The Federalist Society Announces Its Next Leader
The process by which Sheldon Gilbert was selected was full of twists and turns, but turned out well in the end.
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On Saturday afternoon, the Federalist Society for Law and Public Policy Studies aka FedSoc announced its next president and CEO. On January 2, 2025, Sheldon Gilbert, currently Walmart’s senior lead counsel for strategic initiatives, will take the helm of the Federalist Society, the nation’s largest organization of conservative and libertarian lawyers and law students.
Gilbert, 44, has experience in both the for-profit and non-profit worlds. Before joining Walmart, he worked at the National Constitutional Center, the Institute for Justice, and the U.S. Chamber of Commerce’s Litigation Center. Born in a coal mining town in Utah, he graduated from the University of Utah and GW Law. He is married with four children (who “are an absolute delight and run circles around him,” per Sean Marotta).
Orin Kerr described Gilbert as “an improbable choice amidst the more political types who were apparently in the running”—and I don’t disagree. If you compare him to the five finalists I previously reported on, his résumé is less politically inflected. And his credentials are also less “fancy” than some of the other candidates’—e.g., he went to an excellent but non-T14 law school, didn’t clerk, and never worked in Biglaw (aside from a stint as a summer associate at Dorsey & Whitney).
But Kerr nonetheless praised Gilbert as “a very good pick”—and the sources I spoke with agreed. As a former colleague of his told me, “Sheldon is extremely energetic, creative, and forward-thinking. He’s from the next generation of leaders, he can take Federalist Society into the future, and I’m excited to see what he’s going to do.”
FedSoc is large—90,000 members, 50-plus employees, a $25 million budget—and it contains multitudes. So I was struck by the widespread support for Gilbert, from across the ideological spectrum. Positive responses to his selection came from the following (and I’m giving you lots of names, so you can pick the pundit whose opinion you most respect or whose perspective comes closest to your own): Jonathan Adler, Randy Barnett, John Elwood, Robert George, Orin Kerr, Kurt Lash, Sean Marotta, Casey Mattox, Jeffrey Rosen, Carrie Severino, Shoshana Weissman, and Ed Whelan.
So that’s the news. If you came here to learn about who Sheldon Gilbert is and how his selection is being received, you can stop reading here.
But many of my readers love backstory and drama—especially when it’s about the Federalist Society. There’s a reason that one of the five most popular posts in the history of Original Jurisdiction is The Federalist Society And The Capitol Attack: What Is To Be Done, which explored internal tensions at FedSoc in the wake of January 6.
And what follows isn’t just idle gossip (although there’s certainly gossip in it). What happens at FedSoc doesn’t just stay at FedSoc, but instead ramifies throughout the legal world and, ultimately, the nation. I’d venture to say that if not for FedSoc, there wouldn’t be a conservative majority on the Supreme Court, and cases like Roe v. Wade and Chevron v. NRDC would still be the law of the land (for better or worse).
These developments have been possible because, since its founding in 1982, the Federalist Society has grown in size, scope, and influence. It did so under leaders like Eugene Meyer, the outgoing president and CEO, and Leonard Leo, the former executive vice president turned judge picker turned conservative power broker.
But the Federalist Society, like the conservative legal movement more broadly, is at something of a crossroads—and needs to figure out how to remain relevant and influential in the years to come. And the story of how FedSoc selected its next leader sheds light on the past, present, and future of the organization, as well as legal conservatism generally—topics of critical importance to the federal judiciary, the rule of law, and ultimately the nation.
When I learned of Sheldon Gilbert’s selection as FedSoc’s next leader—on Saturday afternoon, from the Twitter feed of Yashar Ali—I was surprised. To be clear, my reaction wasn’t negative; Gilbert and I are friendly, and my interactions with him over the years have been nothing but positive.
But I was caught off guard because he was not known to be in the running—which is why he didn’t appear on my list of five finalists for FedSoc president, published back in October. Was my intelligence bad? I doubted that—I pride myself on having excellent contacts on both the right and the left (most legal journalists have only the latter)—but I wanted to know what had happened.
And I was starting to hear some wild gossip. One rumor went like this (and as you read the next few points, please keep in mind that this was rumor—some of which wound up being accurate but much of it not, as discussed below):
The nationwide “search” was really just a pro forma exercise that would culminate in the selection of Dean Reuter, FedSoc’s senior vice president and general counsel. One theory was that Reuter had the inside track because, having worked at the organization since 2001, he had the greatest institutional knowledge and strongest ties to the Board of Directors. Another was that there was a war going on between different factions inside FedSoc over the future of the organization; more time would be needed to resolve that internal conflict, but in the meantime, Reuter was acceptable enough to both sides and could serve as a caretaker president for a few years, a transitional figure of sorts to FedSoc 2.0.
