What A Day - Democrats Zero In On Midterms

Episode Date: September 1, 2026

The House passed a short-term measure today to fund the federal government into early December, a move designed to avoid a chaotic shutdown as lawmakers campaign for reelection. On today's show, Jane speaks with Slow Boring’s Matt Yglesias about what Democrats need to do – and avoid – to make November really count this year.Show Notes: Check out Matt's work – www.slowboring.com Call Congress – 202-224-3121 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]

You talk about a tsunami, but how far a wave goes depends, you know, like how high the ground is, right? And, you know, if the Senate map was evenly balanced, you would say, okay, with this generic ballot, Democrats will definitely win. But it takes a really big wave to put you over the top in Texas, Iowa, Alaska. You know, these are challenging states to win. It's Tuesday, September 1st. I'm Jane Koston, and this is what a day. Today, Congress avoided a pre-midterm shutdown. I talked to slow boring's Madaglacius about what Democrats need to do and avoid to make November count. Madagalacius, welcome back to what a day.

It's really good to be here. So let's start with where Democrats are right now. We have 63 days until the midterms. Where do you put Democrats' chances of taking the House or, more interestingly, maybe, the Senate? Well, we're going to talk about gambling later. We are. I'm my favorite gambling websites. I think Democrats' odds in the Senate have gone up to exactly 51% when I checked this morning.

So, you know, mission accomplished. Fantastic. What about the House? Like, it feels like the House people seem pretty bought in on. The House seems solid. The redistricting has made it challenging, I think, for Democrats to win, like, a huge landslide in the House. But Trump's broad national unpopularity. means it would be very unlikely.

I mean, something dramatic would have to change between now and election day for Republicans to hold the House. The Senate, I think, you know, your listeners know this is a challenging map. Democrats need to win multiple kind of uphill races simultaneously to take the Senate. The good news is that they are favored in quite a number of those races. So today you wrote about how the GOP has a ton of cash on hand. And I want to break that down a little bit because there is how much money MAGA Inc has, which is Trump's fundraising arm, which Republicans keep being like, please give us some money. And he's like, I don't want to. You all annoy me. But then there's like the RNC and the kind of associated groups. They have lots and lots of money. And Democrats are at a financial disadvantage. First, what does that actually mean? Because I think that we've seen so many examples of. of candidates individually having seemingly money to burn. Like, you know, if you look at the Act Blue number, somebody like James Tallerico or

John Ossoff, they've got cash all over the place. So how do these candidates have so much money, but the DNC doesn't? And secondly, what does that actually mean for the midterms? Sure. So these pots of money come in two different directions. Individual candidate fundraising, there is a cap on how much money any one person can give to one candidate. It's like $2,000-something dollars. So it's not that much money.

And so the way that you as an individual candidate raise a huge sum of money is that you need a really large number of people to cut you a kind of a modest size check. And Democratic candidates are really, really good at that. Asaf in particular is doing amazing. But James Tilariko is doing quite well. Like Abdul Al-Sayyad is doing quite well at that. probably only James Turrick of the frontline Dem candidates is struggling a little bit in the individual fundraising. But then you have these party committees and associated super PACs. So the Democrats Senate Super PAC, Senate Majority Pack, as of midsummer reporting, had raised $126 million,

which is a lot. But the Republican version had raised $239 million. And those super PACs can accept checks of essentially unlimited size. So, you know, a single billionaire can give you a million dollars. They can give you $10 million. They can give you more than that if they want to. And the realignment of the kind of billionaire class over the past few years has made a big difference to these supercommittee fundraising structures. Now, Democrats always think of themselves as like the party of the little guy. But in the past several cycles, their super PACs and party committees had more money than Republicans. And this year, it's different. And so, you know, Mitch McConnell and John Thune and his allies are going to be able to come in with a lot of financial support for the

Republican candidates in these races. Just to add in, James Turrick is running in Iowa. He's a Democrat. Yes. So you, but you just mentioned that it usually is that Democrats are coming in with a lot of money. But, you know, I've been alive for the last 10 years at least. And that seems to a have not really helped Democrats. Like, yes, Democrats have had a lot of money, but I think you even mention if this was all determined by money, Jamie Harrison would be a senator, I believe. Yeah, I mean, money isn't magic, right? I mean, we were talking about the House. You have a lot of not a lot, but many Republicans who are in districts that Trump won by one or two points. And a lot of people who voted for Trump are disillusioned with him. And a lot of Republicans who

hold seats like that are going to lose. And having extra money, you know, it's not going to save them. But money does matter. We got like a really good example of this in the Wisconsin governor's primary where David Crowley ran a lot of TV ads and Francesca Hong didn't run any. And so there's a number of counties in Wisconsin where they actually get their TV from across the border in Minnesota. And Crowley didn't run in those markets, didn't run ads. And Hong did markedly better in those kind of counties. It can move people. And I think especially when you're thinking about these tough races, when you've got a Democrat who's running in Iowa, in Alaska, in Ohio, in Texas, you know, most of the voters in states like that are like primed to receive the message. This guy is a Democrat and he's bad.

