Another One Bites the Dust

More Permanent Injunctions Against Law Firm Executive Orders

In the past week two federal district judges granted summary judgments to law firm plaintiffs and permanently enjoined the punitive executive orders issued by the Trump Administration. The first was an order by U.S. District Judge John D. Bates in the Jenner & Block proceeding, and the second was by Judge Richard J. Leon in the matter of WilmerHale. Although online commentators are having a lot of fun with Judge Leon’s enthusiastic employment of exclamation points and his excellent Cajun food metaphor,¹ both opinions are well worth reading. Although they cover much of the same ground as the previous order in the Perkins Coie proceedings (which I wrote about here), they go beyond that order in interesting ways. In particular, both of the recent orders are more explicit about the constitutional threat posed by targeting lawyers, as opposed to other individuals or groups who may claim First Amendment protection against retaliation for engaging in protected speech.

The Jenner and Wilmer orders were nearly identical in structure and effect, differing only in the specific grievances that Trump had against each firm. The general idea was that the firms were “weaponizing” or “politicizing” their pro bono programs by representing clients in immigration proceedings (grotesquely characterized as “obstruction of efforts to prevent illegal aliens from committing horrific crimes and trafficking deadly drugs within our borders”) or seeking rights for transgender people (construed by the Administration as ““support[ing] attacks against women and children based on a refusal to accept the biological reality of sex”); representing clients in election litigation (engaging in conduct that “furthers the degradation of the quality of American elections”); or having lawyers in the firm such as Robert Mueller, who had investigated allegations of Russian interference in the 2016 election. For these sins the firms were to be punished, basically with a professional death penalty. This was to be accomplished by threatening to revoke the federal government contracts of a client of the firm. In its brief, the government argued that it could consider a contractor’s performance subpar if it engaged a law firm that did the terrible things the Administration was accusing it of doing. In a world of . . . let’s just say “aggressive” arguments, that one is batshit crazy. But along with the denial of access to government buildings, purportedly on national security grounds, the threat of revocation of government contracts of the clients of these firms is the key to the draconian impact of the EOs.

The First Amendment and Its Limits

As a legal matter, what is wrong with these orders? The initial round of commentary tended to focus on broadly conceived and very attractive ideals like the rule of law, the right to counsel, and the role of lawyers in a constitutional democracy. I at least was a wee bit disappointed, therefore, when the summary judgment granting a permanent injunction against the Perkins Coie EO was mostly a First Amendment decision. The analytic keys to that order, both taken from NRA v. Vullo, 602 U.S. 175 (2024), were that (1) while content discrimination draws First Amendment scrutiny, viewpoint discrimination is super-duper disfavored; and (2) the government cannot do indirectly what it is prohibited from doing directly, even though it retains rights as a speaker to express its disapproval of, say, gun manufacturers. (The Jenner opinion, at p. 32, provides a nice tight summary of Vullo when it says the government in that case was trying to “sidestep due process.”) As I said when I wrote about the Perkins Coie summary judgment, this is not meant as a criticism. The First Amendment retaliation claim, grounded in Vullo, is a powerful, analytically clean basis for enjoining the EO. Judge Bates, in the Jenner summary judgment opinion (p. 11), says it is the “most straightforward winner” among the firm’s arguments.

I think that’s right, but still, there seems to be something missing. I strongly endorse the First Amendment anti-orthodoxy principle from W. Va. Board of Education v. Barnette, which is the lead-off quote in the Jenner summary judgment opinion:

In our constitutional order, few stars are as fixed as the principle that no official “can prescribe what shall be orthodox in politics.”

But there are lots of individuals and groups out there holding unorthodox views – the Jehovah’s Witness kids in Barnette; the firearms industry in Vullo; the rock band in Matal v. Tam, 582 U.S. 218 (2017), that wanted to use a racial slur as its name; neo-Nazi demonstrators; distributors of pornographic content; and so on – that don’t seem to play the same positive role in our constitutional democracy as lawyers do. I’m left wanting something more, something about lawyers that sees us as not just dissenting, unorthodox, unpopular actors (although we can be a pain in the ass), but as actors who play a central role in the maintenance of the rule of law.

The trouble is, it’s not obvious how to connect the role of lawyers to the sorts of constitutional rights that the law firms have standing to assert as the basis for their claim for relief. There is a lot of good caselaw under the Sixth Amendment on government interference with the right to counsel in the context of criminal defense. See, e.g., U.S. v. Gonzalez-Lopez, 548 U.S. 140 (2006). And it’s true that these firms do some criminal defense work, mostly in white-collar cases. (Judge Leon makes this point on pp. 66-68 in the Wilmer summary judgment opinion.) Those cases leave a pretty big gap in coverage, however, including civil litigation, representing clients before federal agencies, transactional matters, compliance counseling, and so on.

