What A Day - Are Democrats Saying The Right Things To Win?

Episode Date: October 1, 2026

The midterms are next month, and President Donald Trump's approval rating on issues like the economy is slipping. But are Democrats capitalizing on it? Is their messaging keeping pace with the moment? On today's show, Jane sits down with Sarah Longwell to discuss how Democrats can communicate their policy ideas more effectively and connect with voters. Longwell is the author of the new book, How to Eat an Elephant: One Voter at a Time.Show Notes: Check out Sarah's book – tinyurl.com/3xwu8naa Subscribe to the What A Day Newsletter – https://tinyurl.com/y4y2e9jy What A Day – YouTube – https://www.youtube.com/@whatadaypodcast Follow us on Instagram – https://www.instagram.com/crookedmedia/ For a transcript of this episode, please email [e-mail]

Because there's so much damage being done, there's a wide host of things to choose from for Democrats to say this is what we would do. Again, contrast. Trump is destroying the economy. Democrats can't just say him bad and we're here. They have to say him bad, we good. Like, here's our thing. Here's what we want to do. It's Thursday, October 1st. I'm Jane Koston, and this is what a day. President Donald Trump is hitting the road today. His first stop is Texas, where he's speaking at a Peterbilt truck factory right outside of Dallas. Then he'll head to Oklahoma for a midterm election rally because it's always a good sign when you need to head to Oklahoma to rally Republicans. But, of course, Trump doesn't need to tout his own record when he has senators in his corner like Ohio's John Hustead, who spoke to Fox News today.

Look, it's always tougher in a midterm election once you're governing. But Donald Trump is fighting for lower prices. He's fighting for a stronger economy. And again, is he? I guess he's bad at it. According to a new AP Norke poll, only 17% of American adults approve of Trump's handling of the cost of living. And marking a new low, just 26% approve of his handling of the economy overall.

So he's not good at it, is what I'm saying. The family of Renee Good is suing. the federal government. The 37-year-old Minnesota woman was shot to death by an immigration officer during the federal crackdown in Minneapolis earlier this year. The family filed the suits on Thursday, alleging wrongful death, conspiracy, and other violations. Following up on a story from yesterday, Tennessee governor, Bill Lee, halted the one remaining execution schedule for the rest of the year on Wednesday after officials were unable to put Krista Gail Pike to death. According to Tennessee officials, Pike was alive and loudly snoring after two attempted lethal

injections and was transported to a hospital for treatment. As of the time of this recording, Pike is reportedly still alive. As we mentioned on yesterday's show, Pike's lethal injection was stopped just an hour before it was set to start by an appeals court. Hours later, the U.S. Supreme Court overturned that stay. But I want to talk about voters. Joining me is Sarah Longwell, publisher of the bulwark and author of the new book, How to Eat an Elephant, one voter at a time. Sarah Longwell, welcome back to watch. today. Hey, thanks for having me. So I want to start by talking about Trump's wild corruption. Just today, there are two stories out on Trump and cryptocurrency, which is part of his corruption. One is about a

focus group of young men who are disillusioned with just how much money he's making from cryptocurrency, the industry that's robbing them. Another about a crypto dinner he's holding with holders of his meme coin where you'll never guess, but he gets more money from that. How should Democrats be talking about his corruption? Not just with cryptocurrency, but with pretty much everything. Yeah, so here's the thing about corruption, right? Voters, and I think a lot of people know this who do any kind of consulting, they'll say, voters will tell you everyone's corrupt.

And that's why corruption messaging doesn't work. Wrong. Corruption messaging, contrast works. And so it is true and sort of a bummer, but voters would care a lot less about Trump's corruption, especially Trump voters. if they were doing great. But they're not doing great. In fact, they're doing poorly. The reason that they're mad about his crypto scams is that they're on the losing end of those crypto scams. The fact that people are paying more for gas and groceries and every other item in their lives,

everything having to do with their material well-being, while Trump is enriching himself, they are getting poorer. And that contrast is how Democrats should be talking about all of it. So it's different from you writing your book about this idea of Trump being an honest bullshitter, that yes, he's lying, but everybody lies. And at least he's lying for us. So you're saying essentially that Democrats can say, you know, he's lying for himself while you're getting screwed. That's right. I mean, I talk a lot to people about how voters really look at Trump's first term where they thought he's doing great. The economy's great. I feel good about it. And therefore, I do not care about so many of these other stories. Certainly his voters felt that way. Trump 2.0 with this terrible economy, which people were already frustrated with the economy when Joe Biden was there, he's done nothing about inflation, he's done nothing about grocery prices. Now he started a war and he did the tariffs, both of which voters are very acutely aware are Trump decisions, right? They're not in some rubric that they can't see.

