Brian Lehrer: Brian Lehrer on WNYC. There's been some significant Trump on trial news in the last few days, notably, the gag order yesterday for Trump continuing to target an assistant to the judge in the New York business fraud case. The judge said Trump was putting the assistant at risk of physical violence. Also yesterday, an architect of the election denial plot in Congress, as you probably heard, became Speaker of the House.

Meanwhile, it's probably no surprise to listeners of the show that the conservative legal movement in the United States is stronger than it's ever been. There is, of course, the conservative majority on the Supreme Court stacked up during Donald Trump's tenure. One man has played a far more significant role in pushing the American judiciary to the right and he's done it far less publicly. His name is Leonard Leo. His reach extends far beyond the Supreme Court.

Decades ago, he knew he would have to go deeper than just those nine justices. He decided that jurists need to decide the right cases brought by the right lawyers, lawyers on the right, and heard by the right lower court judges, and all that would head up to a conservative Supreme Court. Then there's his activism at the state court level. He's the subject of a new podcast called, We Don't Talk About Leonard.

Who else could have uncovered such a fascinating covert political operation but our former WNYC colleagues, Ilya Marritz and Andrea Bernstein, known to you probably for their WNYC podcast series, Trump, Inc. Ilya is currently a fellow at the Nieman Foundation at Harvard. Andrea is reporting at ProPublica. She's also the author of American Oligarchs: The Kushners, The Trumps, and the Marriage of Money and Power. They, along with ProPublica's Andy Kroll, are the co-hosts of the podcast, We Don't Talk About Leonard, from ProPublica and our On the Media. Ilya, Andrea, welcome back to the show to talk about your series and the Trump and House Speaker news. Hey there.

Andrea Bernstein: Great to talk to you, Brian.

Ilya Marritz: Hi, Brian. Great to be here.

Brian Lehrer: Starting with Leonard Leo, we've talked plenty on this show about the Federalist Society so instrumental in putting forward a list of conservative judges for Republican presidents charged with filling an empty seat. What's Leonard Leo's connection to the Federalist Society?

Andrea Bernstein: Leonard Leo, was an early staffer of the Federalist Society. The Federalist Society started out in the '80s as a place for conservative legal minds to gather. Leonard Leo was in law school at the time but became an early fan of the Federalist Society and right out of law school almost. Maybe a few years later, he did a couple of things in between, including getting to know Clarence Thomas at the DC Circuit Court of Appeals and working on Clarence Thomas's confirmation.

Very early on in his career, Leonard Leo went to work at the Federalist Society and was the first person to begin to expand the organization, passed a college or, excuse me, a law school organization of legal scholars, legal minds to an organization of lawyers. He worked there for 30 years. His title, he's still the co-chair, but his title when he left the staff position was executive vice president, but everybody understood him as the major force behind the organization.

Brian Lehrer: I want to play a clip from 2007 when Leonard Leo turns his attention to state supreme courts. This is from your podcast. Here's Leo around that time at a Federalist Society forum.

Leonard Leo: State supreme courts and state courts are an incredibly important part of the American jurisprudential scene. In fact, one can very ably argue, I think, that state supreme courts are, in many cases, where the rubber really meets the road.

Andrea Bernstein: Leo travels around making speeches and moderating forums.

Leonard Leo: Somewhere in the neighborhood of 95% to 98% of all litigation takes place in the state courts. I dare say that many of you in this room when you're practicing law may end up trying or arguing one of your most important cases, if not your most important case, before a state supreme court or in some part of the state court system.

Brian Lehrer: Leonard Leo from around 2007. Ilya, the premise of the series, the title of the series, We Don't Talk About Leonard, is that he's behind the scenes. Was it rare to even find that clip of him saying the quiet part out loud?

Ilya Marritz: I'm really glad you played that clip because I think it actually illustrates his genius, which is he really takes the time to understand the whole system. There's a lot of people in Washington who think that power comes with a title and it can. The Leonard Leo model of power is to really understand systems to think about history on a long arc and to play a patient game.

Leonard Leo has been a conservative judicial activist for more than 30 years. There was certainly a long time in the wilderness or a long time, we could say, when one might question whether his strategy was bearing fruit. What we hear in that clip from 2007 is he's saying, "Look at state courts. State courts are where the vast majority of these important matters are being decided."

When you open the newspaper, if you read about a court at all, it's probably the Supreme Court. That strategy of paying attention to where things really happen and understanding systems, that radiated out across the legal system. I spent a lot of time looking at state attorney general offices. Again, that's an office that maybe you know your state attorney general in the state you live in, but you don't necessarily pay attention to state attorneys general all over, and yet they're hugely influential players.