All three of the summary judgment opinions so far cite a D.C. Circuit case called American Airways Charters v. Regan, 746 F.2d 865 (D.C. Cir. 1984). That case involved sanctions against an airline for operating tourist charters to Cuba, in violation of a federal statute called the Trading with the Enemy Act. The Treasury Department took the position that a license was required for any attorney who wanted to represent a “designated foreign national.” The lawyer who wanted to represent the airline sought a declaratory judgment and an injunction. The D.C. Circuit opinion, reversing the district court’s denial of an injunction, was mostly based on the overstepping of its statutory authority by the office within the Treasury Department that refused to grant the lawyer the license. However, the court bulked up its opinion with reference to the “nature and purpose of the attorney-client relationship.” The court said that

in our complex, highly adversarial legal system, an individual or entity may in fact be denied the most fundamental elements of justice without prompt access to counsel. As this court observed in Martin v. Lauer, 686 F.2d 24, 32 (D.C. Cir. 1982): “[W]hile private parties must ordinarily pay their own legal fees, they have an undeniable right to retain counsel to ascertain their legal rights.”

The invalidity of a governmental attempt to deny counsel to a civil litigant was recognized in dictum over fifty years ago in Powell v. Alabama, 287 U.S. 45, 68-69 (1932):

The right to be heard would be, in many cases, of little avail if it did not comprehend the right to be heard by counsel.... If in any case, civil or criminal, a state or federal court were arbitrarily to refuse to hear a party by counsel, employed by and appearing for him, it reasonably may not be doubted that such a refusal would be a denial of a hearing, and, therefore, of due process in the constitutional sense.

This is great stuff, but the difficulty with employing it in the law firm EO litigation is not only that it is dicta in both the American Airways Charters case and in Powell v. Alabama (the Scottsboro Boys case), but that the EO’s here did not deprive any of the firms’ clients of qualified counsel. In American Airways Charters, the Treasury Department was unlikely to license any lawyer to represent the Cuban airline. As the Wilmer opinion pointed out, however, some of the economic harm wreaked by the EO was related to the possibility that the firm’s clients could find other law firms:

[T]he Complaint acknowledges that there are “many similarly situated firms” who have not been targeted by Executive Orders. Compl. ¶ 202; see also Suppl. Berman Decl. ¶ 9 (“Other existing clients have indicated to WilmerHale partners that they are considering whether to replace WilmerHale—or engage an additional firm on ongoing matters . . . .”); id. ¶ 10 (“Clients who need attorneys who can interact with federal government personnel, access federal buildings, and access classified information may well take existing or new business to other firms.”).

I read American Airways Charters to figure out why all three of these courts cited it but then didn’t really do much with it. The answer is, there was a deprivation of counsel for Fifth Amendment purposes by the Treasury Department’s refusal to license lawyers to represent designated Cuban companies, but nothing the government did in connection with the law firm EO’s was going to stop Apple, Citibank, Lockheed-Martin, DuPont, or any other client from obtaining competent representation.

Again, meaning no disrespect to the Perkins opinion, I was happy to see in the Jenner and Wilmer opinions some of the beginnings of a theory of the constitutional significance of the legal profession. To be clear, these are in addition to the First Amendment retaliation argument, based on Vullo, which Judge Bates characterized as the most straightforward argument for invalidating the EO’s. But they’re useful, particularly since (I hope) these summary judgment opinions represent the closing of this chapter in Trump’s war on civil society institutions. I’m a law professor, so my tendency is to ask the question: Going forward, what are the implications of this episode for our constitutional system? I’d like the answer to be that lawyers have a distinctive role to play.

The Constitutional Significance of Lawyers Beyond the First Amendment

The Jenner opinion summarizes the constitutional deficiency in the EO as prohibited viewpoint discrimination (Barnette, Vullo, and all that), but “magnified by the order’s additional Fifth and Sixth Amendment deficiencies” reflected in its attempts to undermine “the essential role that lawyers play in our polity” (p. 9). I’m not sure exactly what that means, but it’s reminiscent of the D.C. Circuit’s reasoning in American Airways Charter, where the core problem is that the Treasury Department exceeded its statutory authority, but that problem is particularly worrisome where the effect of the ultra vires action was to deprive an entity of counsel of its choice (or any counsel at all). Viewpoint discrimination is already pretty high on the list of constitutional bads, but viewpoint discrimination magnified by interference with the attorney-client relationship is even worse. As the court later says (p. 24):

Then there is the fact that we deal here with lawyers. In this context, the forward-looking censorship scheme threatens not only the First Amendment but also the right to counsel’s promise of a conflict-free attorney “devoted solely to the interests of his client.” Penson v. Ohio, 488 U.S. 75, 86–87 (1988) (internal quotation marks omitted). A firm fearing or laboring under an order like this one feels pressure to avoid arguments and clients the administration disdains in the hope of escaping government-imposed disabilities. Meanwhile, a firm that has acceded to the administration’s demands by cutting a deal feels the same pressure to retain “the President’s ongoing approval.” Br. of Legal Ethics Profs. as Amici Curiae in Supp. of Pl. [ECF No. 113] at 6.

