142. How to Win the Midterms

Welcome to the Restless Politics U.S. special New Year's edition. Happy New Year to you, Caddy Kay. Happy New Year, Anthony. I hope you're not too hungover and that you had a good New Year's. holiday hungover is not me as you know but true okay amped up i am i'm i've took some of the trump special sauce today so if i'm a little bit too energetic push back on me okay but we are here

In the Democratic Party situation room, you've got Gavin Newsom pulling AOC's hair, okay, and she's hitting him over the head with a frying pan. I just want to set the visual. But we're here in a strategy session, Caddy, to discuss the midterms and what the Democrats should do to win the midterms. Now, of course, we also should say.

The Democrats may not have to do anything, right? Because some parties lose elections. Okay, the Republican could self-implode, but we don't know that. So let's start with you, Caddy. What should the Democrats do to get their game on? Coming November of this beautiful and bright 2026. So here we are at the beginning of 2026 and the Democrats are playing strategy about how they can win back the House of Representatives and possibly even the Senate.

in November's midterm elections. So we're going to put on our strategist hat and see what our advice to them would be if we were being paid by the DNC, the Democratic National Committee. Okay, so here are the stakes. Midterm elections happen midpoint between presidential elections. So they're halfway between 2024 and 2028. You have a midterm election and it's four.

All of the members of the House, all 435 seats in the House of Representatives are up for grabs because members are only elected for two years. So they were elected in 2024 and now they have to be reelected in 2026. A third of the 100-member Senate is also up for grabs, so 35 senators are battling to hold on to their jobs. Republicans, remember, currently control both the House of Representatives and the Senate.

And it's a big deal because Donald Trump will have been president for two years. And if Democrats take back one of the chambers, the House of Representatives or the Senate or both. Power in Washington suddenly swings away from the White House. At the moment, Donald Trump has the White House. He has the House of Representatives. He has the Senate. If he loses the House of Representatives, which most polls suggest is the most likely and often happens,

happens, by the way, two years into a president's term, then a whole load of things change in Washington. Suddenly, the president could be investigated. You can have subpoenas up on Capitol Hill. You can have more pushback against the president's agenda. There's the possibility even that Donald Trump could be impeached if Democrats feel that he's broken any laws.

Power will shift. And most importantly, the kind of zeitgeist will shift. This guy who came into office on a kind of whirlwind of activity seemed like he was omnipotent for much of 2025. seemed like he couldn't do anything wrong, was a hugely expansionist agenda, all of that will suddenly look less viable because the people will have spoken. And if Democrats can win back the House of Representatives, they will turn around and say, look, the American people do not like what they are seeing.

The first chance they had to vote in big numbers as a referendum on Donald Trump's presidency, this is the opinion that the American people have cast. So that's why this matters to all of our... listeners around the world. Midterm elections are funny things, Anthony, because it's hard for people to get their grips around what are midterms? Why are they even called midterms? But they do.

The House of Representatives obviously can't control policy, and Donald Trump has done a lot by executive orders. He's kind of avoided Congress, so in some ways you might say, well, he doesn't even care about Congress, so... He's just going to carry on doing his executive order thing and running the presidency by fiat and taking on more powers for the presidency. But I actually think these 2026 midterm elections are hugely important for the Democrats.

What do you think the stakes are? Well, I'm going to stipulate here that I think it's going to be very hard for them to win the senate lots of senate seats are also up all of the as you pointed out all the house seats are up but i think it would be hard for them if you go through the math and you look at the charts

The Republicans are benefiting from what I call the tyranny of the minority. The red states that are less populated in the country, they each get two senators. And so it's going to be very, very hard.

But let's go to the House because I think that's where the most likely flip could happen. And I guess if I was sitting in that strategy room with the Democrats and you, Caddy, the first thing I would say is. Let's not go crazy here on each other. Let's try to focus on what I would call super majority. And I would be channeling my Newt Gindridge and just a little bit of history for people.

Way back in 1994, it actually started at the beginning of 1994. Newt Gingrich had something called a contract with America or a contract for America. He listed all the tenants. This was two years into Bill Clinton's term. Yeah, two years into Bill Clinton's term. He said, okay, this is what we want everybody to sign up for, and we're going to coalesce around this. I'm going to come in and be the Speaker of the House if we win the majority.

And then it's going to be me against President Clinton. And I would try to remind people that that works. And so prioritizing a supermajority idea. Don't eat your young caddy. Don't go too far to the left. I know Zoran Mondani won in New York. And I think that's sending a signal to the hard left of the Democratic Party. But as you pointed out on our podcast, there were two centrist wins for the governorship last year.

