Trygve Olson on crossover voters in Wisconsin's 2024 races

Frederica Freyberg:
How will the U.S. Senate and congressional races shape up in Wisconsin, and how will the top of the ticket inform those elections? We turn to Trygve Olson, Wisconsin native, former senior Republican advisor, and now with the anti-Trump organization, The Lincoln Project. And thanks very much for being here.

Trygve Olson:
Yeah, thanks for having me.

Frederica Freyberg:
So you are a former GOP advisor, but no more. Why not?

Trygve Olson:
You know, I still consider myself a conservative, but I don’t really recognize the Republican Party today. And I know Ronald Reagan used to say that the Democratic Party had left him. I feel in many ways like the Republican Party has left me. I had the chance coming out of Wisconsin to get to travel and work and live around the world. And, you know, things like in places like Ukraine and Russia with those fighting for democracy. And, you know, that piece of the Republican Party has left. That Reagan peace through strength sort of bipartisan, the Republican Party is no longer that. So that was really a big piece of it for me.

Frederica Freyberg:
So you know a lot about Wisconsin politics and politicians. What is it about our electorate here that makes Donald Trump run so even in this state, which elected a Democratic governor and one of its U.S. senators?

Trygve Olson:
Yeah. So I think one of the things that I say often to people when we talk about Wisconsin, and I can tell you since, really since 2020, when we founded The Lincoln Project and we started, we’ve been talking about Wisconsin a lot because it’s ground zero. You know, Wisconsin tends to be a right of, slightly right of center state. You have a lot of people. My best friends are all a bunch of — my buddies are all still up in River Falls, and a lot of them voted for Tony Evers and Ron Johnson. A lot of them voted for Trump in ’16 and voted for Biden in ’20. And a lot of them will vote for Tammy Baldwin. Some of them — for some of them, Tammy Baldwin is the first Democrat they ever voted for. They tend to be, you know, traditionally more to the right of center. They don’t like a lot of government interference in their lives. They don’t want government telling them what kind of shotgun they’re going to own. Although more recently, post Dobbs, quite frankly, the ones who have daughters don’t want some theocrat from the state legislature telling their daughters what they can and can’t do. So I just think it’s the nature of Wisconsin. I will say to you, though, one of the things from, from all my experiences traveling around the world, I am glad that if the decision about what happens with democracy in the United States is going to be made anywhere, I’m glad it’s going to be made with people in Wisconsin who take that kind of thing very seriously.

Frederica Freyberg:
As for the U.S. Senate race, of which we just spoke, what do you make of Tammy Baldwin’s prospects for reelection?

Trygve Olson:
Oh, you know, I mean, Tammy Baldwin is probably, and granted, I’m partial since I came out of Tommy Thompson world, I think she’s the most, sort of, organically talented politician we’ve had in the state of Wisconsin since Tommy Thompson. You know, up where I’m from, Tammy Baldwin has lots of support amongst Republicans and sort of those right of center Evers/Johnson voters who, who determine elections in the state in large part because she’s out there working constantly and quite frankly, and this might this might embarrass Tammy Baldwin, but quite frankly, a lot of the guys know that she came by Johnny’s bar during a Packer game and drank a beer with a bunch of them, right? What could be more Wisconsin politician than that? So, yeah, I think Tammy Baldwin’s prospects are pretty strong, you know, and I think Eric Hovde is not only is he, maybe out of step with the state of Wisconsin in terms of his politics being too MAGA, but in addition to that, you know, I think, you know, people in Wisconsin catch somebody who’s from the outside. And I just think he was — he’s been in, in Orange County probably too long to fully get it. Whereas no one’s going to question Tammy Baldwin being a Wisconsinite.

Frederica Freyberg:
So with all of that said, does Tammy Baldwin help Harris in this state and potentially down ballot as well?

Trygve Olson:
I certainly think that she can help Harris and the top of the ticket and quite frankly, that’s something you know, in my Lincoln Project capacity, I really end up spending a lot of time focused on four states: Wisconsin being one of them, Michigan, Pennsylvania and Arizona being the others. In all of those, you have Democratic Senate candidates. Tammy Baldwin, probably the strongest of the bunch, who are running ahead of the National Democratic Party ticket. I think, in the last Marquette poll, you know, Tammy might be a couple points ahead. I think what Tammy Baldwin, Slotkin, Casey and Gallego, who are the Democrats in the others, what they all represent is the ceiling, really for Democrats. And so, you know, one of the things I was saying to some reporters at the convention, I was getting asked about a convention bounce because Harris-Walz has had a couple of, you know, has had probably four unprecedented weeks in terms of bounce. I think there’s still some room to grow in states like Wisconsin because, you know, they can get closer. Harris-Walz can get closer to that 52 that Baldwin is at. I think that’s the ceiling.

Frederica Freyberg:
All right. Well, Trygve Olson, thanks very much for your expertise. Appreciate it.

Trygve Olson:
Yeah. You’re welcome.