Every one of the nine justices on the Supreme Court is a lawyer. They all have connections to law school peers and friends currently in private practice. Positioned at the pinnacle of a judicial system reliant on lawyers to present cases, many justices once thrived as litigators at major law firms, where their success depended on their capability to defend their clients without fear of personal consequences.
Therefore, it is difficult to envision a presidential move more likely to provoke the justices that President Donald Trump needs to support his policies—alongside other federal judges not already aligned with MAGA—than the recent executive orders issued by Trump. These directives are aimed at penalizing law firms that have represented Democrats or clients opposing Trump.
The attorneys singled out by these actions include the justices’ friends, classmates, and professional colleagues. It would likely be straightforward for individuals like Chief Justice John Roberts or Justice Brett Kavanaugh to relate to law partners who perform the same work they once did.
A notable aspect of these law firm executive orders is their lack of substantive justification for Trump’s actions regarding their legality.
For instance, the order targeting Perkins Coie laments the firm’s decision to “represent failed Presidential candidate Hillary Clinton” right in its initial remarks. Meanwhile, the order against WilmerHale alleges that the firm engages in “obvious partisan representations to achieve political ends,” as if Democrats shouldn’t have the same right to secure legal representation as others.
The order directed at Jenner & Block defends its stance, claiming that the firm previously employed Andrew Weissmann, a well-known legal commentator who, as stated in the executive order, “engaged in partisan prosecution as part of Robert Mueller’s completely unwarranted investigation” into Trump. Weissmann departed from Jenner in 2021.
Moreover, the sanctions outlined in these orders are severe. They aim to prohibit the firms’ lawyers and personnel from entering federal buildings, which would hinder criminal defense attorneys from negotiating pleas with federal prosecutors—potentially barring lawyers who practice before federal agencies from appearing in front of them altogether. Additionally, there are moves to revoke security clearances from the firm’s lawyers and to eliminate federal contracts from companies employing the targeted firms.
It’s challenging to find a precedent for such a sweeping assault on a business that has represented a president’s political adversaries. During George W. Bush’s second term, a political appointee at the Defense Department criticized lawyers who defended Guantanamo Bay detainees and suggested those firms’ clients should seek alternatives for legal representation. However, that official quickly apologized afterward and resigned from his position three weeks after his widely criticized comments.
Bush himself never attempted anything comparable to the sanctions that Trump now seeks to impose on law firms.
As Perkins Coie states in its lawsuit contesting the order against them, these sanctions pose an existential risk to the firms targeted by Trump. Perkins mentions that it “has nearly 1,000 active matters that require its lawyers to interact with more than 90 federal agencies,” and it fears many of these representations cannot continue if direct access to government officials is restricted. Likewise, the firm notes that many of its largest clients, including its 15 biggest clients, “hold or are pursuing government contracts” that could be terminated if those clients dismiss the firm.
In essence, Trump asserts the authority to dismantle billion-dollar businesses, employing over a thousand lawyers and just as many support personnel, as a reprisal for actions as seemingly harmless as representing a Democrat in 2016.
It’s difficult to enumerate all the ways these orders breach the Constitution. Perkins, in its legal action, claims violations of the First Amendment concerning free speech and association, due process violations for not being given a hearing or notice of the sanctions, breaches of the separation of powers as no statute permits Trump to impose sanctions of this nature on law firms, and infringements on their clients’ rights to choose their own counsel—among other issues.
Thus far, the Trump administration has not submitted a brief articulating its responses to these claims. However, during a hearing, one of its attorneys suggested that the Constitution grants the president the inherent power to “determine that specific individuals or companies are untrustworthy with the nation’s secrets.”
