Trump's Revenge Tour Could Backfire | Crooked Media
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May 20, 2026
What A Day
Trump's Revenge Tour Could Backfire

In This Episode

A swath of President Donald Trump’s handpicked candidates won their primary elections Tuesday night – and one of Trump’s biggest opponents in Congress, Kentucky Republican Representative Thomas Massie, lost. It was the continuation of Trump’s weeks-long revenge tour against Republicans he views as disloyal. So, for more about what we learned from Tuesday’s primaries, we spoke with Alex Wagner. She’s the host of Crooked Media’s Runaway Country.
And in headlines, President Donald Trump gives a commencement speech to the U.S. Coast Guard Academy’s graduates, the so-called Board of Peace needs money, and the Department of Justice announces charges against former Cuban President Raúl Castro as the Trump administration escalates pressure on the island.
Show Notes:

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TRANSCRIPT

 

Jane Coaston: It’s Thursday, May 21st, I’m Jane Coaston, and this is What a Day, the show that thanks Utah Republican Representative Blake Moore for just saying it out loud on Wednesday. 

 

[clip of Representative Blake Moore] Our Republican priority will always be to be putting government ahead of Americans. 

 

Jane Coaston: Was this what he meant? Probably not. Is this true? Also, yes. [music break] On today’s show, the Department of Justice announces charges against former Cuban President Raúl 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. 

 

[clip of Thomas Massie] I got to watch Fox also for the first time in 18 months. And there was the president 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 the Roman Empire, architecture from the Roman empire. I see a few analogies there. 

 

Jane Coaston: 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. 

 

Alex Wagner: Jane, thank you. I’m happy to be here. What a day. 

 

Jane Coaston: What a say. 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? 

 

Alex Wagner: Self-own is that what it, own goal?

 

Jane Coaston: Yes. Both I think both of those still work, both of those work. 

 

Alex Wagner: Nose cut off, two-spite face. I mean, well, I shouldn’t say that. I think this is gonna free the bar none beast that lives inside Thomas Massie to be even more um engaged on the Epstein scandal and to push for, you know, more oversight in the remaining waning days of this Congress. Um, We are shaping up to have a midterms where there is 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 run run the business of the country. I think it’s like 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. 

 

Jane Coaston: 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–

 

Alex Wagner: Yes. 

 

Jane Coaston: 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. 

 

Alex Wagner: Yeah well, he’s he has he doesn’t have Tillis. He doesn’t have Cornyn. He doesn’t have Cassidy, he 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 disastrous illegal war in Iran. You can say good bye to the ballroom funding, which is I think, basically, a fait accompli as of today, the $1 billion he wants for the ball room 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, pew pew pew, like fuck that on their way out. So I mean, it’s as if Trump has forgotten that there’s six months left on the calendar during which these guys are off leash. 

 

Jane Coaston: 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. But–

 

Alex Wagner: No, I don’t think he does either. 

 

Jane Coaston: No, but these candidates who won do care about the Midterms, and they’re gonna 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.  

 

Alex Wagner: Okay. I got to 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 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 movement, and the economic um maelstrom that Trump has created in his mismanagement of the economy. 

 

Jane Coaston: 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?

 

Alex Wagner: [sigh] 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 forum. 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 Democratic hands 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. 

 

Jane Coaston: Right. 

 

Alex Wagner: But they once they the party does have power they really do need to have a road map. That’s the like most anodyne, broad, 60,000 foot view of like the primaries that I can offer you. 

 

Jane Coaston: 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 and voters didn’t like that. Why is this so different in your view? And it’s been different for a decade.

 

Alex Wagner: Well, as someone who went to a lot of Trump rallies for my work on the circus and otherwise, and for MSNBC, 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 true sense of camaraderie, 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 MAGAism and to a belief in Trump that’s very hard to shake. It is like you know it 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 percent. 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 men, Black men Latinos, young people and 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 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, and who felt desperate, who felt like 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. 

 

Jane Coaston: 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? 

 

Alex Wagner: 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 Talarico is a great candidate. 

 

Jane Coaston: Yes. 

 

Alex Wagner: 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. 

 

Jane Coaston: I know. 

 

–of [?]–

 

Jane Coaston: I think I just have Texas Democrat Senate trauma. 

 

Alex Wagner: 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. His own party doesn’t like him. 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 their this could be the race, this could be the game and it’s all Trump’s fault. 

 

Jane Coaston: Alex, as always, thank you so much for joining me. 

 

Alex Wagner: But it’s great to see you. 

 

Jane Coaston: 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. [music break]

 

[AD BREAK]

 

Jane Coaston: Here’s what else we’re following today. 

 

[sung] Headlines. 

 

[clip of President Donald Trump] 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. 

 

Jane Coaston: 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 U.S. Coast Guard Academy’s graduates in Connecticut on Wednesday? Yes. Was one of those things pointing out the quote, 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 potato. 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. 

 

[clip of President Donald Trump] We’re in the final stages of Iran. We’ll see what happens. Whether they have a deal or we’re gonna do some things that are a little bit nasty. I don’t believe that won’t happened. 

 

Jane Coaston: Trump also told reporters that the war could last a while, saying, quote, “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, quote, “nobody with money and resources wants to work with the Board of Peace.” The source added, quote, “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 Raúl 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. 

 

[clip of Attorney General Todd Blanche] There is a warrant issued for his arrest. So um we expect that he will show up here by his own will or by another way. 

 

Jane Coaston: 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, allege in 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. 

 

[clip of House Speaker Mike Johnson] We don’t know any of the details of that settlement fund. Um. The acting attorney general, Todd Blanche, 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, uh the target of lawfare or weaponization of the federal government. Again, that’s not a partisan proposition either. Everybody should support that. 

 

Jane Coaston: Mike Johnson, a man who never knows anything except that everything is totally fine. So stop freaking out. And that’s the news. [music break]

 

[AD BREAK]

 

Jane Coaston: That’s all for today. If you like the show, make sure you subscribe, leave a review, say toot-a-loo to Stephen Colbert, and tell your friends to listen. And if you’re into reading, and 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 subscribe at Crooked.com/subscribe. I’m Jane Coaston, 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. [music break] What a Day is a production of Crooked Media. Our show is produced by Caitlin Plummer, Emily Fohr, Erica Morrison, and Adriene Hill. Our team includes Hayley Jones, Greg Walters, Matt Berg, Joseph Dutra, Johanna Case, and Desmond Taylor. Our music is by Kyle Murdock and Jordan Cantor. We had help today from the Associated Press. Our production staff is proudly unionized with the Writers Guild of America East. [music break]

 

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