But Reuter’s candidacy got derailed—based on his alleged mishandling of an alleged personnel issue at FedSoc, as well as the prospect, had he been picked, of a revolt among staffers upset over the personnel issue.1
Leonard Leo—viewed by some as the puppet master controlling FedSoc, as well as much of the conservative legal world—seized upon this opportunity to resurrect the candidacy of Sheldon Gilbert, who had been eliminated in a previous round (in part because he lacked some of the super-shiny credentials of the others).
Why did Leo favor Gilbert? First, he was comfortable with him because they are both personally religious: Leo is Catholic, and Gilbert belongs to the Church of Jesus Christ of Latter-day Saints.2 Second, Leo felt that Gilbert—who is younger than the other two finalists, Robert Alt and Dean Reuter, and has less management experience—would be someone that he (Leo) could control.
Through the Marble Freedom Trust, the 85 Fund, and other organizations, Leo enjoys access to more than $1.3 billion in funding, which he directs to various conservative causes.3 Using the leverage associated with this vast amount of funding, which can make a critical difference in FedSoc’s budget, Leo strong-armed the board into picking Gilbert. (Yashar Ali hinted at this in his tweet: Leo “heavily influenced the decision to offer the role to Gilbert, per a source familiar with the process.”)
I outlined a version of this theory (or rumor) and sent it off to FedSoc on Saturday night. I wasn’t necessarily expecting comment; the Society can be tight-lipped at times. So I was pleasantly surprised when, shortly before midnight on Saturday night, I was called on the phone—by none other than Gene Meyer and Leonard Leo.
Gene Meyer and Leonard Leo are sometimes described as leaders of rival factions within the Society, with competing visions for the future of the organization—and maybe even some personal tensions between them. But during our 90-minute call, I was struck by their friendliness and familiarity with each other—which you’d expect from two people who worked together for almost three decades—and how they seemed to be very much on the same page in terms of the future of FedSoc.
I began by asking about some gossip I had heard. Was it true that after Gene Meyer announced his retirement in June, Leo didn’t even want to bother with a search, instead handpicking the next FedSoc leader himself?
Leo responded that that couldn’t be further from the truth. If anything, it was the opposite: at the outset of the process, he advocated for conducting a highly professionalized process, a nationwide search led by an outside firm. Other members of the Search Committee resisted, thinking that they could do the work themselves.
But after the Committee was inundated with applications from approximately 90 candidates, most of them highly qualified, Leo’s view prevailed. FedSoc retained CarterBaldwin Executive Search—on the recommendation of Ed Meese, who had worked with the firm in the past—and CarterBaldwin conducted an initial review of applications, before making recommendations to the Search Committee. (FedSoc has not publicly identified the members of the Committee, but Meyer and Leo informed me that most members of the Board of Directors were on the Search Committee as well—i.e., it wasn’t some small subset of the Board.)
Aided by CarterBaldwin, the Search Committee picked a group of five semifinalists (whom I reported on back in October, although I called them finalists): Robert Alt, president and CEO of the Columbus-based Buckeye Institute; Michael Fragoso, chief counsel to Senate Minority Leader Mitch McConnell (R-Ky.): Ryan Newman, general counsel to Governor Ron DeSantis (R-Fl.); Paul Ray, director of the Roe Institute for Economic Policy Studies at the Heritage Foundation; and Dean Reuter, senior vice president and general counsel of the Federalist Society.
Through further deliberation, the Search Committee whittled down the pool to three finalists: Robert Alt, Mike Fragoso, and Dean Reuter. But in November—shortly before FedSoc’s National Lawyers Convention (NLC), which began on November 14—Fragoso withdrew from the process for personal reasons.
This left only two finalists—which some members of the Search Committee had concerns about, and which CarterBaldwin said was not ideal. So after some discussion, the Committee raised the possibility of bringing back the #6 candidate, who had just missed the semifinalist cut—and that candidate was Sheldon Gilbert. (The Committee had already decided that it didn’t want to go with the two other semifinalists, Newman and Ray, despite their many positive qualities; the Committee wanted to add a new candidate to the mix, to create a final slate of three.)
So at the National Lawyers Convention, two Committee members, Steven Calabresi and David McIntosh, met with Gilbert for coffee,4 essentially to conduct a screening interview—and came away very impressed. After they reported back to the rest of the Committee that it was worth giving him a second look, the Committee conducted a two-hour Zoom meeting with Gilbert, followed by an in-person interview (the same two-step process that the other finalists previously went through).
