We Don't Talk About Leonard: Episode 3
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Millions of dark money dollars are pouring into judicial races across the country, changing the way judges are elected and how they preside. Suddenly there were millions of dollars being put in. It's bad for the system.

It's bad for democracy. From WNYC in New York, this is On the Media. I'm Brooke Gladstone. This week, what conservative power broker Leonard Leo is doing with one of the largest political donations in American history. After one lunch, you can put different kinds of capital together to go out into the world and basically wreck shop. And Leo's vision for American society collides with...

American society. And there is Leonard Leo himself with a security guard standing there chalking my name. He was writing your name on the sidewalk as you were jogging by. Yes, how completely surreal is that? It's all coming up after this.

Thank you.

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That's zbiotics.com slash OTM and use the code OTM at checkout for 15% off. This episode is brought to you by Progressive. Most of you aren't just listening right now. You're driving, cleaning, and even exercising. But what if you could be saving money by switching to Progressive?

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I'm Maria Konnikova. And I'm Nate Silver. And our new podcast, Risky Business, is a show about making better decisions. We're both journalists whom we light as poker players, and that's the lens we're going to use to approach this entire show. We're going to be discussing everything from high-stakes poker to personal questions. Like whether I should call a plumber or fix my shower myself. And of course, we'll be talking about the election, too. Listen to Risky Business wherever you get your podcasts.

From WNYC in New York, this is On the Media. I'm Brooke Gladstone. The first week in October, the liberal majority on Wisconsin's state Supreme Court agreed to hear a case about the state's legislative districts drawn up by Republican lawmakers back in 2011.

And in agreeing to hear one of the most disputed gerrymandering cases in the country, they also reignited a simmering threat. Wisconsin Supreme Court Justice Janet Protasewicz remains under the threat of impeachment by legislative Republicans and Assembly Speaker Robin Voss, who has now created a secret panel of former Supreme Court justices to study the legal issues surrounding the process of impeachment.

Justice Protasewicz was elected to the Wisconsin Supreme Court last April and started her term in August. Before she was elected, she'd made some public comments suggesting that the current electoral maps were rigged. Absolutely positively rigged.

They do not reflect the people in the state. And now... Republicans are saying if she agrees to hear a redistricting case but does not recuse herself, that that would constitute corrupt conduct in office.

This week, two former Wisconsin Supreme Court justices were asked to weigh in on the legality of the impeachment plan. Their opinion? Protus Sawitz had not committed a crime or corrupt conduct that would warrant such an extreme measure. So, state Republicans were thwarted, for now, in their efforts to unseat the justice. But the threat of impeachment has loomed ever since her short tenure began.

What's happening in Wisconsin is an especially stark example of how state courts are becoming increasingly theaters of political war. But in Wisconsin, the judiciary has long been a partisan battlefield.

In this, the third and final installment of We Don't Talk About Leonard, our series made in collaboration with ProPublica, we examine the corrosive influence of money on judicial races and ponder, what's Leo planning for the future? Reporters Andrea Bernstein and Andy Kroll are our guides for this episode. Andrea's up first with more on the Wisconsin situation.

Wisconsin was one of the first states Leonard Leo and the Federalist Society got involved with in around 2007. That was the same time they were unsuccessfully trying to upend Missouri's nonpartisan judicial selection plan. It was designed to take politics out of judicial selection. The plan pushed the court to the center, something Leo opposed.

Leo lost in Missouri, but he did not give up on state courts. They were too tempting a target. In contrast to the power they wield, for example, ruling on voting districts, on gubernatorial edicts and abortion bans, they're pretty low profile. A little can go a long way when you want to change the composition of the courts.

Take Florida, where Leo did figure out how to influence state judicial selections. As soon as he was elected in 2018, Governor Ron DeSantis, a Federalist Society member since law school, brought in Leo to lead a secret panel that reviewed recommendations by the state's public judicial commission. The Florida Supreme Court now has a 6-1 conservative majority. So that's judicial selections. In this episode, we're looking at judicial elections.

These are what Pomona College professor Amanda Hollis Bruski, author of Ideas with Consequences: The Federalist Society and the Conservative Counterrevolution, describes as "low information elections." These are ripe for influence from outside parties who would like to see certain decisions go certain ways.

and can use these judicial elections to populate the state with judges who are going to rule the way they want them to rule. Judicial elections have led to results that have helped erode democracy in some states already. According to a University of Washington study that ranks the health of democracies in individual states, in the last two decades, North Carolina and Wisconsin have plummeted from two of the highest scoring states to scraping the bottom.

Leonard Leo played his part in making that happen. When you have a policy agenda and a policy platform that is not appealing to the majority of Americans, then the courts become a very attractive venue for carrying out your policy agenda. Like an abortion.

