Trump's Revenge Tour Could Backfire

Summary

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Podcast Summary: What A Day

Episode: "Trump's Revenge Tour Could Backfire"

Host: Jane Coaston
Guest: Alex Wagner (Host, Crooked Media's Runaway Country)
Date: May 21, 2026

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Overview

This episode unpacks the aftermath of recent "MAGA primaries," where Donald Trump’s endorsed candidates won key Republican contests, culminating in what the hosts call Trump’s “revenge tour.” Jane Coaston, joined by Alex Wagner, analyzes what Trump’s consolidating control means for the Republican Party, the risks it poses for the GOP and his own agenda, how Democrats should respond, and growing signs that “Trumpism” is an unsustainable strategy for winning national elections. The episode also reviews news on DOJ actions, the complicated "Board of Peace," the situation in Iran, and legal and political drama involving high-profile Republicans.

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Key Discussion Points and Insights

1. Trump’s Primary Night “Revenge Tour” (00:17–04:49)

• Summary:
  A major theme: Trump is successfully pushing out GOP critics by backing challengers against them in primaries, highlighted by Kentucky Rep. Thomas Massie’s defeat and the targeting of others who opposed or criticized Trump.
• Insights:
  • Massie and others may be “lame ducks” but remain in office until January, free to act independently.
  • Trump’s aggressive purges might create short-term party unity but are likely to hurt legislative efforts and future electability.
• Notable Quote:

  “Trump, I think, has said...I don’t think he really cares very much about the midterms.” – Jane Coaston (04:49)

• Memorable Moment:
  Massie’s concession speech compared Trump’s priorities to the “Roman Empire,” highlighting his estrangement from Trump world.

2. Impacts on Policy & Congressional Dynamics (04:49–06:43)

• Summary:
  With moderate or non-Trumpist Republicans leaving, Trump loses reliable votes for his projects in the remaining session.
  • Example: Funding for Trump’s “ballroom” project is likely dead in the water.
  • The GOP is shrinking into a “MAGA minority” as Democrats look set to take a majority.
• Notable Quote (Alex Wagner, 03:58):

  “You have three guys in there who are going to be like Yosemite Sam style, like, fuck that on their way out.”

• Insight:
  Lame duck Republicans may actively undermine Trump’s priorities on their way out.

3. Democrats’ Position & Strategy for Midterms (04:57–07:50)

• Summary:
  The Democratic tent is broad but currently more defined by resistance to Trump than by a coherent policy vision.
• Advice for Democrats:
  • Focus on Trump’s “breathtaking” corruption, including the reported insurrectionist slush fund ($1.8 billion).
  • Make the connection between Trump-era corruption and declining quality of life (e.g., high gas prices, health care costs).
• Notable Quote (Alex Wagner, 05:34):

  “That combination is where Democrats should sit. The injustice of the moment, the moral failing of the moment, and the economic maelstrom that Trump has created in his mismanagement of the economy.”

• Insight:
  Democrats are benefiting simply by serving as a check on Trump, but lack a long-term vision for governing.

4. Understanding Trump Fandom (08:03–10:20)

• Summary:
  Trump’s base isn’t traditionally ideological—it’s a fandom driven by community and identity, resistant to “political gravity.”
• Notable Quote (Alex Wagner, 08:37):

  “We underestimate the desire for community that exists within all of us as homo sapiens… Trump...offered people a true sense of camaraderie and identity and community...almost like a religious revival.”

• Insight:
  While diehards remain, Trump’s coalition isn’t large enough for national victory. Swing voters—drawn to him for economic change—are falling away due to unmet expectations.

5. Texas Senate Race & The Perils of MAGA Candidates (10:20–11:44)

• Summary:
  Trump’s endorsement of the scandal-plagued Texas AG Ken Paxton may jeopardize the GOP’s hold on a Senate seat.
  • Paxton is widely disliked, even among Texas Republicans, making him a weak general election candidate against Democrat James Talarico.
• Notable Quote (Alex Wagner, 10:46):

  “Ken Paxton is the worst possible candidate you could run against James Talarico...he is someone who’s been convicted of bribery.”

