Heartland Inferno: notes and dispatches from a divided state, including the fierce struggle for WI-03
Wisconsin just seems to love having elections. It feels like it was just a few months ago that I was writing a summary of our spring elections. And Wisconsinites love voting: Wisconsin regularly has one of the highest rates of voter participation of any state in the country - in 2020, Wisconsin had the 4th highest voter participation rate in America out of its 50 states. In that election, 76% of eligible voters in Wisconsin voted (Minnesota, braggarts that they are, came in at number one).
NB: This article is lengthier, so I've subdivided it into sections in case there's something in particular you want to read about.
The Heart Of the Inferno: Wisconsin
Wisconsin these days is often a bitterly divided state politically. Donald Trump won it by about 23,000 votes in 2016, and Joe Biden won it by about 21,000 votes in 2020. Both of these margins came out to be just under a percentage point, which is to say both losing candidates came awfully close to winning the state. And while now-President Joe Biden surged in many of Wisconsin's cities and suburbs, he often did worse in rural Wisconsin compared to Democratic presidential candidate Hillary Clinton in 2016. I created a map, shown below, that vividly portrays this. While Biden did improve in a handful of rural counties like Bayfield, Menominee, and Door (all counties with large Native American populations and/or tourism industries), the overall trend was clear: then-President Donald Trump squeezed more net votes out of rural Wisconsin in 2020 than he did in 2016. And it's possible he will perform even more strongly in much of rural Wisconsin in 2024, seizing further political ground in Wisconsin's small towns and villages.
To explain my map a little further: Take, for example, Monroe County - a very rural county, whose county seat of Tomah is directly connected to I-94. Trump won Monroe county by a margin of about 4,300 votes in 2016. In 2020? That number increased to 5,300 - he netted about 1,000 more votes the second time around. In most rural counties in the state, this was the case - netting anywhere from 100 extra votes compared to 2016 to well over a 1,000.
But in historically deep red Ozaukee County, representing Milwaukee's upscale, overwhelmingly white northern suburbs, Trump lost a lot of ground compared to 2016 - he won the county by 10,300 votes in 2016, but only won it by 7,400 votes in 2020. You saw this play out at an even larger scale in Waukesha County, which contains Milwaukee's western suburbs and a county which has been the historic lifeblood of the Republican Party in the state. Trump won it by 63,000 votes in 2016, but only 56,000 votes in 2020. Still a big win, but a loss of valuable ground in a state that is often a knife fight for every vote.
At times, politics in Wisconsin can feel more like an inferno rather than a way of peacefully resolving conflict between groups of people with differing beliefs. And Wisconsin has been no stranger to intense political conflict, even in the pre-Trump era. Anyone who came of age politically in the state during the earlier Obama years can remember the ferocious, polarizing struggle over then-Governor Scott Walker's Act 10, which weakened the power of public sector unions such as firefighters' and teachers' unions. We are still living with the fallout of that law today in the form of out-migration to neighboring states like Minnesota and Illinois, and low morale among public sector employees (as a guy who was a public sector worker of several years until just a few weeks ago, trust me on this one).
And yet, political conflict in Wisconsin has taken on an even more visceral vibe in recent years - Hillary Clinton's loss of the state in 2016 made candidate Donald Trump into President Trump. This was the first time Wisconsin had voted Republican for president since 1984, when Ronald Reagan won every state in the country excepting Minnesota. It delivered an absolute haymaker to the Democrats in this state - no longer could Democrats confidently claim that Wisconsin was a state they could count on winning in presidential races.
Since then, the Wisconsin Democratic Party has let that catastrophic loss fuel a frenzied organizing drive that at times the Republicans here have struggled to counter. 14 out of 17 statewide races here have been Democratic & liberal victories since 2016. But if you're a liberal or a leftie, don't let this make you overconfident - as evidenced by Republican Senator Ron Johnson's narrow re-election victory in 2022 over then-Lieutenant Governor Mandela Barnes, the Republicans can still win crucial elections here.
