Brooke Gladstone: This is On The Media. I'm Brooke Gladstone. Welcome back to our series, We Don't Talk About Leonard. One of the reasons for that name is that so many people who have worked with Leonard Leo do not want to speak with ProPublica's Ilya Marritz, Andy Kroll, or Andrea Bernstein.

Andrea Bernstein: We reached out to hundreds and hundreds of people who had experiences with Leonard Leo, and so many just did not get back to us or wouldn't go on the record. At one point, deep into our reporting, we realized that requests to independent people seemed to be going straight to Leo's PR man.

Andy Kroll: Source after source told me that the reason we were having trouble finding people to talk about Leo is because Leo is funding basically everything. "Everything?" I remember asking in one conversation. "Not literally everything, of course, but you give a guy a billion and a half dollars, and he can bankroll an entire movement."

Andrea Bernstein: To give you a sense of how tightly Leo controls his PR, we put questions to three different groups that are part of this story: the Federalist Society, the Judicial Crisis Network, and Leo himself. They all have the same PR firm, which Leo is a part owner of. The Federalist Society and JCN did not respond.

Andy Kroll: We did find some people to talk to: childhood friends, colleagues, political associates, current and former judges, and attorneys general, some of whom you'll hear from in this series. We spoke to over 100 people who knew Leo on a personal level, worked with him, got funding from him, or studied his rise. Most didn't want us to use their names because they were worried about their careers suffering, or about losing access to donors in Leo's orbit.

Andrea Bernstein: When we asked Leo about this, he said in a statement, "I would assume many people didn't want to speak because they surmised, rightly or wrongly, that you would not be producing a balanced and objective story." We did not interview Leonard Leo. After months of discussions, Leo agreed to speak on the condition we not ask questions about his financial activities or relationships with Supreme Court justices. We declined.

Then we sent him a long and detailed list of questions and a second list of factual assertions. Leo did not correct the vast majority of them; where he did, we made adjustments. He also gave some comments. Leo says he's just trying to keep up with the strategy and spending on the Left. He told us, "To the extent that I have been successful at raising funds, it has been because the ideas I have tried to advance are compelling, and because I have always placed a premium on driving results through highly effective talent pipelines and infrastructure."

He said of his relationship with Supreme Court justices, "The justices who have served on the US Supreme Court since I first started working in Washington in the late 1980s, liberals and conservatives alike, are the most independent and resolute public officials I've known. I've never believed that the relationships or interactions they have outside the Court affects how they do their work."

Andy Kroll: We put this story together based on all of the on-the-record and background interviews we did, plus court records, tax filings, and documents we got from Freedom of Information Act requests. Now on with the story.

Andrea Bernstein: Leonard Anthony Leo was born on Long Island in 1965. His father, who was a baker, died when Leonard was young. His mother remarried an engineer and moved the family to Central New Jersey. This has been described to me as a place with an identity problem, where you weren't sure if your baseball team is the Yankees or the Phillies. I went to see Leo's childhood home. It's modest, one-story on a suburban street where the houses are close together. Leo attended Monroe Township High School, a public school.

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Andrea Bernstein: Hi, how are you?

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Andrea Bernstein: You can still find the 1983 yearbook at the town library. [whispers] Okay, I've got the '83 yearbook. I'm opening it up. The girls have big hair. Some of the boys have mustaches. They're dressed in t-shirts or polos. But there, smiling out from the top of the class page in a shirt and tie and gray blazer, is Leonard Leo. He is senior class president, National Honor Society vice president. His nickname is Moneybags Kid. He says it's, "Because I developed a number of fundraisers that resulted in a significant amount of money for our senior prom and senior trip, with money left over to donate to the high school."

The secretary of the class is Sally Schroeder, now Sally Leo. Leonard Leo shows up many times in these pages, but the picture catching my eye is the one illustrating Most Likely to Succeed. It's Leonard Leo and Sally Schroeder sitting at a table in front of a pile of cash. They're holding more in their hands, fanned out like cards. Superimposed in a lens of each of their eyeglasses, dollar signs.