We come up to today and realize that Leonard Leo has managed to build influence in a lot of places that a lot of people just weren't paying attention to. Andrea and I and Andy, our co-reporter, we thought about Leonard Leo as almost a Robert Moses figure, the man who built many of the highways and parks around New York. He didn't have a fancy title. For decades, many, many, many New Yorkers didn't know who he was.

It was really only once some of the more bruising fights had been played out that his name started to be out there. That, I think, is what is beginning to happen now with Leonard Leo. Yes, that's a roundabout way of answering your question. A lot of people didn't want to talk about Leonard Leo on the record with us. That is why we call this series that. I will say a lot of people were willing to talk on background off the record in some kind of more limited circumstances. That really helped us build this picture of him.

Brian Lehrer: Andrea, is there a liberal or progressive Leonard Leo out there somewhere? Because people might say whether Leo and the Federalist Society and the judges they help to promote to the bench are heroes or villains to any individual American. They have a right to argue their side to try to get their side more empowered. Is there something dark or dirty about this or is this just politics as it's played at the judiciary level? Are there liberal or progressive Leonard Leos out there too?

Andrea Bernstein: We spoke to Caroline Fredrickson, who was the head of the American Constitutional Society, which is a progressive, more left group that set itself up as the liberal response to the Federalist Society. She said, "No, we are court worshipers." Now, this is her saying this, "but we blew it. We did not plan for this. We did not look at this structurally."

She said that she and her allies thought about the court in terms of principles rather than the brass-knuckle ways to get power that Leonard Leo did. One of the things that was striking to us is the ways in which Leonard Leo-- Some of your listeners, I'm sure, have read some of the ProPublica series about Clarence Thomas and Justice Samuel Alito taking trips with these very wealthy donors. Well, one of the things that we learned is that Leo was really the broker for those trips.

It wasn't that he just concerned himself with US Supreme Court justices. He concerned himself personally with state supreme court justices. I know that you did several segments about the recent Supreme Court race in Wisconsin. Well, Dan Kelly, who ran as the conservative candidate, is somebody who's been very close to Leonard Leo. Leo has intervened personally to advance his career.

Just yesterday, North Carolina's State Legislature drew another set of election maps that could give Republicans and Democrats in that state now have seven each Congressional seats. The belief is that these new maps will give Republicans a three-seat advantage. Well, as you know, that is potentially dispositive. That is a direct result of the work of Leonard Leo and his allies who put lots and lots of money into North Carolina dark money to push the court in a more conservative and more partisan direction.

Just back in March, and this comes up in episode 3 of our podcast, We Don't Talk About Leonard, the Supreme Court in North Carolina did something extraordinary, which is they heard a case and ultimately reversed an election-mapping decision that the same court had just made in a democratic iteration. That is the fruit of the kind of work that Leonard Leo has been doing. It spreads not just to the Supreme Court but into state courts and, as we see in a case like this, into politics.

Ilya Marritz: If I could just jump in on that point. Leonard Leo has not gotten in on election denialism per se, right? He hasn't said Donald Trump won the election or anything like that, but being involved in the way that he is in state courts and in these questions about how congressional districts are drawn, there is a real threat to democracy there. There are real questions that people ought to know about. For the most part, they don't.

Brian Lehrer: By the way, Ilya, was the title, We Don't Talk About Leonard, taken from Encanto's We Don't Talk About Bruno?

Ilya Marritz: [laughs] No, but it came up in an early discussion. Those of us like myself who don't have children scratch their heads. I gather that's a very popular movie.

Brian Lehrer: Yes. In our last few minutes, I want to turn to the Trump news. Many people know that the two of you, besides doing the Trump, Inc. podcast with WNYC then, went on to do a lot of January 6th-related reporting for NPR. There was this $10,000 fine that the New York business fraud case judge, Judge Engoron, leveled against Trump yesterday for what the judge felt was threatening, putting at risk the physical safety potentially of the judge's clerk.

I just want to read a couple of these Trump quotes, things that he has said or posted about this clerk, because I wonder if Trump might not even be stoking some anti-Semitism out there with this because that clerk is Jewish. She has an obviously Jewish name. The original Trump quote was with a photo of the clerk with Chuck Schumer and Trump-- This post said, "Schumer's girlfriend," and named her name, "is running this case against me. How disgraceful. This case should be dismissed immediately." He didn't just say that she was biased because she knows Chuck Schumer.