I would include the win in Virginia and the win in New Jersey. And so I would say successful candidates are going to be the ones that stay to the middle. Let's not have an arms race to the hard left. That would be my first thing I would want everybody to stick to. And then let's talk about affordability because I don't think affordability is going away.

Even if prices do come down, oil prices are down, gas prices are down, Federal Reserve will likely be cutting interest rates going into the middle of 2026, and that may mean that prices will be lower. I think what the president really does want when they sit in their strategy sessions is got to get the housing market moving. You know, you got to have a 50, 75 basis point cut in interest rates, which will make housing more affordable.

And remember, and I've said this often, but I want to explain this to people. Small businesses are where the jobs growth is, and 60% of our small businesses, the United States, Caddy, are tied to housing. If you go down to your local... uh main street in every small town there's a hardware store there's a subway shop to feed the contractors there's plumbers there's electricians 60 of small business is tied to housing and so if i'm a democrat

I'm going to accept, I'm going to see to that. I'm going to say, yeah, inflation may be lower, but life is too expensive. And I would go into the ways we as Democrats could lower prices.

or make things a little bit less expensive. Let me play the democratic strategist who's arguing from the left. which I'm not saying is necessarily what I think is the way they have to go. I actually think they have to do a district by district evaluation that the candidate that runs in New York City is not the candidate that can run in rural Virginia, for example.

But let me make the case from the left as I'm sitting here around our crisis meeting for the midterm elections. The left has the energy in the Democratic Party at the moment. Bernie Sanders brought out 300,000 people. With AOC, when they did that Fighting the Oligarchy tour last year, Zoran Mamdani has captured the medium.

of social media we're living in an age where caution is not possible candidates have to take risks because that's what social media and podcasts and the way they get their message out demand they don't like candidates who have too much caution, who play it to the center. The country is divided. Young people want to see people fighting for them, and they tend to be more progressive, and they are the ones that are particularly suffering from the housing.

issues that you've just laid out Anthony the rents that they can't pay so actually all of this stuff what was it that Mamdani said don't bow to the altar of caution we have to actually make sure we galvanize people. It's hard to get people to the polls in midterm elections. There isn't a single candidate that they can rally around.

Turnout tends to be lower in midterm elections. So we need to get fire in their bellies and you don't get fire in their bellies by being too centrist and by being too cautious. What about that argument? I hear the argument, but I want to win. And so what I would tell people is whether you like it or not, the culture has shifted on you. Donald Trump has explained that to people. There were 19 swing districts.

in 2024 swing they're very purple that are now controlled by the republicans and by the way if you look at current polling in those districts it's narrowing again they're becoming purple again And typically those districts have a lot of independence caddy that want centrism and they want common sense more than they want ideology. And so to me, I want to go back after those 19 districts that are now held by Republicans. By the way, there are 14 districts that are...

also swing districts that are very narrow Democratic wins. Okay, so if you look through the whole map, there's 33 districts that are in play, 19 of which are controlled by the Republicans right now. 14 of which are controlled by Democrats, but they're all loosey-goosey.

It's crazy, isn't it? I mean, when you say that, it's still crazy that out of 435 seats, there's only like 30 odd that are actually in the way. Well, that's what's happened through gerrymandering, right? It's so crazy. So we understand this, you know, it's 8% of the house. in swing. The rest of it has been resolved through the fight of gerrymandering. The election was over as a result of the redistricting before the election started.

But you've got to focus on those areas. And so I would be saying to those people, yes, I hear you. Yes, I understand that. I understand that you want purity and you have righteous ideology. And I understand all of that. But I think you want to win. Take a page from Donald Trump's playbook about winning. OK, the Republicans are clearer. OK, the Democrats have always been well-intentioned, Caddy, but more abstract.

And when you're abstract, you're losing the independent voter. That's the thing I would say to these guys, you know. And by the way, housing is going to be a big issue. Trump brought up housing caddy in his pre-Christmas speech from the diplomatic room, that 9 p.m. speech. We're in short supply and the prices are going up.