Trump did them. He did them without Congress. Everybody knows these were his ideas. He did them, and they are the reason that their prices are going up. And voters are, for the first time, I see Trump voters actively mad at Trump. They are mad. And part of it is that he's done all this scummy stuff to them. I had a voter the other day, say the funniest thing. They were like, he told me I was going to get a doge check. He told me I was going to get a rebate from the tariffs.

Now I'm going to get, supposed to get $5,000 if Republicans win. And this voter said, I've been keeping track. And that dude owes me $22,200. Right? And so people are feeling scammed by him now. So winding out to something that's, I mean, it's adjacent to corruption and probably corrupt. But I'm curious to your thoughts as to how Democrats should talk about AI and Trump surrounding himself with the champions of the AI industry. I don't know if you caught that press event earlier this week where he's literally just having these back slapping adventures with Mark Zuckerberg and all these other people for whom, you know, I remember when Mark.

Zuckerberg was like enemy number one for Republicans until that changed for reasons, corrupt reasons, obvious corrupt reasons. It's like I feel like it's a little bit more complicated than Democrats would like it to be because I think that there are a lot of Democrats who were like data centers could provide a lot of money to different communities in my state. You know, AI policy seems like something we should have a policy for. But that kind of the populist answer is burn them all down. and then burn them all down again.

And I think that you're starting to see Democrats being and you're seeing Republicans running scared from data centers and wanting to investigate them or basically never let them darken the door again. So I know that this is a bit of a two-prong question, but first, how should Democrats be talking about AI and kind of the science of AI? But also, how should Democrats be wrangling

with the data center AI issue more generally, given that AI is not going to go away, but everybody, you know, kind of the populist answer is it should. Yeah, I think that it's okay for a short period of time to just demagogue this because they do just want to burn them down. I would say as a political matter, as a practical matter, people are going to want to do their AI things, average people. They're going to want to do their chatbots. They're going to want the internet. And eventually they're going to need, we're going to need more juice.

And there's going to be a moment when voters are ready to have that conversation. but it's not right now. And to be fair to voters, the thing is with the data centers is it's knocking them on three different vectors. Number one, and this is for the rural communities, right? It's one of the reasons that when I go home to central Pennsylvania, there's why parents live out in the country. There's all these anti-data center ads. You know why? Because people are looking for those big, wide open spaces in rural areas, and that's where they're building them. And so those more rural voters are the ones that are angry about them. So there's the physical component of the AI centers. then there is the energy costs and the water costs that people who are nearby deal with. So you get the nimbie part of it. Then there's the third vector, which is, okay, are the billionaires who are making all this money off these data centers, then, and it's going to come take my job. And I'm not going to have a job in 10 years. And I would say voters have gone from zero to 60 on their anxiety around AI and what it's going to mean for them. And so I think that for Democrats right now, a kind of let's slow down. You know, I'm calling for a temporary pause on all data centers until we can figure out

what the heck is going on. Feels like a pretty good place for Democrats to be at the moment. Yeah, I've always been struck by these AI overlords being very surprised. People are worried that AI is going to take their jobs after like five years of, oh, AI is going to take your job. And it'll basically render everything that you've ever done completely meaningless. And they're like, why are people so mad about this? I'm like, I don't know what it could be. So your book lays out a bunch of issues that are challenging for Democrats to talk about. And, you know, from foreign policy to immigration, a host of issues. But a challenge I see I was curious about is that Democrats are not having these debates behind closed doors. Democrats are fighting about them all the time,