And the fact that Republicans will be able to just like, I mean, they'll run stuff that's unfair about Sherrod Brown. about Mary Poltola, about James Telerico, about all of these people. But they'll also just be finding everything in the book to just remind people of baseline partisanship. You've got a Republican against a Democrat. And people are going to be saturated with that. And it matters when you're running against the baseline partisanship of the state. And then conversely, if you were one of these Democrats running in these states, you need to make

people think, you know, I'm a little bit different, right? You know, I've got an Iowa spin, a Texas spin, an Alaska. I'm an independent thinker. And advertising is a good way to tell those stories, you know, and in particular, we talk a lot about, you know, the media environment and attention and how hard it is to sometimes get people to focus on, you know, questions like health care, cost of living that Democrats want people to talk about. Paid media is a really good way to like put something in front of people's eyes that they might not otherwise see, might otherwise not hear about. I was in Maine all summer.

And, you know, Susan Collins has been blanketing the airwaves with like every anecdote of like any time she helped get a bridge repaired, any time she got a school refurbished. Like, you were going to hear about that in Maine. And that's because she has a ton of money behind her campaign. We're going to talk about the media environment a little bit later. But something I've been thinking a lot about is I want to actually go back to 2007. I was about to start my sophomore year of college. Times were different. We were in the midst, deep midst of the Iraq War. George W. Bush was an unpopular president, but Republicans had control of Congress. So I checked. By September 19th of 2006, Democrats were up 6.5 percent, according to real clear politics in the generic ballot. Nate Silver's forecast has Democrats up right now about 7.7 percent in the generic ballot. Reuters has Trump's approval at 33%. Democrats are more excited to vote per Reuters.

And Trump has decided that what everyone wants more of in this election is him, the person who people are literally going to vote against. 2006, as you know, was a massive landslide for Democrats. It was the first time Democrats ended unified control of Congress in a midterm election since 1954. It was great. Nancy Pelosi gained a lot of power. So I want to talk about what has changed and hasn't changed. since 2006 because we have a war no one likes, a very unpopular Republican president,

Republicans who are generally unpopular for their own reasons, all running for re-election, and Democrats are up in the generic ballot at early September. So why are we, you know, I think you and I looking at this, why are we not thinking, wow, this could be a big, big tsunami? I mean, yes, redistricting, but is there anything else that leads you to, put, some caution in your part about this election. Well, I mean, some of it is a map, right? I mean, you talk about a tsunami, but how far a wave goes depends, you know, like how high the ground is, right? And, you know, if the Senate map was evenly balanced, you would say, okay, with this generic ballot, Democrats will definitely win. But it takes a really big wave to put you over the top

in Texas, Iowa, Alaska. You know, these are challenging states to win. And there is the fundraising. I mean, it is striking to me that as much as the public has turned against Trump, he has retained really a lot of the loyalty of, like, Republican donors are very wary of him in 2016, in 2020, even in 2022. And like, they are behind him. And he's gotten a lot of like tech executives, venture capitalists to really be into him. So Republicans are there with this big war chest. And of course, Democrats do not have. the, I don't know how to put it, like pep in their step that they had in 2006. There has been a lot of infighting, a lot of bitterness around some of these primaries, a lot of dissension against party leaders. You know, Nancy Pelosi in 2006 was seen as this like this fresh face who was like exciting and was part of a new era. People don't have that kind of attitude toward Chuck Schumer and Hakeem Jeffries at this point. There's a lot of just uncertainty about where Democrats stand for. And some of that is the fact that, you know,

all throughout George Bush's presidency, Bill Clinton was viewed very positively. All throughout Donald Trump's first term, Barack Obama was viewed very positively. Joe Biden and Kamala Harris are not viewed positively, you know, at this moment. And they haven't been this whole time. So Democrats, you know, they are the alternative to Trump. They're benefiting from Trump's popularity. But it doesn't like go without saying that voters just want to, you know, hand back over the keys of power to them because they have real doubts about the last time Democrats were in office. Let's talk about things Democrats should be doing in advance of Election Day with regard to two issues. Canada apparently are great enemy and gambling.

