A Federal Judge Lists 8 Ways That Trump Violated the Constitution by Punishing a Disfavored Law Firm

The president's crusade against attorneys whose work offends him, which defies the First Amendment and undermines the right to counsel, has provoked several judicial rebukes.

After President Donald Trump began penalizing major law firms that had offended him in one way or another last February, nine of them chose to surrender rather than fight. They agreed to humiliating concessions that included pro bono work, totaling nearly $1 billion, for causes favored by the president. But several firms stood their ground, arguing that Trump's executive orders targeting them violated the First Amendment and undermined the Sixth Amendment right to counsel.

So far the latter approach has proven to be pragmatic as well as principled. Perkins Coie, Jenner & Block, Susman Godfrey, and WilmerHale have obtained court orders barring Trump from abusing his authority to punish law firms for representing his political opponents, supporting causes he does not like, or employing attorneys who have crossed him. The latest example, a permanent injunction that a federal judge in Washington, D.C., issued on Tuesday, underlines the threat posed by Trump's petty vindictiveness. In an opinion peppered with exclamation points, U.S. District Judge Richard J. Leon says Trump's order against WilmerHale defies the First Amendment in four ways, violates the Fifth Amendment's guarantee of due process in two ways, unconstitutionally interferes with the right to legal representation, and flouts the separation of powers.

"The cornerstone of the American system of justice is an independent judiciary and
an independent bar willing to tackle unpopular cases, however daunting," Leon writes. "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."

In his March 27 order targeting WilmerHale, Trump complained that the firm had "engage[d] in obvious partisan representations to achieve political ends." He was alluding to WilmerHale's work for the Democratic National Committee, state-level Democratic organizations, and the presidential campaigns of two Democrats: Joe Biden and Kamala Harris. Trump said WilmerHale was "bent on employing lawyers who weaponize the prosecutorial power to upend the democratic process and distort justice," mentioning former Special Counsel Robert Mueller, who investigated Trump, and two of "his colleagues."

WilmerHale had engaged in "egregious conduct" by "support[ing] efforts to discriminate on the basis of race," Trump averred, referring to the firm's defense of Harvard University's affirmative action practices against a successful challenge by Students for Fair Admissions. He also accused WilmerHale of supporting "the obstruction of efforts to prevent illegal aliens from committing horrific crimes and trafficking deadly drugs within our borders," by which he meant that the firm had challenged some of his immigration policies during his first term. He added that WilmerHale "furthers the degradation of the quality of American elections, including by supporting efforts designed to enable noncitizens to vote." That was a reference to the firm's involvement in challenges to state voter identification and registration laws.

As Leon notes, WilmerHale also has irked Trump by representing "inspectors general
alleging that President Trump improperly fired them" and the House Ways and Means Committee in "litigation resulting in President Trump's disclosure of his personal tax returns." And the firm challenged a fantasy close to Trump's heart by opposing his lawsuits "challenging the results of the 2020 presidential election."

Because WilmerHale had engaged in "conduct detrimental to critical American interests," Trump said, it was appropriate to "suspend any active security clearances" held by lawyers at the firm and restrict their access to federal buildings and government officials. He also ordered the termination of federal contracts with WilmerHale and a review of other contractors' links to the firm. And he threatened the firm with investigations for "racial discrimination" via "diversity, equity, and inclusion" (DEI) programs.

The day after Trump imposed those penalties, which posed a grave threat to WilmerHale's business, Leon issued a temporary restraining order against the president's edict. He noted that the First Amendment prohibits government retaliation for constitutionally protected speech, including "retaliatory actions based on perceived viewpoint." He added that "the retaliatory nature of the Executive Order at issue here is clear on its face," and "there is no doubt this retaliatory action chills speech and legal advocacy, or that it qualifies as a constitutional harm."

Leon reiterates that point in Tuesday's ruling. WilmerHale's legal work is "unquestionably protected conduct under the First Amendment," he notes. "On its face," he says, Trump's order constitutes "retaliation for the firm's protected speech," including its "pro bono practice, 'obvious partisan representations to achieve political ends,' and involvement in immigration and election litigation."