everywhere, and the media is well aware of that. The media loves nothing more than to talk about Democrats being in disarray. I don't want Democrats to be in disarray. I want Democrats to be in array. But how should Democrats, who are running for office in the midterms or in the future, talk about issues where everyone can see that everybody's fighting about them? Because I think that a challenge is, you know, I know what Republicans' immigration policy is. It's mass deportations and closing the border. I don't exactly know how to talk about what Democrats' immigration policy is because there are four different policies and everybody's fighting about them. Where do we go from here? Well, first of all, I do have a whole chapter on immigration in my book. I actually don't think these

issues are that hard because voters tell you exactly how they want them handled, which is, and this is where Democrats, I think, have a new advantage that they didn't have before. Voters want a secure border. So they want to know that they're going to be kept safe. And Donald Trump has done a great job. of hammering into people's heads that immigration means your safety is in jeopardy, your economics, because they're taking jobs, they're bringing drugs, even though, even though fentanyl comes through legal ports of entry, whatever, he's created this rubric. There's a new rubric that can be created. Democrats should go on offense, which is closed border, humane dealing with people who are

here. We're not going to deport people. We're not going to have masked thugs in the streets. Once again, I go back to my contrast framing, which is, it is important that we have a border and that we have a way for people to come here the right way because that's the that's the language that people use they don't not want immigrants to come here they just want them to come here the right way so i'm going to keep you american safe we're going to have immigrants come here the right way but of course we want immigrants to come here this is where democrats can sound different

we're not nativist racist insane people we want immigrants to come here immigrants are a net good but so is a secure border and then uh and i just and we're not going to have massed agents in the streets. Like, you lean into the excesses of the Trump era that people are like, this is too far. They wanted Trump to deport criminals. They didn't want him going after the guy who's been paying taxes working here, is your neighbor, lives down the street. And so Democrats have a new opportunity to kind of seize the middle on the immigration issue. And I don't think it actually sounds that hard to do. I think the challenge, though, is that immigration seems to be a matter of thermostatic popular opinion, which is that, you know, Republican.

if you were in 2023, 2024, you're hearing, like, mass deportations. And now you're kind of like, when I said mass deportations, I didn't mean like mass deportations. I don't like that anymore. It really does seem to be kind of a Goldilocks thing with regard to how voters en masse view the issue of immigration and a host of other issues. And I think that that's something I'd be interested in hearing from someone, you know, you've watched thousands of hours of focus groups. And there are a host of issues like immigration where it does seem as if, one, I like to joke that voters have oppositional defiance disorder, which is that the second they are given something, they decide that they want the exact opposite thing. And they're very mad that you won't give them the exact opposite thing. But also that a lot of these views seem to be thermostatic where you have, you now have Democrats who are positive on immigration for the first time in a long time, where it just seems to be, well, we don't want that anymore. How do you, how do you, how do you, how do you combat. Well, we just don't want that. I don't know. Well, I don't know that I agree with this exact framing because here's what I would say is that the reason that Trump is unpopular on immigration right now

is because he has taken, put us in an immigration regime where there are masked people shooting Americans, deporting the wrong people, deporting Americans that are callously and they're taking people who are following the law, showing up to court, arresting them there, arresting them at schools. They're disrupting communities. That overreacted. overreach, it's not that it's thermostatic, it's that when the overreach happens, people are saying, oh, no, I don't like that. And so that's where the Democrats have an opportunity to kind of resettle in a place that says, we're going to have real border security, and we're going to pair it with a more robust way for people to come the right way so we know who's in the country. But we're not

going to be inhumane and sane people and put mass agents in the streets because now people know what they don't like about the concept of mass deportation. We'll get back to my conversation with Sarah Longwell in just a moment. What a Day is brought to you by Willie's Remedy. An alcohol alternative that actually works. An uplifting euphoric buzz you can really feel with no negative side effects. Most non-alcoholic alternatives promise a great feeling and don't deliver. With Willys, you're relaxed and able to catch a euphoric buzz in about 15 minutes.

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Don't have insurance or don't live in the U.S. You can still get 10% off your first month. Visit betterhelp.com slash WOD to explore your payment options. That's better, H-E-L-P.com. com slash wad. Let's get back to my conversation with Sarah Longwell. So today a new poll came out that found that just 17% of Americans approve of how Trump has handled the cost of living.

