Judicial Notice (06.01.25): Heartburn
Donald Trump v. Leonard Leo, a benchslap of Trump from a prominent conservative judge, and Kirkland’s big raid on a rival.
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Guess what I received in the mail the other day? A membership invitation from AARP, formerly known as the American Association of Retired Persons (and not to be confused with the recent Supreme Court litigant, A.A.R.P.).
Later this month, I’m turning 50—and I’m okay with that. Five years ago, I almost died from Covid—so my general outlook is, “I’m just happy to be here.” If any of you who have preceded me into the second half-century of life would like to share your reflections or advice, please do so in the comments.
Now, on to the news.
Lawyer of the Week: Leonard Leo.
After the U.S. Court of International Trade (CIT) ruled against many of his tariffs in V.O.S. Selections, Inc. v. The United States of America (discussed below as Ruling of the Week), Donald Trump took to Truth Social to vent:
The [CIT] incredibly ruled against the United States of America on desperately needed Tariffs but, fortunately, the full 11 Judge Panel on the U.S. Court of Appeals for the Federal Circuit Court has just stayed the order by the Manhattan-based Court of International Trade.
Where do these initial three Judges come from? How is it possible for them to have potentially done such damage to the United States of America? Is it purely a hatred of “TRUMP?” What other reason could it be?
I was new to Washington, and it was suggested that I use The Federalist Society as a recommending source on Judges. I did so, openly and freely, but then realized that they were under the thumb of a real “sleazebag” named Leonard Leo, a bad person who, in his own way, probably hates America, and obviously has his own separate ambitions.
Leonard Leo is a “sleazebag” and “a bad person”? Finally, Trump and the far left agree on something!
Trump then broadened his attack to include the conservative Federalist Society— the powerful legal organization where Leo worked for many years, whose board of directors he continues to co-chair:
[Leo] openly brags how he controls Judges, and even Justices of the United States Supreme Court—I hope that is not so, and don’t believe it is! In any event, Leo left The Federalist Society to do his own “thing.” I am so disappointed in The Federalist Society because of the bad advice they gave me on numerous Judicial Nominations. This is something that cannot be forgotten!
What did Leonard Leo say in response to Trump’s attacks? Leo took the high road, issuing the following statement: “I’m very grateful for President Trump transforming the Federal Courts, and it was a privilege being involved. There’s more work to be done, for sure, but the Federal Judiciary is better than it’s ever been in modern history, and that will be President Trump’s most important legacy.”
A Cornell Law alum and lawyer by training, Leo served for many years as executive vice president of the Federalist Society, playing a crucial role in its growth in size and influence. He advised then-candidate Trump on judicial nominations, helping him win over traditional conservatives who doubted his bona fides. After Trump won the presidency, Leo took a leave from FedSoc to help the administration pick judges.
But the two men had a falling-out in 2020. And since then, the rift between them has been exacerbated by the fact that various Leo-supported jurists, including Justice Amy Coney Barrett, haven’t always voted with Trump in his second term.
Did Trump have a valid basis for blaming his loss in the tariffs case on Leo? Probably not. The panel in V.O.S. Selections consisted of Judges Gary Katzmann, Timothy Reif, and Jane Restani—appointed by Presidents Obama, Trump, and Reagan, respectively. As a Trump appointee, Judge Reif is the only member of the panel who could plausibly be blamed on Leo. But note this, from my podcast interview of one of Reif’s colleagues, Judge Stephen Vaden (an excellent primer on the CIT, if you’d like to educate yourself about that court):
[Another] unique thing about our court, David, is we have a statute that actually brings politics into play. We are the only Article III court, and I think the only federal court period, even counting the ones that are not Article III, where the statute [28 U.S.C. § 251] says that no more than five members of our court may be affiliated with the same political party….
President Trump had three appointments to the Court of International Trade. I was the last one to be confirmed. My colleague Miller Baker was confirmed before me, and he is also Republican-affiliated. But Tim Reif, who is also a Trump appointee, is a Democrat. He was one of the Democrats’ chief counsel dealing with trade matters in the House Ways and Means Committee, which has jurisdiction over trade matters, and yet he is a Trump appointee.
My guess, then, is that Leonard Leo had little or nothing to do with the selection of Judge Reif. And if you look at his Senate Judiciary Committee questionnaire—which reflects Reif’s solid Democratic credentials, including involvement in the political campaigns of seven candidates, all Dems—you’ll see no mention of Leo or the Federalist Society.
