Joy Powers: This is Swing State of the Union, a podcast all about Wisconsin and why it's so important to U.S. Politics. I'm Joy Powers.
Sam Woods: And I'm Sam Woods. Thank you so much for joining us. The Nov. 3 election is less than a week away, and early voting is open now. All this season, we've been talking to voters living in or near swing districts across the state. Today, we look at the races that will decide the makeup of the state's next legislature and Wisconsin's representatives in Congress.
Powers: Dan Shafer is the founding editor of The Recombobulation Area. Shafer previewed every district in the state up for election this cycle. He joins us to talk about which districts he has his eye on and the odds that either party ends up with full control of the legislature and governor.
A conversation with Dan Shafer of The Recombobulation Area
This interview has been edited for clarity.
Joy Powers: Which swing districts are you looking at most closely right now?
Dan Shafer: Well, I think we have a really, really fascinating election ahead of us in the state Legislature. This is the first fully post-gerrymander election that we have in the State of Wisconsin. So, Tony Evers signed new maps into law in February of 2024. Those were fully in place for the 99-seat state Assembly in the 2024 election, but only half of the state Senate. And so, because the state Senate is on four-year terms, those people have just been elected. Those terms did not run through until this year. And so, the senators in odd-numbered districts who were not on the ballot in 2024 will be on the ballot here in 2026.
So, this is the first election that the gerrymandered maps are fully in the rearview mirror. And so, that means there are a lot more competitive districts than there were under previous maps, because previous maps liked to draw those lines so that there were a lot of deep blue districts and a lot of — or more of — deep red districts. And so now, we're seeing far more swing districts across the state. We're seeing a lot more that may have a slight Democratic lean or slight Republican lean, but ones that could be realistically won by either party.
And so, there are five seats in the Assembly that are represented by a Republican that were districts won by Kamala Harris in the 2024 election. So, those are the ones that most people are pointing to as swing districts in the Assembly. In the state Senate, there are three of those. And the state Senate currently has an 18-to-15 breakdown because Democrats actually did really well on those new lines in 2024 in the state Senate. They won five of the five competitive districts that they had targeted, and now they're in position to flip the state Senate.
The state Senate and the state Assembly have not been in democratic control since the session following the 2008 election. And so, there are three districts in the state Senate that, if Democrats win two of them, they win control of the state Senate for the first time in a long time. The Assembly is a little bit tougher. The factor of having more incumbents is significant. Some of the Democratic flip opportunities are more likely in places where there is an open seat, where there's not a Republican incumbent running for re-election. But, in looking at some of these districts, you see where the most purple parts of the state can really be.
Competitive races in southwest Wisconsin
Sam Woods: So, let's get into some specific districts that you've got your eye on, starting with southwest Wisconsin. I hear there's a couple incumbents out there that could have some type races this time around. Who are they?
Shafer: Todd Novak in the 51st district, which is now includes kind of a sliver of Western Dane County and kind of some of the Southwest counties in the state there. You know, he was somebody that, like, the Democrats thought that they could win under new maps. It was a district that was, I believe, Tammy Baldwin won by about six points or so, but Novak was still able to kind of defy the numbers and win there. And he's running for reelection again. There's a Democratic challenger people are excited about, Ben Gruber. But, you know, Todd Novak has won close election after close election in Wisconsin. And so even though the numbers might suggest he's a pretty vulnerable Republican, he could be in a space where he could defy the odds and win again.
And then in western Wisconsin, the one Democrat who won a Trump-won district is in Onalaska, just outside of La Crosse, Steve Doyle. He's "Mr. Bipartisan." I believe he has the website registered, mrbipartisan.com. And he's the only Democrat to win a Trump-won district. But you know, that's still a toss up district.
Competitive races in southeast Wisconsin
Woods: Moving east to the Milwaukee area, I understand that there's both an Assembly and a Senate seat that you're looking at.
Shafer: We have another state representative here in the Milwaukee area who is much more well-known than your typical state representative: Bob Donovan. And Bob Donavan is a well-known name in southeastern Wisconsin, much more well-known than you're typical Assembly representative. He's in a swing district. He has also outperformed the top of the ticket a number of times now. He is facing a political newcomer, Ben Brist, who won his primary in August. He's an Army veteran. We'll see if he has a chance to win in a different type of environment. But again, that incumbency factor is a big one.