Snehal Shah: I rarely, if ever, saw him in like casual wear. He was always well-dressed, especially at that age.

Andrea Bernstein: This is Snehal Shah, an engineer now, who says Leo was his best friend. From when they met in fourth grade, Shah says Leo wanted to be a lawyer.

Snehal Shah: When you're that age, you want to be a baseball player or a policeman or a fireman. Nobody says they want to be lawyers at 9 or 10 years old, but he did. [chuckles] If you're different at that age, you're going to get bullied a little bit. He was a smart kid. I was a smart kid too. I got bullied. Growing up, in elementary school, junior high, high school, he was probably more of an outcast than someone who was popular.

Andrea Bernstein: When Leo first ran for student government, Shah says, he lost, but then he learned from his mistakes. He won people over.

Snehal Shah: I think he did a better job of not letting the snobbishness come out.

Andrea Bernstein: Shah says he doesn't remember details of their discussions about politics, but--

Snehal Shah: He was always passionate about being anti-abortion. He was very steadfast in that belief.

Andy Kroll: After high school, Leo enrolls at Cornell, where he gets a bachelor's degree and a law degree in just six years, graduating in 1989. I spoke with a half-dozen of his classmates, and here's what I learned. Leonard Leo wore bow ties and a suit to class. No one else did. Many of them consider themselves liberal, but not Leo. Leo told us that as an undergrad, there was a professor in the Department of Government, Jeremy Rabkin, who shaped his views. Rabkin was a rare conservative voice on campus.

Prof. Jeremy Rabkin: The law schools are overwhelmingly tilted to the Left, certainly in the area of constitutional law.

Andy Kroll: This is Rabkin speaking at an event hosted by the conservative Claremont Institute. He points out that the overwhelming majority of justices on the US Supreme Court were appointed by Republicans.

Prof. Jeremy Rabkin: I don't think I'm communicating anything new to anyone in this audience, but let's just remind ourselves. A lot of these appointments were disappointing.

Andy Kroll: Rabkin says, you can't just have a Republican-elected official name a judge and then assume that judge will make the right, that is, sufficiently conservative decisions.

Prof. Jeremy Rabkin: Who was Sandra Day O'Connor? Sandra Day O'Connor was, to put it politely, nobody. There was no reason why people should have trusted that Ronald Reagan's first nominee to the Supreme Court was somebody that conservatives would be happy about.

Andy Kroll: Rabkin made this speech years after Leo graduated, but even back in the '80s, he was criticizing judges who in his view imposed Left-wing policies dressed up as judicial rulings. Rabkin declined to be interviewed for this story.

Andrea Bernstein: When Leo starts law school, there's a new national organization getting off the ground, the Federalist Society. Leo founds a chapter at Cornell. During this period, President Reagan nominates Robert Bork to the US Supreme Court.

Senator Ted Kennedy: In Robert Bork's America, there is no room at the inn for Blacks and no place in the Constitution for women; and in our America, there should be no seat on the Supreme Court for Robert Bork.

Andrea Bernstein: When the Senate kills his nomination, Borked becomes a verb.

Andy Kroll: One of Leo's classmates told me about watching a 1988 presidential debate with Leo. This classmate is complaining about the media's unfair treatment of Jesse Jackson, and Leo says, "Now you know how I feel with the people on my side."

Andrea Bernstein: After graduation in 1989, Leo marries Sally. They move to Washington, where Leo gets a clerkship on the US Court of Appeals. Clarence Thomas is one of the judges. They become lifelong friends.

Leonard Leo: Good afternoon. My name is Leonard Leo, and I am National Lawyers Division director of--

Andrea Bernstein: In this tape from the 1990s, Leo looks like the Jonah Hill character in Moneyball; very young, a full, dark head of hair. He keeps pushing his glasses up his nose.