• Insight:
  Trump’s loyalty tests could give Democrats opportunities even in deep-red states.

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News Wrap-Up & Key Headlines (15:52–19:41)

• Trump Addresses Coast Guard Graduates
  Trump praised national "strength, morale and confidence" (16:13), though Jane Coaston quipped this wasn’t the national mood.
• Iran Conflict & Board of Peace Trouble
  Trump warned the Iran war could "last a while" (16:55); Iran threatened retaliation in “places you cannot even imagine.”
  The “Board of Peace,” designed to aid Gaza reconstruction, fails to attract funding—only 2 of $7 billion pledged arrives (17:04).
• Raul Castro Indicted
  DOJ announces charges against ex-Cuban president Raul Castro for a 1996 shootdown incident (18:22).
• Slush Fund Controversy
  Trump administration’s plans for a $1.776 billion “slush fund” for alleged DOJ weaponization victims face legal challenge
  • Capitol Police officers sue, arguing it financially enables insurrectionists (18:32).
  • House Speaker Mike Johnson deflects on details: “We don’t know any of the details of that settlement fund.” (19:12)

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Notable Quotes & Moments

• On GOP’s Future:
  “The purge of any critic is a bad thing for the Republican Party, but it’s a very bad thing for their electoral prospects and the management of their party moving forward.” – Alex Wagner (02:46)
• On Democrats’ Dilemma:
  “There is no particular guiding principle to the party that I could articulate beyond just we are a check on Trump.” – Alex Wagner (07:50)
• On Trump’s Appeal:
  "Trump fandom is a fandom. It's not a traditional relationship with a politician." – Jane Coaston (08:03)
• On Texas Senate Race:
  “Once you’ve lost Republicans in the Lone Star State...” – Alex Wagner (10:46)

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Timestamps for Important Segments

| Time | Segment/Topic | |--------|------------------------------------------------| | 00:17 | MAGA primaries and Trump’s revenge tour | | 01:46 | Thomas Massie’s concession speech | | 02:26 | Alex Wagner joins to analyze primary results | | 03:58 | Congressional consequences for Trump | | 05:34 | Democratic midterm messaging | | 07:50 | Democrats’ identity and challenges | | 08:03 | Trump’s fanbase as a phenomenon | | 10:20 | Texas Senate race preview | | 15:52 | News wrap: Iran, Gaza, Castro indictment | | 18:32 | Lawsuit against Trump administration slush fund | | 19:12 | Speaker Mike Johnson on "slush fund" |

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Conclusion

The episode delivers an insightful, unsparing look at the consequences of Trump’s obsession with loyalty and the resulting shrinkage of the GOP’s big tent, while warning that such tactics may backfire at the ballot box and in Congress. Coaston and Wagner urge Democrats to seize the moral and practical ground while recognizing the need for post-Trump strategic clarity, and cast Trump’s persistent but shrinking fandom as a spent force unable to reliably deliver electoral victories.

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Transcript

[A]

Foreign

[B]

It's Thursday, May 21st. I'm Jane Coston and this is what a day. The show that thanks Utah Republican Representative Blake Moore for just saying it out loud on Wednesday.

[A]

Our Republican priority will always be to be putting government ahead of Americans.

[B]

Was this what he meant? Probably not. Is this true also? Yes. On today's show, the Department of Justice announces charges against former Cuban President Raul Castro. And President Donald Trump's so called Board of Peace is apparently having a hard time with funding. I wonder why. But let's start with Tuesday's very MAGA primaries. It was a good evening to be Trump as a swath of his hand picked candidates won their primary elections. And one of his biggest opponents in Congress, Kentucky Republican Representative Thomas Massie, lost. Tuesday night was the culmination of Trump's revenge tour against Republicans he viewed as disloyal. Like the Indiana Republicans who opposed his demands to redraw congressional maps. Or Louisiana Republican Senator Bill Cassidy who voted to convict him for inciting the January 6th insurrection. And Georgia Secretary of State Brad Raffensperger who resisted Trump's request to, quote, find votes to overturn President Joe Biden's 2020 victory. Almost all of these politicians lost to Trump endorsed candidates. So yes, this is indeed Trump's Republican Party. But there are a few problems with that, problems that they are going to have to deal with very soon. For one, Massie is still in office and now has few reasons to support Trump on pretty much anything. Here he is speaking during his concession speech on Tuesday.

