Zoe Berg, Senior Photographer

When former President Donald Trump began the review process for nominating a Supreme Court justice in 2017, Leonard Leo — the former vice president and current co-chairman of the Federalist Society — worked with the Trump administration and Republicans on the Senate Judiciary Committee to propose potential candidates.

Under Leo’s guidance in 2018, Trump nominated Brett Kavanaugh ’87 LAW ’90, who has been connected with the Federalist Society for at least 24 years. In 2017 and 2020, Leo’s creation of a list of potential Supreme Court nominees for Trump helped to advise the appointment of two other Federalist Society affiliates, Justices Neil Gorsuch and Amy Coney Barrett.

By 2024, six of the nine Supreme Court justices considered themselves members or affiliates of the Federalist Society — the culmination of a longstanding pipeline connecting members of Federalist Society chapters at America’s top law schools to high-level judgeships and political offices.

But how exactly does this pipeline work, and how has it shaped conservative thought within the American judiciary?

The Federalist Society, a debating organization that hosts political events and acts as a network for conservative and libertarian students and professionals, was founded at Yale Law School in 1982 by three Yale alumni: Steven Calabresi ’80 LAW ’83, David McIntosh ’80 and Lee Liberman Otis ’79. Today, the Society is represented at all 204 ABA-accredited law schools in the country, has established communities of affiliated lawyers in 60 cities and has over 70,000 members.

​​The organization is divided into three divisions — students’ division, lawyers’ division and faculty division — allowing for collaboration between law students, practicing lawyers and judges and law school professors. 

From humble beginnings to political heights

In April 1982, the Federalist Society held its first event: a referendum entitled “A Symposium on Federalism: Legal and Political Ramifications.” Held over the course of a weekend, it featured a series of speaker events, debates and workshops. 

The Federalist Society has since defined itself as a “group of conservatives and libertarians interested in the current state of the legal order,” according to its website. According to its three founders, the Federalist Society’s original goal was to provide a space on law school campuses for debating ideas across the political spectrum.

“It’s fair to say that none of us, when we started it, had any idea how large it would eventually grow to be,” Calabresi said.

With six of the nine current Supreme Court justices serving as members or affiliates of the Federalist Society — Clarence Thomas LAW ’74, Samuel Alito LAW ’75, John Roberts, Kavanaugh, Barrett and Gorsuch — the group’s impact on the national judiciary is notably more significant than its founders anticipated.

Other affiliates include former Supreme Court Justice Antonin Scalia, FBI Director Christopher A. Wray ’89 LAW ’92, former U.S. Attorneys General Edwin Meese ’53 and John Ashcroft ’64 and senator Josh Hawley LAW ’06. 

An “affiliate relationship” to the society is defined by membership in one of its divisions, regular attendance at events or speaking at events.

The idea for the Federalist Society originated when Calabresi, McIntosh and Liberman Otis, all Yale College graduates, started their legal studies — Calabresi at Yale Law School and McIntosh and Liberman at the University of Chicago Law School. They felt that libertarian and conservative perspectives on issues were not represented on their campuses. 

All former members of the Yale Political Union in 1978 and 1979, they noted the “debate and discussion” that fueled their time in the YPU was not present at their respective law schools.

“The Political Union, at the time we were active in it, … was very different from what it is now,” Calabresi said. “We really believed in the value of debate and discussion that the Yale Political Union fostered and wanted to bring it to our law school campuses.”

The three began reaching out to prominent professors and thinkers on the political right to organize their first event: a “Symposium on Federalism” hosted on Yale’s campus. They managed to secure a speaker lineup that included Robert Bork, a candidate for a Supreme Court nomination during Ronald Reagan’s presidency; Scalia, who was a high-level UChicago Law School professor at the time; and Morton Blackwell, president of the Leadership Institute, an organization committed to “turn[ing] principled conservatives into powerhouse leaders,” according to the organization’s website. 

A funding sum of $24,000 from the John M. Olin Foundation and the Institute for Educational Affairs — an organization run by Irving Kristol, a prominent neo-conservative thinker — allowed the Federalist Society to pay for the travel expenses of 60 students and 20 legal scholars to the symposium, which was co-sponsored by the Harvard Journal of Law and Public Policy.