It's not just policymaking through the courts. It's policymaking through the courts that then feeds back into the machinery of democracy in ways that favor Republican electoral outcomes. I'm going to describe a recent event, one that looked like a defeat for Leo. And it was, but it was also a victory. Stay with me. You'll see why.

The most expensive state Supreme Court race in U.S. history ended the night of April 4th, 2023. At least $51 million were spent, including millions from groups associated with Leo. Because of IRS rules, we won't know how much for years. We may not ever know exactly who gave all that money.

But we do know that Leonard Leo personally donated $20,000, the maximum allowable, to the campaign of the conservative candidate, Dan Kelly. Kelly had served once before as a justice, and his opinions fit the profile of the kind of candidate Leo supports against abortion and same-sex marriage, against restrictions on businesses and gun ownership.

Kelly had also aligned himself with those rejecting the outcome of the 2020 presidential election. I wish that in a circumstance like this, I would be able to concede to a worthy opponent. That early night in April, the night of the election in Wisconsin, Kelly takes the podium with a tight smile that looks like a frown. But I do not have a worthy opponent.

to which I can concede. Kelly gives an unusual concession speech, one that accuses his opponent of doing what critics said he had done, threatening the nature of the judiciary and democracy itself. My opponent is a serial liar. She's disregarded judicial ethics. She's demeaned the judiciary with her behavior.

And this is the future that we have to look forward to in Wisconsin. No partisan labels were attached to the candidates, but both the Republican and Democratic parties made clear who they were supporting. It was understood that if Kelly won, he would likely join opinions outlawing abortion, but

uphold political maps that favored Republicans and possibly rule for the GOP in a case determining the outcome of the 2024 presidential election. And that if his opponent, Janet Protasea, was won, she would likely do the opposite. Kelly wraps up his speech, sighing and pursing his lips. And I wish Wisconsin the best of luck, because I think it's going to need it. For years, Leo had made a project of Wisconsin in general and Dan Kelly in particular.

It started when Leo and the Federalist Society launched the State Courts Project and metaphorically put a red circle around the state of Wisconsin. The Federalist Society said in its 2007 annual report that Wisconsin faced an election of some consequence. In early 2008, a Wisconsin conservative named Michael Gableman challenged a sitting justice, Louis Butler.

had voted on a lead paint liability case that outraged a big Wisconsin business group, Wisconsin Manufacturers and Commerce. Yeah, I just thought it was an awful race. It was so different than what we had seen. This is Justice Janine Geske. Now, she's a professor at Marquette University Law School. But back in the 90s, she served as a Wisconsin State Supreme Court Justice.

I'm conservative in the sense that I don't think we should be uprooting laws and changing precedent unless there's a huge reason to do it. And we should do it carefully and slowly. Like many Wisconsin justices, Keske was named to fill a vacancy, in her case, by a Republican governor. ♪

She says the Gableman-Butler race was a real turning point for Wisconsin. Suddenly there were millions of dollars being put in. That was new. The race was fraught, racially charged. Gableman supporters targeted Butler, who is Black, with a barrage of ads suggesting he was soft on crimes.

Lewis Butler worked to put criminals on the street. One commercial run by Gabelman's own campaign showed the mugshot of a convicted rapist next to a picture of Justice Butler. Can Wisconsin families feel safe with Lewis Butler on the Supreme Court?

To have those two pictures of Black men right next to each other, one sex offender, one a justice on the Wisconsin Supreme Court, took our breath away. Most of us looking at that thinking, what have we descended to? Among Gableman's backers, Leonard Leo. These were early days for Leo. He was just building his network. And it was years before Citizens United unleashed rivers of money into campaigns.

But according to a person close to Gableman's campaign, Leo had a big influence. This person told me Leo had a list of wealthy donors passed along to the campaign. The list came with instructions to call the donors and, quote, tell them Leonard told you to call. Each donor on the list, this person said, gave the maximum. When we asked him about this, Leo declined to comment. Gableman won.

This was the first time a state Supreme Court challenger had unseated an incumbent in Wisconsin in 40 years. Lewis Butler blames his loss in part on the negative attack ads from third party groups. It's my hope and my prayer that Wisconsin never has to see a race like we just went through.

In 2010, Republicans turned to Leo again, according to emails. This time, it was to help elect a justice who could back Governor Scott Walker. We've heard it before. Liberal judges letting criminals off on technicalities. Here's an ad from that race for judge. This man had a long criminal history, including beating his wife in front of their two-year-old daughter. The conservative judge won. Walker stayed in power. Leo declined to comment on his involvement in this race.

By this time, Democrats are responding in kind, running their own attack ads. What did David Prosser call one of America's most respected judges? He called her a total b****.

The year after that race, records show, money from Leo-related groups finds its way to Wisconsin. The Judicial Crisis Network, JCN, the dark money group that's been so closely tied to Leo's ambitions, gives hundreds of thousands of dollars to conservative and business groups that spend heavily on Wisconsin court fights. Leo says he doesn't remember this happening.

