Today, Explained

Trump enters his flop era

26 min
Jun 3, 2026about 1 month ago
Listen to Episode
Summary

This episode examines President Trump's recent string of political and policy setbacks, including the collapse of a $1.776 billion 'anti-weaponization' slush fund, stalled Iran negotiations, failed legislative priorities, and cultural missteps like a poorly-received 250th anniversary concert. White House staff and allies describe the administration as being in a 'funk,' with the Iran conflict consuming presidential attention and overshadowing potential wins like prescription drug cost reduction and Trump accounts for children.

Insights
  • Political settlements with personal legal implications can backfire when they lack guardrails; the slush fund's undefined eligibility criteria (potentially including January 6th participants) unified Republican opposition despite initial legitimacy
  • Foreign policy crises can paralyze domestic legislative agendas; Iran negotiations consumed so much presidential bandwidth that marquee initiatives stalled and messaging opportunities were lost
  • Economic anxiety (gas prices, grocery costs) undermines policy wins with voters; Trump accounts and drug pricing initiatives polled well but couldn't compete with cost-of-living concerns
  • Cultural capital erodes quickly; the administration's early momentum with celebrities and institutions reversed when political polarization intensified around controversial initiatives
  • Rhetorical positioning for foreign negotiation (appearing indifferent to gas prices) creates liability in domestic politics; soundbites intended for Iran became Democratic campaign ammunition
Trends
Institutional resistance to executive overreach; Republican lawmakers and federal courts blocked controversial Trump initiatives despite party alignmentPoliticization of cultural institutions; Kennedy Center renovation and anniversary concert became partisan flashpoints rather than unifying eventsVoter prioritization of cost-of-living over policy achievements; messaging disconnect between White House wins and household financial pressuresStaff morale and internal dysfunction signaling policy stagnation; 'funk' descriptor from White House sources indicates organizational malaiseCelebrity and cultural figure depoliticization; performers withdrawing from administration-aligned events citing excessive politicizationLegislative gridlock despite unified government; Senate procedural rules and institutional norms limiting executive agenda advancementMedia narrative management challenges; White House blaming press for not highlighting wins while facing structural messaging obstacles
Topics
Anti-Weaponization Slush Fund SettlementIran Conflict and Strait of Hormuz NegotiationsLegislative Agenda Stalling (Save America Act, Housing Bill, Security Funding)Prescription Drug Cost Reduction (TrumpRx)Trump Accounts for Children (Generational Wealth Initiative)January 6th Pardon and Reparations ControversySenate Filibuster and Parliamentarian RoleKennedy Center Renaming and Renovation250th Anniversary Concert Lineup CollapseGas Prices and Cost-of-Living CrisisMidterm Election Strategy and GerrymanderingWhite House Staff Morale and Organizational DysfunctionIRS Audit Immunity for Trump Family and BusinessesRepublican Party Internal DivisionsTrade Deals and Peace Deals
Companies
Department of Justice
Negotiated settlement with Trump's personal lawyers on tax return disclosure lawsuit and slush fund
IRS
Subject of Trump's $10 billion lawsuit over tax return disclosure; settlement includes audit immunity provision
New York Times
Leaked Trump's tax returns, triggering the lawsuit that led to the slush fund settlement
Kennedy Center
Subject of Trump's attempted renaming and renovation blocked by federal court
People
Shelby Talcott
Discussed the $1.776 billion slush fund fiasco and its origins in Trump's IRS lawsuit
Megan Messerly
Reported on White House 'funk,' Iran stalemate, legislative gridlock, and failed cultural initiatives
Todd Blanche
Testified before Congress that DOJ will not pursue the slush fund; negotiated original settlement
John Thune
Blamed by Trump allies for legislative stalling due to protecting filibuster and Senate procedures
Elizabeth Macdonough
Trump called for her replacement; criticized by administration for allegedly favoring Democrats
Victor Wembenyama
Referenced in opening segment about NBA Finals and flopping analogy for Trump's setbacks
Scott Bessent
Promoted Trump accounts initiative for children and generational wealth building
Sean Ramos
Hosted the episode and conducted interviews with White House correspondents
Quotes
"We hold the world ransom for $1.776 billion."
Host (opening segment)Early in episode
"Pretty much everyone is in a funk... the White House being sort of stuck in this quicksand of Iran."
Megan Messerly (paraphrasing White House source)Mid-episode
"I'm here to bring them together with music. I'm not into politics. I don't have anything to do with circus."
Concert performer (declining to participate)Concert segment
"Okay, these Trump accounts are great, but like, I'm being crunched right now by the cost of gas, by the cost of my groceries."