On April 23, 1982, the News published an article announcing the symposium, which was to be held on the last weekend of April. “Several hundred law students are expected to attend a conference on ‘Federalism: Legal and Political Ramifications’ this weekend,” the News wrote. “The symposium, including speeches, debates, and discussions, will provide students and the speakers with a forum for discussing the proper balance of power among federal, state, and local governments.”

Topics covered at the first symposium included originalism — a philosophy of constitutional interpretation that believes in reading the law as it would have been understood at its birth — and best practices for high-level success for right-wing students.

Blackwell shared reflections on how to get “better people” on law school faculties and how to reshape cultures on law school campuses, according to records by the Harvard Journal of Law and Public Policy. Bork spoke about political issues, including abortion and the “gentrification of the Constitution.” 

At the symposium, Scalia said that “conservatives had been outgunned at the federal level for half a century.” 

On May 2, 1982, the event was featured in The New York Times — an instance of high-profile coverage that foreshadowed the Federalist Society’s subsequent momentum and a new era of conservative thought on law school campuses, one defined by concentrated and organized representation, events and programming. 

Within two years of its first referendum, the Federalist Society had officially filed for national nonprofit status and was operating on dozens of new elite law school campuses, including Harvard, Georgetown University, the University of Virginia and Stanford University. It hosted another symposium in 1983 at Harvard Law School and a third in 1984 at the University of Chicago. By the 1990s, the Federalist Society operated a branch at every law school in the country. 

A pipeline from law school to the courts

As original members began graduating from their respective law schools and entering the national court system, they maintained their ties to the Federalist Society. 

The development of the Lawyers’ Division of the organization in 1986 ensured that graduates could still maintain their intellectual ties to the society through organized speaker events and annual conventions. The creation of a Faculty Division in 1999 allowed law school professors to take an invested stake in “encourag[ing] constructive academic discourse,” according to the Federalist Society’s website.

This led to a high-powered pipeline to the national court system facilitated by the Federalist Society’s vast alumni and affiliate network. 

Noah Feldman, a law professor at Harvard, participated in a number of Federalist Society events as an “arguer on the other side” of the society’s stated political affiliations, he said. A self-identified “liberally-inclined” thinker and debater, Feldman authored the audiobook “Takeover: How a Conservative Student Club Captured the Supreme Court” in 2021 alongside co-author Lidia Jean Kott, wherein they unpack the Federalist Society’s “pipeline” to high-level national politics.

Feldman told the News that the Federalist Society’s community of thinkers with similar intellectual, political and legal commitments enables members to support one another over the course of their careers. 

“It basically creates a framework in which there can be a clear path to go from smart, first-year law student with conservative leanings to law clerk to a Court of Appeals judge or to the Supreme Court,” Feldman said.

High-powered connections like those between the society and national judiciary politics abounded over the course of the society’s early years. During Ronald Reagan’s presidency, Attorney General Edwin Meese was known to give key positions in the Justice Department to members of the society, helping to ensure that judicial nominees were “compatible with the philosophical and policy orientation of the President,” according to an article published by the Federalist Society Review. 

During the presidency of George H.W. Bush ’48, Otis, co-founder of the society, was selected as an associate White House counsel. The role of a White House counsel is to advise the president on all legal issues concerning the president and their administration, including judicial candidates, according to the Federal Register.

“Organizations and institutions, if they’re small enough and have a sense of community, are very good at creating a sense of reputation and of mutual trust,” Feldman said.

Calabresi echoed Feldman’s sentiments.

“The Federalist Society has kind of grown into an extended family, and so it’s a bit of a network of sorts,” Calabresi said. 

He explained that he believes that people with right-of-center political views often feel isolated and marginalized at Yale Law School. According to Calabresi, the society allows people to form friendships with “other people who agree with them.” Additionally, he explained that the society puts students in touch with judges who share similar views, whom students can then “go on to clerk for.” 

This relationship, according to Calabresi, has reciprocally shaped judges’ vetting processes for potential clerks.

“Judges and thinkers who are right of center often find that they’re in a minority in the courts that they’re on, and they equally draw sustenance from being part of a group that is a national group of people who think the way that most Federalist Society members do,” Calabresi said.

Despite this unforeseen pipeline of power, Calabresi emphasized that the Federalist Society’s day-to-day operations still echo its original goal of fostering debate on college campuses.