Around this time is when Dan Kelly enters the scene, a graduate of the devoutly Christian Regent University Law School and an attorney for an anti-abortion group in the Republican Party. Kelly becomes president of the Milwaukee Lawyers Chapter of the Federalist Society. He travels to Washington for Federalist Society conferences. He becomes close to Leo and his team. When we asked Leo about this, he said, quote, "'I have known Dan Kelly for a number of years.'"

In 2016, there's a vacancy on the Wisconsin Supreme Court, and Republican Governor Scott Walker gets to choose who fills out the term. There are three finalists, two Court of Appeals judges and Kelly, who at the time had never been a judge. Then Leo stepped in and said, it's going to be Dan Kelly, a person familiar with the selection process told me, adding, there is zero question in my mind the Federalist Society put the hammer down.

Two other Wisconsin Republicans who learned of the intervention at the time confirmed this account to me. Walker told me in a voicemail message that he never discussed judicial appointments with Leonard Leo while he was governor. Leo says he doesn't remember if he urged Walker to appoint Kelly. Kelly did not respond to requests for comment. Dan Kelly gets the job.

Thank you, Governor Walker, specifically for the appointment. This is an exceptional honor. In 2017, 2018, 2019, really big money from Leo's Judicial Crisis Network starts to flow into multiple Wisconsin Supreme Court races.

millions of dollars. Some of it ends up in TV ads aimed at swaying Wisconsin voters. Radical out-of-state special interest groups are pouring millions into Wisconsin, trying to buy... JCN did not respond to our questions. Go vote for Justice Daniel Kelly to defend the rule of law in Wisconsin. Daniel Kelly! In April of 2020, it's time for Kelly to run for election for the seat he was given by appointment.

It's a complicated political year. Kelly loses. Then he goes to work for the state Republican Party as their attorney.

When Trump loses his second run for the presidency, Kelly gets involved in Trump's efforts to overturn the election. Wisconsin's 10 Republican electors secretly met at the Capitol in December 2020, trying to submit false paperwork claiming Donald Trump won Wisconsin instead of Joe Biden. Then Kelly starts running for Supreme Court justice again. He boasts openly about being the conservative candidate who can pull in tens of millions of dollars in money from outside the state.

money that translates to ads. Justice Kelly supports enforcing the rule of law and keeping our communities safe. As a Milwaukee judge, Janet Protasiewicz has a long history of letting dangerous criminals off easy. Kelly does pull in the money, including from Leonard Leo,

But the candidate backed by the Democrats also raises big bucks. The airwaves are flooded with ads from liberal candidate Janet Protasewicz, who's outspending conservative candidate Daniel Kelly. After the Supreme Court Dobbs decision sent abortion rights to the states, there's a 19th century law banning abortion that could go into effect in Wisconsin. Abortion rights groups and voters rise up. Judge Janet, as she's called, wins handily.

Leo's candidate lost twice. But the idea that Leo had all those years ago, that idea is winning. That judges could be a prize for a political party rather than an independent branch of government. Former Justice Jeanine Geske says it's like the candidates were running to be, quote, super legislators rather than independent arbiters of the facts and the law. Third branch was sort of losing its judicial hat and putting on a legislative hat.

They were making legislative decisions. And that's not what they do. And I know that's not what they do. But I think that's what many voters think. Current and former state Supreme Court justices that I spoke with from all around the country are deeply disturbed with the overt partisanship and boatloads of money that was spent in Wisconsin.

That's bad for the system. It's bad for democracy. It's a very dangerous path to tread down. This is one of those judges. My name is Bob Orr, and I was the justice on the North Carolina Supreme Court. When he was elected, Orr was the first Republican to serve on the bench in North Carolina for almost a century. He joined the Federalist Society for support. It was kind of a sense of

If you're the underdog, it's us against them. Justice Orr left the North Carolina High Court before Leonard Leo got to work on state Supreme Courts. You can trace Leo's interest in North Carolina through the money that starts coming in around 2012. The Judicial Crisis Network was using the same playbook they were using in Wisconsin. And just like in Wisconsin, JCN was part of a first wave of big outside money and negative ads coming into the state.

And so all of a sudden we started seeing these, what I would consider misleading and distortive sort of traditional political ads we all know in politics. But we'd never seen those in judicial races. Over the next decade, JCN, the group that Leo launched and raised money for, kept sending money to another organization, the Republican State Leadership Committee, or RSLC.

Some years, Leo's JCN was RSLC's biggest donor. And that group spent more and more money on state judicial races. Staggering amounts, according to the legal institute, the Brennan Center for Justice. Babour says all of this money coming in has had a clear impact.