We don't know if she knows Chuck Schumer, if she just posed with the senator from New York when they were in the same room one time, but he didn't just say that. He said that she's running the case. Then again, yesterday, when he came out of the courtroom, he said, "This rogue judge, a Trump hater, the only one that hates Trump more is his associate up there. The person that works with him. She's screaming into his ear almost every time we ask a question. A disgrace. It's a disgrace." He's aiming at her, Andrea, and saying she's not only against him. She's this shady person, who happens to have a very Jewish name, calling the shots rather than the judge calling the shots.

Andrea Bernstein: I'll let people draw their own conclusions about the anti-Semitism there. It's part and parcel of this argument that Trump has been making since the beginning of this case, which is that Tish James is politically motivated to do this because she's a Democrat. The judge has ruled that argument out of bounds early on in the case. This does seem to be fitting with that, that Trump is trying to argue, which is an argument that he's making. I've been in court with him a number of times during the course of this trial.

He comes and he sits. Let me tell you that a lot of the testimony, Michael Cohen accepted, but a lot of it is pretty boring. Spreadsheets. You're looking at the lawyers say, "Let me draw your attention to Line No. 948 and this sheet of this spreadsheet," and he is watching that. What he is doing is he's going out into the hallway and he's saying his thing about how it's so unfair to him, he can't be out in the campaign, which he could be. He's getting all of this media attention. This is part of that.

It's part of the way he's trying to use the trial to boost his image as a political partisan victim, but the judge called him out. He said, "You cannot attack my staff." He put a gag order on Trump for that. Trump found out, had maintained a post about her on his website. Last Friday, the judge fined Trump $5,000. Then this week, Trump said something cute, yesterday as a matter of fact. He said, "Well, the person sitting next to the judge is partisan." The AP reported it. The judge saw it during the course of the testimony.

He did something unusual. He put Trump on the stand, swore him in, and Trump said, "I wasn't talking about her. I was talking about Michael Cohen." The judge in effect said, "I don't believe you. I'm giving you a $10,000 fine," which was double the previous fine. "If you do it again, you face consequences." The judge has already said that Trump faces possible jail time if he keeps it up. This is something that we'll have to keep watching. Trump, I guess, thought he could say something cute and get away with it, and the judge said no. We will see what happens from here.

Brian Lehrer: Ilya, I know you have to jump to your next thing. I have one closing question, which I'll give to Andrea. Ilya Marritz, always great to talk to you. Thank you very much. Andrea, on the new Speaker of the House, I'm going to read a New York Times headline about Mike Johnson. It says, "Johnson played leading role in effort to overturn 2020 election."

It goes on to say, "Representative Mike Johnson recruited House Republicans to back a lawsuit to overturn the results, and he was a key architect of his party's objections to certifying President Biden's victory." I guess the question here is, what if we wind up in the same position again with, let's say, Biden beating Trump next year and Trump making up a rigged election claim? This time, Mr. Johnson is the Speaker of the House and the House has to certify the election like they did on January 6th, or really it took them till January 7th. How much of a threat?

Andrea Bernstein: It's certainly a frightening scenario that the litmus test for getting to be Speaker of the US House of Representatives seems to be that you have to say contra all evidence that the 2020 election was stolen. The one candidate who didn't was knocked out by Trump. That is the sad situation we are in. I can't say we didn't see it coming. You see who's gained power in the House and it is that faction. I would add, just bring it full circle to Leonard Leo, one of the things that we talk about in our podcast is that the Republicans and Leonard Leo in particular have focused so much on these state courts, which very much could be in a position 2024 of making a ruling for Republican or Democrat.

That is a scenario that we should enter with eyes wide open. That is where the country is heading sadly. Now, there is opposition. There is a resistance. We do talk about that in the podcast, so I don't want to say there isn't, but it is certainly alarming. All the people who study democracy certainly say that looking at who gains power in your representative bodies is something that you need to pay close attention to.

Brian Lehrer: Andrea Bernstein and Ilya Marritz now with a new series with ProPublica and On the Media called We Don't Talk About Leonard. Thanks for talking about Leonard with us, Andrea.

Andrea Bernstein: [chuckles] Thank you, Brian.

Copyright © 2023 New York Public Radio. All rights reserved. Visit our website terms of use at www.wnyc.org for further information.

New York Public Radio transcripts are created on a rush deadline, often by contractors. This text may not be in its final form and may be updated or revised in the future. Accuracy and availability may vary. The authoritative record of New York Public Radio’s programming is the audio record.