You wrote about how Democrats should, quote, vow to surrender in the Canada trade war. Now, how did this Canada trade war thing start? Because there's there there seems to me there's like the trade war trade imbalance actual thing. And then there's Trump ranting about how it should be the 51st state and not respecting Canada as a country and not treating it as a actual entity and helping Mark Carney win an election that he definitely should not have won. And what happened? And how did we get here? Yeah. I mean, the United States. in Canada obviously have a close trading relationship. We, you know, we are their number one market. They are our number two market. This very, you know, interconnected economic relationship.

Forever, there have been like a couple of disputes on this like bilateral trade docket. And they're really boring. You know, like one of the big ones has to do with how Canadian lumber is priced, which our loggers don't like. And another of them has to do with how American dairy farmers can export dairy products into Canada. People talk about this stuff. They try to negotiate it. It was going to be resolved a little bit in the Trans-Pacific Partnership.

Had that happened, under any normal administration, we would have some talk about that. And then things change in the world, right? The China situation is always changing. America wants to get its trade partners to coordinate with us in our strategic, you know, partnerships.

They're sometimes a little reluctant, et cetera, et cetera. that's all normal. Trump has taken this stuff to 11 by like referring to Canada as the 51st state and then by putting demands on the table about the status of the French language and protection of Canadian cultural content, about Canada's ability to negotiate trade agreements with other countries, things that like an independent country just like can't compromise on. You know, I don't care. You don't care. Like, what is the discoverability of French language movies when you fire up Netflix in Quebec? It's like, who cares? Right? They care. They care a whole lot. The people in

Quebec care a lot, right? Because this goes to the core of like the bargain at the heart of the Canadian Confederation. So normal people understand that this is a trivial financial gain for Hollywood versus the end of Canada. And you just got to let it go. And Trump doesn't want to let it go. He has never explained what the point of picking this huge fight with Canada is. It is completely transformed Canadian politics and turned Mark Carney and the Liberal Party into this dynamo with all of Canada,

you know, united to stand up for its basic existence as a country. And the American people, I mean, all the people, I mean, all the people, polling on this Lake Ontario nonsense and all of this is like voters don't have any problem with Canada, you know, like they don't, they want the cost of living to go down. They don't want tariffs on Canadian auto parts or, you know, to lose sales of American liquor because Canadians are boycotting us. And it's just like a huge, crazy fiasco that even conservatives who are inclined to support Trump. Like, they can't offer any explanation of why he's doing this.

It's just, he's just a, like, he's a crazy person. We'll get back to my conversation with Matt Agglacius in a moment. What a day is brought to you by Delete Me. Have you ever thought, I should really be doing something to protect myself from stalkers, scammers and hackers, but you're not sure what? Here's what you do. Go to www.com.com slash wad and enter code. You'll get 20% off, Delete Me.

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with over 350,000 happy customers and 1 million bottles sold. Order now at drinkwillies.com and use code WAD for 20% off your first order plus free shipping on orders over $95. Or use a store locator to find willies on shelves near you, like your local total wine, specs, ABC, or local liquor store. Let's get back to my conversation with Madagliacius. I want to talk about trade more broadly, though, because a funny trend is that Democrats who support DSA candidates are now the most pro-free trade voting block. And I think that there's been this, if you are a Democratic elected or if you are running for office as a Democrat, talking about trade and talking about tariffs and free trade has become weirdly complicated.

How did Democrats or left-leaning Democrats become super pro free trade? And how should Democrats be talking about the issues of trade? Like should Democrats be saying we got to get back into the Trans-Pacific Partnership? We got to start doing this. Like, should Democrats, left-ling Democrats start talking kind of like how Bill Clinton talked when I was in grade school? I mean, I kind of think so. I mean, you know, I don't know. I was always kind of a free trade Democrat kind of person.

