For the last quarter of a century, an Italian macher from New Jersey has been one of the most powerful people in the United States. If you’re a certain type of nerdy, obsessive, legally inclined conservative, he’s basically Taylor Swift. But most people don’t know who he is because, well, he doesn’t want them to know.
He has never held or sought political office. He does not hail from Silicon Valley or Wall Street. He is not a writer, pundit, or political aide. He rarely does interviews. And yet his influence is hard to overstate. People in power—particularly presidents—trust and listen to him.
I’m talking about Leonard Leo, the animating force behind the Federalist Society and the key node of a growing network of conservative groups aiming to reshape the culture and the country.
Whether you’ve heard of him or not, he has no doubt directly affected your life in some way.
Leo is the person who counseled George W. Bush to appoint Justices John Roberts and Samuel Alito. He had an arguably even greater influence on President Trump. Trump was new to Washington when he first became president. Leo, on the other hand, knew everyone in town. Leo counseled Trump and helped pick and prepare Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett for confirmation.
And that’s just the Supreme Court. Leo has cultivated talent across every level of the judicial system.
Leo understands the levers of Washington. He understands how Congress works, how the press works, and most importantly, how the courts work. He is, in a sense, the architect of the Supreme Court’s conservative majority—the one that overturned Roe v. Wade—which means he has changed American history, for better or worse, depending on your worldview.
Today on Honestly, I ask Leo about all of it: his relationship with Trump and their falling-out (though he disputes this characterization), and how he understands the divide on the right between the old guard like himself and the new characters like Elon Musk and RFK Jr.
I also ask about his so-called dark money groups, a $1.6 billion gift he was given, and the criticism he gets for wielding power and influence of this magnitude.
I ask about Trump’s willingness to defy the courts, if Leo even sees it that way, and if it alarms him. I ask about Trump’s controversial moves like sending accused gang members to El Salvador, and what those choices mean legally. I ask why MAGA has rejected Amy Coney Barrett, and whether gay marriage is settled law—not that I have any vested interest in this one. And most importantly, I ask whether the Supreme Court can remain above the fray.
It was such an original and enlightening conversation that we’re doing something we basically never do: publishing an entire edited transcript of our interview, which comes to some 13,000 words. Paid subscribers can click here to read it all. Or you can just listen and enjoy the edited highlights below. Either way, I hope you find this conversation as fascinating as I did.
Editor’s note: This interview has been edited for clarity; the opinions expressed in this interview are those of the guest’s alone.
On Trump’s political bargain with conservatives:
Bari Weiss: Did Trump have beliefs, or was he outsourcing those beliefs to you, because he knew that you were—to use a Jewish phrase—good at knowing who would and wouldn’t be kosher to a conservative base?
Leonard Leo: Well, as with everything in life, there are oftentimes mixed motives. I do think at some level he chafed at the idea of liberal activist judges. He lived in New York, where there were a lot of problems with crime and the death penalty and other things when he was in the city. The city was falling apart in a lot of different ways. The rights revolution was really wreaking havoc on cities. So I always assumed that it was his experience. We never talked about it, but I always assumed that it was his experience in New York City, with the ravages of this sort of leftist rights revolution in the cities, that kind of caused him to think a little bit about this.
It all became a little more crystallized to me after the election, because the week after he was elected, he summoned me to New York to meet with him, to talk about how we were going to winnow down his list so that he could begin to think about who he would appoint to fill the Scalia vacancy.
And it was at that point that I said to him in that meeting, because I really wanted clarity: Okay, we can winnow this list, but what are your criteria? And I didn’t know what he would say. He could have very easily said, Well, what do you think the criteria should be? But that’s not what he said. What he said was, I want people who are extraordinary in terms of their credentials. Basically out of central casting. Two, I want people who are “not weak.” Then thirdly, I want people who are going to interpret the Constitution “the way the founders meant it to be.”
I will always remember that I didn’t prompt him with that language. That’s what he said. And so that’s how we started talking about the list and getting it down, boiling it down. So at some level, I think he did understand these things, and it was partly a political bargain with the conservative movement.
BW: Of course.
LL: I mean, that’s what politicians do, right? That’s at the very core of the political game and public choice economics and all that kind of stuff. But you know, at some level, I think he did understand that the courts had done damage to our country and something needed to be done about it. And that’s how it all started.
On his goal of “crushing liberal dominance”:
BW: There’s a tape of you going around where you say you want to “crush liberal dominance.” Say a little bit more about that. How’s that war going?
