Wisconsin guv race: high stakes, slow burn

The once quiet contest between David Crowley and Tom Tiffany is ramping up

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Isthmus Cover Stories

On a warm early September evening, Ben Wikler is talking to a group of volunteers packed into a former EVP coffee shop on Mineral Point Road, impressing on them what is at stake in the Wisconsin governor’s race.

“This is a moment that is, simultaneously, one of the most hopeful moments in our state’s history, and one of the most terrifying political moments in all of our political lives,” the former chair of the Democratic Party of Wisconsin tells the room of Madtown O’s, a neighborhood canvass team on Madison’s near-west side.

In Wikler’s view, electing a Democratic ticket is key to “unlocking the shackles” around democracy. A Democratic governor could block an attempted coup on the presidency in 2028 and victories in down-ballot races would give Democrats control over the legislative agenda for the first time in a decade and a half. Wikler has a wish list, with repealing Act 10 at the top.

Wikler is here to kick off canvassing season for the Madtown O’s. They’ll be spending the campaign’s final eight weeks knocking on doors three times a week to squeeze every ballot out of the neighborhoods under their purview.

Around since 2008, the Madtown O’s are one of more than 20 Democratic neighborhood organizing teams in Dane County, a county that Politico, in 2023, described as a “Republican-killing Death Star.” To that, Wikler quips: “I think they got the sides confused. This is definitely the X-wing fighter of the Rebel Alliance.”

The Aug. 11 Democratic primary pitted a Democratic socialist against an establishment Democrat and attracted national attention. Since then the contest between Republican Tom Tiffany and Democrat David Crowley has been relatively quiet, though things started to heat up in late September after the Tiffany campaign barred a Milwaukee Journal Sentinel reporter from an event.

The candidates are ideological opposites, but, with food and gas prices climbing, have both made affordability a centerpiece of their platforms. Their websites contain a host of other policy initiatives they intend to champion, though the details are scarce. The public will have even less opportunity than usual to hear the candidates explain and defend their positions. There will be just one hour-long televised debate before the Nov. 3 election.

On Sept. 8, one day prior to Wikler’s pep talk, Republicans are posting up at the Milford Hills hunting club, located halfway between Madison and Milwaukee in Johnson Creek. It’s a crisp and quiet summer evening — save for the sound of distant gunshots.

Inside the lodge, elk antlers decorate light fixtures and taxidermied bears, wolves, and more look on from a tableau above the bar. Below, former Gov. Tommy Thompson is firing up the crowd.

“This is going to be one hell of a tough election,” Thompson says. “Coming out of Dane County and Milwaukee County, there are going to be huge pluralities.”

“They’re going to play dirty,” someone shouts.

“They always do,” Thompson responds.

The only way to win, Thompson argues, is to get “every man, woman, and child” in rural counties to vote: “I want you to get even your relatives, even those cousins you don’t like. Tell them to come and vote, and vote for the Republicans.”

Democrats are “all socialistic at heart,” he adds. “Good Lord, ladies and gentlemen, vote for this man here who will lead this state in the right direction and bring us back lower taxes, give us law enforcement, and we’ll make sure that we are able to shoot our guns,” Thompson says, fake-exasperated, pointing to Tiffany standing off to the side.

U.S. Rep. Tom Tiffany, 68, has since 2020 represented the vast Northwoods — over 18,000 square miles from Wausau to Bayfield. The former tour boat operator, dam tender, and petroleum distribution manager also spent nine years in the state Legislature under Govs. Scott Walker and Tony Evers, representing parts of northeast Wisconsin from 2011 to 2020.

Tiffany tells the crowd he’s lived the “American Dream,” but it’s slipping away. The son of a dairy farmer, Tiffany says he “got a great education” in Wisconsin’s public schools. He’d go on to operate a tour boat called the Wilderness Queen, and raise three kids, sending them to public school.

“The commitment that I make to all of you is, I’m going to make sure your children and your grandchildren are going to be able to achieve their dreams right here in Wisconsin when I become your next governor.”