And it's been funny because for the longest time, it was more left-wing Democrats were very critical. Yes, I remember the World Trade Organization protests. A lot of cool music was involved. Bernie's campaign in 2016. was very like NAFTA, blah, blah, blah. You know, people remark on this in a bunch of different ways, but there is a younger generation of people who are generally quite left wing, but for whom Trump has defined their political era, he's normalized,

and tariffs and trade protection has, like, been a Trump thing. And all the American people say that they favor free trade agreements, Republicans, independents, Democrats, but the support is highest among Democrats who describe themselves as sympathetic to the Democratic Socialists of America. So I feel like this is a great issue for, you know, old time, the terrible, like, establishment to say something that the, like, left-wing insurgent base agrees with, which is that, like, these tariffs are terrible. It's a regressive tax. It raises people's costs. not that like we could never have any tariff on anything for any reason, but that certainly

friendly countries, like we should buy their stuff and we should sell our stuff to them. And why not? It's like the most common sense thing in the world. But we're seeing still a number of Democrats, including California Governor Gavin Newsom, seem kind of wishy-washy on the idea of tariffs and what they would do theoretically if they were president in 2029 about the issue of tariffs. And going back to the Biden administration, Biden was like, I'm going to protect the American working class and I'm going to do so in part through tariffs. Now that like I do think that many Americans have been anti-tariff-pilled by Trump, which is, you know, Trump will unintentionally anti-you of a lot of things.

But how should Democrats be talking about this moving forward where you still have this idea of we want to protect American workers, we want to protect the working class? tariffs could be a tool in the metaphorical tool shed, but also everybody hates them and it makes everything expensive and they suck. So what do we do? I mean, this is a big and complicated issue. Yes. I don't think all of it can be answered in like a sentence or a podcast segment. But I do want to say in this specific Canada part of it, right? So Governor Newsom made the decision to go on Canadian television and talk about how terrible Trump is, which, you know, good for him. But then he got the question, well, if you were president, like, would you take these tariffs off? And he didn't seem to really have a clear answer to that.

And I think that you can say, and I think that all Democrats could say, without committing themselves necessarily to anything with regard to China or other issues, that, like, yes, we will take these tariffs off of China, that this is just Trump, the Mad King, being deranged, and that we want the Canadian people to hear that, you know, you should stay the course. And that like we want to ride to the rescue and end this and make good on like the promise of American and Canadian friendship. I'm not going to pretend that this is the number one issue in American politics. But it's a very big issue in Canadian politics. And it matters to Americans.

It is the most low hanging fruit of affordability that you can imagine. It's just like let people buy Canadian stuff without paying a special regressive tax on it. the whole rest of it, you know, you got to talk it out. There's a lot of issues with Steelworkers Union and with China in particular that I think have some complexity and some nuance to them. But the Biden administration, you know, didn't remove almost any of Trump's term one tariffs. And so that has left the world wondering, like if Democrats will roll back stuff Trump has done in term two. And I think they should. And especially this Canadian stuff because it is Trump. has, you know, like Kool-Aid man style, re-injected himself into the campaign and made one of his

least popular ideas really salient and newsworthy. And like, I think it's a great gimmy almost for Democrats to talk about, especially because it's something that the left is like aligned with all the boring centrist technocrat wanks on. You know, you got to like seize these opportunities to have every nice kumbaya moment. Should Democrats have a nice kumbaya moment on prediction markets? You posted about this yesterday saying the Trump administration loves gambling, super into gambling, and with regard to prediction markets, Donald Trump Jr. is an advisor to Kalshi and Polly Market and told Republican attorneys general earlier this year not to go after them.

The Trump administration is trying to discourage states from regulating prediction markets, even as Americans have been gradually souring on the concept of gambling in general, which I think is something that you're seeing kind of the like tradish right, common good right and liberals coming together on being like, this is probably not working out so well. So it was like, should Democrats in the year of our Lord 2026 be like, yeah, you should be able to regulate prediction markets. Prediction markets maybe shouldn't be posting like doing paid advertisements without telling people or asking people to vote. on violent events. Yeah, I mean, you know, I have somewhat mixed feelings about this issue. Like, I enjoy a good prediction market about, you know, high-minded events in the world. I find it just journalistically to be useful to have this kind of aggregator of conventional

wisdom. But obviously, in practice, the bulk of the money seems to be in what amounts to sports gambling. And sports gambling has always, always, always been a state-regulated issue. And I think these Trump efforts to say it now suddenly can't be because you're calling it a prediction market, it's like, it's really dodgy and suspicious. And it's really corrupt. You know, like Don Jr., literally working for these companies and then telling Republican state attorneys general that like they should just relinquish their authority over this industry. That seems kind of crazy.

