Trump's other big breakup

Summary

Today, Explained: "Trump's Other Big Breakup"

Episode Release Date: June 10, 2025
Hosts: Sean Rameswaram and Noel King
Network: Vox Media Podcast Network

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1. Introduction: Trump's Rift Beyond Elon

The episode opens with Sean Ramses highlighting the ongoing public focus on Donald Trump and Elon Musk's breakup [00:00]. However, the discussion swiftly shifts to a more profound separation: Trump's strained relationship with the Federalist Society, colloquially known as FedSoc [00:05].

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2. Trump's Breakup with the Federalist Society

Andy Kroll delves into the complexities of this split, emphasizing that Trump's disillusionment stems from FedSoc's influence over judicial appointments. He recounts his initial reliance on FedSoc for recommending judges, only to later perceive them as being controlled by Leonard Leo, whom he labels a "sleazebag" [00:24–00:36]. Kroll argues that Leo's maneuvering threatens presidential authority, asserting, “If allowed to stand, this would completely destroy presidential power” [00:36].

Notable Quote:

“The President of the United States must be allowed to protect America against those that are doing it economic and financial harm.”
— Andy Kroll [00:45]

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3. Judicial Appointments and the Conservative Legal Movement

Kroll provides a historical perspective on FedSoc’s role in shaping the judiciary, noting that Trump had previously relied heavily on FedSoc-backed judges. He points out that despite numerous appointments, FedSoc judges have not supported Trump’s attempts to overturn the 2020 election, ruling against him approximately 72% of the time [03:54].

Notable Quote:

“Conservative legal movement is not what it was then. It is fractured in many of the same ways that the political, the elected Republican world has fractured.”
— Andy Kroll [11:50]

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4. The Supreme Court's Rejection of Trump's Election Lawsuit

The episode highlights a significant judicial event where the Supreme Court dismissed Texas Attorney General Ken Paxton's lawsuit aimed at overturning Joe Biden’s election victory [04:17–04:33]. This decision exacerbates the rift between Trump and FedSoc, as it underscores the judiciary's independence from political pressures.

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5. Leonard Leo’s Expanding Influence into Entertainment

Transitioning from politics to culture, the hosts discuss Leonard Leo's latest endeavors funded by a substantial fortune of $1.6 billion inherited from Barry Seide, a "power strip magnate" [17:53]. Leo is channeling these funds into the entertainment industry to reshape American culture through media projects like the Amazon Prime series "House of David," a remake of "Dr. Dolittle," and the movie "Pinball" [20:12–22:50].

Notable Quote:

“Politics is downstream from culture and that you can win all the elections you want. You can change the Supreme Court. You can start and grow a whole political movement, if you will, talking about the MAGA movement. But if you don't have a cultural influence, you're always losing the war.”
— David French [25:16]

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6. The Strategic Shift: From Judicial to Cultural Influence

David French underscores Leo's strategic pivot from solely influencing the judiciary to embedding conservative values within popular culture. By funding mainstream entertainment, Leo aims to create a lasting cultural impact that aligns with conservative principles, recognizing that political victories alone are insufficient without cultural dominance [24:25–25:16].

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7. Implications for Future Judicial Appointments

Kroll speculates on the long-term effects of Trump's fallout with FedSoc on future judicial nominations. He suggests that Trump may increasingly favor MAGA-aligned lawyers over traditional conservative judges, potentially leading to fractures within the Republican-appointed judiciary [10:12–12:07]. This shift could influence retirement decisions among senior judges, as some may resist being replaced by more ideologically extreme appointees [11:50].

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8. Conclusion: A Fractured Alliance

The episode concludes by reflecting on the deepening divide between Trump and the Federalist Society, highlighting the broader implications for the conservative movement and its institutional structures. The rift signifies a pivotal moment in the interplay between politics and the judiciary, with lasting repercussions for America's legal and cultural landscapes [27:01–27:42].

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Key Takeaways:

• Trump’s Disillusionment with FedSoc: Initially relied on FedSoc for judicial recommendations, but grew resentful due to perceived overreach and lack of support in critical judicial decisions.
• Leonard Leo’s Influence: A central figure in FedSoc, Leo is now targeting cultural spheres like the entertainment industry to expand conservative influence.
• Judicial Independence: Despite numerous FedSoc-backed appointments, the judiciary has frequently ruled against Trump, undermining his strategies to reshape the legal landscape.
• Shift to Cultural Dominance: Leo's new ventures indicate a strategic move to embed conservative values within popular culture, recognizing the limitations of political maneuvers alone.