And you know this, housing is eating the paycheck of the American. It's making it very difficult for Americans that own houses or are renting. It's making it very difficult for them to have other disposable income. due to the rising prices and so you want to talk to people about fast tracking permits multi-family housing starter homes

OK, you know, the Democrats are talking about putting tax penalties on institutional investors that are hoarding single family homes. These big private equity companies have gone into these areas and bought swaths and swaths of. housing and they're pushing the prices up okay you gotta you gotta get in there and talk about these issues and explain to the american people that you have affordability policies

I'm going to say market-based affordability policies, not socialist-based, because the Americans get turned off by that. Maybe that works in New York City, but I don't think it's going to work in the... mainstream american congressional district i think they have realized that affordability is a winning issue for them they'll be talking about that over the course of the new year

22 million Americans will have found suddenly that their health care is a lot more expensive. They'll add that into the affordability issue too and push for things on. more subsidies on healthcare or cheaper healthcare for Americans. I think the other thing they have to figure out what to do and how to talk about it is how to talk about immigration because they've run away since the 2024 election.

Democrats have run away from the whole subject of immigration like it was a burning hot coal that somebody had put in their hands and they don't want to talk about immigration because they realize that Joe Biden didn't do enough to shut the border. Hundreds of thousands of people came across which helped Donald Trump win in 2024, and so they basically dropped the subject. But actually, those elections in New Jersey and Virginia showed a huge swing of Hispanic voters away from Donald Trump.

Hispanic voters are in a way the new swing voter. In 2024, they sided with Donald Trump because of prices. In those off-year elections in Virginia and New Jersey last year, the biggest shift was young voters and Hispanic voters. I think that a lot of the polling suggests that Hispanic voters don't like what they see with these ice crackdowns, particularly when American citizens of Hispanic origin have been picked up and arrested.

And we saw in that Susie Wiles profile in Vanity Fair that you and I spoke about at the end of last year, she actually admitted that... some young person had been arrested who was an American citizen she said oh well that was just an overzealous ICE agent that did that so the White House has a problem around this overactive ICE operations around the country and Democrats I think need to be able to capitalize on that as a

talking point whilst also saying we're going to have border security. So there are things they can talk about. And if they get those themes going, I think this issue of progressivism versus pragmatism, because Abigail Spanberger was the one who said in her race for the Virginia governorship,

It's pragmatism versus partisanship, and we have to go with pragmatism every time. So you've got the kind of two polar opposites there between her and Mamdani. I think they can finesse this in the midterms because they have multiple candidates in multiple states with...

different needs you just got to find the right candidate support the right message for those people but hone in on affordability that's your number one issue find a way to talk about immigration keep the borders safe but highlight the cases of ice deporting or arresting American citizens because that could also play to your advantage in the midterm elections.

Okay, we're going to take a break and come back and talk about specific states. And I want to look at the state of Maine, not just because my son has recently moved out there, because it's got an interesting political case that highlights some of these broader themes. Welcome back to The Rest is Politics US and our democratic strategy session on how to win back something for the Democrats in the midterms. We're trying to give them some advice here.

putting on our democratic strategist hats if we were running this election how would we run it mind you actually no one's called us Anthony to say can you come and run any election which is probably either on the republican side or the democratic side I'd do it no one's ever

called me to run anything no the democrats would probably be more likely to call than the republicans let's face that but let's talk about the republicans for a second because if i was in a republican strategy meeting i would say listen we're not doing great on affordability Obviously, the ICE stuff that you're bringing up, Caddy's hurting us. But there's still a culture war going on out there. And let's create as many trap doors as possible for Democrats to step into.

related to the culture war. Okay. And Trump keeps bringing it up. You know, the transgenders are playing in women's sports, you know, this sort of thing. The military is being mistreated. The immigrants are overrunning the emergency. rooms at your local hospital the crime rate is super high this is stuff that they're going to chant going into the midterms And so what's the best course of action, Caddy? Be the coach and tell people how to avoid the trap doors at the Republicans.

are going to be laying down in late 2026. I think this is the biggest challenge for Democrats, and it's where they haven't got their message sorted out, because they want to be the party of inclusion. They don't want to be the party that says we are against transgender members of our society. But they don't know how to talk about it in a way that...

doesn't alienate centrist American voters and also doesn't alienate the left of their party. And I think actually Gavin Newsom has done a couple of... interesting interviews on this recently where he said look i am for protecting minority groups in our population i think the sign of a healthy democracy is that we look out for people who are in the minority

and who are the disadvantaged. But I also believe that there is a thoughtful debate to be had about transgender women playing in female sports. And he comes down on the line that that is unfair to women. So are we actually also protecting the women and girls in our society if we were allowing transgender women to play in those sports? I mean, ideally.

