Trump enters his flop era

Summary

Today, Explained — “Trump enters his flop era”

Vox | June 3, 2026

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Episode Overview

This episode explores what hosts Sean Rameswaram and Megan Messerly call President Trump's “flop era”—a moment marked by failed policy pushes, legislative gridlock, political backlash, and a string of embarrassing losses. Through in-depth discussions with White House reporters Shelby Talcott (Semaphore) and Megan Messerly (Politico), the episode dissects major recent setbacks for Trump: the collapse of a controversial $1.8 billion “anti-weaponization” fund, the stalled Iran war, legislative futility, culture war stumbles, and plummeting public morale on both sides of the aisle.

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Key Discussion Points & Insights

1. The “Anti-Weaponization Slush Fund” Fiasco

[02:00 – 11:39]

• Origins:

  • The fund began with Trump’s legitimate legal grievance after his tax returns were leaked. He sued the IRS for $10 billion, but as the case wound on, it morphed into a plan involving the Justice Department negotiating with Trump's personal lawyers ("a really unusual situation").
  • Quote (Shelby Talcott, 02:25):
    "This all started back in January when the president filed a lawsuit against the IRS… this slush fund, if you will, was the culmination of those lawsuits."

• How It Was Supposed to Work:

  • A taxpayer-funded account, overseen by a five-person board, to compensate anyone claiming "political persecution" by the government.
  • It raised concerns even among Republicans, especially over the eligibility of January 6 rioters (“They wouldn't necessarily rule that out.” — Shelby Talcott, 05:36).
  • Quote (Sean Ramasubram, 06:43):
    "Under what circumstances would it ever make sense to provide restitution for people who… were found guilty in a court of law? This is just stupid on stilts."

• Mounting Opposition:

  • The fund divided the GOP, hampered Congressional productivity, and became toxic close to the midterms, especially given voter focus on the economy.
  • Legal action led to a judge pausing the fund in court.

• The End (for now?):

  • The White House dropped the fund following the pause order and internal pressure.
  • Quote (Acting AG Todd Blanche, via Shelby Talcott, 09:29):
    “We are not moving forward with the fund, period.”
  • However, controversial immunity for Trump and his family/businesses from IRS inquiry—which was part of the same settlement—remains in place.

2. The Administration’s Legislative & Foreign Policy “Funk”

[14:03 – 19:56]

• White House Morale & the Iran War:

  • The war with Iran drags on with no end in sight, sapping energy from the administration. Staffers reportedly feel “in a funk” and like they’re “stuck in this quicksand of Iran.”
  • High gas prices and White House spin ("somehow the Iran war is good for them") destroy morale and messaging.
  • Quote (Megan Messerly, 15:07):
    “The White House really can’t figure out its path forward here. They just want to find a face-saving way out of this war.”

• Legislative Paralysis:

  • Trump blames Senate Majority Leader John Thune for legislative inertia and rails against the Senate parliamentarian, but hasn’t mounted real pressure.
  • Key bills—like the Save America Act (election reform), a housing bill banning institutional investors, and security funding for Mar-a-Lago—are stalled.
  • Quote (Sean Ramasubram, 17:39):
    “With gas prices where they are, with the president constantly trying to gaslight the American people into believing...that high gas prices even are good for them, it feels like he doesn’t care about the midterms.”

• Midterm Contradictions:

  • Public posturing on not caring about the midterms (“I don’t care about high gas prices, that language is for Iran”) contrasts sharply with ongoing behind-the-scenes tactics: aggressive gerrymandering and endorsements.

3. Cultural and Symbolic Losses

[19:56 – 22:42]

• Sesquicentennial Concert Disaster:

  • An attempt at a major 250th birthday celebration for America falls flat when ‘90s pop acts like Milli Vanilli and Vanilla Ice withdraw over politics.
  • Quote (Megan Messerly, 21:11):
    "I'm not into politics. I don't have anything to do with the circus..."
  • Contrast is drawn with Trump’s previous ability to dominate culture wars and pop culture.