So yeah. If American's fiery, often ugly, politics are in many ways centered on the Midwest these days, we in Wisconsin are at the heart of the inferno. And it will be so for 2024 as it was in 2016 and 2020.
The Republican State Legislature Tries To Undercut Governor Evers - Again
A few weeks ago, Wisconsin had its summer primaries, where candidates for state legislative races and races for Congress by both the Republican and Democratic Parties were nominated. Additionally, we also had a vote on 2 Republican-backed amendments to the Wisconsin state constitution, both of which failed by almost identical margins of 15 points. The amendments, despite failing, represent a new strategy that the Wisconsin Republicans have brewed up in light of recent political defeats for them, including a map that was drawn by them to heavily favor them - i.e., a gerrymander - being replaced with a more balanced one. And that new Republican strategy is this: do everything in their power to cement their power and insulate it from the will of Wisconsin's voters.
Elaborating more: Ever since then-State Superintendent of Public Instruction Tony Evers narrowly defeated Governor Scott Walker in 2018, the Republican Party of Wisconsin - with a heavily rigged legislative majority - has at every turn sought to sabotage Governor Evers instead of finding common ground with him. Often these battles have taken the form of trying to weaken the Wisconsin governor's power to do things, which they notably never did when Scott Walker was the governor. Indeed, just a month after Tony Evers won in 2018, the gerrymandered GOP legislature introduced and passed bills to weaken incoming Governor Evers' power. Scott Walker, soon to be unemployed, gladly went along with this.
So these amendments merely represent their latest scheme to further weaken the power of a governor they don't like, who has now beaten them at the polls twice - indeed, Evers won by a decently larger margin in 2022 than he had in 2018. The amendments would have given the legislature, which has nearly 2/3 of the seats held by Republicans, more control in how federal funds are spent.
This could have had dire consequences in the event of a natural disaster or other emergency - the legislature would have had the capacity to bog down needed relief money from the federal government in red tape (like FEMA funds used for floods or tornadoes), hindering the ability of local and state officials to respond to a crisis ASAP. Was your small town's charming main street totaled by a tornado? Did your pleasant neighborhood in Kenosha flood after a particularly devastating storm? The Wisconsin Republican Party wanted the ability to hold up relief funds if it felt like there was an opportunity to make political hay of it.
And if you think this is hypothetical bloviating from a hardcore partisan, let me use an example of the Wisconsin Republicans already doing something like this in my own community. We recently lost two hospitals, Sacred Heart and St. Joseph's, that had served the Chippewa Valley area for generations. $15 million that had been set aside by the legislature for psychiatric beds were instead going to be used to help Eau Claire, Chippewa Falls, and other communities cope with the fallout of these closures. There was just one problem: The Republicans on the JFC (that's Joint Finance Committee) have not released the funds, owing to a dispute with Evers over how the funds should be spent - specifically, whether or not they can be used in only Eau Claire and Chippewa Counties, or if they can be used more broadly within the western Wisconsin area. These funds, as of writing in late August of 2024, still have yet to be released to our community.
And as someone who has needed a lot of healthcare as of late owing to some of my own health issues, the hospital closures have impacted me quite a lot in the form of increased wait times to get medical care. And one can't help but wonder: if Wisconsin had expanded Medicaid under the Affordable Care Act, would we have had these hospital closures in my area? Many red states like Oklahoma, Kentucky, Indiana, South Dakota, and Idaho have expanded Medicaid, such that only 10 states have not done it yet - Wisconsin being one of them. And according to the nonpartisan Kaiser Family Foundation, hospitals in states that have expanded Medicaid tend to be financially better off than those in states that haven't. This is because of the billions of dollars in federal funds provided to states that accept the Affordable Care Act's Medicaid expansion.
Yet the Republicans in Madison have consistently blocked efforts by the Democrats to expand Medicaid. This is despite the fact that around 70% of Wisconsinites support it. Not to mention the fact that the rural towns that tend to elect Republicans to the legislature in Madison stand to benefit enormously from an influx of federal cash. Billions of dollars in federal money - money provided in part by Wisconsin's taxpayers - have been left on the table as a result of Wisconsin's Republicans blocking the expansion of Medicaid. All of this is a way of saying: you're going to have to forgive me if I do not trust them with more power over how this state spends money.