Now, it's very clear that Trump does not care about the cost of living. He thinks affordability is a word that we made up like groceries. How should Democrats use that issue? But I think more importantly, how should Democrats build on an affordability? affirmative policy to say, this issue you care about, we can fix that. Look, I think that there are, because there's so much damage being done, there's a wide host of things to choose from for Democrats to say this is what we would do. Again, contrast, Trump is destroying the economy.

Democrats can't just say him bad, and we're here. They have to say him bad, we good. Like, here's our thing. Here's what we want to do. We want to raise the minimum wage and index it to inflation. We want to give, you know, even maybe even grab some of, this is what Republicans have done is they grab some of the Democrats policies that were more favorable and they made them their own. Go get some of the Republican policies around making it more affordable for families, talking about more families in child care or elder care. You know, if you're going to put your family, somebody in your family in a home, like one of your parents, your aging parents in a home, you get a $5,000 thing for Medicare.

Why can't that go right to the person who's keeping their loved one in their house? You know, like there's a bunch of issues. And again, I just think that Democrats, if they want to win back working class people, they need to talk about economic and things that hit people's material well-being like 75% of the time. Like one of the best ways to solve the problems that Democrats have by having unpopular opinions on a bunch of other things is to talk about the things that the vast majority of Americans care about and what you're actually actual plan is for them. And I'm not here to be prescriptive about what that plan should be, but I'll tell you that, speaking of issues whose time has come, I think that people are so frustrated

with the state of health care that every single Democrat who runs for office and probably some of the Republicans are going to have a universal option plan of some kind. And this is something where I've kind of changed my own personal view on it because I think it has become so complicated, such a rude goal. People's experiences with health care are so terrible that people want a different option. And I think that politicians should try to provide it. They should lead with that. There's a reason that El Cyanad is focusing on getting money out of politics and on free health care. And by the way, in order to get the health care, you sort of do need to get money out of politics. Right. So he's talking about the structural reform as it relates to the actual policy. I think, and I disagree with him on some other things,

but I think that that's a relatively good frame for how to talk about these issues. So you mentioned that there are, you know, I would say 75%, 80% of issues that people are like, yeah, I agree with Democrats on these issues, economic issues. How should Democrats talk about the 20 to 25% of issues? Like, you know, I go back, you talked about your experience talking about marriage equality to Republicans or, you know, dealing with that issue. And I worked on the marriage equality fight from a public policy percentage. when I was at the human rights campaign. And obviously, you know, marriage equality, pretty important,

love being married. You also love being married. It's great. Highly recommend getting married. It was an issue that you could tell, I mean, when I was in college and after or, and when you were kind of coming up in politics, one, marriage equality was an issue that you couldn't even imagine they're being popular support for. But it was also an issue that you could tell Republicans were going to use as a cudgel forever. That's what it was in 2004. That's what it was in my home state of Ohio. That obviously has changed, thank God. But that's an issue where you could see that there were a lot of Democrats who were like just never talk about it. Fortunately, some did. Fortunately, some people did. Some people were smart and brave. But it looked like terrible politics at the time. So how should we think about

those issues where Democrats are thinking, I know this is the correct way to go. I know that this is what is morally right. But voters, voters don't like it right now. And maybe they won't in the future. But we're right. How do we go from here on those issues? So, well, first of all, we have to be specific about which issues are you right about? Like, are you right about the fact that trans people have dignity and should be treated fairly and that there should not be discrimination against them because in that case, you do have not like overwhelming popular support, but there is majority support for that. It is on trans surgeries, it's on surgeries for minors, right, transition surgeries for minors and some of the hormone stuff. And then on athletics. Those are the two things

where they are 70, 30 issues going Republicans way, basically. And so a lot of Democrats don't approve of them. So the stories that I tell in my book doing marriage equality is Barack Obama, when he ran in 2008, he believed in marriage equality, but he didn't say that. Right. He said, one man, one woman, because it was politically advantageous for him to do that. And frankly, people in the advocacy community gave him the space to do that because we understand that winners make policy, losers go home. And so there does have to be an element of pragmatism to balance out things that are, let's say, you know, you're sure that you're morally right. Now, I think that the marriage equality versus like the trans athlete question are not the same. And I think that a lot of democratic politicians, they were on marriage equality.

