The Last Conservative Judge

By Nick Catoggio

Friday, May 30, 2025

 

There are many stories in literature about people making deals with the devil. Weirdly, in most of them the devil is a square dealer.

 

That is, he keeps up his end of the bargain. He offers the protagonist wealth or power in exchange for something ethereal, like their immortal soul, and when they agree he delivers. The Prince of Lies turns out not to be a swindler. Most of the drama happens after he makes good on his promise and comes to collect.

 

The moral of those stories isn’t that you’re a fool to trade with Beelzebub because you’ll be cheated. It’s that you’re a fool to sacrifice your noblest self for something as fleeting as worldly power.

 

Conservatives made a deal like that in 2016. Donald Trump offered to stock the federal judiciary with their favorite judges, beginning with the vacancy left by Antonin Scalia on the Supreme Court; in return they would set aside their moral, civic, and ideological objections to him and support him in virtually anything he wanted to do, even if it affronted their conservative beliefs. Or basic decency.

 

The bargain was struck—and he delivered. Three eminent conservative jurists were added to the Supreme Court. Hundreds more were confirmed to federal appellate and district courts. The great white whale of social conservatism, Roe v. Wade, was harpooned in 2022 after a 50-year chase. Many other landmark legal victories for the American right have accumulated since Trump took office in 2017.

 

Conservatives weren’t cheated. The devil made good.

 

Fast-forward to last night, when the president broke his unnerving silence about Wednesday’s ruling by the U.S. Court of International Trade declaring his “Liberation Day” tariffs unlawful. He was angry, of course, but it wasn’t chiefly the court that he was angry at. He was mad at the people who had advised him on judicial nominees during his first term, producing a bench of conservative appointees who haven’t been nearly as “loyal” as he had expected.

 

“I was new to Washington, and it was suggested that I use The Federalist Society as a recommending source on Judges,” he explained to supporters on Truth Social. “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.”

 

Leo spent many years as the Federalist Society’s sherpa on judicial nominees, advising Republican presidents on whom to appoint and helping to shepherd candidates through the confirmation process. With the exception of Mitch McConnell, no one has done more this century to build a federal bench of originalist judges. But Trump didn’t want originalists—he wanted flunkies—and so Leo’s influence, and the influence of the organization he serves, have gone up in smoke. “I am so disappointed in The Federalist Society because of the bad advice they gave me on numerous Judicial Nominations,” the president whined in his Truth Social post. “This is something that cannot be forgotten!”

 

Conservatives got the judiciary they wanted in exchange for supporting a man who radiates contempt for the constitutional order. In doing so, they empowered a postliberal movement that despises judges who do their jobs conscientiously instead of dutifully midwifing a Trumpist autocracy. As the Republican Party proceeds further down the path to fascism that those conservatives enabled, eventually the federal judiciary will consist entirely of believers in the “living Constitution,” half authoritarian and half progressive. In the long run, as Reaganites age out and are replaced by younger Trumpists, conservative judges as we’ve known them will go mostly extinct.

 

That’s what conservatives got for their bargain. The devil has come to collect.

 

Sleazebags.

 

It felt meaningful that Trump chose to deride Leonard Leo as a “sleazebag” on the same day that he nominated “highly respected attorney, writer, and Constitutional Scholar” Paul Ingrassia to lead the Office of Special Counsel.

 

I could spend the rest of this newsletter on Ingrassia, but will direct you to Jason Hart’s dossier on him for a deep dive. Briefly, he’s around 30 years old, graduated from law school three years ago, and was sworn into the bar just last summer. He’s a passionate admirer of accused rapist Andrew Tate, has been spotted at a rally held by white nationalist Nick Fuentes, and declared a week after Hamas’ October 7 slaughter of Israelis in 2023 that “Israel/Palestine” was a “psy op.” Per Hart, he’s also accused Nikki Haley, Vivek Ramaswamy, and Ben Shapiro of not being Americans.

 

This is the guy whom Trump chose to head an office that’s supposed to protect federal whistleblowers from retaliation if they come forward to expose wrongdoing.

 

It touched my cynical heart to see people on social media who are mortified by Ingrassia’s selection demanding to know who’s vetting nominees for our dear president, as if he isn’t the platonic ideal of the sort of ruthless amoral toady that Trump adores. Ingrassia got the job for the same reason “Eagle Ed” Martin was elevated to pardon attorney at the Justice Department: He understands the assignment. If forced to choose between the president’s wishes and the ethical obligations of his office, there isn’t an iota of doubt what he’ll do.

 

Postliberalism is an ethic of government that demands impunity for one’s “friends” and persecution of one’s enemies. It can’t coexist with Enlightenment notions of law. And so, logically enough, the great project of Trump’s first four months back in office has been to start undoing those Enlightenment expectations by introducing postliberalism into federal law enforcement. Appointing figures like Ingrassia, Martin, and Kash Patel who’ll prioritize friends over enemies instead of neutrally apply the law is one way to do it. “No MAGA left behind,” as Eagle Ed candidly put it.