In short, these amendments were a power grab, dressed up in garments of legalese. It is a good thing for all communities in Wisconsin, regardless of how they vote or whether they're urban or rural, that these cynical measures failed spectacularly.
The Struggle For Wisconsin's Third Congressional District
But the amendment vote was not the only political battle raging within one of the country's most closely-divided states...
No primary contest in Wisconsin this month drew greater interest than the Democratic primary for Wisconsin's Third District, a House of Representatives district currently represented by former Navy SEAL and January 6 attendee Derrick Van Orden, who is a Republican.
If you want to understand Wisconsin - and American - politics, you could do a lot worse than by looking to WI-03.
Comprised mostly of rural towns - many of them still farming communities - with a smattering of large towns and a few cities, it's been a microcosm of the country's broader political trends over the past ~10 years. Much of the district covers what is known in the Midwest as the Driftless Area: the parts of the Midwest in Minnesota, Wisconsin, Iowa, and Illinois that did not have a glacial ice sheet covering them during the Ice Age some 20,000 years ago. It's an area with both a distinctive identity and geography - with small towns like Viroqua having a distinctly hip, trendy downtown in an area peppered with small dairy farming communities, many of the dairies still family-owned. Or consider Black River Falls, a town of some 3,500 people that is the center of the famous book and later documentary Wisconsin Death Trip regarding the many gruesome events that took place in the area in the late 1800s. I'd definitely recommend it - if you're into that kind of thing.
Represented for just over 25 years by the moderate Democrat Ron Kind, Wisconsin's 3rd District historically voted mostly for Democrats in statewide elections. And Ron Kind himself had a strong history of overperforming other Democrats on the ballot, owing in part due to his efforts to cultivate a large footprint in the district in the form of constant constituent service and outreach.
Then came Donald Trump.
Although it's worth pointing out that rural America had been trending toward the Republicans long before Trump came on to the scene, these trends rapidly accelerated with his political ascent, and were in no small part responsible for his upset victory in 2016.
Take for example Crawford County, a small rural county of about 16,000 people in the southwest of the state and a part of Wisconsin's Third. In 2012, President Barack Obama won Crawford County 59% to 39% for Mitt Romney in his re-election bid - a solid margin of 20 points. In 2016? Trump won it 49% to 44% - an earthquake shift of 25 points toward the Republicans. And in case you think that was the end of it, in 2020, Trump won it yet again - 53% to 45%, even bigger than his previous win.
Yet Ron Kind, despite facing a close race from Republican Derrick Van Orden, retained some residual loyalty from Trump voters in 2020. He carried Crawford County 53% to 47%, despite Trump's improvement there from 2016. That means 100s of Trump voters in the county checked the box for the Democrat for Congress - don't underestimate the power of persuasion, even in such a polarized era. While Trump would ultimately carry the district in 2020 by 6 points - a slight improvement from his 2016 performance of winning it by 5 points - Ron Kind would hang on, defeating Derrick Van Orden by 3 points. He was one of just 8 House Democrats in 2020 to win a district that President Donald Trump won. Ron Kind would later announce his retirement going into the 2022 cycle. The Democrats would nominate Brad Pfaff in 2022, a state senator from the La Crosse area and Ron Kind's former chief of staff. He also has worked as an advocate for mental health initiatives to support farmers in crisis.
Now it's time for a shameless plug: my friend Emerson and I recorded a podcast series about Derrick Van Orden and his many antics, both insurrectionist and not, including his love of yelling at teenagers, shortly before the 2022 midterms. If you want to hear yet more about this district's history and political dynamics, I highly recommend giving it a listen. Unfortunately, our super influential podcast - we have dozens of listeners! - did not stop him from winning 51.8-48.2 that November. Considering he outspent Brad Pfaff massively and that the national Dems left Pfaff for dead, this was not a particularly impressive win. But on some level, a win is a win.
