Leonard Leo stepped onto the stage in a darkened Florida ballroom, looked out at a gathering of some of the nation’s most powerful conservative activists and told them they were on the cusp of fulfilling a long-sought dream.
For two decades, Leo has been on a mission to turn back the clock to a time before the U.S. Supreme Court routinely expanded the government's authority and endorsed new rights such as abortion and same-sex marriage. Now, as President Donald Trump's unofficial judicial adviser, he told the audience at the closed-door event in February that they had to mobilize in "very unprecedented ways" to help finish the job.
"We're going to have to understand that judicial confirmations these days are more like political campaigns," Leo told the members of the Council for National Policy, according to a recording of the speech obtained by The Washington Post. "We're going to have to be smart as a movement."
"No one in this room has probably experienced the kind of transformation that I think we are beginning to see," Leo said.
At a time when Trump and Senate Majority Leader Mitch McConnell are rapidly reshaping federal courts by installing conservative judges and Supreme Court justices, few people outside government have more influence over judicial appointments now than Leo.
He is widely known as a confidant to Trump and as executive vice president of the Federalist Society, an influential nonprofit organization for conservative and libertarian lawyers that has close ties to Supreme Court justices. But behind the scenes, Leo is the maestro of a network of interlocking nonprofits working on media campaigns and other initiatives to sway lawmakers by generating public support for conservative judges.
The story of Leo's rise offers an inside look into the modern machinery of political persuasion. It shows how undisclosed interests outside of government are harnessing the nation's nonprofit system to influence judicial appointments that will shape the nation for decades.
Even as Leo counseled Trump on judicial picks, he and his allies were raising money for nonprofits that under IRS rules do not have to disclose their donors. Between 2014 and 2017 alone, they collected more than $250 million in such donations, sometimes known as "dark money," according to a Post analysis of the most recent tax filings available. The money was used in part to support conservative policies and judges, through advertising and through funding for groups whose executives appeared as television pundits.
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.
Nine of the groups hired the same conservative media relations firm, Creative Response Concepts, collectively paying it more than $10 million in contracting fees in 2016 and 2017. During that time, the firm coordinated a monthslong media campaign in support of Trump's Supreme Court nominee Neil Gorsuch, including publishing opinion essays, contributing 5,000 quotes to news stories, scheduling pundit appearances on television and posting online videos that were viewed 50 million times, according to a report on the firm's website.
In another case, a nonprofit Leo launched in 2016, the Freedom and Opportunity Fund, gave $4 million over two years to a nonprofit called Independent Women's Voice, about half the group's revenue, tax filings show. Leaders of Independent Women's Voice last year spoke at rallies, wrote online commentary and appeared regularly on Fox News to promote another of Trump's Supreme Court nominees, Brett Kavanaugh.
During an on-camera interview for a Post documentary, Leo called himself "a leader of the conservative legal movement" and said, "I have no idea how many groups I've been involved with over the years."
A devout Catholic, Leo said he is driven by his faith and a literal interpretation of the Constitution. He also defended the practice of taking money from donors whose identities are not publicly disclosed, comparing his effort to shape the courts to those of abolitionists, suffragists and civil rights activists.
"[They] were all very much fueled by very wealthy people, and oftentimes wealthy people who chose to be anonymous," Leo said.
But he refused to talk about the money behind his advocacy, saying "I'm not particularly knowledgeable about a lot of it."
"I have a very simple rule, which is, I'm engaged in the battle of ideas, and I care very deeply about our Constitution and the role of courts in our society," he said. "And I don't waste my time on stories that involve money and politics because what I care about is ideas."
Later, 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."
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Leo, 53, wears round, horn-rimmed glasses, tailored suits and monochromatic pocket squares. His office at the Federalist Society is filled with mementos of his career, including a red Trump-campaign-style hat that reads "Make The Court Great Again" and a gold-framed New Yorker profile of himself. On a bookshelf is a photo of Leo and Kavanaugh in tuxedos. A nameplate on the shelf reads, "The Real Boss."
Leo grew up in suburban New Jersey, where his high school yearbook lists his nickname as the "Moneybags kid" and shows a photograph of him holding a handful of cash. He attended Cornell as an undergraduate and law student and founded an early chapter of the Federalist Society, then an all-volunteer organization focused on infusing traditional legal values into the nation's law schools.
His conservative values stood out. When a classmate protesting apartheid in South Africa threw a chocolate cream pie into the face of the university's president, Leo expressed outrage in a letter to the student newspaper. "Although some will dismiss Tuesday as only a pie-throwing incident, it is representative of a more hostile form of expression that has become more common," he wrote.
In 1990, Leo became a clerk for a U.S. Court of Appeals judge in the District of Columbia, where he met Clarence Thomas, then an appellate judge. The two became close friends.
