Today, Explained - Trump's other big breakup

Episode Date: June 10, 2025

President Trump recently blew up his alliance with the conservative legal group that helped him remake the judiciary. But the group’s leader is already moving on. This episode was produced by Gabrielle Berbey and Miles Bryan, edited by Jolie Myers, fact-checked by Laura Bullard and Victoria Chamberlin, engineered by Patrick Boyd and Andrea Kristinsdottir, and hosted by Sean Rameswaram. Listen to Today, Explained ad-free by becoming a Vox Member: vox.com/members. Transcript at vox.com/today-explained-podcast. Leonard Leo, co-chairman of the Federalist Society board of directors. Photo by Nordin Catic/Getty Images for The Cambridge Union. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Breakup-wise, all the attention is on Donald and Elon. I mean, my mind is a storm. 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, Fed Soc. We turn now to Truth Social. Truth Social! The U.S. Court of International Trade incredibly ruled against the United States of America on desperately needed tariffs, but... I was new to Washington, and it was suggested

that I use the Federalist Society as a recommending source on judges. I did so openly and freely, but then realized that they were under the thumb of a real sleazebag named Leonard Leo, a bad person who, in his own way, probably hates America and obviously has his own separate ambitions. If allowed to stand, this would completely destroy presidential power. The President of the United States must be allowed to protect America against those that

are doing it economic and financial harm. Yikes! That's on Today Explained. Thank you for your attention to this matter. This is Peter Kafka, the host of Channels, the show about what happens when media and tech collide. This week I'm talking to Jay Graber, the CEO of Blue Sky. That's the increasingly popular social network that's also kind of a science experiment.

Blue Sky is really part of this moment where me and other people are all saying, let's preserve these early principles of the open web and let's bring that back for the next generation of applications That's this week on channels wherever you get your favorite podcasts Mr. President, do you have any reaction to today's play being named the best new show? I didn't know that I just 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.

David French, New York Times columnist. Okay, David French, are you now or have you ever been a member of the Federalist Society? 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, I 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. I mean, and maybe one of the biggest changes or one of the most conspicuous changes is that Fed Soc has become an enemy of the president of the United States.

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 Fed Soc judges and justices. Today I am keeping another promise to the American people by nominating Judge Neil Gorsuch. Neil Gorsuch is a 49-year-old federal judge, member of the Federalist Society. And central to the president's selection of Judge Brett Kavanaugh last night

was the Federalist Society. Is it your testimony that you don't know what the role of the Federalist Society was in your selection? My experience and my personal experience and what I know is that Mr. that President Trump made the decision. So by the time the election challenge runs or rolls around, he's got three members of the Supreme Court that he's nominated. Who are all members of Fed Soc?

I believe so. Probably all affiliated at some point, been a part of Fed Soc events. And then dozens of appellate judges, I think more than a hundred district court judges, and none of them, zero of them, helped him try to steal the election. Out front tonight, the breaking news this hour, Supreme Court moments ago speaking

and flat out rejecting President Trump's last ditch effort 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. From that point forward, you began to see this drifting apart between sort of Fedsock 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. But you know, you mentioned a whole host of issues here where FedExoc 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? 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 Fed Soc. But like I said, people like me who'd been watching this for a very long time, we're not wondering if this was going to happen. We're 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.

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? 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 most powerful recruiter in the world, the conservative pipeline to the Supreme Court, less kindly perhaps, but just as much emphasizing your influence, the judicial puppet master. I suspect the Federalist Society and lots of other groups and Americans will 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, in helping to foster a robust 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, 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 Fed Soc capitulated. And if you know anything about Fed Soc 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.

Do you think Donald Trump didn't realize that? Oh, I don't think he realized that at all. You know, 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 disagree with them, 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 and the Fed Soc with this like question, what, what's going on? Why is this happening? And I totally understand his bafflement, his bethuddlement, 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.

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? 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. So 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, serious establishment conservatives, Trump 2.0, often mega 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 Third 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 going to 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.

Aha. 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 wanna be replaced by some sort of MAGA figure. Matthew 16

Right. Because most judges, unless there's some 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. Matthew 16 Yes, I do. It is famous only amongst lawyers and it is a song by, 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. I was anointed by the president, a revelation told that I was heaven sent. The Senate in its wisdom wreck did their consent. Appointed forever. David French, opinion columnist at the New York Times. Is that a lifetime appointment? No, no, it is not a lifetime appointment. Ha ha ha.

["The New York Times"] All right, 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. Support for Today Explained comes from indeed the 1927 Yankees, the Apollo space program, Ant's, Sean Romm's firm, and Noelle King. There's nothing more powerful than a great team working together.

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with three-day blinds you can head to three-day blinds comm slash explain for their buy one get 150% off deal on custom blinds shades shutters and drapery for a free no charge no obligation consultation you can head to three-day blinds comm slash explain one last time that's buy one get one 50% off when you head to the number 3, d-a-y, blinds.com slash explained. Today Explained is back. I'm Sean Ramos from Frenchies 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 long time 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. Leo's been up to lately or what season two of his podcast would be about? 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. Where'd he get the money? This is an interesting story.

Around 2020 and 2021, he is 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. Oh my God, that guy would have a lot of money, I assume guy.

That person would have a lot of money. 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. That's right. I'm Abe Froman. The sausage king of Chicago. Yeah's right. I'm Abe Froman. The sausage king of Chicago. Yeah, that's me. And Barry Side is actually in Chicago, so the Chicago connection is 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 triplight 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. So when Mr. Powerstrip gives you a billion dollars and says remake American culture, where do you go first? We see Leonard Leo trying to start entertainment projects,

trying to get movies and television shows off the ground. Are these the people behind Passion of the Christ 2? What are they making? 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. Can one stone change the course of history? Cards! Send me your chaplet!

Goliath! 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. 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, is it finding an audience outside of true believers? Is that the idea though, to find an audience outside true believers, or is the idea to just appeal to the faithful?

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 a remake of Dr. Doolittle. He is enlisting people who worked on the Paw Patrol shows. Huh. Yeah, there's a couple other interesting examples that have come out. One is a movie called Pinball.

And honestly, this is straight up my alley. is a movie called Pinball. And honestly, this is straight up my alley. It's a story of a GQ writer in the 70s 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. This probably sounds weird, but I play pinball all the time. Helps me focus. Are you a reporter?

I just have a question about the pinball banter. Somebody keep these damn kids away from me. 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. Is there any way to know that, you know, what you're watching is, you know, I found it kind of compelling. 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, you know, blend into the wallpaper? 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 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. Doolittle. 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. 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 assigning Mel Gibson and John Voight and whomever else as their Hollywood ambassadors in the White House. It feels like they're trying to do the same thing,

but using different means. My fellow Americans and my peers of Hollywood, I recently met with our President Donald J. Trump. I found out I was some kind of ambassador on a tweet, so I was surprised. But hey, I'm ready, willing, and able to be of service in any way I can. 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 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. And 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 comes of that.

Andy Kroll, friend of the show, ProPublica.org. Miles Bryan and Gabrielle Burbae made the show today, congratulations are in order. Jolie Meyers edited, Victoria Chamberlain fact-checked with Laura Bullard who's back, Patrick Boyd, and Andrea Christensdottir never left. On Tomorrow's Today Explained we'll talk about that other breakup. you