Since Van Orden's victory in the 2022 election against Brad Pfaff, he has continued to engage in his favorite old-man-yelling-at-clouds pastime of yelling at teenagers. This was despite an initial attempt in his early months in office to portray himself as a civic-minded, bipartisan dealmaker focused on the everyday issues facing ordinary people in this district. Even then, I had the sneaking suspicion that this projected image was a carefully stage-managed affair by his staff, and that the true Derrick - the J6 attending Derrick - would soon emerge.
I would not be disappointed. Like when he yelled at a group of Congressional pages during a tour of the US Capitol last year, calling them "pieces of shit" for supposedly violating the sanctity of the Capitol rotunda, which drew criticism from even his own party members - the kids he was yelling at were 16 and 17 year olds. He has refused to apologize for the incident, saying that the teens were defiling the Capitol building. (I trust the irony of Van Orden bloviating about the sanctity of the Capitol, where Derrick was present in a very different context on January 6th, 2021, is not lost on any of my readers). You kids better get off my rotunda!
Van Orden has a remarkably embarrassing inability to resist the urge to yell at teenagers - he also yelled at a teenage library worker back in 2021 in his hometown of Prairie Du Chien over a display of books for LGBTQ Pride month. Particularly offensive to Derrick was the book A Day In The Life Of Marlon Bundo. It's a children's book about a gay rabbit. Combined with his just generally rancid vibes, he has created quite an opening in a district that a less clownish Republican would probably be able to hold onto in all but the biggest Democratic wave years.
Van Orden would later gain even more not-at-all-cringeworthy press for the work he was doing for the good people of WI-03, as when he yelled at President Biden this year back in March for daring to criticize former President Donald Trump at the State of the Union. Damn Derrick, back at it again with the yelling!
Oh, he also accused a protestor of assaulting him at the Republican National Convention in July - an accusation shown by police body camera video to be totally false. He just made it up. A guy who hitches his political wagon enthusiastically to the grift caravan that is the Trump world, being completely dishonest? Will wonders ever cease?
But wait, there's more - he also was given a year's probation for bringing a loaded 9 mm pistol into an airport. Quoting from Wisconsin Watch, an investigative journalism group,
In August 2021, Wisconsin House candidate Derrick Van Orden was cited for carrying a loaded gun into an Iowa airport. Court records show he had a loaded 9 mm handgun in his carry-on bag at the security checkpoint at the Cedar Rapids airport... He pleaded guilty to the charges in December 2021. Van Orden received two fines and had to take a firearms safety course. Van Orden was also placed on unsupervised probation through Dec. 27, 2022.
And the kicker of all what's been said above is this: This is just a smattering of his antics - he regularly gets into petty spats with those who criticize him on social media, like calling Jewish-American Biden voters cult members. To give you an idea of Van Orden's bipartisan, unifying style of politics, you can find that tweet here, which is representative of the posts he tends to make to Twitter. Specifically, he had this to say,
Any American, especially a Jewish American, that votes for Biden is a cult member.
This deeply antisemitic comment, interestingly, seemed to draw no complaint from the Wisconsin Democratic Party. Why am I, a random guy with a keyboard, roasting Van Orden more for his antisemitism than the Democratic Party of this state is? They have more money than god. Seriously - the Wisconsin Democratic Party might well be the best-funded state level Democratic party in the entire country. Go after him on this!
But all of this is to say that, thanks to his big mouth, Van Orden has made himself quite politically vulnerable, opening the way for the Democratic Party to take back this very rural seat. It's almost sad how much he seems to embarrass himself and this district in lieu of actually getting things done for the people here. And because of this, there will be no shortage of material for them to work with in the ensuing weeks of the campaign.
This is a good segue as we now come to the Democratic primary of 2024 for WI-03, which drew two very strong contenders, and who would eventually trade some fairly acrimonious barbs as the primary drew to a close. One thing that stands out to me in hindsight was the fact that every candidate in the running this year on the Democratic side of things was under the age of 40.