LL: The key word is dominance. And in that sense, the Federalist Society is also in the business of crushing dominance, because the Federalist Society started with a deep-seated belief in the idea that there needed to be a robust dialogue and exchange of ideas about the law.
Now, that’s not to say the Federalist Society doesn’t believe in something, because it has a statement of principles. And I’ve told you what those are. But the concern that caused the Federalist Society to arise was this pervasive left dominance in the law schools that completely snuffed out any of this sort of traditional legal thinking and really made it taboo to believe in that stuff.
On conservatives taking over institutions:
BW: There’s an old Marxist theorist, Antonio Gramsci, who wrote about how the left should focus on infiltrating big institutions. This strategy was later called “the long march through the institutions,” an allusion to Mao’s Long March during the Chinese civil war. In a mirror-image sort of way, do you see yourself as doing something similar?
LL: That’s the approach. So what you do is you look for choke points in society. And the academy was the one the left went for first, which was really smart. Because all the captains of industry, all of the major journalists, all of the major politicians—they’re all going to be going to elite universities, right? You’re going to infiltrate those institutions. You’re going to feed them all this garbage, and then they’re going to come out, they’re going to believe in it, and they’re going to do what you want them to do. So it was a really good approach.
BW: And so the left took the universities. You took the law.
LL: I think we are taking the law. For starters, the courts, the legal policy institutions in our country—those are choke points where lots of really important decisions get made. And every time a decision gets made in the law, in particular in the courts or in some of these legal policy institutions, there are multiplier effects, right?
There are huge effects to every decision because they have far-reaching consequences. Universities are a choke point. Now there are others. And that’s why, as I’ve moved on in my career, you know, I’ve expanded the portfolio to include other things. Corporate suites are major choke points of society and culture, as are private equity firms and banks, production studios in Hollywood.
On his first meeting with President Trump:
LL: He clearly had an agenda. And my initial impression was, “Wow.” I had not met a presidential candidate who was as committed to making the courts issue a big deal, like he did. Now, granted, he had the advantage of a vacant U.S. Supreme Court seat, which other presidential candidates didn’t have, and that’s a big deal. But he was very, very focused on the importance of the president’s power of judicial appointment in a way that I never saw in any other candidate.
On his partnership with President Trump:
BW: From the outside, you had an unbelievably fruitful partnership with President Trump. You get Brett Kavanaugh and Amy Coney Barrett on the Supreme Court. And how many other Trump appointees wound up on the federal bench—it was like more than 200.
LL: Yeah, it’s over 200. I mean, dozens and dozens of, honestly, the most talented, intelligent, conservative, originalist jurists we have ever seen on the federal bench in the last 100 years.
BW: So you’re happy, going back in time?
LL: Yeah. What he did, in transforming the federal courts, is probably the most consequential thing he will ever do as a public official that will last 40-plus years. And if there is a revival in the originalist constitution, if there is a rollback of the administrative state and a federal power, it won’t be because of DOGE. It will be because you have jurists who finally put handcuffs on the administrative state and finally require Congress to do its job and not give away its power. And that will all be in the hands of jurists that he appointed to the bench, enormously consequential.
On his relationship with Trump today:
BW: So you have this productive collaboration with Trump for his whole first term. Then you have a falling-out. What causes a falling-out?
LL: Well, I don’t know if I call it a falling-out.
BW: How would you describe it?
LL: As it’s been reported, he was very upset about a number of people in his administration who he felt had really betrayed him and were succumbing to the left in various ways. Then–Deputy Attorney General Rod Rosenstein, then–Attorney General Jeff Sessions. He felt that I was responsible for Rod Rosenstein’s appointment, which is not actually correct. But that was his inclination. And so we had one exchange about that, but afterward, obviously I continue to be of assistance to the administration. I always had a very simple rule, which is I will do things at the pleasure of a president. And so if they reach out, I will respond. If he wanted help, I wouldn’t have refused it.
He’s got a new administration, and I actually am really glad that he’s built an infrastructure that doesn’t have to involve me directly. My whole goal professionally was to build a network or an infrastructure that could function and survive and thrive without me having to micromanage it. And so really, that first Trump administration was the first time that we really were as intensely involved in building and transforming the federal judiciary.
And there was no guarantee that that would perpetuate itself afterward. And it did. And so I’m actually very happy with the way things are shaking out. The lawyers in his current administration are all very good sort of conservatives who understand, you know, the conservative legal project. And I have every confidence that the judicial selection process will go on.