Megan Messerly (paraphrasing voter sentiment)Messaging challenges segment
"We do have things we're doing... but that is all getting overshadowed right now by Iran."
Megan Messerly (summarizing White House position)Wins vs. losses segment
Full Transcript
The NBA Finals tip off tonight. The New York Nicarabaccos have a shot at winning their first championship since 1973, if they can defeat the 7.5 foot Frenchman Victor Wembenyama and his San Antonio Spurs. Nowhere to be seen though, last year's champs, the Oklahoma City Thunder, undeniably elite, but also hated on in just about any city outside Oklahoma because of flups. For those of you who aren't familiar, flopping in the NBA is basically taking a dive. You put up a shot and then on your way back down you fall to the ground in hopes that the ref calls a foul and gives you the opportunity to score a few extra points. And in this particular regard, the Oklahoma City Thunder have a lot in common with the President of the United States at the moment. Not only have they both taken some huge L's in recent weeks, but on Today Explained from Vox, Donald Trump has officially entered his flop era. Support for the show comes from Dell. Remember Dell? Dell PCs with Intel inside are built for the moments you plan. Still, and the ones you don't. Still, they're there for those late night study sessions when you get to the cafe and there's no outlets, all that stuff. Dell is built to adapt to you. It's built with long lasting batteries, you're not scrambling for an outlet, and built in intelligence that makes updates around your schedule, not in the middle of it. And technology built for the way you work at dell.co.uk forward slash Dell PCs built for you. Support for the show comes from Odoo. Running a business is hard enough, so why make it harder with a dozen different apps that don't talk to each other? Introducing Odoo. It's the only business software you'll ever need. It's an all-in-one, fully integrated platform that makes your work easier. CRM, accounting, inventory, e-commerce and more. And the best part? Odoo replaces multiple expensive platforms for a fraction of the cost. That's why over thousands of businesses have made the switch. So why not you? Try Odoo for free at odoo.com. That's odoo.com. We hold the world ransom for $1.776 billion. Today explained here with Shelby Talcott, who's the White House correspondent for SEMIFOR. Shelby, this whole $1.8 or $1.776 billion slush fund fiasco, easy to forget. It kind of started in a legitimate place. Can you remind us where that was? Yeah, so this all started back in January when the president filed a lawsuit against the IRS. He was seeking, I think it was $10 billion in damages over the disclosure of his tax returns. He had also filed a few other claims. And so this was essentially the culmination of that because the Justice Department decided, well, we don't really want to defend the government. So instead, we're going to work with the president's personal lawyers to sort of come to an agreement. And this slush fund, if you will, was the culmination of those lawsuits and what came from those conversations. Someone leaked the president's tax returns to the New York Times. They showed I pay a lot of tax. So the president had a legitimate grievance. Then of course he immediately transmutes this legitimate grievance into something that feels a little lopsided, a $10 billion lawsuit against the government that he runs in which he pits his personal lawyers against Todd Blanche eventually, who is also his former personal lawyer. What pushes the president to settle this lawsuit with himself? Well, I think that he decided that this deal where you have a huge amount of money that is going to go to people who argue that they've been politically persecuted by the government is a good deal because remember that is exactly what he believes as well. This is a persecution of a political opponent. This was never supposed to happen in America. All thing is a witch hunt. It's a disgrace. After he lost the 2020 election, he had a number of lawsuits. He has not stopped talking since then that those were persecutions by the prior administration. So for him, this sort of agreement is personal in a way, I think. By the way, that election was totally rigged. Tell us how this anti-weaponization slush fund was meant to work in theory. It was essentially taxpayer funded fund and it was supposed to come from this account that was going to be overseen by a board of five people. This board of five people were going to decide who had been politically persecuted by the government and then there would be payouts. Pretty incredible setup for January 6th. Other perhaps defenders, allies of the president. Do we have any idea how long this fund was in the works or where it came from? How it originated? The president's idea? Yeah, so I think it was the idea of his legal team of everybody involved. The president obviously signed off on it, but it was a really unusual situation because as you said, there were not really many guardrails about who could theoretically benefit from this fund. Simple question. Will individuals who assaulted Capitol Hill police officers be eligible for this fund? And they wouldn't necessarily rule that out. As was made plain yesterday, anybody in this country is eligible to apply if they believe they were victim of opposition. When we were talking to administration officials, they said, well, there's going to be this board and the board is going to decide who qualifies for this fund. And so this really raised concerns among even Republican members of Congress too for a variety of reasons. One being the January 6th riot is still a very contentious issue within the Republican party. The president has, I think, embraced the rioters, as you saw in his first day of office, when he issued all of those pardons. So this is January 