[C]

I got to watch Fox also for the first time in 18 months. And there was the President. And talking about, by the way, while gas is almost $5 and diesel's almost 6, they're talking about this big ballroom they're going to build. And it looks, it looks like Ro. The Roman Empire architecture from the Roman Empire. I see a few analogies there.

[B]

That does not sound like a man who is inclined to give Trump a billion dollars for his beloved ballroom. So for more on what we learned from Tuesday's primaries, I spoke to Alex Wagner. She's the host of Crooked Media's Runaway Country. Alex, welcome back to what a Day.

[D]

Jane. Thank you. I'm happy to be here. What a day.

[B]

What a day. Okay, let's start with Tuesday's buzziest and most expensive race. Thomas Massie lost his Kentucky primary to Trump's endorsed candidate. What's your takeaway here?

[D]

Self.

[B]

Own.

[D]

Is that what it own goal?

[B]

Yes. Both of, I think both of those still work. Both of those work.

[D]

Nose cut off to spite face. I mean. Well, I shouldn't say that. I think this is going to the bar none beast that lives inside Thomas Massie to be even more engaged on the Epstein scandal and to push for, you know, more oversight in the remaining waning days of this Congress. We are shaping up to have a midterms where there is a, a Democratic majority and a MAGA minority, like just a group of absolutely, totally insane Trump acolytes left in the House and a Democratic majority to keep them, you know, basically to keep, to run, run the business of the country. I think it's like, I think the purge of any critic is a bad thing for the Republican Party, but it's a very bad thing for their electoral prospects and the management of their party moving forward. It's not good.

[B]

I think that that's such an important point that I'm not even sure if Trump really considered, which is that he's like, yeah, I'm ending the careers of my political enemies, but they're all still going to be around until January. So, yes, how will Trump's retribution campaign affect his success in the Hill when he's got Senator Cassidy saying, actually, I don't like the Iran war very much, and he's now got Massie who's like, actually, I hate everything about you.

[D]

Yeah, well, he's, he has, he doesn't have Tillis, he doesn't have Cornyn, he doesn't have. Cassidy has three Republican senators. So that means you can say goodbye to the SAVE Act. You can say goodbye probably to, well, you can say hello to some kind of congressional authorization put in place over the disaster, disastrous illegal war in Iran. You can say goodbye to the ballroom funding, which is, I think, basically a Fed accompli. As of today, the $1 billion he wants for the ballroom has gone the way of the dodo bird as far as Senate Republicans are concerned and, you know, other pet projects, other planks that he demands the Republican Party walk. They don't have to anymore. You have three guys in there who are going to be like Yosemite Sam style, like, fuck that on their way out. So, I mean, as if Trump has forgotten that there's six months left on calendar during which these guys are off leash.

[B]

Yeah, it's, I mean, Trump, I think, has said, and I will say that I don't think he really cares very much about the midterms.

[D]

I don't think he does either.

[B]

No. But these candidates who won do care about the midterms, and they're going to go on to face Democrats in November, and they're in this weird situation, which is that Trump is king in his own party. The thing you cannot do in the Republican Party is cross Trump, but everybody else is pretty much done with him. Given all that, how should Democrats be positioning themselves in the midterms, knowing that, you know, they could win back people who voted for Trump in 2024? And they're kind of in this weird moment where, like, Republicans have to prove themselves to one person, but that one person is disliked by all these other people.