But, there are a couple seats where there have been some very notable retirements. One in particular, Jesse Rodriguez, the Assembly representative in the 21st District, which is in southeastern Milwaukee County. Oak Creek is probably the biggest city there. She had outrun the top of the ticket really significantly. She's been a really reliable over-performer. Tammy Baldwin won her district by seven points, and Jesse Rodriguez as a Republican won by about three points. And so, like, you don't see that type of ticket splitting a whole lot, you know? And the fact that she is not running again means that it's a pretty big flip opportunity for Democrats. And, so, the Democrat who is running there is the mayor of Oak Creek, Dan Bukiewicz, who's running against a political newcomer named Dylan Pfaffenbach. Bukiewicz, I think, has a pretty good chance of flipping that seat.
Competitive races in central & northeast Wisconsin
Woods: So, moving north to the central and northeast areas of the state — including the Fox Valley, Green Bay and Wausau areas — what's going on there, starting with Fox Valley?
Shafer: One of the closest races on the map in 2024, decided by just a few hundred votes in Assembly District 53, that was in the Neenah-Menasha area in the Fox Valley. Republican incumbent, who was the former mayor of Neenah, is not running again because you have the open seat there. That is going to be a pretty significant flip opportunity for Democrats there. So Becky Nichols is the Democrat there. She was a member of the Menasha City Council for 12 years, and she's going against someone named David Daniels, who is a political newcomer who has not run for political office before. He's a business owner in the area. That's going to be an opportunity for Democrats.
In Assembly District 88, there is a close one there as well. Republican incumbent Ben Franklin is running against Brandy Tollefson, and that's a Brown County area. De Pere is, I believe, the biggest city there. In the Wausau area, that's an interesting one. That's the one district in the state, Assembly District 85, that was won by both Donald Trump and Tammy Baldwin in 2024. Again, you have a strong Republican incumbent there who has outrun the top of the ticket in Patrick Snyder. Will he be more vulnerable this time? We'll have to see.
A Democratic trifecta?
Woods: What are the odds that we get a trifecta — so one party wins the governor, state Senate and state Assembly?
Shafer: Yeah. This is the first realistic chance Democrats have had to get a trifecta in a really long time. You know, Republicans obviously had a trifecta from 2010 to 2018, until Tony Evers won, and have maintained control of the legislature since then. So, I think it is a pretty realistic chance for the Democrats to win in the state Senate. I think they can win two of three, if not three of three, of those districts that were carried by Kamala Harris and Tammy Baldwin in 2024. Like I said, if they win two of those, they flip the Senate. I think there's a pretty good chance that they're going to be able to flip at least two of these.
Shafer: I think the Assembly is going to be a little tougher for Democrats. I do this preview at the Recombobulation Area where I look at every last seat. I am the one guy crazy enough to preview more than 115 races in the Wisconsin State Legislature. And I've been doing the work to prepare for that. I think there is a pretty good chance that Democrats are going to be able to pick up some seats in the state Assembly. I think actually winning it outright is going to a little bit tougher. I think there is a really realistic chance that we look at, you know — I think the governor's race is 50-50. Maybe people think that Democrats have a little better chance being in a midterm where there's a Republican president. That's kind of the history of it.
And I think that the Democrats have a good chance of winning the state Senate. I think the Assembly is going be tougher because there are some strong incumbents who have won really close races. I think we could see a pretty realistic outcome where you have a Democratic governor, Democratic Senate, and you have that Republican firewall to having full trifecta control in the Assembly too. But, Democrats, I think, in 2024 with the new maps in the Assembly, they needed to do a little bit better than they did to have some incumbents in these races like the Neenah-Menasha seat, or the De Pere seat in Brown County, or whatever — some of these super, super close races — in order to be in a position to flip the Assembly.
So, I think the Republicans do have more of a clear path to retain control of the Assembly. And there's also the financial factor. And I think some of the billionaire donors who are spending a whole lot on Republican politics in the state — Dick and Liz Uline, Diane Hendricks — they have donated quite a bit to the Republican Assembly Campaign Committee. And they have outraised their democratic counterparts this session thus far.
More gridlock ahead?
Powers: One of the ways I would characterize politics during Governor Evers' time in office is this kind of stalemate of sorts. It's felt like it's been kind of impossible to get things through both the Legislature and the governor. And this kind of tug of war back and forth has ultimately meant a lot of stalling on really important issues for Wisconsinites.