Leonard Leo: I met Justice Thomas in September 1990 as a law clerk on the DC Circuit. Curious as it may seem, one of the first things I noticed upon entering his office was a small statue of St. Jude, who for centuries has been known to many as the patron saint of seemingly hopeless causes.

Andrea Bernstein: This is where Leo becomes a backstage producer in the play that you've already seen. He joins the White House team working on Thomas' nomination to the US Supreme Court. Leo's job is gathering research. Soon, that team is at an all-out fight to discredit Professor Anita Hill's allegations of sexual harassment.

Justice Clarence Thomas: From my standpoint as a Black American, as far as I'm concerned, it is a high-tech lynching for uppity Blacks.

Senate Speaker: The yeas are 52 and the nays are 48. The nomination of Clarence Thomas of Georgia to be Associate Justice of the United States Supreme Court is hereby confirmed.

Andrea Bernstein: Leo, galvanized by the confirmation battle, goes to work for the Federalist Society for the next 30 years.

Andy Kroll: You have the distinction of being a co-founder-

David McIntosh: Yes.

Andy Kroll: -of the Federalist Society. I almost want you to start there. Set that scene. I mean, I've never talked to one of the founders of that organization.

David McIntosh: Oh, really? Oh, okay.

Andrea Bernstein: Andy spoke to David McIntosh at the office where he now works at the Club for Growth. McIntosh says he considers Leo a good friend.

David McIntosh: We were all in law school, and Reagan had just become president. All of us thought, wouldn't it be great if we could have a conservative student group, one that's dedicated to debating what the role of the law is and role of judging?

Andrea Bernstein: The idea was this, elite law schools tilted Left. They were the in-crowd. They had a pipeline sending clerks and lawyers and justices to the US Supreme Court. In 1982, McIntosh and the others organized a conference at Yale.

David McIntosh: And everybody who came had a great time. The students did, the faculty that came [crosstalk]--

Andy Kroll: Was this in some auditorium or ballroom?

David McIntosh: It was at Yale at-- yes, classroom for part of it. I think we weren't even big enough to be in the big law school auditorium.

Andrea Bernstein: The preface to the transcript from that conference belittles professors who "dream of regulating from their cloistered offices every minute detail of our lives." FedSoc, as it becomes known, grows quickly. It hires an executive director, Gene Meyer.

David McIntosh: Gene came to us on the board and said, I want to hire Leonard Leo, here's his background. I got to know Leonard, immediately saw how talented he is.

Andrea Bernstein: That was 1991. As head of the Lawyers Division, Leo spends his first decade with the Federalist Society cultivating relationships with like-minded lawyers around the country and with people in government. McIntosh told us, Leo came to a realization; it takes political activity to nominate a justice.

David McIntosh: You've got to persuade a president that that's the type of justice he or she wants. You then have to persuade the United States Senate to confirm them. I think Leonard's talents there in organizing people who share his beliefs and having them advocate those is a key part of it.

Andrea Bernstein: When George W. Bush becomes president in 2001, Leo seizes the chance to become a bigger player. By 2003, the White House sees him as a key ally. His day job is still with the Federalist Society. One email among Bush aides points out Leo "is now helping to coordinate all outside coalition activity regarding judicial nominations." There's a book about the Federalist Society called Ideas with Consequences: The Federalist Society and the Conservative Counterrevolution. Pomona College political scientist, Amanda Hollis-Brusky, interviewed top Federalist Society leaders, including McIntosh, for the book. The title refers to the organization's mantra; ideas have consequences.

Amanda Hollis-Brusky: But more importantly, that policy is people, right? You have to connect those ideas to the right people who have access to the levers of power to make it happen. Leonard Leo is the policy-is-people guy. When Leonard Leo comes in, it becomes less about creating a sort of pipeline and a counter-elite with their own ideas and shared vision of the Constitution. It becomes about plugging that in very consciously to power.

Andrea Bernstein: Hollis-Brusky noticed something about Leo.