He pointed to an event hosted by the Federalist Society at Yale Law School on Sept. 24, 2024, titled “Where Have All the Trials Gone? The Vanishing Jury Trial and What It Means for the Legal Profession and the American System of Justice,” which saw Judge Richard Sullivan LAW ’90 of the U.S. 2nd Circuit Court of Appeals speak on the future of jury trials in America.

“The Federalist Society contributes vitally to the intellectual life of this place,” Sullivan said at the event. “I’d like to thank them for having me today and for supplementing law school students’ educations.”

Calabresi reflected on the Federalist Society’s importance on campuses, one that he sees as more powerful than the society’s operations in the legal world.

“We are, at our core, a society for debating ideas,” Calabresi said. “I just think it’s informational, both for Federalist Society members and for non-Federalist Society members to come and hear what our speakers, like Judge Sullivan, have to say on law school campuses.”

On a larger scale, the high-powered network facilitated by the society continued to manifest on the national stage. Under former President George W. Bush’s ’68 administration, two new justices with Federalist Society ties — Alito and Roberts — were appointed to the nation’s Supreme Court. Joining Thomas, a Reagan appointee, their appointments ensured that one-third of America’s highest court had ties to the Federalist Society. 

Building ties to the Supreme Court

Eleven years later, in 2017, President Donald Trump began the review process for a successor for the late Supreme Court Justice Antonin Scalia. During the judiciary vetting process, his administration worked closely with Leonard Leo, former executive vice-president of the Federalist Society and current co-chairman, to evaluate potential candidates.

Leo — a Cornell Law School graduate who founded Cornell’s Federalist Society chapter in 1986 — stepped down from his role as co-president of the society in 2017, when the Trump administration had just begun its review process for potential new Supreme Court justices. During this time, Leo devised a list of potential candidate names for the former president that proved to include the three justices Trump would ultimately appoint during his presidency.

As a confidant to Trump, Leo played a considerable role in the 2017 appointment of Neil Gorsuch. Trump’s later appointments of Brett Kavanaugh and Amy Coney Barrett, also Federalist Society affiliates, were under Leo’s counseling, as well. This aligned with a promise that Trump had made earlier in 2016 during his election campaign: if elected, his judicial nominees would “all [be] picked by the Federalist Society.” 

Over the course of the past 40 years, Leo has played a significant role in accelerating the Federalist Society’s rapid growth on the national stage.

After graduating from Cornell, Leo moved to Washington to take on a full-time job with the Federalist Society. He focused on identifying sources of funding for the organization, developing relationships with donors such as the Koch Family Foundation and the Scaife Foundation. As Leo’s personal career developed, he kickstarted The 85 Fund, a group that funds conservative causes nationwide. The 85 Fund donated $5.6 million in funds to the Federalist Society in 2020 and $3.5 million in 2021.

Leo quickly rose within the ranks of the society, becoming vice president of operations in 1990. He took leaves of absence from this position during the judicial review processes for Bush’s Supreme Court nominations in the early 2000s, and he stepped down from his role as operational vice president to become honorary co-chairman of the organization during Trump’s judicial review processes for the Supreme Court.

“When you see that Leonard Leo … took a leave from the Federalist Society to actually go work in the Trump administration on judicial appointments, it just couldn’t be more explicit that there’s a strong tie between the society and our national judiciary,” Feldman said.

Leo, a self-identified conservative who has closely aligned himself with the Christian right, sees his ties with the Federalist Society as a means to realign national politics. 

Leo did not respond to multiple requests for comment.

After receiving $1.6 billion in donations from 2020 to 2022 from Barre Seid, who is a Federalist Society affiliate and political donor, Leo has outlined a plan for a conservative takeover of the courts.

“We need to crush liberal dominance where it’s most insidious,” Leo told the Financial Times.

In Feldman’s opinion, Leo’s connections with the White House and national judiciary processes since his start at the Federalist Society are proof of the society’s strong influence on the national stage.

Calabresi clarified that despite this perceived link, the goals of the organization remain focused on hosting debates and holding conversations that feature different viewpoints.

“The Federalist Society plays no role in judicial selection under either Republican or Democratic Administrations,” Calabresi wrote to the News. “We are a 501(c)3 non-profit organization, which holds debates and conferences in which all points of view are presented as much as is possible.”

