All nine of the Supreme Court justices are lawyers. All of them have friends and law school classmates in private practice. All of them sit at the apex of a legal system that depends on lawyers to brief judges on the matters those judges must decide. Many of them were themselves litigators at large law firms, where their livelihood depended on their ability to advocate for their clients without fear of personal reprisals.
So it’s hard to imagine a presidential action that is more likely to antagonize the justices President Donald Trump needs to uphold his agenda, not to mention every other federal judge who isn’t already in the tank for MAGA, than a series of executive orders Trump has recently issued. These actions aim to punish law firms that previously represented Democrats or clients opposed to Trump.
The lawyers targeted by these orders are the justices’ friends, classmates, and colleagues. It would likely be easy for, say, Chief Justice John Roberts or Justice Brett Kavanaugh to empathize with law partners who do the exact same work they once did.
The striking thing about all the law firm executive orders is that they barely even attempt to justify Trump’s decision with a legitimate explanation for why these orders are lawful.
The order targeting law firm Perkins Coie attacks the firm for “representing failed Presidential candidate Hillary Clinton” in its second sentence. The order targeting WilmerHale accuses it of engaging “in obvious partisan representations to achieve political ends,” as if Democrats do not have the same right to hire lawyers who advocate on their behalf that everyone else does.
The order targeting Jenner & Block justifies that attack because the firm once hired Andrew Weissmann, a prominent television legal commentator who, in the executive order’s words, engaged “in partisan prosecution as part of Robert Mueller’s entirely unjustified investigation” into Trump. Weissmann left Jenner in 2021.
The sanctions laid out in these orders, moreover, are extraordinary. They attempt to bar the firms’ attorneys and staff from federal buildings, preventing lawyers representing criminal defendants from engaging in plea bargaining with federal prosecutors — and potentially preventing lawyers who practice before federal agencies from appearing before those agencies at all. They also seek to strip security clearances from the firm’s lawyers, and to strip federal contracts from companies that employ the targeted law firms.
It’s hard to think of a precedent for this kind of sweeping attack on a business that did some work for a president’s political opponents. During the second Bush administration, a political appointee in the Defense Department criticized lawyers who represent Guantánamo Bay detainees and suggested that their firms’ clients should look elsewhere for legal representation. But that official apologized shortly thereafter. And he resigned his position three weeks after his widely criticized comments.
George W. Bush himself did not attempt anything even resembling the sanctions Trump now seeks to impose on law firms.
As Perkins Coie argues in a lawsuit challenging the order against that firm, these sanctions are an existential threat to the firms Trump is targeting. Perkins says that it “has nearly 1,000 active matters that require its lawyers to interact with more than 90 federal agencies,” and it fears it can’t continue many of those representations if it isn’t even allowed into the building to meet with government officials. Similarly, the firm says many of its biggest clients, including its 15 biggest clients, “have or compete for government contracts” that could be canceled unless those clients fire the firm.
Trump, in other words, is claiming the power to exterminate multibillion-dollar businesses, with over a thousand lawyers and as many support staff, to punish them for things as innocuous as representing a Democrat in 2016.
It’s hard to count all the ways these orders violate the Constitution. Perkins, in its lawsuit, alleges violations of the First Amendment right to free speech and free association, due process violations because it was given no hearing or notice of the sanctions against it, separation of powers violations because no statute authorizes Trump to sanction law firms in this way, and violations of their clients’ right to choose their own counsel — among other things.
The Trump administration has not yet filed a brief laying out its response to these arguments, but in a hearing, one of its lawyers claimed that the Constitution gives the president inherent authority to “find that there are certain individuals or certain companies that are not trustworthy with the nation’s secrets.”
Normally, when a litigant wants the courts to permit something that obviously violates existing law, they try to raise the issue in a case that paints them in a sympathetic light. But Trump has chosen to fight this fight on the most unfavorable ground imaginable.