I’m very happy that an amicus brief I joined is cited in support of this passage.

The court goes on to cite NAACP v. Button, 371 U.S. 415 (1963), which in professional responsibility teaching is mostly thought of as a solicitation case, but which the court here rightly cites for the proposition that vigorous advocacy against government intrusion is the sort of thing that makes lawyerdom proud (p. 12). Notably, Judge Bates says this in responding to the contention in Section 1 of the EO that the firm poses a threat to the national interest because it provides pro bono representation to transgender people and asylum seekers. Putting this in terms of a lot of what I write on legal ethics, the national interest is, or at least includes, vigorous contestation of the government’s official or orthodox policies. This isn’t a “political” position in the conventional Red State/Blue State sense. Rather, it is a substantive position within political theory that comes down on the side of liberalism – the freedom to dissent, to believe things that are out of the mainstream, to challenge majorities, and to refuse to acquiesce in an official statement about what is in the national interest.

Speaking of “national interest,” Judge Bates noticed and called the government out on its slippage between the invocation of national security, which is an area in which courts have traditionally given considerable deference to the Executive, and the much broader concept of national interest. This little sleight of hand comes up in the discussion of the firm’s re-hiring of Andrew Weissman, who left the firm to work on the Mueller investigation. Section 1 of the EO calls out the firm for saying it was “thrilled” to re-hire him (p. 3). Jenner’s “public praise” for Weissman led the Administration to characterize the firm as a national security threat. This is ridiculous, because Weissman was no longer with the firm (p. 24), but right at this moment the government pivots to talking about the “national interest,” which is not the same as national security. (Judge Leon notices this, too, in the Wilmer opinion – see pp. 28-29 – but doesn’t hammer the government as much as he should have for engaging in that little maneuver.) Like Judge Beryl Howell in the Perkins opinion, Judge Bates also dings the government for asserting a national security justification for yanking Jenner’s security clearances when Paul Weiss was able to have all its lawyers’ security clearances restored after denouncing a former partner, changing client selection practices, and promising to do pro bono work to the Administration’s liking (p. 25).

The Wilmer opinion, starting on p. 47, is the first serious consideration I’ve seen by a court of the argument that the EO’s exceeded the President’s authority. This was the leadoff claim in the complaint filed by Perkins Coie, and I always thought it was pretty good. What’s interesting about the ultra vires argument considered here is that it’s not the usual administrative law issue pertaining to Congressional authorization of an agency’s actions. Instead, the separation of powers issue here relates to the judiciary’s inherent authority to regulate the legal profession. It is a bedrock principle of the law governing lawyers that courts are the source of the authority to admit, regulate, and discipline lawyers to practice before them. In the usual case, the state’s highest court prescribes standards for admission to the bar, promulgates rules of conduct (generally based on models drafted by the ABA), and establishes a grievance and disciplinary system to handle claims of misconduct by lawyers. Federal courts have this inherent power, too, but it most often comes up at the trial court level, when lawyers engage in some sort of shenanigans for which rules of procedure do not provide a remedy. Judge Leon does a nice job summarizing the law (p. 49):

The Supreme Court has “outlined the scope of the inherent power of the federal courts.” Chambers v. NASCO, Inc., 501 U.S. 32, 43 (1991). A federal court’s inherent powers include, but are not limited to, the authority to “discipline attorneys who appear before it,” “punish for contempt,” “vacate its own judgment upon proof that a fraud has been perpetrated upon the court,” and “conduct an independent investigation in order to determine whether [the court] has been the victim of fraud.” Id at 43–44. Accordingly, judicial “authority includes ‘the ability to fashion an appropriate sanction for conduct which abuses the judicial process.’” Goodyear, 581 U.S. at 107 (quoting Chambers, 501 U.S. at 44–45).

The kicker, however, is that this authority excludes presidential authority to punish lawyers for professional misconduct (pp. 49-50):

It necessarily follows that this judicial power is exclusive of the other two branches. . . . The Order sanctions WilmerHale and its attorneys for their conduct before Article III courts. This encroaches on the Judiciary’s exclusive power to sanction attorneys. If the President believed that the firm “engaged in improper legal advocacy,” he should have “appeal[ed] to the judiciary to make appropriate findings and fashion an appropriate sanction.” The Executive was not empowered to take it upon itself to sanction this purportedly improper conduct!