[D]

Okay, I gotta say, Democrats actually don't have to do all that much, but I think if they want to have a message, it is this. There's the corruption, which is breathtaking and eye watering. And I think nothing is more exemplary of that than the $1.8 billion insurrectionist slush fund that was announced with some detail this week. And that corruption hand in hand with the lived reality of Americans, which is people who cannot afford hamburger meat to grill burgers this summer, who can't afford the family camping trip to visit grandma because fuel prices are so high, who might not be able to afford air conditioning, and who can't go to the doctor when they get a summer cold because their health insurance costs are too high. That sort of diminution of Americans financial reality and the. And the. This utter numbness that Trump approaches, with which he approaches the pain that Americans are feeling, coupled with the brazen corruption and the thievery of money from American pockets at the same time. That combination is where Democrats should sit. The injustice of the moment, the moral failing of the moment, and the economic maelstrom that Trump has created in his mismanagement of the economy.

[B]

Do you think Democrats have learned anything from their own races on Tuesday? We aren't going to be able to get into those. But I'm just curious as to what you thought about how Democrats did in those primaries.

[D]

Oh, Jane. I mean, I think the Democrats are benefiting right now from the fact that they are the resistance. And I think that the tent is very, very big. And I think Democrats have not had to answer a lot of tough questions. I say this as someone who is going to be moderating an upcoming Michigan Democratic Senate candidate for him. I think the party has not done the hard work of figuring out where it stands and what its priorities are and is going to have to quickly coalesce around some messages once Trump has been sufficiently neutered by having Congress back in Democr. There are going to be some long and hard conversations that need to happen about where the party moves forward because the tent is very, very, very large. And there is no particular guiding principle to the party that I could articulate beyond just we are a check on Trump and I. Right. Let me just say I think that's enough right now.

[B]

Right.

[D]

But once the party does have power, they really do need to have a roadmap. That's the like, Most anodyne, broad, 60,000 foot view of like the primaries that I can offer you.

[B]

The thing I keep thinking about, and I think that Thomas Massie's loss proved, is that Trump fandom is a fandom. It's not a traditional relationship with a politician. Trump's biggest supporters don't care if gas prices go up or down. They root for him. Like you'd support a sports team or how you're like a fan of a band. You know, we've seen so many politicians for whom they get voted out of office because they didn't do something or because they did do something of voters didn't like that. Why is this so different in your view, and it's been different for a decade?

[D]

Well, as someone who went to a lot of Trump rallies for my work on the circus and otherwise and for msnbc, the, the. I think you under. We underestimate the desire for community that exists within all of us as homo homo sapiens. And the fact that Trump for a long time with a, now with a waning number of people, but offered people a true sense of camarade and identity and community. And like, those rallies, as distasteful and appalling as the stuff he said was really were almost like a religious revival. I mean, there was like joy. People were excited to be together. They felt validated in their views. And that has, I think, created almost a cult, like adherence to MAGA ism and to a belief in Trump that's very hard to shake. It is like, you know, I mean, I use the word cult not lightly because it is that kind of thing. To your point where against the laws of political gravity, these people remain stalwart supporters of him and like, that's why his approval rating is at 37%. There's like some quarter of the country that's never going to leave him, but that's not a winning coalition. I mean, the Latinos and the people of color, the black, black men, Latinos, young people, independents who sort of moved more towards Trump in the 2024 election, they're all gone. They weren't voting because they were at the Trump rally and they had the sparkly maga hat they were there because they thought they could, he could make their lives more affordable. And he has failed them over and over again. And so the winning coalition is not just, I mean, it wasn't just diehards. It was people who were Trump curious, who knew, who felt desperate, who felt like they, that the Democratic Party was not giving them what they needed. And, and now the Republican Party certainly is not. And so they will be looking to alternatives.

[B]

So this week, Trump also endorsed Texas Attorney General Ken Paxton in the Texas Senate Republican runoff next week, if history is any indication. And Paxton wins against the incumbent, John Cornyn, who I think a lot of conservatives and Republicans thought had a better chance to beat James Talarico. Does this hand the race to James Talarico or is Texas red enough that it just doesn't really matter?

[D]

I don't know, man. Ken Paxton was impeached by the Texas House. People in Texas don't like Republicans in Texas don't like Ken Paxton. And I think once you've lost Republicans in the Lone Star State. First of all, let's just not shake off the reality that James Tallrigger is a great candidate. It's not like, I mean, he is a very convincing, deeply Christian and very principled individual who I think is really appealing to a cross section.