They would say, well, yeah, I believe in it, but I'm not going to say that out loud because of my political thing. This is one where the actual politicians say, they like actually, they go the other way. They say, yes, we've got to support trans athletes, but actually personally, they don't think it's good policy or they don't like it. And so they think it's a fairness issue, the way a lot of voters do. And so I don't know. I think it's more complicated than that. Something I'm really glad that you brought up in your book is the idea of vice signaling, which I think is one of the most reprehensible aspects of the last 10, 12 years of politics,

especially on the right. And vice signaling is essentially saying that, like, everyone is actually terrible. And anyone who's trying to perform being not terrible is virtue signal. that you should actually be as transgressive and terrible as possible. And I think that you can see this all over the place all the time, this idea that the best thing to be is cruel and mean and awful all the time because that's real, that's authentic. I, you know, we have so many examples from even this midterm cycle of candidates running who, you know, call mothers who get involved in politics come dumpsters.

Like this idea that, yeah, I'm terrible. I'm based. That's real. That's authentic. How do we even begin to counter that? Because I think that there are some Democrats who, you know, they were like, this is not who we are or something like that. But that doesn't feel strong enough.

It doesn't feel adequate to challenge this idea that the best thing to be is the worst possible person. Yeah. I talk a lot about this book. because I've done so many focus groups with Democrats who say some version of, ah, I'm tired of us bringing a pillow to a gunfight. I'm so mad that our politicians are so weak and they don't stand up to them. And then in the same breath, they say, I mean, I don't want to be like them,

but I want us to have some of that energy. I want us to push. And so I do think that there are, I think what people are asking for where they, but they haven't quite got their arms around it is I would like to take that darkness that they put in there. I would like to take that vitriol and I would like to counter it with something energetic, but also decent, where they have all the lies, we're going to tell the truth. But we're going to do it without sort of an apology. Like, we're going to go. And this is why I think people are gravitating to Assov. Assov is going on offense against the corruption. He's telling a story

about the things they're doing wrong, but he's not doing it by, and this is where I think Gavin Newsome's sort of performance art in trying to sort of be like Trump. played well for a minute on Twitter, but didn't have staying power. Because people liked holding the mirror up, but they don't want to be that, actually. They want to be better. They just don't want to say, when they go low, we go high. They just want to say, when they go low, we're going to find a way to kick their ass, but not be just like them. Right. And I think another important point is that John Alsav showed that so much of this vice signaling is so fragile. You know, you reference Trump's favorite assistant once and you get a host of people weeping in the closets for like two weeks.

So I think that you're right that it's about like don't become them, but be better than them at everything, including winning elections. Yes. I think sometimes people are like, why would we have this former Republican, you know, telling us Democrats about how to win? And I'm like, you know, why? Because Republicans are mercenaries and I came up above them and they built their own media ecosystem and they have figured out how to do dominance narratives. And I do think that Democrats, and look, what am I? I'm an American who desperately wants to see Donald Trump and his entire mega experiment just consigned to the asheap of history. It's the only thing I want and then I'll walk away from all of it. I just want that to happen. And the way to do it is to build a big broad

coalition, is to build a big community around the Democratic Party and to not do, like, do you want to be right about everything? Or do you want to win? Win. Winning matters a lot so you can do the things you want to do. Sarah Longwell, thank you so much for joining me. Thanks for having me. That was my conversation with Sarah Longwell, author of the new book, How to Eat an Elephant, one voter at a time. Before we go, we are in the final countdown to Election Day.

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I'm Jane Koston and do not let Elon Musk hear about this. What Today is a production of Crooked Media. produced by Emily 4, Erica Morrison, and Adrian Hill. Our team includes Haley Jones, Greg Walters, Matt Berg, Adam Lippurg, Johanna Case, and Desmond Taylor. Our music is by Kyle Murdoch and Jordan Cantor. We had helped today from the Associated Press. Our production staff is proudly unionized

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