Notable Quotes:

• “The President of the United States must be allowed to protect America against those that are doing it economic and financial harm.” — Andy Kroll [00:45]
• “Politics is downstream from culture...” — David French [25:16]
• “Conservative legal movement is not what it was then...” — Andy Kroll [11:50]

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This comprehensive summary encapsulates the critical discussions and insights from the "Today's Explained" episode on Trump's significant breakup with the Federalist Society and the broader implications for American politics and culture.

Transcript

[Sean Ramis]

Breakup wise, all the attention is on Donald and Elon.

[David French]

I mean, my mind is a storm.

[Sean Ramis]

But it's not Trump's only breakup of note. There's also his breakup with the Federalist Society, or as it's known to its friends, FedSoc. We turn now to Truth Social, Truth Social. The U.S. court of International Trade incredibly ruled against the United States of America.

[Andy Kroll]

On desperately needed tariffs.

[Sean Ramis]

But.

[Andy Kroll]

I was new to Washington and.

[Sean Ramis]

It was suggested that I use the Federalist Society as a recommending source on judges. I did so openly and freely, but.

[Andy Kroll]

Then realized that they were under the.

[Sean Ramis]

Thumb of a real sleazebag named Leonard Leo, a bad person who in his own way probably hates America and obviously.

[Andy Kroll]

Has his own separate ambitions.

[Sean Ramis]

If allowed to stand, this would completely destroy presidential power. The President of the United States must be allowed to protect America against those.

[Andy Kroll]

That are doing it economic and financial harm.

[Sean Ramis]

Yikes. That's on Today. Explained.

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[David French]

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[David French]

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

[Sean Ramis]

Wow, I didn't know that.

[Andy Kroll]

I just.

[Sean Ramis]

You're telling me now for the first time. Let's just have you start by saying your name and how you'd like us to identify you on the show.

[Andy Kroll]

David French, New York Times Columnist okay.

[Sean Ramis]

David French, are you now or have you ever been a member of the Federalist Society?

[Andy Kroll]

I am not now, but I have been a member of the Federalist Society. I was a member of the Federalist society when I was believe it was either all three years of law school or the first two years of law school. But it was also a very, very, very different time. I think the Federalist Society at the law school at that time when we would have meetings, maybe 10 or 12 people would show up. Definitely things have changed, no question about that.

[Sean Ramis]

I mean, and maybe one of the biggest changes or one of the most conspicuous changes is that FedSoc has become an enemy of the President of the United States.

[Andy Kroll]

So if you're familiar with how the conservative legal movement has interacted with maga, you have seen this coming for a while. You knew this was coming really after 2020, because it's in 2020, after Trump had really stocked the federal judiciary with an awful lot of FedSoc judges and justices. Today, I am keeping another promise to the American people by nominating Judge Neil Gorsuch.

[Gabrielle Burbay]

Neil Gorsuch is a 49 year old.

[Sean Ramis]

Federal judge, member of the Federalist Society, and central to the President's selection of Judge Brett Kavanaugh last night was the Federalist Society.

[David French]

So is it your testimony that you.

[Andy Kroll]

Don'T know what the role of the Federalist Society was in your selection?

[Sean Ramis]

My experience and of my personal experience and what I know is that President Trump made the decision.

[Andy Kroll]

So by the time the election challenge rolls around, he's got three members of the Supreme Court that he's nominated who.

[Sean Ramis]

Are all members of FedSoc?

[Andy Kroll]

I believe so, probably all affiliated at some point, been a part of FedSoc events and then dozens of appellate judges, I think more than 100 district court judges, and none of them, zero of them, helped him try to steal the election out front.

[David French]

Tonight, the breaking news this hour.

[Gabrielle Burbay]

Supreme Court moments ago speaking and flat.

[Andy Kroll]

Out rejecting President Trump's last ditch effort.

[David French]

To steal the election from Joe Biden. Tonight, the Supreme Court has just rejected Texas Attorney General Ken Paxton's lawsuit to overturn Joe Biden's victory.

[Andy Kroll]

From that point forward, you began to see this drifting apart between sort of FedSoc and MAGA. And so then when Trump comes back into office and he doubles down on being Donald Trump, all of this became very, very predictable. Because if the Trump administration's argument dovetailed, say, with their originalist legal philosophy, they would rule for it. But if it was just simply Trump's lawless demands, they were going to reject it. And Trump is baffled by this distinction. I mean, he's baffled by it because the Congressional Republicans haven't drawn this line at all. Not at all. When Trump's demands conflict with conservative principles, they will yield to Trump's demands every time. And the judges and justices have taken the opposite tack to such an extent that Republican nominated judges have ruled against Trump about 72% of the time, which is remarkably close to about the 80% or so of the time that Democratic appointed judges have ruled against Trump.