Tiffany promises that if elected he would protect and expand the “hunting traditions” guaranteed by the state Constitution, and create “more opportunities to hunt, fish and trap in Wisconsin.” He reminds the room that he has introduced federal legislation to delist the gray wolf. He is also in favor of a sandhill crane hunt.

Tiffany also promises to audit the Wisconsin Department of Natural Resources, along with all other state agencies and “every corner” of the state budget, to ensure that taxpayers aren’t getting “ripped off.” 

When asked about campaign strategy, Tiffany says his campaign is following a successful playbook. “I would say our template is the 2024 election. If you look at President Trump’s win in 2024, how did he win? It’s places like this in rural and small town Wisconsin, where people came out in incredible numbers.”

Tiffany is endorsed by Trump and has rarely diverged from voting with the president. In 2020, Tiffany voted to decertify election results in two states in Trump’s favor. In the August 2026 Marquette Law School poll, 69% of registered voters described Tiffany as a MAGA Republican.

Brandon Scholz, a former executive director of the Wisconsin Republican Party who no longer identifies as a Republican, says Tiffany is “super comfortable in any area” of the state and “works the room well.” He notes his time running a tour boat business. “When you work with customers, you have a different attitude in terms of working a room, reading people, reaching for their hand to shake their hand [with a] big smile on your face, and [getting] them to talk,” Scholz says. “That’s a skill.”

On Sept. 7, one day prior to Tiffany’s hunt club talk, David Crowley is also all smiles as he works the crowd under a big white tent at Madison’s LaborFest on Park Street. In celebration of Labor Day, he’s sporting a shirt that reads “It’s better in a union.”

Crowley was raised by a master electrician and a food service worker who both became addicted to crack cocaine. His family was evicted three times before he graduated from high school.

“You get someone who was as hot-headed as my mother back in the day, and someone as neutral as my father, you put those two together — this is the spark that you get,” says Crowley, who tells Isthmus he’s “the son of labor.”

“But I know what a union does, right? Being able to grow up in a union household, even with challenges, gave my father dignity.”

Crowley wants to raise the minimum wage to $15 and restore the right to collective bargaining by repealing Act 10. “You’re not going to get that when it comes down to my opponent,” he says.

Crowley works the big tent counterclockwise, moving table by table. To the chagrin of campaign staff, he’s going well over his allotted time. He’s chatting up 99-year-old former state Sen. Fred Risser and taking selfies with Frances Huntley-Cooper, the former Fitchburg mayor who broke the glass ceiling as the first elected Black mayor in Wisconsin. Crowley says his work is ultimately about building relationships: “No one cares how much you know until they know how much you care,” he says, attributing the quote to Teddy Roosevelt.

Crowley, 40, was elected Milwaukee County executive six years ago, the youngest ever to assume the post. The former community organizer worked on U.S. Sen. Russ Feingold’s re-election campaign in 2010, then as a legislative aide in Milwaukee County and the state Senate. He lost a race for Milwaukee city council before winning a state Assembly seat in 2016. Earlier this summer, following an endorsement from Gov. Tony Evers, he clinched the Democratic nomination, beating presumed frontrunner Francesca Hong by 3,796 votes.

Straight-laced on the outside, those who know Crowley say he, like Tiffany, is good at working a room. State Rep. Mike Bare (D-Verona) remembers meeting Crowley when Bare was research director for the Feingold campaign and Crowley was a campaign field organizer. “In pops this jubilant, bouncy, big-smile David Crowley,” someone who was “looking for advice” and “really wanted to do it right.”

He recalls one time during the campaign when Crowley accompanied Feingold on a Sunday tour of Black Milwaukee churches. Bare remembers watching Crowley connect with pastors and “light those rooms up.”

Scholz says Crowley is clearly at ease “in his element,” but his challenge is proving he can connect with voters far beyond Milwaukee and Dane counties.