After his clerkship, Leo joined the Federalist Society as one of its first paid employees. But he delayed the start date to help Thomas through his contentious confirmation process for the Supreme Court.
At the Federalist Society, Leo took a leading role in the conservative legal movement, part of a burgeoning effort to counter the influence of the 1960s and liberals on education, law and politics.
With the election of George W. Bush, Leo began working as an outside adviser for the White House on initiatives related to judicial nominations. Among his allies was Kavanaugh, then White House associate counsel.
In January 2003, Leo called White House officials, including Kavanaugh, to object to a plan by Bush to weigh in on affirmative action. Bush was going to criticize the practice but praise racial diversity. Leo complained that praising diversity would "disgust any conservative who thinks that this is a matter of principle," according to a previously unreported email by a White House official describing one of the calls.
About 15 minutes later, Kavanaugh wrote back: "Leonard just called me and gave me the same earful."
Leo told The Post that from the accounts of the calls, "it appears I was conveying the widely shared belief among conservatives that discriminating on the basis of race is always wrong and inconsistent with the dignity and worth of every person."
Leo came to be known in the White House as coordinator of "all outside coalition activity regarding judicial nominations," according to a 2003 email by a White House aide to Kavanaugh and others.
Leo also developed a reputation as a conservative moneyman. When Kavanaugh and other Bush aides were looking for someone to pay for a press event aimed at supporting the stalled judicial nomination of Miguel Estrada, they turned to Leo.
"Leonard Leo will know," a White House aide wrote in an email obtained by The Post. "We probably don't want the fed soc paying for it, but he might know some generous donor."
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Leo's behind-the-scenes activism came at the same time he was helping to grow the Federalist Society, which describes itself as nonpartisan. Leo told The Post he has taken steps to avoid any conflict.
"I separate my advocacy from the educational work of The Federalist Society," he said in his 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."
Leo told The Post he has employed techniques liberals used to derail the nomination of Robert Bork to the Supreme Court almost three decades ago.
In 2005 and 2006, Leo served as the leader of the campaigns supporting Supreme Court nominees John Roberts and Samuel Alito. He and other members of an advocacy coalition spent about $15 million in donations from undisclosed donors on ads, telemarketing and the mobilization of "grass roots" groups, Leo later told a Federalist Society chapter at the University of Virginia. They conducted polls to help craft the most persuasive messages and arranged dozens of "background" briefings for reporters.
A key part of those efforts was a new nonprofit called the Judicial Confirmation Network, or JCN. Tax filings show it was based at the home of Ann and Neil Corkery, close allies of Leo who have served as board members or treasurers of organizations run by Leo and a small group of interconnected activists.
One radio spot paid for by JCN in Arkansas featured a local minister who warned listeners that liberals wanted to curb religious freedom, including Christmas celebrations. "Now these extremist groups want our senators to vote against Judge Alito for the United States Supreme Court," the ad said.
In the interview with The Post, Leo said he took time off from the Federalist Society - a charity that says it does not endorse specific nominees - during the nomination fights in 2005 and 2006. The group's tax filings show that his compensation in those two years jumped by nearly 50%, to about $328,000 annually. Leo did not respond to a question about how his compensation was affected by his time off. 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 was $419,000.
Documents show that Leo never assumed a formal position at JCN, which eventually changed its name to the Judicial Crisis Network. But he told The Post he is "very supportive" of the group.
The ties between JCN and Leo are opaque. JCN's office is on the same hallway as the Federalist Society in a downtown Washington building, though JCN's website and tax filings list a mailing address at a different location, an address shared by multiple companies.
JCN board director Gary Marx told The Post the two organizations share similar goals but have "different boards, different missions, different functions and do very different things."
When a Post reporter visited the JCN offices to ask questions, a security guard contacted a longtime employee of the Federalist Society to see whether anyone at JCN was available. A Federalist Society employee then escorted the reporter to JCN's office.
The group's president, Daniel Casey, has worked closely with Leo for years. Casey receives no pay from JCN or three other nonprofits in the network that he helps to lead, tax filings show. He received more than $1.5 million in fees from the Federalist Society over nine years for media training through a firm based at his home in Front Royal, Virginia.
In an interview with The Post, Casey declined to discuss that firm, DC Strategies. He said all of the nonprofit groups he is affiliated with followed the law. "Everything is up and up," he said.
Leo told The Post that Casey has been "a highly skilled provider of strategic consulting services in the legal policy space for over 30 years."
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Leo's influence and political connections continued to expand even as President Barack Obama took over the White House.
He routinely attended galas and black-tie Federalist Society events that included justices Thomas, Alito and Antonin Scalia, as well as McConnell and other leading lawmakers, according to interviews and annual reports by the Federalist Society.