[B]

I know. I think I just have Texas Democrat Senate trauma.

[D]

Oh, of course, rightfully so. But I mean, Ken Paxton is the worst possible candidate you could run against James Talarico. I mean, he is someone who's been convicted of bribery. I mean, the guy has the spottiest record ever, though his own party doesn't like him. The, the Senate Republicans didn't want to see him in the race and the Senate Majority Leader didn't want to see him in the race. They're not saying that just because they really like John Cornyn, though. They did, but they think they're. This could be the race.

[B]

This could be the ball game, and

[D]

it's all Trump's fault.

[B]

Alex, as always, thank you so much for joining me, but it's great to see you. That was my conversation with Alex Wagner, host of Crooked Media's Runaway Country. We welcome all newcomers to the Trump Hate Train, even you, Bill Cassidy. So make sure to subscribe, leave a five star review on Spotify and Apple Podcasts, watch us on YouTube and share with your friends. More to come after some ads. This podcast is brought to you by Wise, the app for international people using money around the globe. When it comes to sending money abroad, many providers claim to offer free fees and competitive rates. But don't be fooled. This can be code for inflated exchange rates. With the WISE account, you can send, spend and receive money in over 40 currencies without ever having to worry about hidden fees. Sending pounds across the pond. Most transfers arrive in 20 seconds or less. Spending reals in Rio. The wise travel card gives you the mid market rate on every purchase. No costly markups on your bill. Getting paid in dollars for your side gig. Avoid hidden fees and get the real exchange rate every time. With 24. 7 access to live support, your international transactions with WISE are quick, transparent and safe. Plus wise runs over 7 million daily checks to catch and prevent fraud. 15 million people already trust wise to manage their money internationally. Be smart. Get Wise My husband and I have used WISE when we've traveled out of the country and it's been a total game changer. Download the Wyze app today or visit wyze.com Terms and Conditions apply. What a Day is brought to you by Casper Sleeping is one of my top tier talents and priorities. If you're not waking up feeling like a functioning human, your mattress might be the problem. Casper makes reliable, high quality mattresses designed to deliver consistent, comfortable sleep night after night. Casper's mattresses are highly rated by Consumer Reports and out of 99 mattresses, Consumer Reports named Casper's the 1 Mattress their top rated all foam mattress of 2026. If you're in the market for a new mattress or a mattress Upgrade, head to Casper.com and save up to 30% on the mattress you deserve. Casper's mattresses are built to be durable and long lasting so you're not replacing your mattress every few years. Their products are designed to withstand the test of time, maintaining support and comfort over the long haul and Casper has their 100 night risk free trial so you can give Casper's mattress a try. Risk free although with 110,000 five star reviews, I'm sure you're going to love it like I do. My Casper mattress keeps me cool at night so that I can get the sleep I need to be able to report on all of this. Casper offers a wide range of mattress types, so whether you like your mattress firm, soft or somewhere in between, there's something for you at Casper.com/ I really love Casper and I'm excited to get to share them with you. Plus they just launched a brand new kids mattress so even the youngest sleepers in your family can get the same comfort and quality that you do right now. Save up to 30% on mattresses and up to 35% on everything else. When you go to Casper.com one last time, that's C-A-S-P-E-R.com and save up to 30% on the mattress you deserve.

[E]

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[B]

Here's what else we're following today.

[D]

Head Aligns

[C]

the things will happen and I believe for the best. Hopefully for the best, but I believe for the best. But things will happen that you can't even imagine. And it's going to be very exciting. But the way that's going to happen is through thinking big.

[B]

Inspiring. No, we will not be sane Washing Trump's comments today did the president say a slew of things during his commencement speech to the US Coast Guard Academy's graduates in Connecticut on Wednesday? Yes. Was one of those things pointing out the muscles on this guy? Also yes. Trump also told the cadets that they were graduating at a time he described as a resurgence of national strength, morale and confidence for our country. Not exactly how I'd describe it, but potato, potahto. Trump's trip to and from Connecticut on Wednesday gave him a lot of time to talk in front of Air Force One. Here he is talking to reporters about the war.

