What A Day - Trump's Revenge Tour Could Backfire

Episode Date: May 21, 2026

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: Check out Runaway Country – tinyurl.com/mrmmsw8d 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 visit crooked.com/whataday

It's Thursday, May 21st. I'm Jane Koston, and this is what a day, the show that thanks Utah Republican Representative Blake Moore for just saying it out loud on Wednesday. Our Republican priority will always be to be putting government ahead of Americans. 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 mega 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 Massey, 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 Raffensberger, 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, Massey 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. 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 six, They're talking about this big ballroom they're going to build, and it looks like the Roman Empire, architecture from the Roman Empire. I see a few analogies there. 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. Jane, thank you. I'm happy to be here. What a day. a day. Okay, let's start with Tuesday's busiest and most expensive race. Thomas Massey lost his Kentucky primary to Trump's endorsed candidate. What's your takeaway here? Self-own. Is that what it?

Own goal? Yes. Both of, I think both of those still were. Both of those were. Nose cut off to spite face. I mean, well, I shouldn't say that. I think this is going to free the bar nun beast that lives inside Thomas Massey 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 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 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. 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 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 Massey who's like, actually, I hate everything about you. Yeah. Well, 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 goodbye to the ballroom funding, which is, I think, basically a Fed accompli as of today. The $1 billion he wants for the ballroom is 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 the calendar during which these guys are off leash. 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. No, I don't think he does either. 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. 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 American, 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 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. 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 practices. Mary's. 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. Right. But once the party does have power, they really do need to have a roadmap. That's the most anodyne, broad, 60,000-foot view of, like, the primaries that I can offer you. The thing I keep thinking about, and I think that Thomas Massey'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 a voters didn't like that.

Why is this so different in your view? And it's been different for a decade. Well, as someone who went to a lot of Trump rallies for my work on the circus and otherwise and for MSNBC, I think we underestimate the desire for our community that exists within all of us as homo homo sapiens. And the fact that Trump for a long time, 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, 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 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 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, who knew who felt desperate, who felt like the Democratic Party was not giving them what they needed. And now the Republican Party certainly is not. And so they will be looking to alternatives. 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 Tolarico. Does this hand the race to James Tolarico? Or is Texas read enough that it just doesn't really matter? I don't know, man. Ken Paxton was impeached by the Texas House. People in Texas don't like Republicans in Texas don't. 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 Salarico 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. I know. I think I just have Texas Democrat Senate trauma. Oh, of course. Rightfully so. But I mean, Ken Paxson is the worst possible candidate you could run against James Salarico. I mean, he is someone who, you know, who's been convicted of bribery. I mean, the guy has the spot-iest 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 liked John Cornyn, though they did. But they think this could be the race. This could be the ballgame. And it's all Trump's fault. 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

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casper.com. Well, last time, that's C-A-S-P-E-R-com and save up to 30% on the mattress you deserve. Here's what else we're following today. 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. Inspiring.

No, we will not be sanewashing 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. We're in final stages of Iran. We'll see what happens. Well, did they have a deal or are we going to do some things there? I don't believe that won't happen. 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 a tax, 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. The 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, Raou Castro, as the Trump administration escalates, on the island. The indictment was related to Castro's alleged role in the shootdown 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. A warrant issued for his arrest, so we expect that he will show up here by his own will or by another way. 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, an officer Daniel Hodges of D.C. Metropolitan Police alleged in their suit that the funds 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. We don't know any of the details of that settlement fund. 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 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. 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 L.A. 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 Tignataro, Todd Glass, Apana Natrilla, Never Have I Evers, Purna Jaganathan, and more. Get tickets at crooked.com slash events. And if you're not in L.A., 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 Tudaloo 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, Water Day is also a nightly newsletter. Check it out and subscribe at crooked.com

slash subscribe. I'm Jane Koston 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. Water Day is a production of Crooked Media. Our show is produced by Caitlin Flummer, Emily 4, Erica Morrison, and Adrian Hill. Our team includes Haley Jules. Jones, Greg Walters, Matt Berg, Joseph Dutra, Johanna Case, and Desmond Taylor. Our music is by Kyle Murdoch and Jordan Cantor. We had helped today from the Associated Press. Our production staff is proudly unionized with the Writers Guild of America East.