Amanda Hollis-Brusky: Through the course of interviews with other Federalist Society folks, it became clear that the president of the Federalist Society was more of a symbolic figurehead, whereas the real power in the organization was with the vice president, Leonard Leo.

Andrea Bernstein: One top Republican strategist told us, his key to success in Washington is that he doesn't have the typical Washington ego. He's a real cause guy, he's just in it for the cause. In this lead-from-behind role, Leo cultivates wealthy conservative donors, which makes him important to the White House, which in turn, makes him important to the donors, and the less people know about what he's doing, the more he can get done. One of the ways he organizes is by hosting powerful people, bring them together over food and wine and their commitment to conservative causes.

David McIntosh: He has very good taste-

Andrea Bernstein: Federalist Society, co-founder David McIntosh.

David McIntosh: -and opinions about food and wine, but he's solicitous of his guests and really makes you feel this sense of warmth. That he cares about you. He wants you to enjoy the same things he's enjoying and to be part of, in the moment, a larger sense of enjoying a great meal.

Andrea Bernstein: When Leo invited people to work with him, it was the same.

David McIntosh: And be part of a coalition of people that are aiming at that same goal for liberty and constitutional order. It's a collegiality that the public image doesn't show.

Andrea Bernstein: On a cold night in Washington in 2004, shortly after Bush was reelected, that collegiality suffused a private dinner at an upscale Italian restaurant. The meal came at a turning point in American political life, the founding of a little-known group that would become immensely powerful. The dinner went under the radar for years until Peter Stone of The Daily Beast and Viveca Novak of the nonpartisan group OpenSecrets figured it out.

Viveca Novak: At this dinner in 2004-

Andrea Bernstein: Viveca Novak.

Viveca Novak: -you had Leo, you had Scalia, you had Robin Arkley, you had other big donors. Scalia was obviously the headliner and the draw for the dinner.

Andrea Bernstein: It's a celebration. Robin Arkley II is a major Federalist Society donor from California. He owns a mortgage servicing company. He gets a prime seat next to Justice Scalia.

Viveca Novak: It was right around that time that JCN was started.

Andy Kroll: JCN, the Judicial Confirmation Network. Like the Federalist Society, JCN is a nonprofit but it's a different kind, the kind that is allowed to be involved in partisan politics and without disclosing its donors; a big advantage for the kind of behind-the-scenes work Leo is doing. In response to our questions, Leo confirmed that he helped launch JCN.

Viveca Novak: He was hanging around with a lot of deep-pocketed donors who were involved in the Federalist Society, and he realized that these kinds of groups could be very helpful.

Andy Kroll: Groups like JCN.

Viveca Novak: What you had was kind of a daisy chain where donors were giving money to one group, the group didn't have to disclose its donors. They'd give money to another group, that group didn't have to disclose its donors.

Andy Kroll: As Novak came to learn, Leo, in his role as Federalist Society vice president, was cultivating donors for the Federalist Society and also cultivating donations that flowed to JCN.

Viveca Novak: He was certainly a broker. He was the guy who orchestrated these sorts of events; the donations, where the donation should go, how they should be spent. He's the brains behind the operation.

Andrea Bernstein: We got an email from Robin Arkley, the early JCN donor. He told us, "Nothing has been more consequential in transforming the courts and building a more impactful conservative movement than the network of talented individuals and groups fostered by Leonard Leo. The agenda of the Left can no longer take success for granted." Over the dinner where he was seated next to Scalia, Arkley wrote that Leo was "always introducing me to people I admired, like Justices Scalia and Alito, engaging with such accomplished intelligence and, most of all, compassionate Catholics, impacted how I see the world and I am thankful for it."

One more thing about Leo's role with JCN. It's informal. He's not on the board or in any of the paperwork, but you can trace his ties. Board members and contractors and donors lead back to him. Sometimes JCN hires or gives money to or gets money from groups that Leo runs or supports. In his statement to us, Leo did not dispute any of this.

