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Brooke Gladstone: 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-Brusky.

Professor Amanda Hollis-Brusky: 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.

Brooke Gladstone: 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 Trump.

Professor Amanda Hollis-Brusky: I think he makes the calculation to 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 an Icarus moment too, where they're getting really close to the sun now.

Brooke Gladstone: Andy Kroll and Andrea Bernstein pick up the story.

Andy Kroll: 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 for the $1.6 billion fund Leo controls.

Andrea Bernstein: 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 more groups that those groups fund, like the Republican Attorneys General Association.

Andy Kroll: 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.

Andrea Bernstein: Leo started coming a couple of decades ago as a visitor, eventually he bought a home.

Edward Tomic: 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?

Leonard Leo: Well, we have a long history here.

Andy Kroll: Here's Leo in an interview he did in the summer of 2023. It's with The Main Wire, a Conservative media outlet.

Leonard Leo: 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. She invited us to use her home when she wasn't there, and we started coming for vacations. Of course, we were first attracted by the beauty.

Andy Kroll: At one point, Clarence Thomas and his wife, Ginni Thomas come up to visit, but it didn't get much attention.

Andrea Bernstein: That changes when Leo holds a fundraiser for Maine US Senator Susan Collins in 2019 That was after she gave a deciding yes vote for US 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.

Demonstrators: Pro-life, that's a lie. You don't care if people's die. Pro-life, that's a lie. You don't care if people's life

Andrea Bernstein: At the end of July of 2020, 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 was from a police body cam recording. It's pretty hard to hear.

Leonard Leo: A gentleman pulled up who I'm very familiar with because he's been harassing us for weeks

Andrea Bernstein: 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 Durant."

Leonard Leo: He's in the passenger seat. He yells out--

Andrea Bernstein: "He's in the passenger seat. He yells out, pardon my language, 'You're [censoreed] 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.

Protestor: Leonard Leo is confronting women.

Leonard Leo: They had Leo's signs and stuff like that. That's not a political protest.

Andrea Bernstein: Leo says this isn't a political protest. Instead, he says it's harassment. The protesters are saying, "You don't belong here."

Leonard Leo: You don't belong in this neighborhood.

Andrea Bernstein: Leo says, "With Eli Durant-McDonnell. He's reached his limit."

Leonard Leo: I feel as though it's time to take some action personally.

Andrea Bernstein: After the cops finished taking Leo's statement, he walks out to the front of Leo's house.

Cop Kevin: Eli, you got an ID on you real quick?

Eli Durant-McDonald: No, I don't actually.

Cop Kevin: All right. Well, you're coming with me.

Eli Durant-McDonald: What's that?

Andrea Bernstein: The demonstrators start to yell.

Cop Kevin: Disorderly conduct on Main Street today, not here. Not here. Don't get in the way. Don't get in the way.

[background conversation]

Bow Green: Kevin, this is not cool. You know it's not cool.

Andrea Bernstein: The woman speaking Bow Green taught calculus at the high school the cop's kids went to. That's how small this town is.

Bow Green: 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.

Protestors: Are you kidding me?

Bow Green: Kevin, what are you doing?

Andrea Bernstein: Almost a year after the arrest, the case against Eli Durant-McDonnell 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 DOM's 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."

Bettina Richards: I have definitely talked to him a couple of times when he was walking his dog by my front yard, which is really surreal.

Andrea Bernstein: 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."

Bettina Richards: His neighbor across the street allowed us to hang a pink fist flag across from his house.

Andrea Bernstein: 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.

Bettina Richards: I hopped on my bike and went down there, called the guy and said what are you doing?

Andrea Bernstein: She gets to work rehanging the flag.

Bettina Richards: I was on a ladder repairing the flag because he'd broken the grommets and the security guard comes back out with Leonard Leo.

Andrea Bernstein: Leo tells her the flag is offensive.

Bettina Richards: I said well, you have a flag hanging out in front of your house.

Andrea Bernstein: Leo rotates flags with Catholic iconography. Richards says "Don't touch my flag."

Bettina Richards: I'm going to know if you've touched it. I have evidence that you've touched it. Then he said to me, "I will allow it."

Andrea Bernstein: Leo told us "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." Richards said another household member had okayed the pink fist flag. It was taken down. That was encountered 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.

Bettina Richards: I go running often in the morning and I was running about 8:00 AM. I was running down the street and there, bent over halfway, is Leonard Leo himself with a security guard standing there chalking my name.

Andrea Bernstein: He was writing your name on the sidewalk as you were jogging by?

Bettina Richards: 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?

Andrea Bernstein: He was writing your name over and over?

Bettina Richards: Yes. Each chalk drawing, he had written our names so he had written it at least four or five times by the time I got there. I think he continued on until he had attributed each chalk drawing to us.

Andrea Bernstein: Leo's spokesperson told us Leo was responding to messages, including one that said, "You should not be enjoying your life here while you destroy other's lives. Get out." Another message is probably best not repeated on the radio. Leo added, "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."

Andy Kroll: 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. He's become a rallying cry, a uniting force that's bringing his opponents together.

Andrea Bernstein: When he's spoken about his place in American society, Leo has consistently sounded one note, 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.

Brooke Gladstone: 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. 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 exposes were merely, "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, 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 total victory, but he's made huge strides, and all the while, almost no one was watching.

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This series is reported by Andrea Bernstein, Andy Kroll, and Ilya Marritz, and edited by OTM executive producer Katya Rogers, and ProPublica's Jesse Eisenberg. Molly Rosen is the lead producer with help from Shaan 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 Kutner, and Sarah Matthews. If you missed parts one and two of We Don't Talk About Leonard, you'll find them On The Media feeds wherever you get your podcasts. You could read much more at our partner site, propublica.org.

Andrea Bernstein: 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. ProPublica's Eric Umansky, Megan O'Matz, Lindenbaum, Doris Burke, Alex Mierjeski, Ken Twinkie, Ruth Talbot, Nick Weenies, Justin Elliott, Josh Kaplan and Brett Murphy.

Also for our visual production, Nick Schweitzer, Lisa Larson-Walker, Anna Donlan, Alex Bandoni, and Zisiga Mukulu. Ed Pilkington, David Daley, Lisa Graves, and Evan Vorpahl of True North Research. Sailor Jones of North Carolina Common Cause, Nick Sergei and the team it documented, and Becky Harper. 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 in 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

Brooke Gladstone: I'm Brooke Gladstone.

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