If I don't rule a certain way in certain cases, this is going to come back to really hurt my career. Like Justice Janine Geske in Wisconsin, Justice Orr told me that the rank politics in court races confuses the public about the role of the justice system in civic life.

about what judges are supposed to do. The whole confidence in the judiciary is critical in the sense of that's supposed to be the umpire. But if you have no confidence in the courts...

then you undermine the whole process. He says that's what the ads are doing. Well, the ads are going to be, "Judge so-and-so voted to release a child molester who did this or that." There was actually an ad about child molesting?

I'm trying to remember. After a while, you want to put them out of your mind. Negative ads have long focused on Democratic judges being soft on crime. In 2020, Chief Justice Cherie Beasley was running to retain her seat.

I mean, I felt powerless to fix the trajectory of my race. I could do the very best I was going to do, but I also understood that the impact of outside money in my race was going to be determinative in so many ways. Unlike in Wisconsin, judges run on party lines in North Carolina. Beasley ran as a Democrat, and for a long time, her party controlled the majority in North Carolina's Supreme Court.

Beasley says even though she raised a lot of money and even though Democrats are now spending in judicial races, conservatives have had a huge head start. Democrats and moderate-leaning groups long delayed being informed around the importance of judicial elections and why it was important to make sure that the electorate is informed about these races.

In 2020, Chief Justice Beasley lost her race to Republican Justice Paul Newby by 401 votes. Then, more money comes in from Leo's groups. In 2021, according to tax returns, nearly all of JCN's funding came directly from a group Leo controls. JCN donates millions to RSLC. RSLC spends record-breaking amounts on state court races.

In November of 2022, a year that was generally unfavorable to Republicans, RSLC and JCN and Leo win big. The North Carolina court is flipped from 4-3 Democrat to 5-2 Republican.

The Honorable Chief Justice... In early February of 2023, the newly Republican-controlled court did something extraordinary. It said it would re-hear two voting rights cases that the court had decided just two months earlier when it was controlled by Democrats. Same court, same facts, same law, different partisan makeup. This is the logical outcome of the court system Leonard Leo helped create.

After the first hearing in a windswept plaza between the court and the Capitol, voting rights advocates looked grim, staring at the ground. Good afternoon. My name is Sam Hirsch, H-I-R-S-C-H. I traveled to Raleigh to watch the hearings in the two cases, which were held on two unusually cold mid-March days.

The first to be heard was Harper v. Hall, which just a few months earlier had green-lit electoral maps that more closely reflected the state's roughly even partisan division. The lawyer for the plaintiffs in that case didn't even pretend things had gone well. In the state of North Carolina and in the United States of America, elections are supposed to matter. They're the way that we translate the popular will, the sovereignty of the people, into government power.

But if the Supreme Court of North Carolina overrules the Harper decisions from last year, it'll be saying to the people of North Carolina that only one election matters, and that's the election for the seven members of that court. That's not our democratic system. Can you tell us how it felt to be in the court today? Quick.

Some of the justices did not seem to want to spend time hearing about the key issues. The next day wasn't any better for the plaintiffs. This case was over whether voter ID laws discriminated against Black voters. Plaintiff lawyer Paul Brockman cited case law showing that to prove voter ID laws discriminate...

you don't need to have someone explicitly saying they're meant to discriminate. We are fortunately well past the time where we expect to find blatant statements of racially discriminatory motive in the legislative record. I hope we get back there. I'm sorry, Counsel. If I understand, you are indicating that there is no direct evidence of racial animus in Senate Bill or the legislative Bill 824. This is Justice Phil Berger, Jr., a Republican. He's

He disregards what Brockman says. He wants the direct evidence. Brockman tries again. We hope in 2023 that we are well past the point where legislators are going to stand up on the floor of the General Assembly and proclaim an intent to disenfranchise African-American voters. And you agree that the legislation on its face is...

In April, Berger Jr. wrote the 5-2 decision overturning a precedent that had stood for just five months. He wrote, quote, "...plaintiffs here have failed to prove beyond a reasonable doubt that SB 824 was enacted with discriminatory intent, or that the law actually produces a meaningful disparate impact along racial lines."

the prior opinion is withdrawn. — Major victories for the state Republicans today. — Yeah, the state Supreme Court issuing big rulings with major implications on how North Carolina votes. — The North Carolina Supreme Court has reinstated the voter ID law. — This 5-2 decision likely means that a photo ID mandate will be enforced in the 2024 election. — Neither the Judicial Crisis Network nor the Republican State Leadership Committee nor Justice Phil Berger Jr. had any comment.

Leonard Leo wrote in answer to our questions, I think the state Supreme Courts are more independent and impartial today than they were when trial lawyers and unions dominated state judicial races without any counter. If the name Phil Berger Jr. is ringing a bell, here's why. He was among the justices who attended the big party in Leonard Leo's mansion in June of 2022, the one by the Cove, protected by U.S. Marshals and the Coast Guard.