There’s not as much to do now as there was in the first administration. And there are only several dozen vacancies. But I feel very satisfied that the process has ended up where it is today, which is a new, young, generational shift in terms of who’s doing this work.
On the ideological tensions within the White House:
LL: I think what you’re seeing in the Trump administration, in terms of its appointments and where it’s heading with policy, is really a manifestation of a broader trend that’s occurring both on the right and on the left. On the right, you have these tensions between some traditional conservative ideas about trade, the role of government, foreign policy, and the prominence of social issues in the political agenda.
And that view is now in tension with what I would call sort of the more populist movement within the conservative world. And so what you see in the administration is to some degree an amalgam of these different forces.
On threats against judges:
BW: Over the weekend, the Trump administration sent hundreds of accused gang members to El Salvador, and it justified many of these deportations by pointing to the—at least as far as I know—rarely invoked Alien Enemies Act of 1798.
Stephen Miller is going around on cable news talking about it. Judge James Boasberg blocked the deportation and the White House ignored him. And they didn’t just ignore him. House Republicans, at Trump’s urging, called for the judge’s impeachment. And they still are as of today’s conversation. It got so insane that John Roberts put out a statement, and I’m just going to read it to you.
“For more than two centuries, it has been established that impeachment is not an appropriate response to disagreement concerning a judicial decision. The normal appellate review process exists for that purpose.”
What do you think of this?
LL: Yeah. Well, this is all, for a lot of different reasons, coming from both directions. This is a big mess. So let me try to unpack this. First of all, I’m not surprised this is where the debate is. If we all put on our thinking caps for a minute, for the past two or three years, we’ve had Democrats and leftists all over the country using the I word, impeachment, and talking about criminal convictions of conservative Republican judicial appointees.
You know, sometimes saying that the hospitality—which members of Congress accept in spades—somehow taints the decision-making of these judges. And they’ve been waving around impeachment. They’ve been waving around criminal conviction. We had comments from Senator Schumer on the steps of the U.S. Supreme Court talking about the whirlwind that was going to occur if the court overturned Roe v. Wade, and shortly thereafter, Brett Kavanaugh finds a potential assassin at his doorsteps. So the escalation has been occurring for several years.
On where the pro-life movement goes now:
LL: The pro-life movement is, in my view, at its lowest point in history.
BW: I’m just shocked to hear you say that after Dobbs.
LL: But look at what has happened after Dobbs. You’ve had constitutional referenda in states like Ohio and Missouri, which are deep-red states, that enshrine abortion. So the movement is at a weak point.
BW: Just to clarify it, for people who don’t know about Dobbs, that Dobbs kicks abortion back to the states. And you’re saying the states are deciding in favor of what some call choice, what you would call pro-abortion.
LL: So the pro-life movement is coming into the 2024 cycle in a relatively weak position. Overturning Roe v. Wade was a huge victory for the culture of life. But what do you do now? And how much credibility and reputational capital does a pro-life movement have? And so you’re going into the 2024 cycle with a movement that is trying to find its new voice, and find a new way of doing business.
On the Federalist Society prosecutor who quit Trump’s Justice Department:
BW: I want to ask you a few things very quickly. I’m going to describe a bunch of actions that Trump or the White House has taken, and you just kind of tell me, in the Leonard Leo Court: kosher or not kosher. Sending migrants to Guantanamo Bay. Legal?
LL: Yeah, probably.
BW: Shutting down the southern border to asylum seekers.
LL: Don’t know whether it’s legal or not.
BW: Threatening to take funds from sanctuary cities that don’t cooperate with federal immigration enforcement.
LL: Probably okay.
BW: I want to ask you about Danielle Sassoon. Do you remember that name?
LL: Oh, I know who she is.
BW: Yes, so, member of the Federalist Society. She was the acting U.S. attorney in the Southern District of New York. And she resigned a few weeks ago after she was ordered by the Trump administration to drop the corruption case against New York City mayor Eric Adams. Was she right to resign?
LL: Yes. I think the honorable thing to do when you’re an administration official and you can’t carry out what the administration wants you to do, the right thing to do is to resign. That’s sort of how I think you should do it. And my recollection is that she basically sent a letter to the attorney general saying, look, I’d like to meet with you to discuss this, you know, the Southern District of New York here in the city is a really important U.S. attorney’s office. This is a really important case. I wouldn’t normally bother you, but I think this is one we need to discuss because it has political ramifications. And if you’re not prepared or not willing to have a discussion with me about it, I am certainly prepared to tender my resignation.