6th. These are the hostages. Approximately 1,500 for a pardon. Yes. Full pardon. But a lot of Republican lawmakers are still very uncomfortable with that reality. And so you saw kind of that tension within the Republican party start to really explode. Look, under what circumstances would it ever make sense to provide restitution for people who were either pled guilty or were found guilty on a court of law? This is just stupid on stilt. And it really, it was blowing everything up on Capitol Hill. There were, they couldn't get anything passed essentially because Republicans were so perturbed by this agreement. But it was also over the fact that we're really close to the midterms, quite frankly. And this is a tough road for Republicans. And so there were lawmakers who were just simply concerned because this is a nearly $1.8 billion fund that is taxpayer funded. And it comes at a time when the economy is at the top of mind for voters. And so there was an argument to be made from lawmakers of, is this really the right time to be pushing something like this when voters are asking, well, why is my gas so high? Why are my grocery bills like this? So what actually derails this fund ultimately? Is it that Republican opposition or is it the legality constitutionality of the fund itself? A little bit of both. So there were lawsuits, this was going through the courts last Friday, a judge ruled essentially paused the fund and said, you can't move forward right now with distributing the money from this fund. And I think lawmakers initially thought, well, this is great. This is going to kind of solve our problem. But they were still pushing. And really, the president and his advisors met and realized that this was extremely contentious, that lawmakers were not letting go of this. This was also going to go through the courts. And there were people inside Trump's orbit, I think, who just thought it wasn't worth it effectively. And so the president had a conversation earlier this week with some of his team and ultimately decided that they were not going to pursue this fund. Is it really, really dead or is it just dead for the moment because it's so incredibly unpopular? Do we know? That's the big question. So initially, the DOJ had issued a statement saying that they were going to comply with this court order that had come down on Friday. But the court order lasts essentially until I think mid June. And so the question was still, OK, well, does complying with the court order mean it's dead? A lot of people said it doesn't. I think I agree with that. But then acting attorney general Todd Blanche on the Hill yesterday was specifically asked, are you going to pursue this? Like is this over? And he said, we are not moving forward with the fund period. But he also said, I think there'll be a transcript to what I say here so that will be right. So the question I have is, there's still that court situation going on. And so are we going to see the DOJ formally file something to the courts saying it's dead? And I think that is when people who are still concerned about this will say, OK, finally, we can put this to rest. I mean, one sign that this might not be completely dead is that one part of it, a part of it that we haven't really discussed thus far, is very much still alive, which is this idea that Trump and his family and his businesses are immune from IRS inquiry. Yes. And actually, Todd Blanche was asked about that specifically. And he said that the only part of this settlement that the Justice Department was not planning to enforce was going to be this nearly $1.8 billion fund. So that indicates that every other part of the settlement that the Justice Department came with, decided on with the president's personal lawyers, including that provision that will bar the IRS from auditing the president, his family, his business, that stands. Which I guess it remains to be seen if that in and of itself is legal or not. Correct. And I also think when I think about this in terms of, OK, will this satisfy Republicans? It's not going to satisfy Democrats. But will it satisfy Republicans? I think yes, because I think their main concern was this nearly $1.8 billion slush fund. They don't particularly mind the rest of it. So they're going to take the win and probably give the president something back in return, get something passed and move on. OK, that was the one big, beautiful flop of the week. But there's a bunch of other ones that we're going to get into when today Explained returns. Support for the show today comes from select quote. 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You can save more than 50% on term life insurance at select quote.com slash explained today. If you want to get started, that's like quote.com slash explained. Support for the show comes from Dell. Remember Dell? Dell PCs with Intel inside are built for the moments you plan. Still, and the ones you don't still. They're there for those late night study sessions when you get to the cafe and there's no outlets, all that stuff. Dell is built to adapt to you. It's built with long lasting batteries. You're not scrambling for an outlet and built in intelligence that makes updates around your schedule, not in the middle of it. Find technology built for the way you work at Dell.co.uk forward slash Dell PCs built for you. Support for the show comes from Odoo. Running a business is hard enough. So why make it harder with a dozen different apps that don't talk to each other? Introducing Odoo. It's the only business software you'll ever need. It's an all-in-one fully integrated platform that makes your work easier. CRM, accounting, inventory, e-commerce and more. And the best part? Odoo replaces multiple expensive platforms for a fraction of the cost. That's why over thousands of businesses have made the switch. So why not you? Try Odoo for free at odoo.com. That's