The one where the mood was jubilant, where guests drank champagne and whiskey and consumed a three-course meal. The party that came at the end of a U.S. Supreme Court term, where conservatives made gains on gun rights, on religious rights. And the day after the party: abortion. Now there was something else to celebrate. Decisions that could protect Republican majorities in the North Carolina state legislature for years to come.

Coming up, Leo is hard at work building the, quote, Federalist Society for Everything. This is On the Media. On the Media

This episode is brought to you by Progressive. Most of you aren't just listening right now. You're driving, cleaning, and even exercising. But what if you could be saving money by switching to Progressive?

Drivers who save by switching save nearly $750 on average, and auto customers qualify for an average of seven discounts. Multitask right now. Quote today at Progressive.com. Progressive Casualty Insurance Company and Affiliates. National average 12-month savings of $744 by new customers surveyed who saved with Progressive between June 2022 and May 2023. Potential savings will vary. Discounts not available in all states and situations. ♪

I'm Maria Konnikova. And I'm Nate Silver. And our new podcast, Risky Business, is a show about making better decisions. We're both journalists whom we light as poker players, and that's the lens we're going to use to approach this entire show. We're going to be discussing everything from high-stakes poker to personal questions. Like whether I should call a plumber or fix my shower myself. And of course, we'll be talking about the election, too. Listen to Risky Business wherever you get your podcasts.

This is On the Media. I'm Brooke Gladstone. You're listening to our investigative collaboration with ProPublica, We Don't Talk About Leonard. In early 2020, the news website Axios reported a story with the headline, Leonard Leo to Shape New Conservative Network.

Leonard had plans, he told Axios. He was leaving his day job as the Federalist Society's executive VP to set up a group called CRC Advisors, a group inspired, Leo said, by an outfit called Arabella Advisors, described by Axios as a, quote, "...little-known yet powerful consulting firm that advises liberal donors and non-profits about where to spend their money."

Leo said that he planned to work with two existing groups that we've talked so much about in this series, the Judicial Crisis Network and the Judicial Education Project. Only they were getting new names, the Concord Fund and the 85 Fund. One of Leo's first projects, a $10 million campaign focusing on judges.

Soon he would quietly set in motion a plan to transfer a $1.6 billion donation from an obscure electronics manufacturer to a political non-profit that Leo alone controlled.

Another thing Leo kept mum about was that he'd soon be taking over the Teneo Network, a private national networking group. ProPublica and the investigative journalism project Documented obtained hours of internal videos and hundreds of pages of documents from Teneo, which, taken together, provide a roadmap of exactly what Leo wants to do.

which, simply put, is to create a Federalist Society for everything. Here's Andy. When we started reporting this series, there were some big driving questions. What does Leonard Leo do with $1.6 billion? People who work with Leo, like Federalist Society co-founder David McIntosh, said that Leo had a choice. Take the Barry side money to the Federalist Society or create his own new thing.

He decided, new thing. He, in his own thinking of, should he stay at the Federalist Society, or should he give up that position and move to heading up the network? The network. Among Leo associates we spoke with, that term refers to the broader network, but also a specific one, the Teneo network.

One former leader of that group told me that it was, quote, high on his priority list. Leo not only funded it, he took it over.

Teneo shapes the broader culture by building networks of conservatives that can roll back or crush liberal dominance in key areas of American life. This is Leo in a promotional video from not too long ago. He's sitting on a couch wearing a charcoal gray jacket, no tie. I spent close to 30 years, if not more, helping to build the conservative legal movement.

And at some point or another, you know, I just said to myself, well, if this can work for law, why can't it work for lots of other areas of American culture and American life where things are really messed up right now? Leo ticks off a few of those areas. What he calls wokeism in the corporate environment, one-sided journalism, entertainment that's, quote, corrupting our youth.

He lays out the philosophy that's driven his work for the past three decades. At the end of the day, the movements that have been most successful in human history have been the ones where relationships were built, where bonds were built, where friendships were made, where people had people's backs.

If you can build talent pipelines of people who believe in the ideals around which our country were founded, and you can unite those people in common purpose. We've seen Leo do this, hosting parties, bringing people together, building networks.

spotting talent and making calls on their behalf to high government officials. One person who worked closely with Leo told me, "It's not like normal Washington networking where you get a business card and then add the person to your contacts list." This person, who Leo scouted in law school, told me, "He'd always make time. He'd see you at an event and come over and say hi. You always knew he was in your corner."

Leo, this person said, has a, quote, generational time frame. Those judges he's recommended, quote, he had known some of them for life. Teneo had been around for about a decade before Leo took it over. Its co-founder was a conservative entrepreneur named Evan Baer. There's this one video made late in the Trump administration where Baer explains why he formed the group.