That wasn’t, I don’t think, meant to be a slap in the face. I think that’s the honorable thing to do when you think you can’t really pursue the administration’s objectives. And so, yeah, that was the right thing for her to do.
On the January 6 pardons:
BW: The administration, as you know, and as everyone who is listening to this knows, didn’t just pardon six nonviolent protesters in January. They also pardoned people who had violently rioted that day. What did you think of those pardons?
LL: Certainly, if you were pardoned and you engaged in violent behavior, I wouldn’t be in favor of that. I mean, so, anyone who engages in violent behavior, in my view, should not have been pardoned.
On the right’s vilification of Amy Coney Barrett:
BW: One of the things that I see as an early warning sign—maybe not even that early—that things are not necessarily going in the right direction, is when you see parts of the right turning against Amy Coney Barrett, and turning her into a kind of villain, because she caucused recently with the liberal justices. They’re sort of throwing her under the bus, like she’s not pure enough for MAGA loyalists. Where does that go?
LL: Well, first of all, to give credit where credit’s due, I was heartened by the fact that when asked about this, President Trump showed real respect to Justice Barrett and said she was a very capable and smart judge, and that she shouldn’t be criticized. So I thought that was a good signal to his community about where he stood.
I think part of the reason he probably said that was because she is, when you think about it, probably one of the most prominent conservative jurists in the last hundred years of our court. I mean, on every major issue that is of importance to conservatives, be it abortion, religious freedom, the administrative state, the Second Amendment, presidential immunity, separation of powers. She has been a major figure in the conservative jurisprudential tide. So to say that she’s “a rattled law professor” or—
BW: Who called her that again, Steve Bannon or somebody in Steve Bannon’s world?
LL: I don’t remember. So somebody said she was around a law professor and had her head in places where we normally don’t put them. That’s just not—that’s not consistent with who she is and what she’s done on the court. And look, the fact of the matter is, we’ve always seen these small disagreements. And what we’re seeing—we saw in this particular instance with Justice Barrett was a relatively small disagreement over what is really a procedural matter.
On the future of the right:
LL: Just by virtue of my own sort of background, and my training, and what I’ve done my whole professional life, I’m always worried about the rule of law and threats to the rule of law and threats to the dignity and worth of the person by not respecting either sort of traditional cultural guardrails or the Constitution itself.
I’m always worried about that. And I’ve never believed, and never will, that those threats come only from the left. They can just as readily come from the right. So for any good conservative, that’s sort of built into who you are and how you think. So I worry about that a lot.
And there’s good reason to be worried about the sparring that takes place now, because of the environment that we’re in. We didn’t just get to these nasty comments about Amy Barrett because Donald Trump was elected and because the MAGA movement wants certain things out of the Supreme Court. That isn’t the reason why we’re hearing this kind of invective. We’re hearing it because of a broader cultural problem.
Going back now 25 or 30 years, the gloves have been off in the law. The politics of personal destruction, the use of law as a weapon—that’s been around and it’s been used by both sides. And those are now the rules of engagement. So that worries me.
On why the right is better with money:
BW: Who’s your model on the left? You’re saying that your model was created by the left. You’re just trying to imitate it. Who is it? Is it George Soros or somebody else?
LL: Actually, there is no model on the left in the sense that we’re much better than anything they do. Why? Because for every $6 they could spend, I can do it with $1.
BW: Because they’re so few. Because conservatives were so hard up.
LL: Yeah. It’s just we’ve never had as much cash. And honestly, we have truth on our side.
BW: But the point is your side is hungrier.
LL: We’re hungrier. But also, honestly, you know, I think our art, our beliefs are more consistent with the natural order and that makes it easier. That’s a long conversation. But I think that’s true. And the other thing I will say is, we just really do have an incredible pool of talent right now, an incredible pool of talent.
On gay marriage, IVF, and abortion:
BW: Is gay marriage settled law?
LL: [Long pause] Yes. Probably.
BW: Should IVF be illegal?
LL: I mean, I’m against IVF.
BW: I know, but should it be illegal?
LL: Yes, because it’s, in my view, killing of human life.
BW: So should abortion be decided at the state level or banned nationally?
LL: Unless you can get a constitutional amendment adopted. I don’t think it’s in the Constitution.
To read the full transcript of Bari’s conversation with Leonard Leo, click here.