Angela Lang, co-executive director of Milwaukee-based nonprofit BLOC, or Black Leaders Organizing for Communities, has known Crowley for roughly two decades since his days as a community organizer. She says he is “not afraid to go into rooms where people disagree with him.”

Lang was herself unhappy with the agreement Crowley negotiated in 2023 with Republican lawmakers that allowed Milwaukee to implement a sales tax and other measures to help fix long-term fiscal issues in the county. She understood the need for revenue, but had issues accepting the deal’s “poison pills,” including the restoration of school resource officers into Milwaukee public schools and gutting of DEI initiatives. “It never got to a point where we fully agreed,” Lang says. But, she adds, “I was able to relay some of the information to the community when I got questioned.” They continue to have a good relationship.

While Act 12 was once applauded as a rare instance of bipartisanship — the deal was negotiated with Assembly Speaker Robin Vos and Senate Majority Leader Devin LeMahieu, both Republicans — it is now fodder for Tiffany to attack. His campaign has called Crowley the “taxman” who “nearly doubled” the sales taxes and “raised property taxes five times” in Milwaukee County. (“Say hello to David Crowley,” one 30-second spot begins, “and say goodbye to your hard-earned money.”)

After the deal, Milwaukee County’s sales tax rose to .9%, the highest of any county in the state. The city of Milwaukee also established a 2% sales tax; both went into effect in 2024. 

Property taxes also went up under Crowley, from 2019 to 2025, confirms Jason Stein, president of the nonprofit Wisconsin Policy Forum, which tracks tax data for Wisconsin’s municipalities and counties. But Stein adds that inflation outpaced Milwaukee County’s tax increases during the same time period. “If you’re angry that David Crowley raised property taxes by 2.7%, which is a bit more than one-tenth  of what inflation did over that period…how could he have done less than that?”

Both Tiffany and Crowley have been staking out positions in dribs and drabs. Their take on data centers — an issue that’s been defining midterms nationwide — both buck popular opinion.

According to a Marquette Law School Poll conducted after the Aug. 11 gubernatorial primary, 78% of Wisconsin voters think the costs of data centers outweigh their benefits. Candidates in other states have taken the opening to run against overwhelmingly unpopular projects, and dozens of Wisconsin municipalities have adopted local moratoriums. Yet neither Tiffany nor Crowley support the establishment of a statewide moratorium on data centers.

Tiffany is in favor of repealing the state’s sales and use tax exemptions for data centers; Crowley has not followed suit on that, but has called for data centers to cover their increased cost to the grid, something the PSC did in April by establishing a tariff rate for “very large customers.” He also supports using renewable energy to power data centers even as large solar and wind projects have become increasingly unpopular in rural Wisconsin. 

Both candidates say local communities should have the final say on data centers, but neither have outlined the specifics of what that means. 

Tiffany has not always supported local control. As a state rep, he was the chief sponsor of a 2013 bill blocking local governments from creating their own rules for nonmetallic mining. Tiffany told Wisconsin Watch at the time that local governments were “trying to establish mini-DNRs.” The bill did not pass but some of the provisions preempting local regulation of existing quarries were later included in Evers’ 2023 shared revenue overhaul.

Four years later, in 2017, Tiffany co-sponsored a repeal of Wisconsin’s “Prove it First” mining moratorium for metals like copper, gold and zinc, signed into law by Gov. Thompson in 1998. The repeal was signed into law by Gov. Scott Walker.

In an ad released this summer ahead of the Democratic primary, Tiffany is serving up a plate of scrambled eggs at an outdoor breakfast. He’s peppered with questions from his siblings, including a nurse who asks about his plan to fix healthcare and a Realtor who asks about his plan to fix housing affordability.

He responds to each question with folksy charm, promising to make healthcare more transparent, to stop Wall Street from “buying our homes,” to repeal Gov. Evers’ veto that locked in annual increases in revenue limits for education funding until 2425, and to audit every state agency to “protect our tax dollars.” One sibling warns that their mom, who gestures saltily at the end, is going to hold Tiffany to his promises. “I wouldn’t have it any other way,” Tiffany responds.