He said Leonard Leo was an inspiration. And the secret sauce behind Leonard's work is the following. So there's about 75,000 members of the Federalist Society. Baer says there are about 3,000 people that are in Leo's inner core. And with those people, he is mostly identifying them and recruiting them for either specific roles to serve as judges or to spin up and launch critical projects, often which you would have no idea about.

Bayer is telling us exactly how it works. Recruit and mentor conservatives and get them in top jobs where they can really have an influence. We have a lot of people in the White House, White House Counsel's Office, State Department, Ag, Pentagon, DOD. They're everywhere. And that's really cool. In 2021, Leo takes over as chair of the board of the Teneo Network. Soon, new members join. Federal judges, an attorney general, a solicitor general, deputy solicitors general.

and also people who work for Leo's business, CRC advisors. The leaders of the Republican Attorneys General Association and the Republican State Leadership Committee, top staffers for Republican governors and senators,

and a lot of conservative media figures, athletes, academics, venture capitalists, and bankers. All these new members are a diagram of the people that are important to Leo, the leaders he wants to connect with one another to bring about a new era of social change. In one video, Evan Baer explicitly lays out how they want to do this. We think the left gets us right all the time, and we're learning from them.

In the video, Bear's wearing a navy polo shirt, standing at a clear plastic podium in front of a couple of potted plants. He wears a watch on each wrist and gesticulates a lot. Consider this case study. Imagine a group of four people sitting at the Harvard Club for lunch in midtown Manhattan. And you have a billionaire hedge funder. You have a film producer. You have a Harvard professor and a New York Times writer. It's a conspiratorial view of the left.

It's Taneo's model. The billionaire says, wouldn't it be cool if middle school kids had free access to sex change therapy paid for by the federal government? Well, a filmmaker says, I'd love to do a documentary on that. It'll be a major motion film. The Harvard professor says, we can do studies on that that say that's absolutely biologically sound and safe. And your Times person says, I'll profile people who feel trapped in the wrong gender. After one lunch, you can put different kinds of capital together to go out into the world and what? Basically, wreck shop.

That is our approach for how we're trying to advance our ideas. In a statement, Leo told us, Spanning across many major professional sectors in American life.

Leo added he's excited to, quote, level the playing field in this country for a fairer fight over the direction of public policy, media and other areas. When the Federalist Society started in the 1980s, it wasn't obvious how powerful it would become. Leo was identifying and promoting talent and making connections for decades before some of his efforts came to fruition. Leaders on the left told me, shame on us. We should have been working on this, too.

Leo's only been in charge of Teneo for a couple of years. It's hard to see exactly what the group has accomplished. But what we can see, Leo's getting ready to make a move should the pieces fall into place. Coming up, Leo has moved his family to a coastal mansion in Maine, but it has not been smooth sailing. This is On the Media. On the Media

This episode is brought to you by Progressive. Most of you aren't just listening right now. You're driving, cleaning, and even exercising. But what if you could be saving money by switching to Progressive?

Drivers who save by switching save nearly $750 on average, and auto customers qualify for an average of seven discounts. Multitask right now. Quote today at Progressive.com. Progressive Casualty Insurance Company and Affiliates. National average 12-month savings of $744 by new customers surveyed who saved with Progressive between June 2022 and May 2023. Potential savings will vary. Discounts not available in all states and situations.

I'm Maria Konnikova. And I'm Nate Silver. And our new podcast, Risky Business, is a show about making better decisions. We're both journalists whom we light as poker players, and that's the lens we're going to use to approach this entire show. We're going to be discussing everything from high-stakes poker to personal questions. Like whether I should call a plumber or fix my shower myself. And of course, we'll be talking about the election, too. Listen to Risky Business wherever you get your podcasts. This is On The Media. I'm Brooke Gladstone.

You're listening to our investigative collaboration with ProPublica, We Don't Talk About Leonard.

As the title of this series points to, up until a few years ago, few people really knew about Leonard Leo. And that was by design, Pomona College professor Amanda Hollis Bruski. If you can operate below the radar in ways that aren't apparent to the average citizen and sort of achieve your goals in a way that doesn't invite backlash and scrutiny...

then that's the most desirable way to go about doing politics. But things began to change with the whole list situation and Donald Trump. In order to keep his Supreme Court project going, Leo has to send a big signal to conservatives that he, Leonard Leo, is advising.

I think he makes a calculation to kind of come out from the shadows and put himself front and center because he knows that that will give Republican voters confidence to vote for Donald Trump in the 2016 election. But that's sort of an Icarus moment, too, where they're getting really close to the sun now. Andy Kroll and Andrea Bernstein pick up the story.

Leo's coming out more publicly in other ways, too. We can see from tax records that in 2021, the Judicial Crisis Network, which is now called the Concord Fund, is getting basically its entire budget from the $1.6 billion fund Leo controls. Leo seems to be thriving. The Concord Fund, formerly JCN, and the 85 Fund, formerly the Judicial Education Project, or JEP, are hiring Leo's business, CRC Advisors.