One of the candidates was Rebecca Cooke, who is from the Eau Claire area. She's a non-profit owner and former business owner who has often played up her rural roots, noting often in her campaign's ads and promotional materials that her parents are still dairy farmers on the farm she grew up on. She has also worked as a waitress. Notably, she has never held elected office before. She ran back in 2022 as well, coming in 2nd to Brad Pfaff in the Democratic primary then. At the time, I recall being impressed by her showing against the strongly favored Pfaff - she kept the race against him to just the single digits, getting 31% of the vote to Pfaff's 39% (a lot of people ran that year).
In the the interests of full disclosure, I have personally met Rebecca, and she struck me as an intelligent, forceful advocate for the issues that matter to a lot of people in this district. The fact that she had a sort of quiet charisma to her doesn't hurt either. During the course of our conversation, she also noted that she regularly spoke with Trump voters in the district, some of whom she said compared her to him favorably, saying that they admired her business sense - she and I both expressed amazement at such comments. I think anyone who has actually studied Trump's business record, which now includes 34 felony convictions of falsifying business records, would perhaps come away with a different conclusion about the business acumen - and ethics - of one Donald J. Trump.
The other major candidate this time around for the Democratic nomination was Katrina Shankland, a state representative from the Stevens Point area since 2012. Shankland emphasized her long history of experience lawmaking in Madison, and also touted her ability to get legislation passed in a Madison often paralyzed by gridlock. She also played up her strong ties to organized labor in the district, rolling out a lengthy list of union endorsements at the start of her campaign, including such union heavyweights like the AFL-CIO, UAW, and IBEW. She also would later earn the lion's share of endorsements of local and federal elected leaders in Wisconsin, including both of Wisconsin's congressional Democrats, Mark Pocan of WI-02 and Gwen Moore of WI-04. She also landed the endorsement of the legendary Dave Obey, who represented WI-07 (Wisconsin's northwoods) for 40 years - a district I will be writing more about later.
Both major candidates had their pluses and minuses, though I was personally of the opinion that Shankland was more battle-tested, with a history of outperforming other Democrats on the same ticket as her. That is no mean feat in a day and age where the number of people splitting their ballots has practically cratered. She won her moderately Democratic district 57-42 back in 2022, a solid margin and better than other Democrats on the same ballot. And Wisconsin's Third is the type of district where one should expect 110% Donald Trump to win it again this year, so any Democratic victory would be predicated on winning over a small-but-significant portion of people checking the box for Trump at the top of the ticket. Persuasion remains decisive, even in a highly partisan age.
As mentioned earlier, one thing that became notable about WI-03's Democratic primary was the fact that it turned rather acrimonious in its closing weeks. Criticism of other candidates in competitive primaries is the norm, so I tend to take lamentations about "going negative" with a grain of salt, yet it is true that the tone of the attacks often veered into the personal.
There's an element of "she said, she said" to this in terms of who you could credibly accuse of starting the negativity train, but basically: Shankland criticized Cooke for having no legislative experience in an ad, especially since Cooke often highlighted her not being a career politician as a political plus. Moreover, Shankland had pointed out that Cooke's outsider status might be more political mirage than anything else - Cooke has never held elected office, but she does have experience as a fundraiser for other political candidates.
Cooke shot back, saying that Shankland's much-touted lawmaking record had its warts, including a bill she voted for that included an amendment from the GOP that banned the expansion of Medicaid in the state without the approval of the state legislature. That does indeed sound bad, but it's important to realize that the state legislature does have to approve the Medicaid expansion as it is. It's merely doubling down on that - and Shankland has been a strong supporter of expanding BadgerCare, introducing bills to do just that. Personally, I don't think this attack had merit and took Shankland's vote massively out of context, especially since she voted against the Medicaid restriction amendment in committee, but pro-Rebecca Cooke PACs took this line of attack against Shankland and ran with it - hard.