 

The president is also using his own powers to normalize treating friends and enemies differently. Every time he punishes an adversary by rescinding a legal privilege or rewards an ally by granting unjustified clemency, he reinforces public expectations that whether the law will be followed depends on whether someone has caused him trouble or not. The New York Times published a story on Friday that described his approach as nothing more or less than trying to “redefine crime,” which sounds hysterical but in fact describes the new reality. If you’re accused of a federal offense, Donald Trump’s opinion of you is now a crucial variable in whether you’ll serve time—or even be able to find a lawyer willing to represent you.

 

Authoritarians face a big problem in overcoming Enlightenment norms about law, though. In a word: judges.

 

Most elements of federal law enforcement answer to the president, and Trump has taken full advantage—purging DOJ prosecutors and FBI officials, firing the Pentagon’s top lawyers, letting DOGE run roughshod over the IRS and other federal bureaucracies. He has enormous discretion to make personnel changes that will imprint postliberal priorities on how American law is carried out …

 

… until the process reaches the courthouse door, where his power ends. He can’t replace the personnel there, as federal judges famously serve for life. And when he did have a chance to replace them in his first term, Leonard Leo and the Federalist Society pushed conservative nominees on him instead of the postliberal ones he thought he was getting.

 

I almost sympathize with him. To a man addled by sociopathy, who assesses merit entirely through the lens of whether someone is favorable to him or not, being told that so-and-so would make a “great judge” must have sounded indistinguishable from a pledge that so-and-so would dependably rule in his favor. That’s certainly the vibe one gets from his Truth Social post about Leonard Leo. The sense of betrayal, never mind resentment, is palpable.

 

The president could have created a judiciary that respects him more than it respects the Constitution and instead the Federalist Society duped him into creating one that did the opposite. It’s a momentous missed opportunity that’s left him with no good options. If he goes full authoritarian by ignoring court rulings, the public (and markets) won’t like it. But if he follows court rulings, the authoritarian project will founder.

 

Postliberalism can’t coexist with Enlightenment notions of law, and thanks to the Federalist Society, the Enlightenment retains an enormous advantage. What now?

 

They want flunkies.

 

The president is going to have to start filling judicial vacancies with the sort of servile flunkies he thought he was getting the first time around.

 

His advisers figured that out a while ago, actually. As far back as November 2023, Trump cronies like Russell Vought were complaining to the media that “the Federalist Society doesn’t know what time it is,” using a bit of autocratic lingo that’s in vogue among postliberal bootlickers. “Trump allies are building new recruiting pipelines separate from the Federalist Society” for his second term, the Times reported at the time, in hopes of finding attorneys “willing to use theories that more establishment lawyers would reject to advance his cause.”

 

The new administration would look beyond Leo-approved “squishes” who were “too worried about maintaining their standing in polite society and their employment prospects at big law firms to advance their movement’s most contentious tactics and goals,” the story continued. If it isn’t clear from all that what sort of lawyer Trump and his team are looking for, the Wall Street Journal got specific in a piece published last October: “This ascendant faction [in his orbit] wants more judges like U.S. District Judge Aileen Cannon, the controversial Trump-appointed Florida jurist who dismissed one of the criminal cases against Trump.”

 

They want flunkies. True to form, they intend to emulate the worst tendencies of the left by appointing judges who’ll approach the Constitution as a sort of “living” document whose meaning shifts as their political needs do. Remember the conservative rallying cry “no more Souters!” that sank Harriet Miers? The new version, essentially, is “no more Amy Coney Barretts”—never mind that Barrett, Brett Kavanaugh, and Neil Gorsuch did precisely what Souter notoriously declined to do by striking down Roe.

 

The postliberal right wants flunkies. Which brings us to Emil Bove.

 

Last week rumors spread that Trump was considering Bove for a vacancy on the 3rd Circuit Court of Appeals. A smart conservative lawyer I know scoffed that “a lot of people are ‘considered,’” seemingly skeptical that a character like him might end up on the federal bench. Bove helped defend Trump from criminal charges last year and was rewarded for it with a high position at the Justice Department. You may remember that he used that position to pressure prosecutors in Manhattan’s U.S. attorney’s office to drop criminal charges against New York Mayor Eric Adams, in part because Adams was useful politically to the White House.

 

Several lawyers in that office resigned in protest over the grossly unethical nature of the request. But Emil Bove, rumor had it, was in line for a promotion. And why not? By postliberal logic, the “sleazebags” in that story are the ones who refused to accord Adams the legal privileges due to an ally of the president. Emil Bove, Trump “henchman,” understood the assignment.

 

On Wednesday the rumors were confirmed. Bove is officially the president’s nominee for a seat on the 3rd Circuit. They want flunkies and they’re going to have them.