Both candidates have made affordability a central campaign issue. It’s a smart move: 43% of the registered voters surveyed in the August Marquette poll said that their top issue was “inflation and cost of living.”

In an ad released by Crowley in September, the candidate ticks off what weighs on his mind as his family gets ready for dinner: the mortgage, utility bills, and the “financial stress of raising three beautiful daughters.” He says he gets voters’ financial struggles because “we’re going through it, too.” He promises to lower healthcare costs, make gas and utilities cheaper, fully fund public schools, cut property taxes, and make housing more affordable.

Both candidates’ ads are 30 seconds, compressing a host of complex policies to exactly one minute. What else do the candidates say?

According to his campaign website, Tiffany also promises to cut income taxes by 10% for families making under $150,000 a year; end taxes on tips and overtime; return Wisconsin’s budget surplus of nearly $3 billion to taxpayers; and repeal the state’s minimum markup on gas.

Big-ticket items from Crowley include capping childcare costs at 7% of household income for families with children under 5; providing property tax relief by expanding eligibility for a low-income tax credit; and expanding enrollment in Wisconsin’s Medicaid option, BadgerCare, to any household that wants it.

Both candidates have dozens of planks outlined in bullet points on their campaign websites, summed up in a few sentences. There are some oddities — state protection for racetracks (Tiffany), a new energy accountability office (Crowley).

According to the August Marquette Law School Poll, the candidates are tied at 44% while 12% of registered voters are undecided. Conservative blogger David Blaska argues that Tiffany and Crowley need to play to that middle-of-the-road voter. “It’s a tightrope that both candidates have to walk,” he says.

“I predict that Tom Tiffany will not invite Donald Trump to Wisconsin,” he says, adding that Tiffany needs to break out of the “MAGAsphere” but not alienate it. At the same time, Crowley needs to appeal to Hong supporters. Blaska thinks Tiffany should turn to culture issues: “That’s where he’s got Crowley by the short hairs.”

There will be limited opportunity to hear either candidate defend or expand on their positions. Tiffany has agreed to just one debate, on Oct 21, less than two weeks before the election. Tiffany has declined others. One, set for Oct 9, was to have been hosted by the Wisconsin Broadcasters Association, which has hosted a debate in every gubernatorial election since 1990. “One debate is sufficient to be able to cover the issues that need to be covered,” Tiffany told conservative talk radio host Dan O’Donnell.

Another debate, proposed by the Milwaukee County Intergovernmental Cooperation Council (ICC) and set to be aired by TMJ4, was cancelled after Crowley presented scheduling issues and Tiffany then declined the invitation. Glendale Mayor Bryan Kennedy, who helped organize the debate on behalf of ICC, calls the cancellation a “disappointment” and says it’s a missed opportunity to highlight important issues that “often get overlooked,” including the state’s role in funding local government.

“We wanted to be able to ask really tough questions that often are not questions that get asked, like, why your property tax bill keeps going up and up and up, and it’s going up because the state keeps cutting funds to local municipalities and school districts,” adds Kennedy. “Those kinds of questions just don’t ever get asked.” 

Tiffany has continued to follow a Trump-like pattern of blaming the press for perceived bias; on Sept. 24, the campaign refused to allow Milwaukee Journal Sentinel reporter Mary Spicuzza into a campaign event. An official campaign account on X called her a “liberal activist” while claiming to welcome other “balanced journalists.” In response, Greg Borowski, executive editor of the Journal Sentinel, wrote that restricting press access “blocks the public from vital information.”

More journalists could be on their way. The national press swarmed Wisconsin when it looked like a Democratic socialist might pull off a victory in the Democratic primary. Hong lost, but the stakes, as Wikler warned the Madtown O’s, are still high. He predicts the race will heat up and there will be “more and more attention” by the end, especially if polls show the race is likely to be close. “I think it’s going to come flooding back.”