odoo.com. Mr. President, do you have any reaction to today's play being named the best news show? Wow. I didn't know that. You're telling me now for the first time. My name is Megan Messerly and I am a White House reporter at Politico. And you recently wrote for Politico about how the president and his administration's kind of in a funk and not just the slush fund fiasco we just talked about. So remind us how else we're seeing this funk for those who have disassociated. We are now three months, more than three months into the Iran war. And this is just not going anywhere anytime soon. We have seen the president over the last week. We can half now say that he sees close on a deal to extend this ceasefire with Iran that still has not come through. We're getting what we want slowly. They're very tough negotiators. It takes a long time. I'm in no hurry. When negotiating, whether we make a deal or not, makes no difference to me. There was this two-hour situation room meeting on Friday. Nothing came out of that after two hours. And so the White House really can't figure out its path forward here, right? Talking to folks in and around the White House. They just want to find a sort of face-saving way out of this war, right? But they have been unable to do that. They've been unable to get Iran to agree to something that would open the Strait of Hormuz and get us out. And in the meantime, everyone's just very over it. And according to my reporting, that's including staff inside the White House who one of my sources described to me and said, pretty much everyone is in a funk, used that word funk, which was always, always fun. And described it as sort of the White House being sort of stuck in this quicksand of Iran. Is there like a legislative funk too with this administration? Because it doesn't feel like we're getting anything done. Yeah. And that was one of the big things that I was talking to folks about for this story is this idea that Iran has really taken up so much of the president's time that it is in some ways distracting from some of these other priorities. And that includes the president's legislative agenda. Of course, some allies I spoke with also blamed that squarely on Senate Majority Leader John Thune and said, you know, Thune is being too much of an institutionalist protecting the filibuster, you know, the president has called for firing the Senate parliamentarian. Shockingly, Republicans have kept the very important position of quote, parliamentarian in the hands of a woman, Elizabeth Macdonough, who was appointed long ago by Barack Hussein Obama and a vicious lunatic known as Senator Harry Reid, who ran the Senate for the Democrats with a quote, iron fist. Over the years, she has been brutal to Republicans, but not so to Democrats. So why has she not been replaced? That has not happened yet either. And so you have a very frustrated Trump, but a frustrated Trump who has, you know, rhetorically turned the screws a bit on Thune, but really hasn't, you know, put the full force of pressure on Thune to get his legislative agenda through. And we should say that includes things like the president has talked a lot about the Save America Act, right, an elections-focused piece of legislation. That's one of his top legislative priorities. It's called the Save America Act. We've changed your name. It's the Save America Act. And the Democrats are against it. I heard one of them say, we will stop the Save America Act. No, we're trying to save America. There's this housing bill that includes this institutional investor ban that he wants to see across the finish line. And then, of course, he wants to see security funding for his ballroom slash bunker. This will be the entrance into the ballroom. The ballroom will be right here. This is a glass, beautiful glass tunnel, beautiful tunnel that goes right into the ballroom. Ballroom's right there. Pretty good, right? I mean, with the Iran War in this sort of quagmire, especially coming from a president who rallied against the Iraq and Afghanistan wars with gas prices where they are, with the president constantly trying to gas like the American people into believing that somehow the Iran War is good for them and that high gas prices even are good for them. It feels like he doesn't care about the midterms, but then there's all the gerrymandering that he's pushing. I mean, which implies that he very much cares about the midterms and his endorsement of candidates. What's your read on what's going on with the president when it comes to the midterms? Yes, it definitely feels like those two things are at odds with one another. I think the way that White House allies view it is, you know, he needs to, the president needs to be able to say, I don't care about the midterms. I don't care about high gas prices because that language is for Iran, right? He's saying like, I'm willing to take this gamble because he needs Iran to believe that he will take the maximalist position, that, you know, he will let gas prices rise however high they need to rise in order to not deal with that, right? So White House allies would say that that's a negotiating tactic. On the flip side, those are now sound bites that Democrats can run in every single ad across the country. I don't think about Americans financial situation. I don't think about anybody. We're fighting wars. We can't take care of daycare, Medicaid, Medicare, all these individual things. So, you know, what might be helpful rhetorically with Iran is not helpful rhetorically with Republicans as, you know, they're fighting it out in these really key midterm races. Tough spot he's in. It feels like it's such a tough spot that even the things that should be easy wins, like a sesquicentennial concert on the National Mall or whatever, are like big L's right now. You can't even like land a Millie Vanilly booking. What is going on with this