Since its founding, JCN has changed its name twice. The money flows are hard to track and hard to describe, but one thing is clear, JCN is a key component of Leo's machine. In his answers to our questions, Leo confirmed that JCN has been an integral part of his efforts to build a more conservative judiciary. In 2021, nearly all of JCN's revenue came from a group that is entirely controlled by Leo. We don't have numbers for any years after that. In July of 2005, Leo and JCN have their opportunity to work on a US Supreme Court nomination.

Andy Kroll: Justice Sandra Day O'Connor resigns; President Bush nominates John Roberts.

Steve Schmidt: I was flying back from somewhere with Cheney on Air Force Two and I got called forward to the cabin, and there were these two giant duffel bags and they were filled with binders.

Andy Kroll: This is political operative Steve Schmidt. Schmidt was tasked with reading through the binders on potential Court nominees. At the time, he worked in the White House as a deputy assistant to President Bush.

Steve Schmidt: I was leading the two Supreme Court confirmations in the Bush administration for Chief Justice Roberts and Justice Alito.

Andy Kroll: He calls a meeting with key stakeholders. It's held in the Eisenhower Executive Office Building adjacent to the White House. That's where Schmidt meets Leo. At first, Leo was just one of the crowd, but then Schmidt gets a read on him.

Steve Schmidt: If you take it down to like a school committee, like the PTA committee, who's going to be the chairperson of the committee? It's going to be the person who cares the most and shows up to all the meetings. This is what Leonard Leo did.

Andy Kroll: JCN treats the confirmation battle like a political campaign with ads.

Steve Schmidt: You're making TV ads, you are trying to communicate, trying to make sure that no one is getting wobbly on you, right? I can't explain to you why this stuff works, but it does.

Andrea Bernstein: I'm just curious, though, like you're the guy in the White House, you're responsible for getting this through the Senate. Here's the Judicial Confirmation Network. That was clear to you that this was a group associated with Leo, that he was [crosstalk]--

Steve Schmidt: Yes, 100%. Leonard was the guy.

Andrea Bernstein: That's the behind-the-scenes part. Publicly, there's just a glimpse Leo was involved.

Leonard Leo: Judge Roberts did a fine job today.

Andrea Bernstein: He speaks to the press after Roberts testifies. There's Leo, hair cropped short, glasses well-fitting.

Leonard Leo: We are very happy with the way today went and--

Andrea Bernstein: The next nomination is choppier. Bush nominates his counsel. Her name is Harriet Miers. Conservatives, Leo's allies, suspect Miers is not firm enough on abortion. Leo publicly defends the President. Bush ultimately withdraws her nomination and picks a hard-Right conservative from New Jersey.

President George W. Bush: I'm pleased to announce my nomination of Judge Samuel A. Alito, Jr. as Associate Justice of the Supreme Court of the United States.

Andrea Bernstein: Democrats push back, but JCN gears up again, running pro-Alito ads, shoring up specific senators' support.

Ad Voice: You know who they are, the folks who sue towns for putting up nativity scenes and menorahs. Now these extremist groups want our senators to vote against Judge Alito for the United States Supreme Court.

Andrea Bernstein: The nomination passes the Senate 58 to 42. The Moneybags Kid had arrived.

[applause]

Leonard Leo: It is a pleasure to stand before 1,500 of the most little-known and elusive of that secret society or conspiracy we call the Federalist Society.

Andrea Bernstein: This is Leo at a Federalist Society gala soon after Alito is confirmed. Long before the term was coined, his speech sounds like he's owning the libs.

Leonard Leo: Thanks so very much for your support and involvement. You may pick up your subpoenas on the way out.

[laughter]

Brooke Gladstone: Coming up. After Alito's nomination, there would be no more US Supreme Court nominees for the remainder of Bush's presidency, so Leo and the Federalist Society turn their attention to the state supreme courts.

Michael Wolf: It's not enough to own a House and own a Senate and own a governor. We've got to own the courts too. It is a power grab. There's no question about that.

Brooke Gladstone: This is On The Media.