With this election and with all of these swing districts, let's say you get a Democratic governor, a Democratic state Senate, but you have a Republican Assembly, as you say could happen, how is that going to likely change the way that politics is done here in Wisconsin?
Shafer: Yeah, I think we can only speculate, of course. But, I think it would be a dynamic that we have not seen here in a really long time. So, it's really hard to kind of map what that would look like. But if, let's say, there's a Democratic Senate and a Republican Assembly, you'd have a more balanced Joint Finance Committee, right? Right now, it's 12-to-4 Republican because it's Republican control for both chambers. You'd have different committee approvals. The Senate is the chamber that approves the governor's appointments to various places. If that was Democratic controlled, those appointments would sail through, right? But you might have some contentious budget arguments, a whole lot of other legislation that could stall in various ways in the state if you had divided government in a different sense there too.
Van Orden vs. Cooke
Woods: So, we've talked a lot about state government implications and state races. But, for federal races, if we have a congressional district flip, what does that mean for the U.S. Congress?
Shafer: As always, Wisconsin's elections are going to be a major factor in what happens there. And so, I think the 3rd Congressional District is the one that everyone has circled right now — as one that Democrats have an opportunity to flip, as one that is the most competitive in the state of Wisconsin. We are a purple state, but sometimes that means you have a lot of deep red districts and a lot of deep blue districts. And you also see that in the state Legislature, and you see that in Congress too.
And I think the Western Wisconsin district and the 3rd Congressional District currently represented by Republican Derrick Van Orden. He'll be facing Rebecca Cooke for the second time. She was the candidate in the 3rd Congressional District in the 2024 election. And all things considered, she did pretty well because she outran the top of the ticket. She did better than Kamala Harris did there. She actually did better than Tammy Baldwin did there, which I thought was a pretty impressive electoral feat, even in defeat. And so, I think she won her primary by a pretty significant margin — even by bigger numbers than I think what some were expecting — and is coming into this with the support of the Democratic congressional committees that have not always been there for Wisconsin congressional races. Sometimes those coastal Democrats tend to forget about certain districts in Wisconsin from time to time. I don't think they're forgetting about the 3rd this time.
And Derick Van Orden has not been a particularly strong electoral performer in the two terms that he has won there. He did worse than many expected in 2022. And then, he again underperformed the other Republicans running in that part of the state in 2024. But, it's Wisconsin. It's a toss-up. We have so many toss-ups here. I think, if you look at the governor's race, you look at these state legislative races, you look at that particular congressional race, we might not have the results for that until the wee hours of the night. And it could be decided by decimal points yet again.
Looking ahead to Nov. 3
Woods: You're talking about Congressional District 3. And Republican Derick Van Orden has run a number of very clearly AI-generated attack ads against Rebecca Cooke — something that stood out to me in that race. But, as you're looking at swing districts across the state for Congress and state level, are there phenomenon or races or something like those AI attack ads that make you say, like, "This is really 2026?"
Shafer: I think the rise in data centers as just a real splinter issue in this election, that's going to be, certainly, a very 2026 story. But I think so much of it, too, is just going to come back to traditional issues as well. Like, Medicaid isn't a specifically 2026 issue. You could make the case that it is, but it's also been an issue in many other elections before it as well.
I think so much of this one, too, at the state level, is about the potential for Democrats to win control of state government for the first time in such a long time. And like I said, I think the Assembly is going to be a tough road. But I also think the potential is there. And if Democrats do win a trifecta, that is going to absolutely change everything about the state.
I think Dianne Hesselbein, the Senate majority leader, was quoted in the New York Times saying that she thinks this is the most important election Wisconsin has ever seen. And I think there's always that rhetoric of "the most-important election of our lifetime" every time we get to after Labor Day, before an election cycle. But I think, for Democrats in Wisconsin, it has been this meticulous, election-by-election, incremental shift of digging out from the Scott Walker years. And whether it's flipping the state Supreme Court in election after election, toppling the gerrymander, making the gains that they have, having an opportunity to elect a Democratic governor and have a Democratic state legislature, that to me is the biggest story going into this fall — of just the potential of that and how seismic that would be for the state Wisconsin and be able to really change the trajectory of the state in such a significant way.
Powers: Well, Dan, thank you so much for joining us and sharing so much of your work. Good luck. Good luck as we head into November.
Shafer: Good luck to you as well.
Woods: That was Dan Shafer, founding editor of the Recombobulation Area. Election Day is Nov. 3.