Around this time—i.e., sometime during November—CarterBaldwin received an anonymous email flagging a potential issue regarding Dean Reuter. Specifically, the email raised the possibility that Reuter allegedly mishandled a certain personnel issue involving FedSoc staff—and suggested that the Committee look into the situation further, as part of its review of Reuter’s candidacy.
The Board retained Gibson Dunn—which had done work for FedSoc in the past, and was a trusted outside law firm—to look into the matter. After conducting an investigation that lasted almost four weeks, including interviews of multiple FedSoc staffers and leaders, Gibson exonerated Reuter of any malfeasance, sharing their findings in an hour-long presentation to the Board (with a written report to follow).
The Committee then faced the task of choosing a new leader from among three impressive finalists: Robert Alt, Sheldon Gilbert, and Dean Reuter. I asked Leo whether, as rumored, he coerced the Board into picking Gilbert at this point—and threatened to pull millions of dollars in FedSoc funding if Gilbert was not selected.
Leo emphatically denied this. He acknowledged that yes, Gilbert was one of his early favorites in the process—based on the excellent professional and personal qualities that led to his ultimate selection. But contrary to the rumor that he was single-handedly responsible for selecting Gilbert, Leo said that bringing Gilbert back into contention and ultimately giving him the job were consensus decisions that enjoyed broad, perhaps even universal, support—consistent with how FedSoc has historically operated over the years, as a consensus-driven organization.
On the issue of funding, Leo acknowledged that yes, he controls a huge amount of funding, and yes, he deploys it strategically—and in recent years, he has reduced or paused some of the funding he provides to FedSoc. Why? Since 2022, he has been conveying to the Board his concerns that FedSoc needs to evolve as an organization and transition leadership successfully to the next generation—and once that process has been completed to his satisfaction, he will provide a significant infusion of financial support to the Society.5
I asked Leo how the selection of Sheldon Gilbert as president and CEO might affect the funding that he and his entities provide to FedSoc. Leo said that the selection of a bold young leader like Gilbert is definitely part of what needs to happen at the Society—and that if Gilbert succeeds in moving FedSoc into the future, making it relevant to the next generation of leaders, more funding from Leo will be forthcoming.
So if Leo did not install Gilbert by fiat, how did the Search Committee settle on him as the next president and CEO? They certainly had no shortage of information about the three finalists, after two-hour Zoom meetings, in-person interviews, and dinners with each (which allowed the Committee members to interact with the finalists in a more relaxed setting).
CarterBaldwin also created an online dossier for each candidate, where Search Committee members could log in at any time to review the finalist’s application materials, past writings, and recommendations from outside sources. And, of course, the Committee members were doing their own work, speaking directly with personal references for the finalists and having side conversations amongst themselves, comparing notes about the various candidates.
Last Friday, December 13, the Board convened to select and vote upon the new president and CEO. The meeting, which started around 10 a.m. and concluded around 3:30 p.m., was not contentious—and, in fact, was surprisingly straightforward. Although the Board thoroughly evaluated the three finalists and their respective advantages and disadvantages, as it was required to do, there was a broad consensus that Gilbert was the best choice—culminating in a unanimous vote to offer him the role as FedSoc’s next president and CEO.
The rollout got a little… messy. The original plan was to announce on the morning of Monday, December 16—a logical and popular time for major announcements. But after Yashar Ali tweeted out the news, the Society decided it was best to accelerate the announcement and make things official—and the rest is history.
The selection of the Federalist Society’s new leader raises recurring questions: Where does FedSoc go from here? What are the possible directions in which it might evolve? How can it enjoy continued success in a rapidly changing political and legal climate?
In the words of Professor Josh Blackman, “People today may think FedSoc harbors something close to a monopoly on conservative legal thought. But history teaches that the dominance of market share is not permanent…. Organizations that fail to innovate become punchlines…. Nothing lasts forever.”
Struck by how much they agreed with each other during our 90-minute call, I specifically asked Meyer and Leo: what are the differences between the two of you and your competing visions for the Federalist Society? Surely there must be some daylight between you, right?
“There might be, at the margins, some slight differences in our visions,” Meyer said. But he said that on the whole, during the 29 years that he and Leo worked together, they operated by consensus.
Similarly, Leo could not recall, off the top of his head, any major disagreement that turned into an argument or fight between the two of them. It was “a great partnership,” he said—and “although we didn’t see eye to eye on every issue, we had an excellent working relationship.”