• Kennedy Center Rename Stymied:

  • Another defeat: Trump’s efforts to rename and renovate the Kennedy Center as the “Trump Kennedy Center” hit a legal wall, prompting angry Truth Social posts.

4. What Remains & Attempts at a Win

[22:42 – 25:41]

• Some Actual Policy Wins:

  • Trump RX (prescription drugs), new investment accounts for children (“Trump accounts”), and various peace/trade/tax deals—White House claims these as real progress.
  • Quote (Sean Ramasubram, 23:22):
    “For the next four years, every child getting $1,000 put in an index fund in their Trump account. They’re going to learn about the markets...”
  • However, these wins aren’t breaking through with voters worried about immediate concerns like gas and food prices.

• White House Mood & the UFC Fête:

  • Administration is so desperate for a win that hosting a UFC brawl on the White House lawn for the President’s birthday is raised as a possible morale booster.
  • Quote (Megan Messerly, 24:45):
    “Something like that really could raise his mood—and honestly produce sort of a policy breakthrough because he has been stuck for so long…”

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Notable Quotes & Memorable Moments

• On the Slush Fund’s Absurdity:

  • “Under what circumstances would it ever make sense to provide restitution for people who… were found guilty in a court of law? This is just stupid on stilts.”
    — Sean Ramasubram, [06:43]

• On the White House Mood:

  • “Pretty much everyone is in a funk… the White House [is] stuck in this quicksand of Iran.”
    — Megan Messerly, [15:07]

• Describing Legislative Frustration:

  • “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… put the whole full force of pressure on Thune.”
    — Megan Messerly, [17:03]

• On Failed Pop Culture Outreach:

  • “You can't even, like, land a Milli Vanilli booking.”
    — Sean Ramasubram, [20:14]

• On White House Hopes for a Win:

  • “Something like [the UFC fight] really could raise his mood—and honestly produce sort of a policy breakthrough…”
    — Megan Messerly, [24:45]

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Important Timestamps

• Slush Fund Origins: [02:00 – 03:37]
• Eligibility & Republican Revolt: [04:32 – 06:54]
• Legal & Political Defeat of Fund: [07:42 – 11:39]
• Iran War Quagmire & White House Funk: [14:03 – 15:52]
• Legislative Stagnation: [15:52 – 17:29]
• Flailing Culture War (“flop era”): [19:56 – 22:42]
• Policy “Wins” That Aren’t Landing with Voters: [22:49 – 24:34]
• UFC on the Lawn—Looking for a Win: [24:34 – 25:34]

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Tone & Style

The episode is lively, wry, and direct—leaning into humor about Trump’s dramatic political downturn, but consistently grounding discussion in reporting and policy substance.

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For listeners (or non-listeners): This episode paints a vivid scene of a beleaguered White House, drifting from one headline-grabbing defeat to another, fighting on too many fronts, and failing—at least for now—to regain its narrative or legislative momentum.

Transcript

[Sean Ramasubram]

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[Shelby Talcott]

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[Sean Ramasubram]

We hold the world ransom for $1.776 billion today. Explained here with Shelby Talcott, who's the White House correspondent for Semaphore. 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?

[Shelby Talcott]

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. So Instead, we're gonna 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?

[Sean Ramasubram]

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 DOL 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?

[Shelby Talcott]

Well, I think that he decided that this deal, where, you know, you have a huge amount of money that is going to go to people who argue that they've been, you know, politically persecuted by the government is a good deal, because, remember, that is exactly what he believes as well.

[Megan Messerly]

This is a persecution of a political opponent. This was never supposed to happen in America.

[Sean Ramasubram]

Whole thing is a witch hunt.

[Shelby Talcott]

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 this sort of agreement is personal in a way.

[Sean Ramasubram]

I think, by the way, that election was totally rigged. Tell us how this anti weaponization slush fund was meant to work.

[Shelby Talcott]

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.

[Sean Ramasubram]

Pretty incredible setup for January6. There's 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? Was it the President's idea?

[Shelby Talcott]

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.