He also became more adept at managing media campaigns. In a previously undisclosed email, Leo boasted to a colleague in 2009 about his savvy generating free publicity through the Federalist Society.
"I'm very familiar with the media," Leo wrote to Tom Carter, then a spokesman for the U.S. Commission on International Religious Freedom, a government agency created to promote religious liberty abroad. "I spend probably close to $800,000 annually on a PR team at the Federalist Society, and we generate press that has a publicity value of approximately $146 million each year."
Leo, then a commissioner, said the Federalist Society had learned to sidestep pointed questions about judicial nominees - and he urged Carter to do the same in his work for the commission. "We get around these inquiries quite well, and I am sure you can find a way to do so as well," he wrote.
Leo joined additional advocacy groups that expanded his influence following the Supreme Court's landmark Citizens United decision in 2010, which lifted restrictions on spending by corporations, unions and nonprofits on politically oriented advertisements and media campaigns.
His growing network was composed mostly of nonprofits called "social welfare organizations," which are allowed to engage in politics as long as it's not their primary activity. It also included some public charities, which can receive tax-deductible donations and are prohibited from backing or opposing candidates for office.
In 2010, Leo served on the board of a tea party group called Liberty Central. Ginni Thomas, wife of Supreme Court Justice Clarence Thomas, received $120,511 as the start-up's president that year. She later stepped down following questions about possible conflicts of interest, saying the issue had become a distraction for the group.
In 2012, Leo joined the boards of the nonprofit Catholic Association and an affiliated charity, the Catholic Association Foundation. They funded campaigns to rally Catholic voters and stop states from recognizing same-sex marriage.
The two Catholic nonprofits launched a third organization called Catholic Voices. Its stated mission was to train Catholic lay members to advocate for religious and conservative causes, some of whom later wrote letters for publication in major newspapers condemning the Affordable Care Act and Roe v. Wade, the Supreme Court decision that made abortion legal.
The next year, Leo joined forces with wealthy conservative donor Rebekah Mercer and Stephen Bannon, then the chairman of Breitbart News, on the board of a small charity known as Reclaim New York. Mercer and Bannon would go on to play central roles in Trump's insurgent campaign, Mercer as a leading financial backer and Bannon as campaign chief.
In the year Leo joined Mercer's group, and in the two following years, the Mercer family became a leading benefactor of the Federalist Society, donating a total of nearly $6 million, tax filings show.
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In March 2016, Leo met with Trump and Federalist Society member Donald McGahn at the Washington law firm Jones Day, just as Trump was beginning to prevail in his quest to be the Republican nominee, Leo told The Post.
Justice Scalia had just died, and the men were mulling the implications. McGahn had come up with the idea of generating a list of potential Supreme Court nominees that Trump could disclose to win over moderates. Leo said he briefed Trump about the current composition of the court, the ideology of the justices and the like.
As Leo tells it, Trump was open to one of his long-held goals: A federal court system dominated by conservative judges who believe the Constitution must be interpreted literally.
Leo later gave the president a list of possible Supreme Court nominees. Trump released the list during the primary campaign, a gesture that helped him win the support of skeptical mainstream Republicans. Gorsuch and Kavanaugh were added to the list later.
JCN, the group that has office space on the same hall as the Federalist Society, launched a $7 million media campaign to bolster the Republican-controlled Senate in preventing Obama from filling the seat, according to a JCN news release at the time. Working on the campaign was Creative Response Concepts, a firm that was hired by multiple nonprofits in Leo's network, tax filings show. CRC's president, Greg Mueller, describes himself as a friend of Leo. Mueller's firm gained prominence during the presidential campaign of 2004 for helping to promote the "swift boat" allegations, unsubstantiated claims that Democratic candidate John Kerry's war record in Vietnam was exaggerated. Among its clients now is the Federalist Society.
Mueller said in a statement that the firm does not discuss its work for clients.
As the 2016 election campaign heated up, Leo became president of three new nonprofits whose tax filings and incorporation records illustrate how his network sometimes operates.
The groups - called BH Fund, the Freedom and Opportunity Fund and America Engaged - were formed by an employee at Holtzman Vogel Josefiak Torchinsky, a Warrenton, Virginia, law firm with deep ties to the conservative movement.
The nonprofits reported having no employees and no websites. They had virtually no public presence. Leo's role as president of all three groups was not disclosed for nearly three years because of lags in how nonprofit groups report their annual operations to the IRS.
All three hired CRC for public relations and consulting.
In 2016 and 2017, the three nonprofits raised about $33 million, with the BH Fund taking in $24,250,000 from a single donor whose identity is still not publicly known, documents show. BH Fund then gave a total of almost $3 million to the two other Leo groups, Freedom and Opportunity Fund and America Engaged. The Center for Responsive Politics published details about the groups' spending in February.