concert? Yeah, it's been really fascinating to actually see even conservative commentators come out and say like, first of all, the folks that were slated for this lineup to your point, Millie Vanilly and others, you know, these are not like, you know, the pop culture stars of today. These are pop culture stars of, you know, three decades ago. So there was that to begin with. And then legitimately like vanilla ice. Ice, ice baby. Oh my stop. Right. Exactly, exactly. And what we're seeing is even some of those folks now pulling out and saying, hey, you know, we were interested in sort of celebrating America's 250th anniversary, but this is far too political for us. This is not what we wanted. This is not what we signed up for. This is not what I signed. I'm here to bring them together with music. I'm not into politics. I don't have anything to do with circus. And to me and many of the folks that I spoke with, this is just such a deviation from where we were at the beginning of the president's term last year when he was just really taking the culture by storm. He was, you think about, he was just, you know, steamrolling these law firms and Ivy League institutions. And you've seen other pop culture figures come on board to the president's agenda like Nicki Minaj. I am probably the president's number one fan. This is not that, right? This is a moment where the president wants to be taking a victory lap and yet he's, you know, stuck in this quagmire that is Iran, one that he desperately wants to get out of. And while we're on concerts, he even lost the Kennedy Center? Yeah. I mean, this has been one that has been, you know, near and dear to the president for months now. His fight to rename it the Trump Kennedy Center and this, you know, planned massive renovation of the center all put on hold by a federal court last week. We saw the president take to true social to express his sincere displeasure at that decision. Unfortunately, Judge Cooper and the radical left would rather see it die than have President Trump transform it into something that everyone could be proud of. But just another loss in this sort of string of challenging circumstances for the White House right now. Do they have any wins that they should be celebrating right now that they could be parading in front of the American people? So some White House allies I spoke to said, you know, this is the challenge is that it's not like they don't have any wins. And the White House as well, this was their pushback to me in the story was we do have things we're doing. For instance, their efforts to reduce the cost of prescription drugs through TrumpRx, the coming launch of Trump accounts for millions of children, Treasury Secretary Scott Besant, you know, was was on the road last week in California and elsewhere, touting these investment accounts right that are supposed to sort of build generational wealth for the next generation. For the next four years, every child getting $1,000 put in an index fund and their Trump account, they're going to learn about the markets, their parents going to learn about it. And the president has done peace deals, trade deals and tax deals. But I think this could be his most enduring legacy. But that is all getting overshadowed right now by Iran. And so the White House blames the media for not doing more to sort of highlight these things. But ultimately, I think the challenge, and this is what I hear when I'm sort of talking to regular voters is, okay, these Trump accounts are great, but like, I'm being crunched right now by the cost of gas, by the cost of my groceries when I'm buying ground beef. And it's, you know, nine, $10 a pound. So like this is these wins are great. And it's not that the American people, you know, that polling is, you know, very high around both of these issues, drug prices and these Trump accounts. But when the pressing concern is putting food on the table and, you know, making ends meet and paying the bills, that has been sort of cold comfort. And that sort of exposes some of the challenge of the White House's efforts to message here. Do you think watching some like half naked men brutally beat the living daylights out of each other on the South Lawn will make the president feel better on his birthday, no less? You know, the president is a longtime fan of the UFC. And we are certainly seeing him celebrate his 80th birthday, which is the day of the UFC fight in accordance with that. You know, the president is sort of this mercurial figure and something like that really could, you know, raise his mood and honestly produce sort of a policy breakthrough because he has been stuck for so long talking to allies. Like I think they think that if the president, you know, gets a win, that could sort of put them back on this track to passing the president's agenda. And that could be a policy win or it could just be a sort of, you know, triumphant UFC fight on the White House lawn, right? Sometimes that's all it takes. Yep. Megan, the writer Politico is where you can find they're pretty much in a funk Trump's agenda hits a summer stall. Earlier in the show, you heard from Shelby Talcott, who writes about the White House for semaphore. I'm Sean Ramos from the show is made by Kelly Wessinger and Dustin DeSoto. I'm an Al-Sadhi edited Gabriel Dunatab was on facts and David Tadashore and Patrick Boyd were on the mix. This is today explained. I see why am I. Del PCs with Intel inside are built for the moment you plan and the ones you don't. For the time you forgot your charger at the gate passengers, we are now on our initial ascent or when you're bouncing between projects like a ping pong ball. We build PCs with long lasting battery life so you're not scrambling for a charger and built in intelligence so you can stay focused on whatever you're doing. Dell Technologies built for you. Dell.co.uk forward slash del PCs.