[Megan Messerly]

Simple question. Will eligible individuals who assaulted Capitol Hill police officers be eligible for this fund?

[Shelby Talcott]

And they wouldn't necessarily rule that out.

[Sean Ramasubram]

As, as. As was made plain yesterday, anybody in this country is eligible to apply if they believe they were victim weapons. Mr. Transgender.

[Shelby Talcott]

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.

[Sean Ramasubram]

So this is January 6th.

[Megan Messerly]

These are the hostages. Approximately 1,500 for a pardon.

[Sean Ramasubram]

Yes, full pardon.

[Shelby Talcott]

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.

[Sean Ramasubram]

Look, under what circumstances would it ever make sense to provide restitution for people who were either pled guilty or were found guilty in a court of law? This is just stupid on stilts.

[Shelby Talcott]

And it really, it was blowing everything up on Capitol Hill. 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?

[Sean Ramasubram]

So what actually derails this fund ultimately? Is it that Republican opposition, or is the legality, constitutionality of the fund itself?

[Shelby Talcott]

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 know, 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, you know, 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.

[Sean Ramasubram]

Is it really, really dead, or is it just dead for the moment because it's so incredibly unpopular? Do we know?

[Shelby Talcott]

That's the big question. So initially, the DOJ had issued a statement saying that they were gonna 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, okay, 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

[Sean Ramasubram]

forward with the fund, period.

[Shelby Talcott]

But he also said, I mean, I

[Sean Ramasubram]

think there'll be a transcript of what I say here, so that will be in writing.

[Shelby Talcott]

So the question I have is, you know, 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, okay, finally we can put this to rest.

[Sean Ramasubram]

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.

[Shelby Talcott]

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 gonna be this nearly $1.8 billion fund. So that indicates that every other part of the settlement that the just 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.

[Sean Ramasubram]

Which I guess it remains to be seen if that in and of itself is legal or not.

[Shelby Talcott]

Correct. And I also think when I think about this in terms of, okay, 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.

[Sean Ramasubram]

Okay, that was 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. It's never a bad time to start taking your financial future more seriously. And one thing that often gets overlooked in the mix is term life insurance. You know what I mean? But figuring out coverage can feel complicated. How much do you need? What does it cost? And where do you even start? But select QUOTE wants to make things easier and more affordable for over 40 years. Like me, Select Quote has helped more than 2 million Americans secure over $700 billion in coverage. I haven't done that, but I've been around for more than 40 years as of as of late actually. Sounds like I should get some life insurance. Their goal is simple. Help you find a term life insurance policy that fits needs and budget. They do the shopping for you so you can save time and money. And in many cases, Selectquote can give you same day coverage up to $2 million, no doctor's visit required. You can get the right life insurance for you for less and save more than [e-mail] explained. You can save more than 50% on term life [e-mail] explained today to get started. That's SelectQuote.com explained.

[Megan Messerly]

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[Sean Ramasubram]

Mr. President, do you have any reaction to Today Explain being named the best news show?

[Megan Messerly]

Wow, I didn't know that.

[Sean Ramasubram]

I just.

[Megan Messerly]

You're telling me now for the first time. My name is Megan Messerly and I am a White House reporter at Politico.

[Sean Ramasubram]

And you recently wrote for Politico about how the president and his administration's kind of in a fight 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

[Megan Messerly]

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, week and a half now say that, you know, he's, he's close on a deal to extend this ceasefire with Iran. That still has not come through. We're getting what we slowly, very tough negotiators. It takes a long time. I'm in no hurry.

[Sean Ramasubram]

We're negotiating. Whether we make a deal or not makes no difference to me.

[Megan Messerly]

There was this two hour situation room meeting on Friday. Nothing came out of that after, 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, use that word, funk, which is always fun, and described it as sort of the White House being sort of stuck in this quicksand of Iran.

[Sean Ramasubram]

Is there like a legislative funk too, with this administration? Because it doesn't feel like we're getting anything done.

[Megan Messerly]

Yeah. And so that was one of the big things that I was talking to folks about for this story is this idea that, you know, 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.

