Leonard Leo in 2016. (Carolyn Kaster/AP)
8 min

In the more than 30 years since he became friends with Supreme Court Justice Clarence Thomas, the conservative judicial activist Leonard Leo — who once described himself to The Washington Post as “a leader of the conservative legal movement” — has used his influence to help bring a right-leaning majority to the Supreme Court.

Leo’s relationship with Thomas is under scrutiny after Leo arranged for Virginia “Ginni” Thomas, the Supreme Court justice’s wife, to be paid tens of thousands of dollars for consulting work just over a decade ago, specifying that her name be left off billing records, according to documents reviewed by The Post. Reporting by The Post shows that Leo instructed the conservative pollster Kellyanne Conway in 2012 to bill the Judicial Education Project, a nonprofit group he advises, and use that money to pay Ginni Thomas. Leo told Conway that he wanted her to “give” Ginni Thomas “another $25K,” the documents show. He emphasized that the paperwork should have “No mention of Ginni, of course.”

Critics have called that relationship, and others involving the Thomases, a conflict of interest for Clarence Thomas.

Leo, 57, defended the Thomases in a statement to The Post, saying, “It is no secret that Ginni Thomas has a long history of working on issues within the conservative movement, and part of that work has involved gauging public attitudes and sentiment.” He also addressed why he left Ginni Thomas’s name off the documents: “Knowing how disrespectful, malicious and gossipy people can be, I have always tried to protect the privacy of Justice Thomas and Ginni,” he wrote.

So, who is Leo, and how did he become one of Thomas’s key allies? Here’s what we know:

Who is Leonard Leo?

Leo was born in November 1965 on Long Island and raised in an Italian American family of Catholics. His father died of cancer when he was in preschool, according to a 2017 profile in the New Yorker. After his mother remarried when Leo was 5, the family moved to central New Jersey. His nickname in high school was “Moneybags kid,” and a yearbook photo shows him holding a handful of cash, The Post reported in a 2019 profile.

He has credited his father, who emigrated from Italy and went from being a tailor to a vice president at Brooks Brothers, as a major influence in his political life.

“He understood America as being a land of opportunity, understood the value of capitalism, the value of hard work, personal responsibility,” Leo said to the New Yorker. “My grandparents were deeply religious people, they were daily Mass attendees. So I got all of that.”

Leo attended Cornell University and graduated with a bachelor’s degree in 1986 before landing an internship with Sen. Orrin G. Hatch (R-Utah). He returned to Cornell Law School and got a law degree in 1989.

Around this time, he married his high school sweetheart, Sally Schroeder, and returned to Washington to clerk for a federal appellate judge, A. Raymond Randolph, on the D.C. Circuit.

How did Leo become close with Thomas?

Leo has said he met Thomas in September 1990, when Thomas had just started on the U.S. Circuit Court of Appeals. When he walked into Thomas’s office, Leo said in a September 1995 speech, he saw a statue of St. Jude that made him think of his great-grandmother and the principles in which she believed.

“Perhaps it should not have been a surprise then that Justice Thomas would play some of the same inspirational role that my great-grandmother did,” Leo told the Federalist Society, an organization promoting causes for conservative and libertarian jurists. “Justice Thomas demonstrates a tremendous abiding faith in the capacity of the human spirit to rise above adversity.”

When Leo joined the Federalist Society as one of its first paid employees, he delayed his start date to gather research in support of Thomas’s nomination to the Supreme Court in 1991. The sexual harassment allegations against Thomas by Anita Hill turned the confirmation hearing into contentious and bitter proceedings. Hill, a lawyer, had worked with Thomas at the U.S. Education Department and the Equal Employment Opportunity Commission.

From 2011: For Anita Hill, the Clarence Thomas hearings haven’t really ended

After the Senate confirmed Thomas to the Supreme Court in a 52-to-45 vote that was at the time the narrowest margin in a century, Leo started at the Federalist Society.