So are groups that those groups fund, like the Republican Attorneys General Association. Leo has gone from being a leader of a nonprofit with a modest home in McLean, Virginia, to living in a mansion in Northeast Harbor, Maine. Leo started coming a couple of decades ago as a visitor. Eventually, he bought a home. How does somebody who is so stridently conservative, a very religious Catholic, how do you find yourself in Maine, in Bar Harbor of all places?

Well, we have a long history here. Here's Leo in an interview he did in the summer of 2023. It's with The Main Wire, a conservative media outlet. Not as long as some people do, but we started coming here 20 years ago. We had a dear family friend and a house here on Mount Desert Island. And she invited us to use her home when she wasn't there. And we started coming for vacations. And of course, we were first attracted by the beauty. At one point, Clarence Thomas and his wife, Ginny Thomas, come up to visit.

but it didn't get much attention. That changes when Leo holds a fundraiser for Maine U.S. Senator Susan Collins in 2019. That was after she gave a deciding yes vote for U.S. Supreme Court Justice Brett Kavanaugh. There's a protest outside his house. The local press starts paying attention to Leonard Leo. Three years later, when the Dobbs abortion decision leaks, the demonstrations get more intense. That's a lie! That's a lie! You don't care if people die!

At the end of July of 2022, five weeks after Roe v. Wade is overturned, Leo calls the police. He'd been walking to the town's business district with his wife and daughter. The following audio is from a police body cam recording. It's pretty hard to hear. A gentleman pulled up who I'm very familiar with because he's been harassing us for weeks. He says, a gentleman pulled up who I'm very familiar with because he's been harassing me for weeks. His name, I think, is Eli Durand. He's in the passenger seat.

He yells out, uh... He's in the passenger seat. He yells out, pardon my language, you're a f***ing a**hole and you're going to hell. The backstory is that for weeks, protesters have gathered outside Leo's mansion on weekends. Leo has a video. He shows the cops. They watch it together.

All right, when they have Leo signs and stuff like that, that's not political protesting. Leo says this isn't a political protest. Instead, he says it's harassment. The protesters are saying, you don't belong here. They're not welcome in this neighborhood. Leo says with Eli Durant McDonald, he's reached his limit. And I feel as though it's time to take some action personally.

After the cop is finished taking Leo's statement, he walks out to the front of Leo's house. Eli? Yeah? You got an ID on you real quick? I don't, actually. Okay. All right, will you come with me? All right. What's that? Disorderly conduct. The demonstrators start to yell. Disorderly conduct on Main Street today. Not here. Not here. Don't get in the way. Don't get in the way. Leonard Leo's rights. He's made a line again.

Kevin, this is not cool. You know it's not cool. The woman speaking, Bo Green, taught calculus at the high school the cop's kids went to. That's how small this town is. This guy is ruining your country that you say that you stand up for. And you're talking about this young man? Come on, Kevin. Kevin, what are you doing? I don't know.

Almost a year after the arrest, the case against Eli Duran McDonald, a recent Oberlin grad who works for a nonprofit and runs a landscaping business, was dropped. He was banned from protesting Leo in town while his case was pending, but now he's back. In June, he dressed up as Justice Samuel Alito, carrying a giant salmon. It's based on a picture first published in ProPublica of Alito and hedge fund billionaire Paul Singer. ♪

This protest is on the first anniversary of the Dobbs decision. It draws a pretty big crowd, despite an unpleasant rain. One of the other protesters here is named Bettina Richards. She's wearing bright pink cargo pants.

and carrying a sign that says, you claim it's not about control, but you're banning birth control. It was always about control. I've definitely talked to him a couple times when he was walking his dog by my front yard, which is really surreal. Richards runs a record company in Chicago and lives on the island for the summers.

just down the road from Leo, where she has a sign that says, Google Leonard Leo. His neighbor across the street allowed us to hang a pink fist flag across from his house. The flag was on private property.

But one day, Richards gets a call that Leo's security guard is in the process of tearing it down. So I hopped on my bike and went down there, caught the guy and said, what are you doing? She gets to work rehanging the flag. And I was on a ladder repairing the flag because he'd broken the grommets. And the security guard comes back out with Leonard Leo. Leo tells her the flag is offensive. I said, well, you have a flag hanging out in front of your house. Leo rotates flags with Catholic iconography. Richard?

Richard says, "Don't touch my flag." I'm going to know if you've touched it. I have evidence that you've touched it. So, and then he said to me, "I will allow it." Leo told us, quote, "The owner of that property came to us some weeks later stating that whoever put the flag up did not have permission and that the property owner would be taking it down." Richard said another household member had okayed the pink fist flag. It was taken down.