Democrats would find a way to have this conversation, move on from it very fast, but not fall into the trap of just playing to the left of their party. I think that was the problem they had in the 2024 election. They got themselves caught up in knots. They didn't know where to push back. They became tarnished with this, Kamala Harris is for they, them, we're for you.

it really damaged them because it just played into this perception that they're the woke party. So they've got to find a way to move on from that. Drop the moral superiority. I mean, that's, I think, at heart, I've been thinking about this issue of wokeism recently. At heart, the problem with it is it makes one group sound like they have all the moral cards to play and that they are the better people.

and that we know best and if you believe this you're a bad person if you want the border shot you are racist if you don't allow transgender women to play in sports you're kind of against minorities i mean that is what they it's tonal they've got to get over that moral superiority tone and there is an opportunity i agree with you in some of these races around the countries in the midterms if i'm playing republican strategist now i'm saying push democrats hard on that because that's

They can't resist sounding like they're morally superior and voters find that a real turnoff. You know, first of all, I agree with you, but how likely or how willing. Will the Democrats be in terms of accepting that sort of strategy? See, that's that to me is the problem right there. I think there's a big rub. Take somebody like Bernie Sanders. Bernie Sanders is not particularly woke.

Right? I mean, this is the horseshoe theory of populism that, you know, you bend it around far enough and Bernie Sanders starts sounding like Steve Bannon at certain points. He's not interested in wokeism. He's interested in economic populism.

And that is the card you have to play. You've got to play the affordability card. And there's a very interesting place. Let's dig into this because in the last half, you said that you don't think the Democrats will take back the Senate. I tend to agree. But there are states, Maine, Massachusetts, Michigan, Minnesota, I don't know why they all begin with Ms. Anyway, a whole bunch of states where actually the Democrats have some chance of winning back.

the Senate. And there's a very interesting race happening up in Maine that gets to some of these issues of pragmatism versus political purity and being. On the left of the party, there's both a kind of generational fight going on and this progressive... versus centrist fight going on. You've got Susan Collins, who's the 73-year-old sitting senator who's been there.

since the dinosaurs as long as i can remember she's a frequent critic of donald trump she's kind of a moderate republican senator one of the few left in this swing state in maine She is being now challenged by the Democrats. They think they can unseat Susan Collins, which would be kind of seismic in Senate history. That's getting in a little bit.

in the weeds and nerdy but anyway in washington terms that counts as big news and she's being challenged by the democrats but the democrats have their own fight going on and the Two people who are trying to unseat Susan Collins who are fighting for the nomination. One of them is Governor Janet Mills, who's been a critic of Donald Trump. She is also a popular, moderate governor. Normally, she would be a shoo-in.

for the opportunity to unseat Susan Collins, but she's 77 years old and she's being challenged now by a 41-year-old who has a super interesting background, Graham Platner, who is a former oyster farmer. former military veteran who is coming at this much more from the kind of

economic populist point of view. He's not a particularly woke progressive, but he's talking about things like affordability. All of those issues, Anthony, that you're talking about that young people are really concerned about, about housing, about rent, about child care and he's going around Maine I've seen him speaking and he's very kind of down to earth very folksy very Maine he's a great candidate for that state he's had some controversial issues around text messages about

uh the police um and about racial issues but he's popular and even despite that he's super popular in maine because he has that sort of authentic populism that Mamdani manages to embody as well. And he's really talking about the affordability issues. And he's got the age thing. There's a big generation, don't underestimate that, too, in these midterm elections, young candidates saying to older candidates, particularly in the Democratic Party, it's...

Time for you guys to step out of the way. It's our time now. We are the ones that understand how hard it is to make rent, how hard it is to pay for childcare. I think it's very well said. But again, going to those 30 or so districts.

Let's look at the demographics of those districts. Okay, most are suburban. Most of those districts are housing stressed. These are places like upstate New York, Westchester County, suburban Philly. suburban pittsburgh okay these are people that in my mind are tired they're overworked and they're not necessarily ideological moreover

The Trump style rhetoric helps GOP turnout. We know this. You know, you can sit there as a Democrat and say, oh, Trump is a liar and Trump's lying about this. Trump's lying about that. But Trump knows how to. press launch codes he knows how to press buttons on his base to get them to vote and you know these elections are so tight caddy that there's an incremental swing voter

That if Trump's rhetoric is bringing out the GOP, you've got to be in a position to try to throttle that down. So you've got to talk about cost of living competence. You got to talk about housing and how you're going to improve their ability to buy a house, secure a house. You got to go after the healthcare situation, okay, at the end of this congressional term.