In 2017, America Engaged passed on almost $1 million to the lobbying arm of the National Rifle Association. That same year, the NRA announced a $1 million ad campaign in support of Gorsuch. The ads targeted lawmakers in Montana, Indiana, Missouri and North Dakota who had supported Obama's calls for gun control. "Your freedom is on the line," the ads stated.
The media blitz coincided with yet another campaign to promote Gorsuch's nomination, by Judicial Crisis Network. JCN announced that it would spend $10 million, calling it "the most robust operation in the history of confirmation battles." CRC, its media consultant on the campaign, later boasted that online videos, television ads, pundit commentary, opinion essays and other material supporting Gorsuch had been viewed 1.2 billion times.
Leo's Freedom and Opportunity Fund, meanwhile, distributed $4 million to Independent Women's Voice over two years.
The leaders of Independent Women's Voice appeared frequently on Fox News, speaking in support of Trump and his judicial nominees. They spoke at rallies, according to videos, and they bought Facebook ads that reached hundreds of thousands of users, according to a Facebook political advertising database.
Heather Higgins, the group's president and chief executive, expressed doubts on Fox News about the memory of the woman accusing Kavanaugh of sexually assaulting her decades ago. "If you have a weak standard of evidence, then what you are doing is guaranteeing that future nominations will all be last-minute character assassinations and circuses," said Higgins, who records show is paid $311,000 as the leader of Independent Women's Voice.
Higgins did not respond to requests for comment.
She once described her group as a weapon in the "Republican conservative arsenal" that caters to "donors who want a high return on their investment for their political dollars," according to a video of a speech she made at the nonprofit David Horowitz Freedom Center.
"We have worked hard to create a branded organization . . . that does not carry partisan baggage," Higgins said in 2015. "Being branded as neutral but actually having the people who know, know that you're actually conservative puts us in a unique position."
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Leonard Leo's work in the nonprofit world has proved lucrative.
The Federalist Society, a charity, has regularly paid Leo more than $400,000 in annual compensation in recent years, tax filings show. In 2016, the Catholic Association paid him $120,000 for management consulting.
Leo's only other publicly known employer is an obscure for-profit start-up called the BH Group. It was registered in Virginia on Aug. 22, 2016, by the same law firm employee who incorporated the BH Fund and the two other nonprofits Leo started earlier that year. The firm is based out of a virtual office suite used as a shared mailing address and meeting space for unrelated companies.
In the two years following its formation, the BH Group received more than $4 million from the Judicial Crisis Network, a related group called the Judicial Education Project and a third nonprofit in the network called the Wellspring Committee, all of them connected to Leo through funding, personnel and the same accountant, IRS filings show. The groups described the payments in IRS filings as consulting, research and public relations fees.
Leo, who disclosed BH Group as his employer in a campaign finance filing, declined to say how much money he received from the company or provide any other details about it.
"BH Group is a private firm whose team of professionals, which includes Leonard Leo, provides management and consulting services to philanthropists and nonprofits," a CRC spokesman for Leo said in a statement. "Like similar firms on the Left, its clients are private as are the details of the work for them."
In December 2016, while Leo worked on Trump's transition team, BH Group donated $1 million to Trump's inaugural committee, according to a campaign finance disclosure.
The next year, Leo and his wife, Sally, were named Stewards of Saint Peter by the Papal Foundation, an honor given to those who pledge to donate $1 million or more for Vatican initiatives worldwide.
Leo, his wife and their six children have lived in a McLean, Virginia, home that was purchased in 2010 for $710,000, according to real estate records. They paid off a 30-year mortgage last August and two months later bought a $3.3 million summer home with 11 bedrooms in an affluent seaside village on the coast of Maine. In a statement, Leo described the mansion as "a retreat for our large family and for extending hospitality to our community of personal and professional friends and co-workers."
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Leo's work to influence judicial nominations has made him a hero to some conservative activists. The esteem was evident in February at the closed-door meeting of the nonprofit Council for National Policy, where Leo serves on the board of governors.
"He is one of us. He cares about the Constitution. He understands that elections may come and go, but judges with lifetime appointments . . . are going to be here for a long time," Rebecca Hagelin, a board member, told the assembled activists and donors.
"And this is perhaps where Donald Trump is making his greatest, longest-lasting effort. But he's doing it based on a lot of the work by Leonard Leo. And today I'm so pleased to introduce him," she said. "Welcome him to the stage, and thank him for all the work that he is doing to help save America."
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The Washington Post’s Dalton Bennett, Alice Crites and Andrew Tran contributed to this report.