But Leo did acknowledge some distinctions: “We are different people, and we have some stylistic differences. I tend to be a little more edgy and operational, while Gene can be more cautious. We complemented each other.”
“Working with Gene was a great experience, and my departure from the Federalist Society in 2020 was bittersweet,” Leo added. “I felt called to do the philanthropy and other work that I’m doing now. But I love the Federalist Society, and I never had any reservations about going into the office every day and working with Gene.”
We concluded with a discussion of the future of the conservative legal movement more generally—and where FedSoc fits into it. There are definite tensions, both in the movement and in the Society—rifts that could very well grow during a second Trump administration, without a Democratic White House to serve as a common foe.
“At the Federalist Society, we have a lot of these tensions because we have a pretty big tent and don’t take institutional positions on issues,” said Meyer. “In fact, our typical response to disagreement is, ‘Let’s have a debate.’ I believe that in some ways, the opportunities we have now are greater than they have ever been—and I’m excited about the future because I believe that Sheldon has the vision and leadership ability to turn our hopes into reality.”
“The future of the Federalist Society depends on successfully addressing several distinct opportunities and challenges,” Leo explained. “One is the issue of generational change. If you accept that FedSoc is a talent pipeline or infrastructure or network, it’s obviously very important that the baton be passed from one generation to the next. There are some amazing thirtysomething and fortysomething people who are rising up in the legal profession, who are ready to engage and to lead—and Sheldon is an excellent example.”
“There have always been divisions in the conservative movement—that is nothing new—and I can’t tell you how they are going to be resolved,” Leo said. “But FedSoc has always been very good at bringing together cross-cutting factions and finding areas of agreement and consensus.”
“Things are obviously very different today,” he continued. “We’ve moved from a world where conservatives and libertarians were critical of the governing institutions to one where conservatives and libertarians are now running many governing institutions—and that has implications for FedSoc’s programming and membership that need to be figured out.”
“But it doesn’t matter what I think or what Gene thinks about these issues,” Leo concluded. “What matters is what Sheldon Gilbert and the next generation think about these issues. And I’m excited to find out.”
As discussed below in greater detail, an investigation by outside counsel cleared Dean Reuter of any malfeasance. But I’d urge Sheldon Gilbert to go on a “listening tour” of the FedSoc offices, meeting with staffers individually or in small groups—because not all campers there are happy right now, as I learned during the course of my reporting.
Even if he is personally religious, Gilbert might be best described as a “libertarian conservative” in his politics, per Sarah Isgur of Advisory Opinions (starting around 1:02:00). But because he is so charming and has such high EQ, Gilbert can talk to members of different factions and make them feel heard and respected—which explains why he enjoys support from libertarians like Randy Barnett, social conservatives like Robby George, moderates like Sean Marotta, and liberals like Jeffrey Rosen.
For more on how Leonard Leo acquired control over these eye-popping sums and how he deploys them, see, e.g., Thomas Edsall and Ken Vogel of The New York Times, or We Don’t Talk About Leonard, the podcast by ProPublica reporters Andrea Bernstein, Andy Kroll, and Ilya Marritz. While I can’t vouch for every fact and don’t agree with every opinion contained in these extremely voluminous sources—which I suspect many conservatives might take issue with, since they’re not flattering to Leo—the big-picture takeaway can’t be disputed: Leonard Leo is one of the most powerful figures in the entire conservative movement.
I’m guessing that Gilbert, a member of the Church of Jesus Christ of Latter-day Saints (LDS), did not drink coffee at this meeting. Fun fact: it’s a common misperception that LDS members don’t drink coffee because of a caffeine prohibition; it’s actually a prohibition against coffee and tea specifically. So if you see an LDS friend eating chocolate, you don’t need to narc them out to their local bishop.
Leo added that he has been open about his philosophy of giving, explaining how he wants to deploy his funding to maximum effectiveness. Some of Leo’s concerns are reflected in a leaked letter that the 85 Fund sent to recipients of its funding, which articulated his “growing concern that conservative philanthropy is too heavily weighted in the direction of ‘ideation’—the development of and education about conservative ideas and policies”—and not enough financial support is going “toward operationalizing and weaponizing those ideas and policies to crush liberal dominance at the choke points of influence and power in our society.” (Query whether FedSoc, at least in its “we’re just a debating society” incarnation, is too focused on “ideation” and not focused enough on “crush[ing] liberal dominance.”)
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Sheldon is a personal friend. He's a great guy. Really happy for him and for what he can bring to FedSoc.
Thanks for this article, David.