Typically, when a litigant seeks court approval for actions that clearly contravene existing law, they construct their case in a way that makes them appear sympathetic. Yet Trump has chosen to engage in this battle on the least favorable ground possible:
There may be an unsettling logic to Trump’s choice to contest such unfavorable territory. If he successfully gains the authority to penalize law firms for representing a well-known Democrat from years past, it is improbable that the Supreme Court would stop him from taking further action in the future. Most lawyers may refrain from pursuing lawsuits against Trump due to fear of retaliation. Already, one of the firms Trump targeted, Paul Weiss, seems to have yielded by agreeing to undertake $40 million worth of pro bono work aligning with initiatives endorsed by Trump’s administration. (Similar to Perkins, Wilmer, and Jenner, this firm has also initiated legal action to obstruct the orders against them.)
And, of course, if Trump’s ultimate objective is to openly challenge the courts, an obviously unconstitutional executive order targeting law firms that litigate against the government could rapidly serve that goal.
These shocking executive orders challenge the courts to either render themselves irrelevant or provoke what might become the conclusive battle over the rule of law.
The anti-Thurgood Marshall strategy
To comprehend how litigants typically proceed when aiming to persuade the courts to enact bold changes to the law, consider Sweatt v. Painter (1950), a case presented by future Justice Thurgood Marshall shortly before he successfully urged the justices to declare public school segregation unconstitutional in Brown v. Board of Education (1954).
Marshall aimed to convince the justices that, as they ultimately decided in Brown, “separate educational facilities are inherently unequal,” even when a state puts forth efforts to equalize resources available to segregated schools for Black and white students. Before he presented the tougher challenge against K-12 segregation, however, Marshall opted for a more favorable battleground to argue for integrated educational institutions: law schools.
In Sweatt, a Black man was denied entry to the University of Texas Law School purely due to his race. Rather than integrate UT, Texas created a separate law school for potential Black lawyers, asserting that this establishment resolved the constitutional issue by allowing Black law students to receive an education comparable to that of the state’s flagship institution.
However, the justices, all of whom understood the nuances of the legal profession—where a law school’s prestige can significantly shape a lawyer’s career path—were not deceived by this arrangement.
The Court’s unanimous ruling articulated that “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 distinguished reputation and a robust alumni network filled with successful lawyers eager to support UT graduates.
In essence, Marshall realized that by appealing to the professional sentiments of the justices, he could help them grasp that the idea of “separate but equal” is fundamentally contradictory. Once those justices could easily empathize with law students denied access to an esteemed institution, it became more straightforward for them to imagine the plight of elementary school students relegated to inferior schools.
Trump has executed the complete reverse of what Marshall achieved in Sweatt. Consequently, the same empathy that benefited Marshall’s clients in Sweatt and Brown is likely to work against Trump.
Moreover, the justices who will ultimately deliberate on this case may possess a unique sympathy for lawyers attacked by a politician trying to undermine their credibility, as many of them faced similar situations during their own confirmation hearings.
For instance, when Chief Justice John Roberts was nominated to the Supreme Court, one of the few controversies surrounding his nomination was whether the positions he took while representing clients could be attributed to him personally. Having been a judge for just about two years at the time of his nomination, Roberts had a relatively sparse judicial record, and some Democrats hoped to utilize his work as a lawyer to discredit his nomination. Among other matters, they referenced a brief that Roberts signed while at the Justice Department, which contended that Roe v. Wade should be overturned.
At that time, the defense from the White House and Senate Republicans was that a lawyer’s role is to represent their clients’ interests, regardless of personal agreement with the client. Thus, it was unjust to hold a lawyer responsible for their former client’s views. This argument was sound! The Constitution guarantees everyone the right to secure legal representation for their cases. If lawyers who represent unpopular clients or perspectives face professional consequences for doing so, the entire system collapses.
The key takeaway is that the most powerful judge in the nation, along with numerous judges who’ve had their careers scrutinized by the Senate Judiciary Committee, has a deeply personal interest in the question of whether lawyers can be punished simply because the wrong elected officials disapprove of their clients.
While this does not imply that the drafter of the Court’s appalling Trump immunity decision will suddenly have a change of heart and oppose Donald Trump, if Trump’s intention is to alienate Roberts (and many other judges), targeting lawyers who find themselves in very similar situations to those Roberts experienced 20 years ago is a solid strategy.