He suffered a tragedy in that period. His first child, Margaret, was born with spina bifida, a condition that affects the spine, and it brought about other medical complications, according to the New Yorker. Margaret died in 2007 at age 14. Leo told the Washington Examiner in 2018 that Thomas had sometimes said Margaret was the justice’s best friend. Thomas also kept Margaret’s drawings under glass on his desk, Leo told the New Yorker.

What made Leo ‘a leader of the conservative legal movement’?

Conservatives are winning the battle for America’s courts, a triumph decades in the making. This is how they did it. (Video: Dalton Bennett, Jesse Mesner-Hage, Jorge Ribas/The Washington Post)

For nearly three decades, Leo has helped and led campaigns in support of the Supreme Court nominations of all the conservative judges now on the high court — John G. Roberts Jr., Samuel A. Alito, Neil M. Gorsuch, Brett M. Kavanaugh and Amy Coney Barrett.

He also has had the ears of the most recent Republican presidents. When President George W. Bush planned to praise racial diversity in his 2003 criticism of affirmative action, Leo called to complain that supporting diversity in a speech would “disgust any conservative who thinks that this is a matter of principle,” The Post reported in 2019. Leo later told The Post that “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.”

At a 2017 speech, Kris Mauren of the right-leaning think tank Acton Institute, introduced Leo as having “a significant leadership role in the selection and successful confirmation of a third of the currently sitting justices on the Supreme Court” after Gorsuch was confirmed earlier in the year, according to the Examiner. The introduction made Leo grin, but he insisted there was more work to do.

“I’ve seen that comment about the third of the Supreme Court — I prefer controlling interests,” Leo said to the crowd, which laughed in approval. “But we haven’t quite been able to launch a hostile takeover yet.”

In 2018, Thomas jokingly said Leo had helped reshape the nation’s court, becoming “the Number Three most powerful person in the world.”

“God help us,” Leo replied at the Federalist Society event in Fort Worth, smiling as Thomas and the attendees laughed.

But perhaps the most important piece of Leo’s rise is his fundraising ability. Between 2014 and 2017, Leo helped conservative nonprofits raise $250 million from mostly undisclosed donors — such funds are sometimes known as “dark money” — according to a Post analysis in 2019. The money was used in part to support conservative policies and judges, through advertising and funding for groups whose executives appeared as television pundits.

He left the Federalist Society in 2020 to start a new group, CRC Advisors, but kept his seat on the society’s board of directors. Last year, Leo and CRC Advisors scored a $1.6 billion donation from Barre Seid, an electronics manufacturing mogul, that was among the largest contributions ever made to a political nonprofit, according to the New York Times. The donation was possible thanks to an introduction from the Federalist Society, whose tax status forbids political activism, Politico reported.

What are the reactions to Leo’s leaving Ginni Thomas’s name off payment filings?

Among the details revealed by The Post is that the Judicial Education Project, the nonprofit that Leo advises that is connected to the payments to Ginni Thomas, filed a brief to the Supreme Court in 2012. The case, Shelby County v. Holder, challenged a landmark civil rights law aimed at protecting minority voters. The court struck down a formula in the Voting Rights Act that determined which states had to obtain federal clearance before changing their voting rules and procedures. Thomas was part of the 5-to-4 majority in the 2013 ruling in the case.

Thomas issued a concurring opinion, arguing that the preclearance requirement itself was unconstitutional. Thomas’s opinion, which was consistent with a previous opinion he wrote, favored the outcome the Judicial Education Project and several other conservative organizations had advocated in their amicus briefs. He did not cite the Judicial Education Project’s brief.

Democrats and media pundits have criticized Thomas and Leo for what they say is a clear conflict of interest. Sen. Sheldon Whitehouse (D-R.I.) said he has been tweeting about Leo since 2018 as part of an effort “to explain to the American people how billionaires are working to grow their influence at SCOTUS to bend our democracy to their will.” (The acronym SCOTUS refers to Supreme Court of the United States.)

“It needs to be clear,” Whitehouse tweeted. “[Leo’s] business isn’t *before* the Court; his business *is* the Court.”

Emma Brown, Shawn Boburg, Jonathan O’Connell and Robert O. Harrow Jr. contributed to this report.