[Sean Ramis]

But, you know, you mention a whole host of issues here where FedSoc judges have perhaps not given Trump what he wanted. Does the one that finally tips Trump off to start ranting? I guess maybe he's ranted before, but he really goes for it on Truth Social. Does the case study here sort of surprise you?

[Andy Kroll]

No, it doesn't, because what really set him off was striking down tariffs. To the extent that Trump loves a policy, he loves tariffs. I always say tariffs is the most beautiful word to me in the dictionary. And when the, you know, Court of International Trade and then followed up by other judges struck it down, and it was pointed out to him that one of the judges on the Court of International Trade that struck down the tariffs was appointed by him. This he had been ranting about judges in general. Now he got specific. He got specific with Leonard Leo, he got specific with the FedSoc. And but like I said, people like me who'd been watching this for a very long time were not wondering if this was going to happen. We were just wondering when this was, what was going to be the tipping point. Was it going to be a Supreme Court case? Was it going to be a appellate court? Turns out it was Court of Trade that brought us to this moment.

[Sean Ramis]

So Trump gets mad at the judges of this court and also a guy named Leonard Leo, who we have spoken about on this program before. Leonard Leo did not author a decision from this court. Why is he mad at Leonard Leo?

[Andy Kroll]

Well, Leonard Leo has long been sort of a key, not the only key, but a key figure in the Federalist Society and was very much a part of the first Trump administration, working closely with the administration to put forward judges. You've been described by some as the.

[David French]

Most powerful recruiter in the world.

[Andy Kroll]

The conservative pipeline to the Supreme Court, less kindly perhaps, but just as just.

[David French]

As much emphasizing your influence. The judicial puppet master, I suspect the.

[Andy Kroll]

Federalist Society and lots of other groups and Americans who want to weigh in because the Supreme Court is such an important institution in our country, is decisive on so many important issues. So we'll play some role, I'm sure.

[Sean Ramis]

In helping to foster a robust and.

[Andy Kroll]

Discussion and conversation about the role of the court. And so for a Long time, Trump looked at his judicial nominations and sort of waved them like a flag to the American conservative public, saying, look, look, look, look what I did. But the more the American conservative public started loving Trump as Trump versus Trump, as what kind of policy objectives or policy wins he could deliver, the less he started waving these other ideological flags, and the more it became all about him. And so this meant that this marriage was going to be temporary almost from the beginning, unless the FedSoc capitulated. And if you know anything about FedSoc and the people who belong to it and the people who've come up as judges, I knew they weren't going to capitulate. It's just a different culture than political conservatism. It's a very different culture from political conservatism.

[Sean Ramis]

Do you think Donald Trump didn't realize that?

[Andy Kroll]

Oh, I don't think he realized that at all. If you think about it like this, he's had this entire history politically of when Republicans disagree with him, they either fall in line or they're steamrolled. Just steamrolled. And so it's so interesting to me that he actually began that truth social rant that lacerated Leonard Leo in the Fed society with this, like, question, what? What's going on? Why is this happening? And I totally understand his bafflement, his befuddlement, because all of the political people had surrendered, all of them or almost all of them. And so when he turns around and these judges and justices just keep ruling against him, you can understand why I think he would take that as what's going on here. I don't get this. I don't understand this. I've been assured that these were good judges. But when Leonard Leo says good judge, he doesn't mean Trump loyalist. He means honest, originalist. And those two things are very, very different. And so that's where you get to that real tension.

[Sean Ramis]

Do you think this rift that he's had or that he has with the Federalist Society will affect how he appoints judges going forward?

[Andy Kroll]

I think the short answer to that question is yes. The longer answer to that question is heck, yes. So a lot of people were worried about this because they were thinking, okay, wait a minute. Trump 1.0, he has General Mattis as Secretary of Defense. Trump 2.0, he has Pete Hegseth. So you can just do this all day long. The Trump 1.0 early nominations sound ser establishment conservatives, Trump 2.0 often MAGA crazies. Right. So the question was going to be, is this same pattern going to establish itself in Trump 2.0 on judges. And then he appointed to the 3rd Circuit Emil Beauvais, this DOJ enforcer of his, who was responsible for the effort to dismiss the Eric Adams case, caused that early in his term conflict, which a number of even conservative lawyers resigned from the DOJ as a result of this. And so he puts him on the Third Circuit, he's nominated him for the Third Circuit. And a lot of people are now saying, oh, now that's your harbinger right there. Right now the conservative legal movement is not what it was then. It is fractured in many of the same ways that the political, the elected Republican world has fractured. And so there's just a lot more MAGA lawyers now. There's a lot more MAGA wannabe judges now. And so I do think you're gonna see Trump tilting in that direction pretty dramatically. And the interesting thing about this is it might impact the retirement decisions of senior Republican nominated judges.