There may be a perverse logic to Trump’s decision to fight on such unfavorable terrain. If he wins the right to punish law firms for representing a prominent Democrat a decade ago, it is unlikely that the Supreme Court will stop him from doing anything at all in the future. Most lawyers will be too scared of retaliation to even bring lawsuits challenging Trump’s actions. Already, one of the firms targeted by Trump, Paul Weiss, appears to have caved to him by agreeing to do $40 million worth of free legal work on causes supported by Trump’s White House. (Like Perkins, Wilmer and Jenner sued to block the orders targeting them.)
And, of course, if Trump’s endgame is to openly defy the courts, an obviously unconstitutional executive order targeting law firms that are in the business of suing the government is a good way to bring about that endgame quickly.
These stunning executive orders dare the courts to either make themselves irrelevant, or to trigger what could be the final showdown over the rule of law.
The anti-Thurgood Marshall strategy
If you want to understand how litigants normally proceed when they want to convince the courts to make audacious changes to the law, consider Sweatt v. Painter (1950), a case brought by future Justice Thurgood Marshall a few years before he successfully convinced the justices to declare public school segregation unconstitutional in Brown v. Board of Education (1954).
Marshall’s goal was to convince the justices that, as they eventually concluded in Brown, “separate education facilities are inherently unequal,” even if a state attempted to equalize the resources provided to segregated Black and white schools. Before he brought the much more difficult challenge to K-12 segregation, however, Marshall chose a more favorable ground to fight for integrated educational facilities: law schools.
In Sweatt, a Black man was denied admission to the University of Texas Law School solely because of his race. Rather than integrate UT, Texas opened a new law school for aspiring Black lawyers, and argued that this facility solved the constitutional problem because now Black law students could receive a similar education to the one they would receive at the state’s flagship university.
But the justices, all of whom were lawyers, understood the subtle hierarchies of the legal profession — in which where you go to law school can determine the entire trajectory of your career — all too well to be fooled by this arrangement.
As the Court’s unanimous decision explained, “the University of Texas Law School possesses to a far greater degree those qualities which are incapable of objective measurement but which make for greatness in a law school” — qualities like a reputation for excellence, and an alumni network full of successful lawyers eager to lend a hand to UT’s graduates.
Marshall, in other words, understood that, by appealing to the professional sensibilities of the justices, he could make them see that the concept of “separate but equal” is at odds with itself. And once those justices took the easy step of empathizing with law students denied access to an elite school, it was much easier to get them to see themselves in grade school students shunted into an inferior elementary school.
Trump has done the exact opposite of what Marshall did in Sweatt. And that means that the same empathy that Marshall’s clients benefited from in Sweatt and Brown is likely to cut against Trump.
Not only that, but the justices who will ultimately hear this case are likely to have unique sympathy for lawyers attacked by a politician seeking to discredit them, because many of them experienced just that in their confirmation hearings.
When Chief Justice John Roberts was nominated to the Supreme Court, for example, one of the few controversies surrounding his nomination was whether the positions he took as a lawyer representing a client could be attributed to him personally. Roberts had been a judge for only about two years when he was nominated for the Supreme Court, so his judicial record was quite thin, and some Democrats and their allies hoped to point to his work as a lawyer to discredit him. Among other things, they pointed to a brief Roberts signed as a Justice Department lawyer, which argued that Roe v. Wade should be overruled.
The White House and Senate Republicans’ defense of Roberts at the time was that a lawyer’s job is to represent their clients’ interests, even if they do not agree with the client. So it is unfair to attribute a former client’s views to their lawyer. And this was an excellent defense! The Constitution gives everyone a right to hire legal counsel to represent them before the courts. This entire system breaks down if lawyers who represent unpopular clients or positions face professional sanction for doing so.
The point is that the most powerful judge in the country, like numerous other judges who’ve had their careers probed by the Senate Judiciary Committee, has a very personal stake in the question of whether lawyers can be punished because the wrong elected officials don’t like their clients.
That does not mean that the author of the Court’s unconscionable Trump immunity decision will suddenly have an epiphany and turn against Donald Trump. But if Trump’s goal is to turn Roberts (and numerous other judges) against him, attacking lawyers who stand in very similar shoes to the ones Roberts wore 20 years ago is a pretty good way to do it.