In response, Shankland doubled down on her barbs against Cooke - saying it was unfortunate that she was taking the race in a negative direction, and continued trying to portray her as an inexperienced upstart. Anecdotally, I tended to notice that Shankland got a lot of heat from Cooke supporters on social media for these criticisms. There were definitely some hard feelings.
Former Democratic congressman for WI-03 Ron Kind himself, now an elder statesman, weighed in, saying he was concerned the negativity could set the wrong tone for the general election. He commented,
All this can backfire on you in a primary, and that's why primaries are hard. You try to make a point of distinction of what you're offering versus your primary opponents, but you don't want to do it in a way that's going to alienate your opponents' supporters at the end of the day.
I will say this: this primary was indeed quite different from the one that was held in 2022, despite that also being an extremely competitive race. I had a conversation with a nice woman in her 80s who canvassed my house for Katrina Shankland not long before the election, and I could tell that Eleanor was not happy with the attacks Cooke and her allies were making on Shankland.
Ultimately, Cooke would go on to win the primary on August 13th by 50.5-41.6 - about a 9 point margin. Not quite a blowout, but not a nail-biter either for an open seat. Eric Wilson, the third candidate in the running that I have not mentioned, ran a more progressive-focused campaign that struggled to gain much traction - he did not even break into the double digits district-wide. So I did silo him off into the category of, "seems like a nice guy who means well, should probably run for local office instead though."
One way to think of it would be this: Cooke's campaign tended to emphasize her roots, whereas Shankland's tended to focus more on her record. And when looking at the actual results, there was a very stark divide within the district. Shankland won big league in her neck of the woods - Portage County, where Stevens Point and its surrounding area is, voted for her by an absolute landslide margin of 84-13. She is clearly popular among the people she represents.
But Shankland's fundamental problem was that her appeal was far more limited outside her stomping grounds - Cooke won big in most of the rest of the district. Take for example tiny Pepin County, just a smidge west from Cooke's home base of Eau Claire - Cooke romped here, beating Shankland 67-29. And within Eau Claire County itself, Cooke still ran up the score 56-33. Shankland only broke 40% of the vote in 3 counties, and ultimately won just 2 of out of the 19 counties in this very rural district.
I was personally disappointed that the candidates never had a debate - a common point of criticism against Van Orden back in 2022 was that he pointedly refused to debate Brad Pfaff, clearly worried about what an open airing of his record to the public could do to his tough guy, ex-Navy SEAL image. All the most patriotic people show up to an attack on the Capitol which killed cops, I hear. Generally, when campaigns do things like this, it's because they know there's a risk of it hurting them somehow. And the Democratic candidates did have a debate back in 2022 during their primary, in contrast to this time.
But in a heartening development for those of us who want to see Derrick Van Orden defeated, considering the man is a menace to teenagers and ordinary working people more broadly, the Democratic candidates have staged several campaign events together in the aftermath of Cooke's victory, and Shankland herself has said she's ready to focus on defeating Van Orden.
The Final Analysis
Okay, you've read this far. You presumably want to know the answer to the question: who's likely to win this district? What are some of the policy stakes?
Wisconsin's Third is a big district. You can drive in this area for hours and still be in it. It stretches from River Falls on the western end, to Stevens Point on its eastern end. From Eau Claire to Platteville, Viroqua to Prescott - there are a lot of communities here, many of them with radically different economies and needs. What Eau Claire needs might not be what tiny Boscobel or Black River Falls needs.
And from the collapse of family dairies to the loss of hospital systems and with them healthcare access, this district has real issues. Take it from someone who knows: even in the district's biggest city, Eau Claire, making a living can be hard. A lot of places in this district might be described as great to go to school in, great to visit... but hard to make a living.
Cooke has real plans to address some of this - from breaking up large agricultural monopolies crushing the relatively few family farms that still remain, to tackling rising costs for prescription drugs and healthcare. I've read her policy page and liked a lot of what I've seen. She wants to make it easier to unionize and will vote to uphold and expand abortion rights protections, including ensuring that Planned Parenthood remains federally funded. She supports the price negotiations for commonly-used-by-seniors drugs that Biden has implemented under the Inflation Reduction Act and wants to see this expanded, so that all people don't have to pay as much for the medicine they need. She also would vote to end the Hyde amendment, a law from the 1970s that makes it so federal funding cannot pay for abortion services under Medicaid or Medicare. And she would support the banning of stock trading by members of Congress.