[Sean Ramis]

Aha.

[Andy Kroll]

Because a lot of these guys who are now old enough to retire were appointed by Reagan or Bush. So you have a layer of Bush appointed judges who might be reaching that age of retirement and they may not want to be replaced by some sort of MAGA figure.

[Sean Ramis]

Right. Because most judges, unless there's some, you know, terrible turn of events and an impeachment process, get to hang out as long as they want. Which you remind us of in your piece in the Times through song Yes I Do.

[Andy Kroll]

It is famous only amongst lawyers and it is a song by an. Oh gosh, what is the name of the group? It might be the Bar and Grill Singers, something along those lines. And it's set to the music of the Turtles, Happy Together. And I believe it's called Appointed Forever. And here's some of the lyrics.

[David French]

I was anointed by the President a revelation Told that I was heaven sent.

[Andy Kroll]

The Senate in its wisdom ranked the consent Appointed Forever.

[Sean Ramis]

David French, opinion columnist at the New York Times. Is that a lifetime appointment?

[Andy Kroll]

No. No, it is not a lifetime appointment.

[Sean Ramis]

Alright, so Trump's wicked mad at the Federalist Society and Leonard Leo. But it may not matter because Leonard Leo is moving on. You might be surprised. Where to though? We'll tell you when we're back on Today Explained.

[Gabrielle Burbay]

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[Sean Ramis]

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[Andy Kroll]

Oh yay.

[Sean Ramis]

Oh yay.

[Andy Kroll]

Oh yay, oh, yay.

[Sean Ramis]

Today explain is back. I'm Sean Ramis from Frenchie's Gone, but we've got friend of the show Andy Kroll. Andy's an investigative reporter for ProPublica who also once helped make a podcast for them called We Don't Talk about Leonard. It was all about longtime Fed Soc VP Leonard Leo. We asked him what Leo's been up to lately or what season two of his podcast would be about.

[David French]

Season two is all about Leonard Leo taking all the lessons that he learned in the trenches of the American legal world and applying them to a whole bunch of other parts of American life, including Hollywood and the entertainment industry. And now he's got more than a billion dollars to spend on trying to accomplish that mission.

[Sean Ramis]

Where did he get the money?

[David French]

This is an interesting story. Around 2020 and 2021, he is, you know, rolling off of his work advising then President Trump on who to put in the courts. And right around the time that he's wrapping up that work, he comes into possession of the entire fortune, $1.6 billion of, I kid you not, the power strip magnate of America.

[Sean Ramis]

Oh, my God. That guy would have a lot of money. I assume guy, that person would have a lot of money.

[David French]

He's a guy. His name's Barry side. No one will have heard of him. And that is very much by design. He has even more so than Leonard Leo operated completely out of the public eye for the entire time that he has been a businessman, industrialist, whatever. You know, it's funny, when I think about him, I just, I can't not think of the Ferris Bueller scene where they talk about, you know, I'm Abe Froman, the sausage king of Chicago.

[Andy Kroll]

That's right. I'm Abe Froman, the sausage king of Chicago. Yeah, that's me.

[David French]

And Barry Seide is actually in Chicago. So the Chicago connection's there. He's the power strip magnate of America. If you look under your desk and you see a power strip or any kind of electrical product that says trip light on it, two piece. That is Barry's side. And the fortune that he amassed selling power strips and all kinds of other electrical supplies and Gadgets and stuff. That money got transferred to Leonard Leo about four or five years ago with essentially the mandate to go out and do whatever Leonard Leo wants to do with the money in service of this larger mission.

[Sean Ramis]

So when Mr. Powerstrip gives you a billion dollars and says remake American culture, where do you go?

[David French]

First we see Leonard Leo trying to start entertainment projects, trying to get movies and television shows off the ground.

[Sean Ramis]

Are these the people behind Passion of the Christ too? What are they making?

[David French]

They're making what they say is more sort of family friendly, wholesome entertainment. But that still appeals to a broad enough swath of folks. So one of them is a show called House of David. It's a series, tells the biblical story of David.

[Sean Ramis]

Can one stone change the course of history? Cowards. Send me your channel.

[David French]

Goliath.

[Andy Kroll]

The premiere for Amazon Prime's House of David series finally delivers on what I've wanted from biblical fiction on the screen for decades. I'm Peter Franzen from Christiangeekcentral.com and Spirit Blade Productions.

