Leonard Leo, seen on a video screen, speaks at the National Catholic Prayer Breakfast in Washington in April. (Michael Robinson Chavez/The Washington Post)

President Trump and Senate Majority Leader Mitch McConnell are rapidly reshaping the federal courts by installing conservative judges and Supreme Court justices. No one outside government has more influence over this transformation than Leonard Leo, an executive at a Washington-based organization called the Federalist Society.

Leo has a highly public role as Trump’s outside judicial adviser, and in that role, he recommends nominees for the federal bench. But he also has a less visible role, raising and spending millions of dollars to generate support for those same nominees.

Here are five takeaways from The Washington Post’s examination of Leo’s influence over the changing composition of the courts.

1. Leo has connections to a group of nonprofits that raise millions from people whose identities are not publicly known.

Leo has worked with a network of nonprofits that promote conservative judges and values. A dozen key groups in that network brought in a total of more than $250 million in contributions between 2014 and 2017, including a single $24 million donation from an undisclosed donor, an examination of tax filings shows.

Because the law does not require that contributors be publicly identified, it is unclear how many donors there are and what their specific interests and goals may be. 

2. Leo’s role behind the scenes is not readily apparent.

During confirmation battles over Trump’s two Supreme Court nominees, Neil M. Gorsuch and Brett M. Kavanaugh, nonprofits affiliated with Leo funded an influence campaign that relied on advertisements, television pundits, social media and other measures to create pressure on Congress to support the nominees. 

Independent Women’s Voice, which describes itself as a grass-roots organization for women, received about half its revenue from two nonprofits run by Leo while its executives appeared regularly on Fox News and promoted Trump’s nominees. 

Though they are formed as separate entities, the groups in Leo’s network often work in concert and are linked to Leo and one another by finances, shared board members, phone numbers, addresses, back-office support and other operational details, according to tax filings, incorporation records, other documents and interviews. The nonprofit Center for Responsive Politics has revealed some of these relationships.

In response to written questions about the interlocking nonprofits, Leo described the network as “an effective and highly successful judicial coalition that’s organized just about the same as the Left’s, except that their coalition is significantly bigger and better funded.”

Conservatives are winning the battle for America’s courts, a triumph decades in the making. This is the story of the ideologues, activists and undisclosed donors who made it happen. (REF:bennettd,REF:mesnerhagej,REF:ribasjl/The Washington Post)

3. Leo’s success under Trump is part of an effort to remake the Supreme Court that goes back many years.

While working for the Federalist Society in the early 2000s, Leo also became an outside organizer of initiatives related to judicial nominations for the George W. Bush White House. Among his allies was Kavanaugh, then White House associate counsel, according to emails obtained by The Post.

The White House relied on him to organize a coalition of nonprofits in support of Bush’s judicial nominees, the emails show. Leo also earned a reputation for raising money from wealthy contributors. He came to be known in the White House as coordinator of “all outside coalition activity regarding judicial nominations,” according to an email by a White House aide to Kavanaugh and others.

4. The Federalist Society says it does not advocate for specific judicial nominees, and Leo say he keeps his advocacy separate from his work at the society. But there are links between the two through shared personnel and office space.

One of the nonprofits, Judicial Crisis Network, has an office on the same hallway as the Federalist Society, an organization for conservative and libertarian lawyers, in downtown Washington. The JCN president’s consulting firm has received $1.5 million from the Federalist Society since 2010, according to tax filings. JCN’s president said all payments and work have complied with the law.

In an interview with The Post, Leo said he took time off from the Federalist Society, a charity that says it does not advocate for particular policies or nominees, during Supreme Court nomination fights in 2005 and 2006. The group’s tax filings show that his compensation in those two years jumped by nearly 50 percent, to about $328,000 annually. A spokesman for the Federalist Society said Leo’s pay went up — despite the time off — because of the organization’s “extraordinary revenue growth.” Back at the Federalist Society the following year, his compensation went up again, to $419,000.

“I separate my advocacy from the educational work of The Federalist Society,” Leo said in a statement. “I put in a full day’s work for the Society and spend a substantial amount of my personal time on the other public service work I also love.”

5. Leo has been well compensated for his work with nonprofits.

In addition to Federalist Society compensation that has regularly exceeded $400,000 in recent years, a group called the Catholic Association paid him $120,000 in 2016 for management consulting. Leo’s only other publicly known employer is a for-profit entity called the BH Group. In the two years following its 2016 formation, the BH Group received more than $4 million from nonprofits with connections to Leo, according to tax filings that described the payments as consulting, research and public relations fees.

Leo declined to provide any other details about the firm. “BH Group is a private firm whose team of professionals, which includes Leonard Leo, provides management and consulting services to philanthropists and nonprofits,” a spokesman for Leo said in a statement. 

Leo, his wife and their six children live in a McLean home that was purchased in 2010 for $710,000, according to real estate records. They paid off a 30-year mortgage in August, after eight years, and two months later bought a $3.3 million summer home with 11 bedrooms in a seaside village on the coast of Maine, records show. In a statement, Leo described the home as “a retreat for our large family and for extending hospitality to our community of personal and professional friends and co-workers.”