Feldman, though, described the past 20 years under Leo’s leadership at the Federalist Society as a “conservative constitutional revolution.”

Politicians like Sen. Sheldon Whitehouse ’78, United States senator for Rhode Island since 2007 and chairman of the Senate’s Judiciary Subcommittee on Federal Courts, see Leo’s political influence as setting a dangerous precedent.

In a statement to the News, Whitehouse, who has been outspoken in his criticisms of the Federalist Society pipeline, critiqued Leo’s contributions to national judiciary politics.

“Leonard Leo’s secretive judicial selection and confirmation operation use[s] the Federalist Society’s name as a cover,” Whitehouse wrote to the News. 

He described Leo’s influence as an advisor to President Trump as a “covert operation … to control Republican judicial appointments.” 

Whitehouse claimed that the Federalist Society is a “pawn” in what he perceives to be Leo’s efforts to expand conservative influence over the national court system. In Whitehouse’s opinion, Leo’s actions do not align with the stated goals or values of the national Federalist Society as it operates today. 

Calabresi specified that the role of independent actors like Leo in judicial processes did not reflect the stances or positions of the society at large. 

“Contrary to the press reports, the Federalist Society plays no role at all in judicial nominations and never has,” Calabresi wrote to the News.

He said that while individual members of the society’s board of directors have sometimes played a role in judicial decisions, this has been in a strictly private capacity. 

What does this mean for the 2024 election?

Noah Feldman drew a connection between the 2024 election and the future influence of the Federalist Society.

Feldman said he believes the Federalist Society perceives conservatism as being an “underdog” in national politics. This perception, he said, is subject to change depending on the outcome of the 2024 election. 

Given Trump’s strong connection to the Society, Feldman said that a Trump victory would challenge the society’s position as an “underdog” in national politics, draining energy from the movement in the long-term. 

When asked about how the society might operate differently in an election year, Calabresi clarified that the Federalist Society intends to be strictly apolitical.

“The Federalist Society … takes no positions on pending legislation, cases pending before the Supreme Court or any other court, or on judicial nominations,” Calabresi wrote to the News.

Irrespective of the Federalist Society’s intentions, Feldman discussed the organization’s wide-ranging — but perhaps, inadvertent — impact on national politics. Feldman said he sees the past five years as the “apex” of the Federalist Society’s influence, with the 2024 election representing an essential turning point.

He pointed to splinterings within the national court system that exemplify this decline.

“Once you’ve gotten your main objectives, it is much harder to hold on to your place of influence,” Feldman said. “Right now, the conservative justices are starting to splinter in terms of their jurisprudential and ideological commitments, and you can see that in the court’s opinions.”

In the past, the Federalist Society was committed to the three elements of modern legal conservatism: textualism in statutory interpretation, originalism in constitutional interpretation and judicial restraint. According to Calabresi, while the society is committed to hosting debates featuring multiple perspectives, members “tend to agree on how to interpret the law.” 

Feldman echoed this idea. “If there’s any other group that wants to achieve similar influence to the Federalist Society, it similarly has to have cohesion in its ideological commitments and the long time horizon and the patience to get there,” Feldman said. 

However, Feldman sees this shared interpretation as being at risk. He cited examples of how justices associated with the society, like Alito and Gorsuch, have begun to deviate from textualism, contrary to the society’s stated goals. 

In Feldman’s opinion, this loss of a cohesive legal stance and philosophy, coupled with the rapid growth of conservatism in national judiciary politics in the last 10 years, could foreshadow the Federalist Society’s downfall.

According to Feldman, should Trump win the 2024 election, Trump’s close ties to the Federalist Society’s network would ensure that any judge appointments within the next four years are members of the tight-knit society. 

Two judges — Thomas, 72, and Alito, 74 — are approaching the age of retirement, and politicians expect a Supreme Court vacancy to open during the upcoming 60th presidency.

Alongside the presidential election, 305 appellate court seats are on the ballot in 2024, including 69 state supreme court seats this November. 32 of the candidates running for state supreme court positions are affiliated with the Federalist Society.

Feldman’s notion of the society’s “apex” cannot be disentangled from the organization’s long history of judicial impact. 

As the 2024 election approaches, the Federalist Society provides a new lens by which to view the growth of conservatism as a concentrated body of thought on the national scale. 

This April will mark the 43rd year since the Federalist Society’s founding.