Instead, according to Reif’s SJC questionnaire, his name was forwarded to the White House by Robert Lighthizer, U.S. trade representative in the first Trump administration. Reif served as general counsel of the Office of the United States Trade Representative, appointed by President Obama, and he remained at the Office and worked with Lighthizer after the change in administration. I’m guessing that he made a positive impression, convincing Lighthizer that he was a “good” Democrat—so when the Trump administration had to appoint a Democrat to the CIT, they probably figured that Tim Reif was the kind of Democrat they could work with.
Given this, there’s probably little or no legitimate reason for Donald Trump to blame Leonard Leo for Judge Reif and the loss in the tariffs case. And even if Reif had voted the other way, Trump still would have lost, 2-1.
But Trump lashing out against Leo is revealing, as noted by The New York Times and Politico (via Howard Bashman of How Appealing). It suggests that the growing rift between the Federalist Society and MAGA—i.e., between the conservative legal establishment, which still has a commitment to the rule of law, and Trump loyalists, who want Trump to win at all costs—might now be a more serious and lasting rupture.
Trump’s broadside against Leo, FedSoc, and some of his first-term judicial appointments struck some prominent legal conservatives as counterproductive. As Professor John Yoo told The Times, “Calling for the impeachment of judges, attacking Leonard Leo personally and basically calling him as traitor, as far as I can tell—Trump is basically turning his back on one of his biggest achievements of his first term.” Or as John Malcolm of The Heritage Foundation said to Bloomberg Law, Trump’s comments about Leo risk “needlessly offending an ally.”
And could Trump’s comments have negative practical consequences for his administration—including its judicial appointments? According to the Wall Street Journal editorial board (gift link), Trump’s “attacks on judicial conservatives will hurt his own agenda and legacy,” making it less likely that they’ll retire on his watch—“lest they be replaced by partisan hacks.” In fact, as conservative commentator Ed Whelan tweeted, “Just yesterday, a very conservative appellate judge told me that s/he wouldn't take senior status because of concerns over who would be picked as successor.”
Now, there is a counterargument here—at least as to Justices Clarence Thomas and Samuel Alito, whom some conservatives would like to retire under Trump. As Professor Josh Blackman wrote at The Volokh Conspiracy, “In Trump-related cases, Justices Thomas and Alito are dissenting alone…. If I had to guess, Justices Thomas and Alito would not want someone like the three Trump appointees to replace them. They would want someone who votes like them…. Indeed, if the same sorts of people are advising Trump on his next batch of Supreme Court nominee who advised on his first batch, Thomas and Alito would just as well hold on.”
But as to Justices Thomas and Alito, I don’t believe that recent events will affect their plans very much, in either direction. I believe they’ve made up their minds—and I’m sticking to my prediction from last year that we won’t see a SCOTUS retirement during Trump’s term. And on that note, I’m hearing that Justice Alito, who has completed his hiring of law clerks for October Term 2025, has even started hiring for October Term 2026—which is on the early side for him. If you have names to share—I now have all of his OT 2025 clerks, but none for OT 2026—please email me, at davidlat at substack dot com.
Other lawyers in the news:
Congratulations to the lawyers who won the big tariffs case: Jeffrey Schwab, who argued the case for the private plaintiffs (five U.S. businesses harmed by the tariffs); Reilly Stephens, James McQuaid, and Bridget Conlan, Schwab’s colleagues at the Liberty Justice Center; Professor Ilya Somin of Scalia Law, who has been working with the LJC lawyers; Brian Simmonds Marshall of the Oregon Department of Justice, who argued the case for twelve plaintiff states; and the many other attorneys, from state AG offices across the country, who collaborated with Marshall on the case.
Kudos as well to prominent SCOTUS advocate Kannon Shanmugam on joining the Harvard Corporation, the senior governing board of Harvard University (Shanmugam’s alma mater, for both college and law school). He’s filling the seat being vacated by his partner at Paul Weiss, fellow HLS alum Ted Wells. Considering all of Harvard’s courtroom battles with the Trump administration, the Corporation will benefit from the addition of another great legal mind.
Two top deputies to Texas Attorney General turned U.S. senate candidate Ken Paxton, former solicitor general Judd Stone and former assistant attorney general Chris Hilton, were forced to resign from the Texas AG’s Office in 2023 over allegations of harassment—according to a lawsuit filed by Jordan Eskew, another former employee of that office.
Donald Trump nominated Paul Ingrassia—a 30-year-old who graduated from Cornell Law in 2022, most well-known for hosting a right-wing podcast—to lead the Office of Special Counsel (OSC), an independent agency that protects federal whistleblowers. The OSC was recently in the headlines because of litigation over Trump’s firing of its former head, Hampton Dellinger.
Judge of the Week: Judge Richard Leon!
