Brooke Gladstone: This is On The Media. I'm Brooke Gladstone. You're listening to our series reported in collaboration with ProPublica called, We don't talk about Leonard. As we just heard, at the same time, Leonard Leo was helping to promote and credential new legal talent. He was also attending to practical matters, fundraising, and cultivating the kind of relationships with wealthy donors that can fuel a movement for years and even decades. ProPublica's Andy Kroll and Andrea Bernstein have this part of the story.

Andrea Bernstein: One illustration of how Leo cultivated relationships among donors and justices is a fishing trip Justice Samuel Alito took to Alaska. It happened in 2008, but the world didn't learn about it until this year. It made a splash.

News Presenter 8: A new report from ProPublica claims Samuel Alito accepted a lavish vacation from a conservative billionaire with frequent business before the high court.

News Presenter 9: See the guy in the red in the middle of the picture holding the gigantic fish, that is Justice Samuel Alito.

News Presenter 10: Now in an unusual move, Alito is defending himself in the press, writing in a Wall Street Journal op-ed, that the seat on the plane on Paul Singer's private jet would otherwise have been unoccupied.

Andrea Bernstein: It was our ProPublica colleagues, Justin Elliott, Josh Kaplan, and Alex Mierjeski, who broke the story. They figured out that Alito had taken a flight on a private plane paid for by a hedge fund manager named Paul Singer. Singer and Alito stayed at a fishing lodge at the invitation of Californian Robin Arkley. He owns a mortgage servicing company. Josh says, "At first it wasn't clear what linked Alito and Singer and Arkley." Then it came to them.

Josh Kaplan: The only common thread between the prominent guests on that trip was that they were all connected to Leonard Leo.

Andrea Bernstein: Singer was a big-dollar federal society donor. Robin Arkley provided seed money for the judicial crisis network, that Leo connected group. Leonard Leo himself was on the trip. There's a photo of Leo with other guests holding a big fish in front of a seaplane. Another guest on the outing was a federal judge named Raymond Randolph. Leo clerked for him after law school.

Josh Kaplan: As we were digging on this, we learned that Leo actually-- He helped organize it. He played an important role in connecting Alito with this billionaire. Leo was the one that invited the billionaire, Singer on the trip. Leo asked Singer if he and Alito could fly there on the billionaire's jet.

Justin Elliott: Leo actually secured these very expensive private jet flight across the country for a sitting Supreme Court justice.

Andrea Bernstein: That's Josh's co-reporter, Justin Elliott. They got their hands on an email chain.

Justin Elliott: In which after they got back from the fishing trip, Paul Singer had apparently expected to receive a shipment of salmon, and it never arrived in New York where Singer lives. Singer actually sent an email to Leo about this half-jokingly saying, "The salmon, they've escaped." Then Leo in turn forwarded that along to another donor, this guy Rob Arkley, who owned the fishing lodge where they hosted Alito where the fishing trip happened, to take care of it and get Paul Singer his salmon.

Andrea Bernstein: Justice Alito has acknowledged the trip and said there was no need to inform the public because "accommodations and transportation for social events were not reportable gifts." If Alito had chartered the plane himself, people in the industry estimate, the flight alone could have cost him $100,000 one way. Singer told ProPublica he did not organize the trip and did not discuss his business with Justice Alito.

Andy Kroll: This Alaska trip was the first time Singer and Alito met, and Alito must have impressed Singer because by 2010 he was introducing the Justice at a black-tie dinner.

Paul Singer: Dessert this evening comes with a lecture by one of America's greatest and most influential legal minds, the Honorable Samuel Alito.

[applause]

Andy Kroll: Singer calls Alito a "Model Supreme Court Justice."

Samuel Alito: Thank you all very much. Thank you. Thank you for the very warm welcome and thank you, Paul, for the very kind introduction. How is that? Can you hear me okay?

Andy Kroll: Alito and Singer intersect again in 2014 when Singer has a case before the US Supreme Court. A unit of Singer's hedge fund had purchased distressed Argentinian debt years earlier. Argentina's repaying its other creditors pennies on the dollar.

Andrea Bernstein: Singer insists his fund must be repaid in full.

News Presenter 11: Argentina will default on its obligation to bondholders tomorrow if nothing changes. Argentina's president, Cristina Fernández de Kirchner blames the brinksmanship on, "Vulture capitalists picking at the bones of Argentina's economy." Paul Singer, the billionaire bondholder calling in Argentina's loan says any damage is self-inflicted.

Andrea Bernstein: Singer takes the fight all the way to the US Supreme Court, and he prevails. Justice Alito votes with the 7 to 1 majority in favor of the hedge fund. There was quite a bit of press coverage at the time. Justice Alito has said he didn't know Singer was involved since Singer, as an individual, was not a named party to the lawsuit. When our colleagues asked Leonard Leo about the fishing trip. He said of the justices, "No objective and well-informed observer of the judiciary honestly could believe that they, the justices, decide cases in order to call favor with friends, or in return for a free-plane seat or fishing trip."

Andy Kroll: There's another way to look at the Justice Alito, Leonard Leo, Paul Singer triangle. Getting close to a Supreme Court justice, people in Washington have told me, is a huge flex. Andrea and I spoke to someone who did this, an evangelical minister, the Reverend Rob Schenck. He was a longtime anti-abortion activist but came to regret some of his tactics.

Andrea Bernstein: Reverend Schenck and Leo were not in the same circle, though they worked on the same issues. Schenck told us how he first got close to Supreme Court Justices Thomas and Alito. He uses the term, feet of clay, a biblical reference to weaknesses in powerful people.

Reverend Rob Schenck: It didn't take long for me to see their feet of clay, but it was my experience in pastoral work, in congregations, that helped me to appreciate that every human is fragile, every human is corruptible. Just because someone dawns a robe, just because they are one of a rare nine, just because they sit so far removed from average people, does not make them superhuman. They are human in every way.

Andy Kroll: "He could use that closeness," Schenck says, "To appeal to donors."

Reverend Rob Schenck: How many people do you know who have set a prayer with a justice in chambers? How many people do you know who have taken a justice on a vacation trip and talked into the late night hours over a drink, traded stories? I'm going to guess none. That's what makes our work unique, and it makes the impact of our work unique.

Andrea Bernstein: As ProPublica has learned, Leo himself brought wealthy donors to the US Supreme Court, a secretive group put together by Paul Singer. It was March of 2017.

Andy Kroll: This is actually an organized group of rich Republican donors who meet twice a year. That spring, they were in Washington DC, and Leonard Leo arranged a private meeting with Clarence Thomas inside the court. Afterwards, the donors, including Paul Singer, were treated to a gala dinner inside the Library of Congress, which is a beautiful historic building right next door.

Andrea Bernstein: "A year and a half later," this person said, "When Brett Kavanaugh, Supreme Court nomination was running into trouble, Leo turned to the group of wealthy donors to raise money for an ad campaign to counter all the negative press. Leonard Leo acknowledged the meeting with Thomas at the Supreme Court. In an email, he said some of the people in the group were not his donors. "But they are thought leaders who should know more about the Constitution and the rule of law. I was happy to arrange for them to hear about these topics from one of the best teachers on that I know, Clarence Thomas."

Brooke Gladstone: Coming up, what Leo did when Congress passed a law that one of his donors hated. This is On The Media.