There's a word for this type of platform: populist. Someone embracing positions that take on established institutions and elites, and that are focused on the needs of ordinary people. This was a term that often will still get used to describe a guy like Donald Trump, despite the fact that his main legislative achievement in office was a 2017 tax bill that mostly was a giveaway to the richest people in this country.
Cooke clearly wants to represent the people of this district, since she's now run for this seat twice, and I say: let her. I'm frankly tired of having to read headlines about Derrick Van Orden's latest bullshit. He is clearly not focused on helping the many people who need it in this district and is instead beclowning himself.
And Cooke does have a real chance in this district, and it does have areas where she can grow her support, like Eau Claire and La Crosse, which Van Orden lost by huge margins in 2022 (26.5 and 34 points, respectively). And there are even some small towns where Dems do win, like Viroqua, which Pfaff won about 62.8-37.1, or in Prairie Du Chien, which Pfaff won 53.6-46.3 (recall that this is Van Orden's hometown, where he harassed that teenage library page. I guess that's not a vote-winner, Derrick!).
But here's the hard truth: if there's one thing the political campaigns of Donald Trump have shown us, it's that Republicans in the era of Trump have a strong capacity to mine as many votes out of rural America as possible. I will use just one example here: the city of Tomah, population about 10,000. It's a popular stopping spot on right off of I-94, and in recent years Republicans have improved their showing here. President Barack Obama won it about 52-46 in 2012 against Mitt Romney. 4 years later? Trump won it 53.4-38.4 - a swing to the right of 21 points. And in 2020, despite carrying Wisconsin, Biden posted up a near identical performance - losing it to Trump 56.1-41.4. A lot of towns and cities in this district have trended rightward... and mostly stayed that way. Some have kept getting redder.
Think of oranges. The Republicans basically have a lot of tiny oranges - representing small rural counties with few voters - that they try to squeeze as much juice out of as possible to make a bigger glass of orange juice than the Democrats. They have dozens of these tiny oranges (and a few large ones, representing places like the Waukesha burbs... but mostly tiny ones).
The Democrats, on the other hand, mostly have a few jumbo oranges (and a few tiny ones, like the counties along Lake Superior... but mostly jumbo ones). They try to squeeze as much juice out of these jumbo oranges to make a bigger glass of juice than the Republicans. These represent the urban and suburban counties that vote for them - much more populated, but also fewer in number than the many rural counties in a state like Wisconsin.
This metaphor was intentionally silly, but the point is this: don't underestimate how much juice the Republicans can squeeze out of the rural vote. Derrick Van Orden will be on the same ballot as his favorite aspiring dictator, which means he will get a serious boost in rural turnout, perhaps even bringing new or very infrequent rural voters to the polls. The Democrats should not assume that this will help them; in fact, in heavily white, rural counties, higher turnout will likely help Republicans like Van Orden and Trump on balance instead. Cooke will need to try to cut into Van Orden's margins in rural areas, something she has been positioning herself as capable of doing by emphasizing her rural roots and policies in her campaign.
But ultimately, this is why Van Orden has a great chance of winning again: the district he represents is mostly rural in population, and has gotten redder in recent years. He does have many self-inflicted political wounds, but I am not sure how much they will end up mattering to a lot of people in this district. I'd like to believe his volatile temperament and tendency to be cruel toward those with less power, like teenagers, will count for something, and I do think he will underperform Trump. And there are areas in the district that just plain don't like him, like Eau Claire, La Crosse, Stevens Point, Viroqua, River Falls, and his own damn hometown of Prairie Du Chien. Will it be enough to kick him out of the House? That remains to be seen. This race could well end up coming down to just a few 100 votes - so it's worth repeating: your vote does matter.