[David French]

House of David is a Leo backed entertainment play. You know, I watched the trailer for it. I've watched a little bit of the show itself. Can't say that it necessarily appeals to me. I wouldn't say that we're talking like HBO level television viewing here, but it did hit the top of the Amazon prime streaming list at one point earlier this year. So clearly it's finding an audience. The question is it finding an audience outside of true believers?

[Sean Ramis]

Is that the idea though, to find an audience outside true believers, or is the idea to just appeal to the faithful?

[David French]

Oh, I think it's absolutely intended to appeal to folks beyond the faithful. Leo is too smart to think that you can have the kind of change that he wants. Preaching to the converted, that doesn't get you really anywhere. You're just hardening the folks who already agree with you. And if you look at some of the projects that he's funding, you know, some of them, House of David, it's a biblical story. Like, you kind of get where they're going with that. But then there's, you know, a remake of Dr. Dolittle. He is enlisting people who worked on the Paw Patrol shows.

[Sean Ramis]

Huh?

[David French]

Yeah. There's a couple other interesting examples that have come out. One is a movie called Pinball. And honestly, this is like straight up my alley. It's a story of a GQ writer in the seventies in New York City who makes it his mission to convince the New York City Council that pinball is not a gambling game. Not A game of chance, but it's a game of skill.

[Andy Kroll]

This probably sounds weird, but I play pinball all the time. Helps me focus.

[Sean Ramis]

Are you a reporter?

[Andy Kroll]

I just have a question about the pinball dancer. Somebody keep these damn kids away from me.

[David French]

Pinball was essentially treated like slot machines at that time in New York City. If you think about it for a sec, you realize, oh, maybe this is a story about big government and regulatory overreach, you know, stomping on a beloved pastime. But honestly, I actually, you know, I found it kind of compelling.

[Sean Ramis]

Is there any way to know that, you know, what you're watching is, you know, brought to you by Leonard Leo, or is part of the strategy to sort of just, you know, blend into the wallpaper?

[David French]

That's definitely his modus operandi. I think these movies, these television projects, the other things that he's working on, very much the goal is to try to, say, fund filmmakers or fund studios. It's not going to be Leonard Leo Productions brings you the animated version of Dr. Dolittle. That's just not plausible, credible. There's no way that would work. But if you say it's through the Motion Picture Institute or if you're funding a studio that has a whole bunch of different projects, then I think you can accomplish both things. You can help fund the content that you want, but also doesn't look like, again, this is Leonard Leo Productions coming to your big or small screen.

[Sean Ramis]

You know, it's funny, we started the show talking about this truth social post from the president that calling Leonard Leo a sleazebag, and yet you're talking about his plans in Hollywood. And the one thing it's reminding me of is, like, Donald Trump's ambitions to reshape Hollywood by, you know, negotiating where productions can be filmed abroad or at home or, you know, assigning Mel Gibson and Jon Voight and whomever else as, like, their Hollywood ambassadors in the White House. It feels like they're trying to do the same thing, but, you know, using different means.

[Andy Kroll]

My fellow Americans and my peers of Hollywood, I recently met with our President, Donald J. Trump. I found out I was some kind.

[David French]

Of ambassador on a tweet, so I was surprised. But, hey, I'm ready, willing, and able.

[Andy Kroll]

To be of service in any way I can.

[David French]

The real connection between what Leo's trying to do and what Trump seems to be trying to do here is this recognition. And I think Andrew Breitbart put it best many years ago, the belief that politics is downstream from culture and that you can win all the elections you want. You can change the Supreme Court. You can start and grow a whole political movement, if you will, talking about the MAGA movement. But if you don't have a cultural influence in the way that Netflix does or in the way that iconic filmmakers do or famous actors do, you're always losing the war. Winning the battle maybe, but losing the war. And I think Leo recognizes that. Trump, I think, probably wouldn't put it in such precise terms, but you know, he's a guy who's been around actors in the entertainment industry for a really long time, long predating his political career. So surely he gets it too. Now, I don't know whether that will work. There's a long history of piecemeal efforts to try to make Hollywood more conservative that kind of seem to miss the way culture and art and entertainment work. But again, Leo's got this fortune and he's got 40 years of hard won lessons to bring to this. So it'll be really, really interesting to see what he actually invests in and what, if anything, come to that.

[Sean Ramis]

Andy Kroll, friend of the show propublica.org Miles Bryant and Gabrielle Burbay made the show today. Congratulations are in order. Jolie Myers, edited Victoria Chamberlain fact checked with Laura Bullard, who's back. Patrick Boyd and Andrea Christian's daughter never left. On tomorrow's Today explained. We'll talk about that other break.

[Andy Kroll]

Sam.