are asking voters to reelect them to the state Legislature in November while simultaneously campaigning to become the county’s next executive in a December special election.

Paul Farrow, who had served as the Waukesha County executive since 2015, was a former state lawmaker and previous chair of the Republican Party of Wisconsin, died in July after a two year battle with a rare and aggressive abdominal cancer. Tom Farley, who previously worked as the county’s lead attorney, was sworn in to serve as the interim county executive on July 30 after being nominated by the county board.

The race to serve the last few months of Farrow’s four-year term has so far attracted the attention of two longtime GOP lawmakers who are also currently running for reelection to their respective seats: Rep. Adam Neylon (R-Pewaukee) and Sen. Chris Kapenga (R-Delafield).

But the lawmakers concurrently running for two offices sets up a tangle of filing deadlines and election dates. The deadline to file nominating signatures to get on the special election ballot is Oct. 20 and if they both gain access, a primary election will be held Nov. 17 — just over two weeks after they’ll both be on the ballot in the midterm elections on Nov. 3.

Kapenga announced his candidacy on July 13 in an interview with conservative radio host Dan O’Donnell.

“Usually, you get excited about announcing, but this is just unfortunate,” Kapenga said, adding that he was praying for Farrow’s family.

Neylon announced his campaign in early September. Neylon, who said Farrow was a mentor of his, said he spent time grieving and then mulling the decision.

“I believe our families deserve leaders who put community first and show up, listen, work well with others, and deliver results to protect the values that built this place, and I think that, given my experience, my background, that I’m the right person for the job,” Neylon told the Wisconsin Examiner.

After the special election, a regular election for a full term as the county executive will happen in April 2027.

Both will appear on ballots in November in races for their respective legislative seat. Within 60 days following the certification of the election as county executive, a lawmaker would need to resign from their position. State law prevents legislators from serving in the Legislature and as a county executive.

Kapenga and Neylon’s decision to seek the job outside the Legislature follows a wave of Republicans opting to not run for reelection this year, including Senate Majority Leader Devin LeMahieu (R-Oostburg) and Assembly Speaker Robin Vos (R-Rochester). Though state lawmakers regularly run for open county executive seats.

Kapenga or Neylon’s departure from the Legislature would be one fewer Republican with legislative experience and would trigger the need for a special election to fill the seat.

Farrow was a state senator when he ran in 2015 and his election created a vacancy that Kapenga filled by winning a special election for the Senate seat that July. Democratic gubernatorial candidate David Crowley, then a state Assembly member, was elected to be Milwaukee County executive in May 2020, and former Senate Minority Leader Melissa Agard ran to be Dane County executive after deciding not to run for reelection.

With control of the Senate and Assembly at stake in November, the possibility of a legislative vacancy adds another variable for the next legislative session.

Kapenga did not respond to requests for an interview from the Examiner, but during his interview with O’Donnell, he said he expects another Republican to be elected to his seat if he wins the special election and resigns.

“It’s almost statistically impossible unless somebody really makes a major mistake in this seat to lose it to a Dem so that risk is very low,” Kapenga, who won his last reelection effort unopposed, said.

Kapenga is facing a challenge for the state Senate seat from Mike Van Someren, a Democrat and attorney from the Town of Delafield, in the race for state Senate.

Van Someren has knocked Kapenga for campaigning for county executive while running for the state Senate, saying in a video posted to TikTok that “it’s clear we’re both out there working for the job we really want.”

“So in this instance, I just want to wish both luck,” he said.

The Examiner spoke with Neylon about his campaigns. He said he is focused on winning reelection to the Assembly and then will turn his focus to the county executive race.

“It’s going to be a sprint,” Neylon said of the turn around time between elections. “There’s not a lot of people paying attention to the county executive race right now when you have the general election on the horizon. People are talking about the governor’s race. People are talking about the majorities, and I’m part of that.”

In the race for the Assembly, Neylon faces a challenge from Democrat Stephen Tryon, an author. He won his 2024 election in a 59.1% to 40.9% vote against his Democratic opponent.

Neylon said wants to help Republicans keep their majority as Assembly Democrats are seeking to flip five seats and put Republicans out of power for the first time in 16 years, but that he also has unfinished business in the Assembly that he’d like to work on.

“When I left Madison at the end of last session, I didn’t leave thinking it was over,” Neylon said. “I think it’s actually a positive thing, not something that I’m going to apologize for.”

With Vos and other GOP leadership retirements, Neylon said he wants to be involved in choosing a new leader for Assembly Republicans. He said there is also some legislation that he would want the opportunity to propose, including on AI and regulating Flock license plate readers.

Neylon said it was a difficult decision, but there wasn’t much strategic thought put into running for both seats. He said he sees an opportunity in the county executive role and thinks he is best suited for the job due to his ability to listen to people and work collaboratively.

“At the end of the day, the ultimate consideration was, do I want to do this? And I do,” Neylon said. “I think that when you look at the opportunity that Waukesha County Executive presents to be able to be an advocate and a leader in a community that I love, that I care about, that I want to protect for my kids to make sure that they have the same opportunities that we do. It just felt like I had to raise my hand and step up, and I felt a sense of commitment and responsibility to do so.”

Kapenga is known for being a staunch conservative and fiscal hawk, who wants to cut taxes and reduce government services. He has at times been the lone “No” vote on bipartisan legislation, including a law to provide additional coverage for breast cancer screenings. He’s also been part of hardline Republican obstinance that led to legislation failing or Republican leaders turning to Democrats for help getting bills across the finish line.

One issue that has defined the race so far is taxes. Waukesha County is one of two counties in the state that do not impose a local county tax on top of the state sales tax of 5%. During his tenure, Farrow had proposed a plan to implement a sales tax to avoid steep cuts in services. It was withdrawn in January 2025.

Neylon and Kapenga have said they are opposed to implementing a sales tax.

“Things cost more. Based on the last budget projected deficits into the future at the current levels of spending, so there’s been an interest in looking at different ways to increase government revenues,” Neylon said. “I think we need to be more innovative about the solutions we’re offering to people instead of always just going back to we need to raise tax.”

Neylon said he wouldn’t look to shared revenue from the state to help with the county’s fiscal issues, however, he said he would lobby state lawmakers to allow the county to keep more revenue from fees that currently go to the state.

Neylon has said he would also bring his focus on regulatory reform to county government, including to rising housing costs by looking to ease zoning and permitting rules that he says slow construction. He has spent much of his legislative career focused on rulemaking, including as the the lead author of the REINS Act, the Walker-era law that requires state agencies to halt the rulemaking process for any proposed administrative rule estimated to cost $10 million or more. He also served as the chair of the Joint Committee for Review of Administrative Rulemaking.

Kapenga, who has worked as a certified public accountant, told O’Donnell that his experience would help provide a different perspective to county government.

“I think it really works well with the challenges that we’re facing as we go forward,” Kapenga said.

Wisconsin Examiner is part of States Newsroom, a nonprofit news network supported by grants and a coalition of donors as a 501c(3) public charity. Wisconsin Examiner maintains editorial independence. Contact Editor Ruth Conniff for questions: info@wisconsinexaminer.com.