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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 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.”
Leo’s remarks: ‘We stand at the threshold’
The Washington Post obtained audio of Leonard Leo speaking to members of the
Council for National Policy.
“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.
Leo, seen on a video screen, speaks at the National Catholic Prayer Breakfast in
Washington in April. (Michael Robinson Chavez/The Washington Post)
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 Washington, D.C.,
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.
Leo and Mother Assumpta Long of the Dominican Sisters of Mary Mother of the
Eucharist watch President George W. Bush speak at the National Catholic Prayer
Breakfast in 2007. (Jim Watson/AFP/Getty Images)
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.”
Leo, center, attends the National Catholic Prayer Breakfast in April. (Michael
Robinson Chavez/The Washington Post)
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 three decades ago.
In 2005 and 2006, Leo served as the leader of the campaigns supporting Supreme
Court nominees John G. Roberts Jr. and Samuel A. Alito Jr. 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.
The Supreme Court justices, from left: Stephen G. Breyer, Clarence Thomas, John
G. Roberts Jr., Ruth Bader Ginsburg and Samuel A. Alito Jr. Back, from left: Neil M.
Gorsuch, Sonia Sotomayor, Elena Kagan and Brett M. Kavanaugh. (Jabin
Botsford/The Washington Post)
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.
[Read five takeaways from The Post’s investigation.]
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 percent, 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.
Leo speaks at the National Catholic Prayer Breakfast in April. (Michael Robinson
Chavez/The Washington Post)
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, Va.
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.”
Supreme Court Justices Roberts, left, Thomas, Breyer and Alito attend President
George W. Bush’s State of the Union address in 2006. (Melina Mara/The
Washington Post)
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 at
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.
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, Va., 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 detailsabout 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.”