The Trump administration is now 0-3 in the federal courts when it comes to defending its executive orders (EOs) aimed at law firms. On Tuesday, Judge Richard Leon (D.D.C.) ruled that Trump’s EO against WilmerHale was unconstitutional—violative of the First Amendment’s protections for free speech and free association, the constitutional rights to counsel and to due process, and the separation of powers.
Here’s the opening to his 73-page opinion, striking down the order “in its entirety”:
The cornerstone of the American system of justice is an independent judiciary and an independent bar willing to tackle unpopular cases, however daunting. The Founding Fathers knew this! Accordingly, they took pains to enshrine in the Constitution certain rights that would serve as the foundation for that independence. Little wonder that in the nearly 250 years since the Constitution was adopted, no Executive Order has been issued challenging these fundamental rights.
Now, however, several Executive Orders have been issued directly challenging these rights and that independence. One of these Orders is the subject of this case. For the reasons set forth below, I have concluded that this Order must be struck down in its entirety as unconstitutional. Indeed, to rule otherwise would be unfaithful to the judgment and vision of the Founding Fathers!
Exclamation points in the original—in fact, this benchslap of an opinion boasts 26 exclamation points (not counting one included in a direct quotation of Trump). But those who know Judge Leon shouldn’t be surprised; he’s an excitable guy. Back in 2013, he was spotted having lunch with Chief Justice John Roberts at Carmine’s, by an Above the Law reader who described Judge Leon as “a rather rotund, strangely dressed fellow, who kept yapping and waving his arms at Roberts.”
Judge Leon, a George W. Bush appointee, is the most conservative jurist to rule against a Trump Biglaw EO to date. He is also, according to Sarah Isgur of Advisory Opinions (AO), a highly respected trial judge—so his ruling against one of these EOs is yet another sign of their constitutional infirmity. (Despite her praise for Judge Leon, Isgur did take issue, as a former Fifth Circuit clerk, with his comparison of the EO to a gumbo that “gives the Court heartburn”—questioning what a D.C.-based, Massachusetts-born judge would know about gumbo.)
In other judicial news:
Chief Judge Steven Colloton (8th Cir.) dismissed a judicial-misconduct complaint against a district judge who participated in a clerk hiring boycott aimed at graduates of Columbia. But in his decision, Chief Judge Colloton stated that “a substantial question” exists as to “whether judges cross an important line when they… begin using their power as government officials to pressure private institutions to conform to the judges’ preferences”—and that “[t]he matter may be appropriate for study by those who revise and interpret the Code of Conduct.” (The judge who was the subject of the complaint isn’t named in the opinion, but according to Reuters, it’s Judge Daniel Traynor of North Dakota.)
Conservatives tend to be more critical than liberals of legal academia—which isn’t surprising, given the leftward leanings of most law professors. But according to an interesting study by Brent Newton of Penn State Dickinson Law, conservative Supreme Court justices are citing law-review articles more than liberals nowadays.
In nominations news:
In another departure from how judicial nominations were handled during Trump’s first term, the administration is further curtailing the role of the American Bar Association (ABA) in reviewing judicial nominees. As Attorney General Pam Bondi declared in a letter to ABA President William Bay, the Justice Department’s Office of Legal Policy (OLP) “will no longer direct nominees to provide waivers allowing the ABA access to nonpublic information, including bar records,” and “[n]ominees will also not respond to questionnaires prepared by the ABA and will not sit for interviews with the ABA.” (Although the ABA didn’t get a “sneak peek” or early access to nominees’ identities during the first Trump administration, as the organization did during the Obama administration, the ABA did get access to bar records, and nominees did respond to questionnaires and sit for interviews.)
What I mentioned as a possibility in last week’s Judicial Notice has now come to pass: Donald Trump announced that he’d be nominating one of his former defense lawyers, Principal Associate Deputy Attorney General Emil Bove, to serve on the Third Circuit (despite Bove’s lack of significant ties to either New Jersey or Delaware, the two states in the Third Circuit with vacancies). Trump praised Bove on Truth Social as “SMART, TOUGH, and respected by everyone.” (Well, maybe not everyone—Ed Whelan is not a fan.)
Bove will face some skepticism from the Senate. Trump’s picks for five district-court seats in Florida should be more well-received: Magistrate Judge Kyle Dudek (M.D. Fla.); Florida chief deputy attorney general John Guard (M.D. Fla.); and three Florida state appellate judges, Judges Jordan Pratt (M.D. Fla.), Anne-Leigh Gaylord Moe (M.D. Fla.), and Ed Artau (S.D. Fla.).
In memoriam: Justice J. Michael Eakin, who served on the Pennsylvania Supreme Court from 2002 until 2016, passed away at 76. May he rest in peace.
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