I don't know like exactly what I would do with this topic, which sometimes is exactly why you want to have federalism and, you know, like different states doing doing different things and trying to find their way there. Because, you know, I know a lot of people who have had fun wagering on stuff in a low stakes way. And I know a lot of people who are intensely concerned about particularly younger men spending like all their time on gambling apps. I think the empirical evidence is that when you open up sports betting, it leads to bad financial outcomes for people. I think the sort of lowest hanging fruit is a lot of these sports gambling sites will kick you off if you're too good at winning. Because, you know, they're not in the business of paying you. They're in the business of you losing. And, you know, in a lot of industries, you might say, well, you know, we need to balance like consumer regulation against, you know,

well, it'll like restrict supply, right? But if you make the betting websites play fair and allow skilled participants to keep playing and keep winning, that sounds good. That's like customer friendly. And if it makes these sites a little bit less lucrative and they're like less dominant advertisers and they're not present everywhere, like that also seems good, right? Because the value proposition right now is, of course, in the marketing, it's like, come bet on draft kings and you'll win all.

all this money. But if you actually win a lot of money, they're going to kick you off. And, you know, that doesn't sit right with me. And I don't think it sits right with anybody who thinks about it. No. And it seems telling. I want to go back to something you said earlier, talking about the media environment, which we're working in. And I know, I think we've talked about this before. It's kind of a general thing. Democrats in general are held to a different standard than Republicans. That is, for any number of reasons, people can argue about it in any number of ways, but that's kind of the environment we're in. We are in an environment in which you can have entire panels yelling about streamer Hassan Piker and his associations or perceived

associations with a host of Democratic-Kandidates or Democratic-aligned candidates or DSA-aligned candidates or DSA members. Meanwhile, Laura Lumer can get people deported or fired while screaming about how a Supreme Court justice is a quote, ghetto entitled race-obsessed, destructive black bitch. Like, that's just that's just where we are. So how should Democrats respond to that double standard? And is there a way to start breaking that double standard down where it's like, we are aware that Randy Fine can say things and people are like, oh, that seems bad, but there's really nothing we can do about it. And a Democratic elected could not say the same things. It just, that's just where we are. So what do we do about it? You know, I mean, I think you always have to be careful with like double

standards and what it is you're trying to say, right? Because part of the reason why Randy Fine, I think, could get away with like, egregious sort of Islamophobic statements is that, like, the mass public is just not that averse, at least in his district, to those kinds of statements, right? So, like, we can jump up and down. I mean, I remember when I, when I worked at Think Progress, you know, we did a lot of, like, look at this crazy thing Michelle Bachman said. Yes. And like, we made a really big deal out of it. And her constituents just kept voting for her because they like that. Yeah.

Right. Yeah. And, you know, the reason that Hassan Piker controversies gain some teeth is that there's a meaningful number of Democrats in blue districts who are bothered by some these allegations. things that he says. So that's like it manifests itself in the media environment, but it like reflects the fact that the Democratic Party is more diverse. You know, it is more evenly split between moderates and progressives. It has, it's constituted by the members of lots of different religious and ethnic and racial minority groups. And it requires a kind of an internal praxis of like liberalism and kindness and togetherness that the Republican coalition doesn't.

And so it's totally fair. It's like accurate to say, well, this seems like a double standard. Like it seems like we're not in a level playing field. But like we're not. You know, and like that I think like can't change. It's a genuine asymmetrical relationship between the political parties that, you know, is both challenging, but it also reflects what I think. think in our reflective moments like Democrats like about the Democratic Party, that like it's

not just a party of like us versus them inside or outsider resentment mobilization. Matt, as always, thank you so much for joining me. Thank you. That was my conversation with Matt Iglesias, publisher of Slow Boring. That's all for today. If you like the show, make sure to subscribe, leave a review. Never ever tell me anything about Sean Duffy's personal life. and tell your friends to listen.

And if you're into reading, and not just about how our transportation secretary and his wife discussed, among other things, their love playlist and Sidney's Body on Fox News Radio, like me, What Today is also a nightly newsletter. Check it out and subscribe at crooked.com slash subscribe. I'm Jane Koston and Ewe. What Today is a production of Crooked Media.

Our show is produced by Caitlin Plummer, Emily 4, Erica Morrison, and Adrian Hill. Our team includes Haley Jones, Greg Walters, Matt, Joseph Dutra, Johanna Case, and Desmond Taylor. Our music is by Kyle Murdock and Jordan Cantor. We had helped today from the Associated Press. Our production staff is proudly unionized with the Writers Guild of America East.