Starting in 2027 January, 22 million people are coming off the healthcare. Those people may be in your swing district. You've got to explain to them what's going to happen to them. if they don't get the check of a democrat coming into the house and that's i think where you're going to see uh all of the money that will be spent in these midterm elections and there's probably going to be

I don't know if it's going to be a billion that gets spent totally, but I wouldn't be surprised given how much presidential elections cost. All of that money that is already being raised and is already being spent in these. key swing districts is going to focus on those things right it has to if it's going to cut through because you've got 45 percent of american voters saying that the most important factor deciding their vote

is a candidate's position on the cost of living. So I feel so bad for you, but if you live in one of those swing districts, expect an avalanche of ads between now and November. You are going to be inundated with ads telling you what a... candidate's position is on things like housing on things like health care um so a couple of the ads where people they're already spending money because it's interesting i've been told by democratic strategists that

They are spending money earlier this year for this year's midterm elections than they ever have done before. They're targeting about 50 races around the countries where they're really spending big money. And they have already started putting ads up in some of those races. They're running independent expenditure ads in the Senate seat in Pennsylvania.

They are already targeting New York's 17th district. That's very near you, Anthony, the Republican-held swing district of Mike Lawler. They see that as a realistic pickup. They're a bunch of... house seats in Pennsylvania that they're targeting. There's an interesting house seat down in Florida, Florida's 13th district. They're already targeting that one. So they're dotted around the country. You're suddenly going to see an avalanche of these.

political ads, all targeting, I think, issues like healthcare and housing. Remember this, the president's strategy, as we're sitting here talking to you at the dawn of this new year, inflation is trending down. A recent CPI number was 2.7 down from 3.1. And so it's trending down. That's going to give some space to the new Federal Reserve chairman to lower rates going into the midterms.

Trump is going to take credit for all of that. You've got to speak to these people and say, hey, man, we're here to cut your costs. We're here to cut your drug costs. We're here to help you with your rent. Okay, we're here as the competence party. Republicans are shouting, but we can cut the costs. The housing is going to be a big issue, Caddy. Trust me, that's, to me, I think that there's, it's just not well understood.

outside of a certain genre especially amongst young people we're hearing it all the time people in their 30s who can't afford houses focus on the housing guys try to get people to believe okay that you're going to be the party of cost-cutting competence. You're going to be the party that's going to make sure that people get their healthcare restored. You're going to be the party that's going to help clear the housing supply-demand mix and make more housing supply.

So Anthony, you're in the White House and we're now putting you back in position of playing strategist in the White House. Oh my God, I'm breaking, I'm breaking out. Pass me the anti- Yeah, the hives, the hives are coming up. Pass me the hydrocortisone. Slathering, slathering, preventing the hives.

You've got a phone call from Speaker Johnson who's saying, Susie Wiles, quickly, quickly, we need to get together a strategy meeting because we have to determine how the president is going to help us hold on to the House. in these midterm elections um what should we do with donald trump during the course of this year again what they're going to do is roll him out he wants to be rolled out because he wants all the attention

Susie's going to roll him out. We've seen that Johnson, Speaker Johnson, is a little bit of a wallflower. He's going to allow Trump to do whatever he wants. And so you're going to see Trump on the stump. And, you know, Democrats, because they dislike Trump, they're like, yeah, that's great. Bring him on. We want to see him out there because we despise him. But time out, fellas. OK, he brings out the vote. He brings out his base.

And so you better recognize he's coming for you and he's coming for you with a lower interest rate for sure. There'll be five to 50 to 75 basis points. OK, and you know this and I know this. It is not normal for a lame duck president to be out there beating the drum for his party. But what has been normal about Donald Trump? He's going to go do this one way or the other, Caddy. And don't underestimate the SOB.

Well, that's the midterm elections. I don't know how we did as Democratic strategists or Republican strategists. I haven't got anyone picking, you know, my phone is not ringing off the hook saying. God, you're a genius. Come and win the elections for me. But there we go. That's our advice to both parties. That's all we have time for this week. We'll be back on Monday with our regular episode.

And as a New Year's treat, if you sign up at therestispoliticsus.com and become a founding member, you can get an episode of Anthony and I answering your... personal questions katie's favorite part of the podcast aunt agony and by the way it's not called it's not called uncle agony okay because katie she is asserting herself here with aunt agony trust me

Sign up at therestispoliticsus.com. Happy New Year to everybody. It'll be hopefully a healthy and prosperous year for everybody listening in. Bye, everybody. Bye, everybody.