[C]

We're in the final stages of Iran. We'll see what happens. We'll either have a deal or we're going to do some things that are a little bit nasty. I don't believe that won't happen.

[B]

Trump also told reporters that the war could last a while, saying, I'm in no hurry. Meanwhile, Iran's Revolutionary Guards warned that it would launch attacks, quote, in places you cannot even imagine if the country is struck again. That's according to a statement reported by Iranian state media on Wednesday. I regrettably can imagine quite a number of places. There has been no reconstruction in Gaza since Trump's ceasefire went into effect seven months ago and the so called Board of Peace is struggling to collect funds, according to the Guardian. Countries have pledged more than $7 billion to the project, but only two have sent funds, a source told the Guardian. Nobody with money and resources wants to work with the Board of Peace, the source added. Lump on the conflict with Iran and the people with deep pockets now have an excuse not to pay. The DOJ announced charges against former Cuban President Raul Castro as the Trump administration escalates pressure on the island. The indictment was related to Castro's alleged role in the shoot down of two small planes operated by the exile group Brothers to the rescue. Castro, now 94, was Cuba's defense minister at the time. The charges included murder and destruction of an airplane. Here's Acting Attorney General Todd Blanche speaking at a press conference announcing Castro's indictment on Wednesday.

[C]

A warrant issued for his arrest.

[B]

So we expect that he will show

[C]

up here by his own will or by another way.

[B]

This is a major escalation by Trump's team against Cuba, which is bracing for possible military action by the United States. Two police officers who tried to stop the January 6th insurrection sued the Trump administration on Wednesday over its planned $1.776 billion slush fund for victims of alleged DOJ weaponization. The two officers, former U.S. capitol Police officer Harry Dunn and Officer Daniel Hodges of D.C. metropolitan Police, alleging their suit that the fund created by Trump will, quote, finance the insurrectionists and paramilitary groups that commit violence in his name. Here's House Speaker Mike Johnson talking about the slush fund on Wednesday.

[A]

We don't know any of the details of that settlement fund. The acting Attorney General, Todd Blanch, testified yesterday and he gave a lot of detail and I'll just defer to what he said because he obviously knows a lot more about it than I do. He said, let me, let me, let me tell you what he said. He said they are setting up a fund to compensate all Americans who have been the subject, the target of lawfare or weaponization of the federal government. Again, that's not a partisan proposition either. Everybody should support that.

[B]

Mike Johnson, a man who never knows anything except that everything is totally fine. So stop freaking out. And that's the news. Before we go, if you're in the LA area, come catch a live taping of Love it or Leave It. They've moved over to Interwoven Studios and have an exciting lineup of guests, including the hilarious stand ups Tig Notaro, Todd Glass, Aparna Naturla. Never have I ever's Purna Jagannathan and more. Get [e-mail] events and if you're not in LA, you can watch love it or leave it on YouTube or listen wherever you get your podcasts. That's all for today. If you like the show, make sure you subscribe, leave a review, say Toodaloo to Stephen Colbert and tell your friends to listen. And if you're into reading, not just about how Colbert will end his run as the host of CBS's Late show tonight after 11 years, definitely not because he made Trump mad. Like me. What a Day is also a nightly newsletter. Check it out and [e-mail] subscribe I'm Jane Kostin, and in general, it's a little amusing to me that at the end of the day, Donald Trump is just a humorless scold who can't take a joke. Snowflake Behavior. What a Day is a production of Crooked Media. Our show is produced by Caitlin Plummer, Emily Foer, Erica Morrison and Adrienne Hill. Our team includes Haley Jones, Greg Walters, Matt Berg, Joseph Dutra, Johanna Case and Desmond Taylor. Our music is by Kyle Murdoch and Jordan Kanter. We had help today from the Associated Press. Our production staff is proudly unionized with the Writers Guild of America EAS.

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