The Recombobulation Area is a 19-time 21-TIME! Milwaukee Press Club award-winning opinion column and online publication founded by Milwaukee journalist Dan Shafer.
With less than a month to go before the everything-on-the-line, fork-in-the-road election in Wisconsin, there are two dominant competing forces at play.
One is the reality of the times and the current moment in American politics. There’s the economy, where costs continue to rise, the job market continues to slow, and affordability concerns continue to escalate. There’s the history of midterm elections, where the president’s party almost always loses seats in Congress. There’s this particular midterm election, where the president is more unpopular than at any point over his two terms in office, and is a drag on his party up and down the ticket. Even in many red states, Democrats are favored or competitive in statewide races, which says plenty about the national environment. On the generic ballot, Democrats lead Republicans by a nearly 10-point margin, per Nate Silver’s latest model at Silver Bulletin.
So, being that Wisconsin is typically a 50-50 state, with the history of midterm elections and the current national environment suggesting Democrats are in an advantageous position this year, it seems to suggest that Democratic nominee David Crowley is the favorite to win the race for governor and Democrats are favored to win control of the state legislature. Consider what happened last time there was a Trump midterm, in 2018, when Tammy Baldwin won re-election to the U.S. Senate in a nearly 11-point landslide, Tony Evers toppled Scott Walker to win the governorship, and Democrats swept every statewide election. Trump is even more disliked than he was then, and the president and his party’s marks on the economy are far worse now. Trump is also uniquely tied to the Republican gubernatorial nominee, Tom Tiffany, a Trump loyalist who has been in 100% alignment with the president.
That should all add up to a Democratic advantage in the first open race for governor since 2010. But this national environment is running up against another major factor in our elections: money.
Republicans clearly have a clear financial advantage in Wisconsin’s elections right now. A WisPolitics analysis found that Tiffany and his allies have been outspending David Crowley and those supporting him by a 2.5-to-1 margin. Tiffany’s campaign is boosted by astronomical spending from three billionaires — Dick and Liz Uihlein, the founders of Pleasant Prairie-based Uline; and Diane Hendricks, the co-founder of Beloit-based ABC Supply Co. — who spent a combined $24.2 million in the most recent reporting period, which, when transferred through the state party to Tiffany’s campaign, adds up to more than 93% of Tiffany’s overall fundraising haul. Hendricks and the Uihleins have spent more than $73 million backing Tiffany and Republicans in Wisconsin this year. The degree to which these mega-donors are propping up Tiffany goes orders of magnitude beyond even what Elon Musk was doing in the 2025 state Supreme Court race.
That discrepancy goes a long way toward explaining why, in a year when Democrats should be favored in a 50-50 state, the gubernatorial race remains a toss-up. While Democrats have raised their share of money from wealthy donors over the years, too, there is nothing remotely comparable to what is happening now with Hendricks and the Uihleins now. Per WisPolitics, “no individual Dem donor has contributed as much over the past 17 years as each of the three GOP billionaires have donated in 2026 alone.”
And it’s not just the governor’s race that is seeing such a funding discrepancy and this overwhelming support from these three megadonors. Up and down the ticket, the Uihlein and Hendricks money is going a long way in efforts to counteract a potential blue wave. They have spent a combined total of nearly $25 million to back the Republican Assembly Campaign Committee (RACC) and the Committee to Elect a Republican Senate (CERS). Hendricks contributed the majority of RACC’s funds ($5.5 million of its $6.2 million total) and CERS’s funds ($1.75 million of its $2.3 million total) from July through September.
Up and down the ticket, you’re hearing the same story from people. Democrats are in position to make major gains, win the governor’s race, and potentially flip the legislature and deliver the first trifecta in a generation. They are even looking to broaden the map, seeking to unseat Republican Bryan Steil in the 1st Congressional District and are eyeing several legislative races not thought to be in play months ago.
But the Uihlein/Hendricks money is everywhere, and it is making a real impact.
To a certain extent, this is a double-edged sword. The outrageous volume of spending coming from just three people backing Tiffany’s campaign could be a motivating factor for Democratic voters, not unlike what happened in 2025 when Elon Musk’s astronomical spending became the dominant story in the spring race for Wisconsin Supreme Court. The Uihleins, in particular, are in the same mega-donor stratosphere as the world’s richest person. According to OpenSecrets, the Uihleins ranked fourth among the biggest donors in the 2024 election, spending more than $140 million backing Republicans. Hendricks ranked 16th, spending more than $33 million.
While these billionaires are in Musk territory for overall spending, they’re not exactly in the same kind of public spotlight that Elon has been in. I certainly would not expect Dick Uihlein to be waving around a chainsaw or wearing a cheesehead at a rally in Green Bay and handing out million-dollar checks. So, the public backlash might not match what it was when DOGE was running rampant and Musk’s oligarchical takeover was among the dominant stories in American politics at the outset of Trump’s second term.
But what this can do for Democrats is play into an already-salient narrative about what’s been happening under a Trump presidency and Republican control of government. The billionaire protected class is being taken care of, while life becomes more and more unaffordable for the rest of the country. With the cost of living issue being far and away the No. 1 issue in this election, there’s certainly a case to be made there. After all, Tiffany’s vote in the “One Big Beautiful Bill” made tax breaks benefitting Hendricks and the Uihleins — ones that Ron Johnson advocated for when this was first passed — permanent.
But even as redder states like Ohio and Iowa and Texas are seeing statewide races where Democrats have a fighting chance, Wisconsin remains close. There are a myriad of reasons for this, of course, but in this particular moment, the biggest one certainly has a lot to do with the checkbooks of Dick Uihlein, Liz Uihlein, and Diane Hendricks.
There’s so much that could be said about the state of the race in Wisconsin right now. Elections for governor and for the Senate and Assembly will determine the state’s future on so many issues — from health care to public education to the environment to every local government in every corner of Wisconsin, and so much more. As the final few weeks are set to unfold — the lone debate, the inevitable get-out-the-vote push, any number of spotlight events and rallies set to occur — the state of the race is dominated by the competing forces of billionaire money from right-wing megadonors and the on-the-ground reality of an unpopular president, a challenging economy and a broken political system.
Which of these forces will ultimately prevail? Wisconsin’s future is riding on that very answer.
Dan Shafer is an independent journalist from Milwaukee who writes and publishes The Recombobulation Area. He worked with Civic Media from 2024 to 2026. He’s written for The New York Times, The Daily Beast, Heartland Signal, Belt Magazine, WisPolitics, and Milwaukee Record. He previously worked at Seattle Magazine, Seattle Business Magazine, the Milwaukee Business Journal, Milwaukee Magazine, and BizTimes Milwaukee. He’s won 24 Milwaukee Press Club Excellence in Journalism Awards. He’s on Twitter at @DanRShafer.
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