[Shelby Talcott]

Truth Social.

[Sean Ramasubram]

Shockingly, Republicans have kept the very important position of, quote, parliamentarian in the hands of a woman, Elizabeth McDonough, 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?

[Megan Messerly]

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 whole 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.

[Sean Ramasubram]

It's called the Save America Act.

[Megan Messerly]

We've changed the name.

[Shelby Talcott]

It's the Save America act, and the Democrats are against it.

[Sean Ramasubram]

I heard one of them say, we

[Shelby Talcott]

will stop the Save America Act. No, we're trying to save America.

[Megan Messerly]

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. His ballroom slash bunker.

[Shelby Talcott]

This will be the entrance into the ballroom. The ballroom will be right here.

[Sean Ramasubram]

This is a glass.

[Megan Messerly]

Beautiful glass tunnel.

[Sean Ramasubram]

Beautiful tunnel that goes right into the ballrooms right there.

[Shelby Talcott]

Pretty good, right?

[Sean Ramasubram]

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 gaslight 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. 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?

[Megan Messerly]

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, 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 notch a deal with them. Right. So. 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.

[Sean Ramasubram]

I don'. American financial situation, I don't think about anybody.

[Shelby Talcott]

We're fighting wars we can't take care of daycare, Medicaid, Medicare, all these individual things.

[Megan Messerly]

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.

[Sean Ramasubram]

Tough spot he's in, and 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 Ls right now. You can't even, like, land a Milli Vanilli booking.

[Megan Messerly]

I'm gonna miss you.

[Sean Ramasubram]

What is going on with this concert?

[Megan Messerly]

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, Milli Vanilli and others, you know, these are not like, you know, the pop culture stars of today. These are pop culture stars of three decades ago. So there was that to begin with,

[Sean Ramasubram]

and then legitimately, like, Vanilla Ice.

[Megan Messerly]

Ice, baby. All right, 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. This is not. This is not what we wanted. This is not what we signed up for. Not what I sound. You know, I'm here to, you know, to bring people together with music.

[Shelby Talcott]

I'm not into politics.

[Megan Messerly]

I don't have anything to do with the circus because, you know, 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 store. And 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 presidential 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.

[Sean Ramasubram]

And while we're on concerts, he even lost the Kennedy Center.

[Megan Messerly]

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 planned, massive renovation of the center, all put on hold by a federal court last week, we saw the president take to Truth Social to express his sincere displeasure at that decision.

[Sean Ramasubram]

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.

[Megan Messerly]

But just another loss in this sort of string of challenging circumstances. For the White House right now, do

[Sean Ramasubram]

they have any wins that they should be celebrating right now that they could be parading in front of the American people?

[Megan Messerly]

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 this story was we do have things we're doing, for instance, their efforts to reduce the cost of prescription drugs through Trump rx, the coming launch of Trump accounts for millions of children. Treasury Secretary Scott Bessant, 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.

[Sean Ramasubram]

For the next four years. Every child getting $1,000 put in an index fund in their Trump account. They're going to learn about the markets,

[Megan Messerly]

their parents going to learn about it. And the President has done peace deals,

[Sean Ramasubram]

trade deals and tax deals, but I

[Megan Messerly]

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, yeah, know, nine, ten dollars a pound. So, like, this is, these wins are great. And it's not that the American people, you know, that polling is very higher on 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,

[Sean Ramasubram]

Do you think? I 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.

[Megan Messerly]

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, is sort of this mercurial figure, and something like that really could raise his mood and honestly produce sort of a policy breakthrough because he has been stuck for so long talking to allies. I think they think that if the President 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 triumphant UFC fight on the White House lawn. Right.

[Sean Ramasubram]

Sometimes that's all it takes.

[Megan Messerly]

Yep.

[Sean Ramasubram]

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 Ramasburum. The show was made by Kelly Rose Wesinger and Dustin De Soto. Aminah Al Saadi edited Gabriel Dunatov was on fax, and David Tadashore and Patrick Boyd were on the mix. This is today, explained Icymi.