That was encounter number one. Encounter number two involves some chalk drawings, which protesters have taken to writing on the street outside Leo's home. Like, dirty money lives here.

Because she lives so close, Richards sees Leo often. He now walks with a security guard and is often accompanied by a priest with a cassock and a collar. I go running often in the morning, and I was running about 8 a.m., and I was running down this street, and there...

Bent over halfway is Leonard Leo himself with a security guard standing there chalking my name. He was writing your name on the sidewalk as you were jogging by. Yes. Yes. Again, how completely surreal is that? The fact that someone that you would assume, if you have a billion dollars, that you don't have time to go out and chalk people's names. He was writing your name over and over? Yeah. So each time...

chalk drawing, he had written our names. So he had written it at least four or five times by the time I got there. And I think he continued on to he had attributed each chalk drawing to us. Leo's spokesperson told us Leo was responding to messages, including one that said, quote, you should not be enjoying your life here while you destroy others' lives. Get out. Another message is probably best not repeated on the radio. Leo added, quote,

I chalked the names of protesters next to the hateful, vulgar, and offensive statements they had chalked right in front of my family's house. But I washed their names off virtually immediately because I regretted that my behavior was churlish and undignified. When Andrea and I visited Bar Harbor in June of 2023, we encountered something we really haven't found in our reporting. Regular people who know who Leonard Leo is. It was like going through the looking glass.

The town knows him. His name is familiar. Some of those people like him. Many don't. And some of those people are pushing back. To them, Leo is the face of the conservative takeover of the courts. And he's become a rallying cry, a uniting force that's bringing his opponents together. When he's spoken about his place in American society, Leo has consistently sounded one note since, well, since he was in college and maybe even in high school.

that he's losing and needs to catch up. In his response to us, he's still saying the same thing.

So, here we are. As we've heard throughout the series, courts in America are becoming politicized. One person or seven or nine can overturn the will of the majority. And if you're in the political minority, but you can control the courts, well, then you can control democracy through an ultra-minoritarian institution.

ProPublica's reporting on undisclosed lavish trips and gifts bestowed on Supreme Court justices has provoked a sharp response. Justice Samuel Alito took to the Wall Street Journal editorial page to charge ProPublica with misleading readers, even before the story about him had been published. He didn't dispute any of the facts in his op-ed, nor has he since.

Leo says that the exposés were merely, quote, bait for reeling in more dark money from woke billionaires who want to damage the Supreme Court and remake it into one that will disregard the law by rubber-stamping their disordered and highly unpopular cultural preferences.

Meanwhile, the Democratic-led Senate Judiciary Committee has begun investigating ethical lapses on the high court, requesting information from Leo and Paul Singer and Robin Arkley. So far, it seems the senators aren't getting through.

In August, Politico reported that the District of Columbia's attorney general was investigating Leo for possibly enriching himself through his network of tax-exempt nonprofit groups. Leo's counsel says Leo has done nothing wrong and will not cooperate with the probe. Leonard Leo hasn't achieved a total victory, but he's made huge strides, and all the while, almost no one was watching.

This series is reported by Andrea Bernstein, Andy Kroll, and Ilya Meritz, and edited by OTM executive producer Katya Rogers and ProPublica's Jesse Isinger. Molly Rosen is the lead producer, with help from Sean Merchant. Jennifer Munson is our technical director. Jared Paul wrote and recorded all the original music, which included Lily Parker on viola and Sophie Baum on violin.

Our fact-checkers are Andrea Marks and Hannah Murphy Winter. Our legal team is Ivan Zimmerman, Lauren Cooperman, Jeremy Kuttner, and Sarah Matthews. If you missed parts one and two of We Don't Talk About Leonard, you'll find them on the On the Media feed, wherever you get your podcasts. And you could read much more at our partner site, propublica.org.

We'd like to say some thank yous to people who helped us report the story, but whose names you won't hear in the show. For Publica's Eric Umansky, Megan O'Mance, Lynn Dombeck, Doris Burke, Alex Meyer-Jeske, Ken Schwenke, Ruth Talbot, Nick Lanise, Justin Elliott, Josh Kaplan, and Brett Murphy. Also, for our visual production, Nick Schweitzer, Lisa Larson-Walker, Anna Donlan, Alex Bandoni, and Sisiga Mukulu.

Ed Pilkington, David Daly, Lisa Graves, and Evan Vorpaul of True North Research, Saylor Jones of North Carolina Common Cause, Nick Sergei and the team at Documented, and Becky Harper. And the many, many current and former justices, judges, elected officials, Trump administration appointees, and others who spoke to us confidentially for fear of the consequences to their careers or livelihoods if we use their names and we don't talk about Leonard.

Tracy Weber is the managing editor and Steve Engelberg is the editor-in-chief of ProPublica. Thanks for listening. I'm Andrea Bernstein. And I'm Brooke Gladstone.