This observation about exclusive judicial authority to regulate lawyers is connected with the language from Legal Services Corp. v. Velazquez, which is quoted in all of these opinions, i.e. that “An informed, independent judiciary presumes an informed, independent bar.” Judge Leon makes the connection clear, citing an amicus brief by a number of former judges (p. 51):

“Efforts to use governmental power to bend lawyers to the political interests or views of an administration may impair the candor on which judges rely and usurp judges’ role in regulating the conduct of lawyers who appear before them. The adversarial system cannot function properly with such an incursion into the judicial role.”

The idea seems to be that the judiciary needs to be able to enforce standards of conduct for lawyers, without any mucking around by the other branches, so it can perform its function of deciding cases on the merits, on the basis of a reliable factual record and good-faith legal argument.

Finally, and returning to the invocation of the “national interest,” the Wilmer opinion takes more seriously than the other opinions the due process doctrine of void for vagueness. The order says that Wilmer’s conduct is contrary to “bedrock American principles” and “the interests of the United States” (p. 58). How, exactly? What are the bedrock principles and interests that are opposed to the firm’s representation of immigrants and transgender people? In one sense, the answer is simple: The principles are those that Donald J. Trump, in his capacity of President of the United States, says they are. He has the sole authority to decide what is in the interests of the United States and then to punish anyone whose conduct he regards as antithetical to those principles.

If you see why that is a woefully inadequate answer, congratulations, you understand what is meant by the rule of law, and how it contrasts with the arbitrary exercise of power. You could read Gerald Postema, Jeremy Waldron, Andrei Marmor, or Joseph Raz to learn more about the rule of law, but you’re most of the way there if you can see what is so screwy about the idea that there is no other way of determining when you’re going to be punished for conduct that goes against the national interest than to try to get inside the head of the President and figure out what he thinks would be bad (p. 59):

The Order directs agency officials to take action against WilmerHale to ensure “consistency” with the “national interest,” “the goals and priorities of [the] Administration,” and “the interests of the United States.” Read in the context of the Order, these phrases are most narrowly construed to mean those interests which the President condones or, in their broadest construction, whatever an agency head thinks is in the interest of the American people. To say the least, the Order is fraught with the risk of arbitrary or discriminatory enforcement!

Another exclamation point! To which I’ll add my own: Yes! This is exactly the right way to understand the rule of law!

I’ll probably end up writing something longer and less tossed-off-in-the-moment on what we can learn from the law firm EO’s about the constitutional and normative significance of the legal profession. Implicit in that project is a limitation of the First Amendment analysis: I want to understand what is distinctive about lawyers that can’t be reduced to the opposition to viewpoint discrimination or the protection against retaliation for speech the government disfavors. The Jenner and Wilmer opinions are a helpful beginning of the project of clarifying the role of the legal profession in a constitutional democracy.

1. Footnote 4 to Judge Leon’s order observes:

The Order is akin to a gumbo. Sections 2 through 5 are the meaty ingredients — e.g., the Andouille, the okra, the tomatoes, the crab, the oysters. But it is the roux — here, § 1 — which holds everything together. A gumbo is served and eaten with all the ingredients together, and so too must the sections of the Order be addressed together. As explained in this Memorandum Opinion, this gumbo gives the Court heartburn.

There is actually a serious issue here, discussed on pp. 12-14, and p. 34, of the order, concerning whether the constitutionality of the EO should be considered section-by-section. The government sought that approach, because it wanted to be able to justify each section based on established precedent permitting the President to pursue policy objectives through conditions on government contracts (as in the Biden and Obama affirmative action requirements for government contractors) or on the broad discretion afforded to the Executive Branch in matters of national security. Reading the EO as one, unified gumbo, rather than looking at individual ingredients, makes it more clearly an unconstitutional instance of retaliation for engaging in protected activities.

From a bit of quick Googling, it appears that Judge Leon grew up in Framingham, Massachusetts, and went to Holy Cross and Suffolk Law School, so I’m not sure where he acquired his familiarity with Louisiana cuisine. However, his description of a gumbo is mostly on point, except that Cajun cooks would generally use either a roux or okra as a thickener (or possibly gumbo filé, which is a powder made of rubbed sassafras leaves). In any event, I very much appreciate the metaphor and from now on will be trying to think of ways to analogize legal concepts to Texas culinary icons like brisket, breakfast tacos, and chicken-fried steak.