 

That probably also explains why Attorney General Pam Bondi notified the American Bar Association on Thursday that it’ll no longer be given special access to judicial nominees to assess their fitness for the bench. That’s not the first time that a Republican president has punished the ABA for liberal biases by rescinding its privileges in the confirmation process; George W. Bush did it as well. But in light of Bove’s nomination and the clamor among the worst people on the right for judges who “know what time it is,” it’s likely not so much the ABA’s “liberal” bias that Bondi is worried about as its bias against nominees who really are frighteningly ethically or intellectually unfit.

 

The right wants flunkies. Having a well-known legal gatekeeper raising public alarm about flunkies who are in the judicial pipeline is unhelpful to that project.

 

The long march.

 

Conservatives voted for this.

 

Many will claim that they didn’t, that they assumed they’d be getting the same caliber of jurist that they got during Trump’s first term, but in that case they’re as guilty of not paying attention to politics as the chumps who now complain that they didn’t vote for higher prices on foreign goods. The president’s interest in appointing flunky judges in a second term was as inevitable as his trade war was, as stories like the Times piece from 2023 demonstrate.

 

It’s the logical result of his descent into go-for-broke postliberalism that began with trying to overturn the 2020 election, a topic explored in, oh, the last 600 or so editions of this newsletter. When you voted for a guy who attempted a coup, who spent the whole campaign burbling about “retribution,” who’s casually called for suspending the Constitution, did you really expect him to do things by the book and keep appointing rule-of-law conservatives to the bench?

 

The good news for conservatives is that the postliberal program to create a judiciary full of fascists will take time, possibly decades. Trump will fill scores of vacancies before 2029, but he won’t come close to replacing every conservative with a gavel. His demagoguery of the Federalist Society might even backfire by spooking some Republican judges who were thinking of retiring but don’t want to be replaced by a clown. If you’re Samuel Alito, how might it influence your career plans to know that Emil Bove is waiting to take your seat?

 

The Federalist Society won’t wield much influence over future judicial appointees, but originalism will continue to be the default approach for most right-wing judges for the rest of Trump’s term, and for the next Republican administration, and maybe even for the one after that. The march through the institutions of the judiciary by right-wing Stalinists will in fact be long.

 

The president and his fans aren’t known for patience, though, so here we can make a few easy predictions. First, if the Supreme Court thwarts him by limiting his authority over matters that he cares about, like tariffs or immigration, Trump and his MAGA cheerleaders will call for court-packing. The fact that they derided the idea when Democrats took it up during Joe Biden’s presidency won’t matter to them any more than that they derided Kamala Harris for endorsing price controls before Trump did.

 

Another easy one: Trump will continue to appoint Federalist Society members to some judicial vacancies, mainly because there still aren’t enough prominent lawyers on the postliberal farm team to fill every open seat. The most influential appointments will be reserved for flunkies, however. We’ll see Paul Ingrassia land on the Supreme Court—or Aileen Cannon, more likely—before we see someone in the Paul Clement mold.

 

Another, easier than the first two: If conservatives on the court really do thwart Trump in a major ruling limiting his executive authority, the American right’s hatred of Neil Gorsuch, Brett Kavanaugh, and especially Amy Coney Barrett will exceed the hostility they feel for any Democrat. (Barrett’s extended family is already receiving veiled threats.) MAGA has learned to live with liberals in power, but they’ll never abide someone who accepted Trump’s invitation to join the court and then ungratefully insisted on holding him accountable to the law.

 

Last but not least: Most conservatives will be just fine with seeing their party’s judges become contemptible stooges for a contemptible strongman.

 

That’s the lesson of the last 10 years of right-wing politics, no? We’ve learned that the Republican Party consists of a small but powerful minority of actual fascists atop a much broader base of people who identify as “conservatives,” but assign no intellectual meaning to the term. To be a “conservative” means to favor owning the libs; whatever form that lib-owning takes, whatever moral demands it makes, matters not a bit.

 

Even conservatives who do assign ideological content to the term will find ways to rationalize supporting the Boves and Cannons. It’ll be the same old story: Yes, Trump is flawed, but better him than Hillary Clinton, Joe Biden, or Kamala Harris. Yes, Justice Bove is flawed, but better him than Justice Sotomayor. If we’re doomed to have a “living Constitution,” we should prefer to have fascists rather than communists bringing it to life.

 

Eventually, I expect, the Federalist Society will be known not as a platform for conservatives who favor originalism but as a platform for postliberals who believe the law should do whatever the president—a Republican president, at least—wants it to do. (That’s basically what happened to the Heritage Foundation, no?) The group has always attracted ambitious young lawyers in part because the networking it offers can advance their careers. If advancement in the GOP now requires showing loyalty to the president, not to the Constitution, why should we assume that the supply of right-wing legal talent won’t shift to meet the demand?

 

The devil is forever offering deals to American conservatives and they’re forever accepting, no matter how often he comes to collect. In the end, they’ll have traded away everything they ever claimed to care about.