The order imposes "a kitchen sink of severe sanctions on WilmerHale for this protected conduct!" Leon writes. "Any one of those sanctions would cause clients to strongly reconsider their engagements with WilmerHale. Taken together, the provisions constitute a staggering punishment for the firm's protected speech! The Order is intended to, and does in fact, impede the firm's ability to effectively represent its clients! For example, WilmerHale attorneys may not be able to enter federal courthouses for trial, meet with federal regulators, or access classified materials necessary for working on national security matters."

Leon notes that "clients have already begun ending or curtailing their relationships with WilmerHale." In addition to the direct restrictions on the firm's work, the order's contracting provisions threatened "severe economic consequences for the firm," he says. "The impact of losing federal contractor clients would be staggering, as '[a]t least 21 of WilmerHale's 25 largest clients in 2024 have contracts with federal agencies. These 21 clients accounted for more than 30% of the Firm's revenue in 2024—nearly $500 million.'"

WilmerHale also alleged that Trump's order violated the First Amendment by discriminating against particular viewpoints. Leon agrees. "WilmerHale's representation of clients in litigation is speech," he says. "The Order attacks the viewpoints WilmerHale expressed over the course of these representations, describing WilmerHale's work as 'partisan' and 'political,' and maligning WilmerHale's advocacy on behalf of causes disfavored by President Trump." It "both threatens and imposes sanctions and uses other means of coercion to suppress WilmerHale's representation of disfavored causes and clients."

In addition to freedom of speech, the First Amendment guarantees the right to "petition the government for a redress of grievances." Leon says Trump's order blatantly violates that right as well.

"WilmerHale has both alleged and shown that the Order violates the Petition Clause
by (1) punishing the firm for its past representation of clients in litigation and (2)
undermining the firm's ability to pursue litigation in the future," Leon writes. "The
Order explicitly targets WilmerHale at least in part for the litigation it has pursued,
including election and immigration lawsuits." In addition to "punishing WilmerHale for past petitioning," he notes, the order "creates hurdles to prevent the firm from pursuing future lawsuits" by revoking security clearances and restricting access to federal buildings and agencies, which "would severely hinder WilmerHale's ability to effectively bring cases."

Leon is not impressed by Trump's invocation of national security. "Other than a passing reference to WilmerHale's involvement in election and immigration litigation, the Order does not explain how WilmerHale's conduct has threatened national security or how restricting its access to federal buildings or federal employees would remedy those threats," he writes. Rather, the order is "plainly motivated by the President's desire to retaliate against WilmerHale for its protected activity," which is "not a legitimate Government interest."

The First Amendment also has long been understood to protect freedom of association. "Compelled disclosure of affiliation with groups engaged in advocacy can violate this First Amendment right," Leon notes. "WilmerHale alleges that the Order compels the firm's federal contractor clients to disclose their affiliation with WilmerHale, which engages in advocacy on their behalf and on behalf of other clients. I find that this disclosure violates the First Amendment [right to] freedom of association."

Regarding WilmerHale's Fifth Amendment claims, Leon notes that the firm has "a protected liberty interest in its right to petition the Government under the First Amendment." WilmerHale "has shown that the Government deprived the firm of this protected liberty interest," he writes, and Trump "issued the Order without any due process."

The order also violates due process because it is unconstitutionally vague, failing to provide "fair notice of conduct that is forbidden or required," Leon says. The order "does not provide WilmerHale with notice of how it should act in the future to avoid these sanctions," he notes. "The Order's invocation of concepts such as 'bedrock American principles' and 'the interests of the United States' leave WilmerHale and its employees guessing about how to modify their conduct to avoid the Order's sanctions….The Order essentially leaves it to WilmerHale to predict which causes and which attorneys the President personally dislikes and then steer clear of those causes and attorneys. This chilling effect triggers serious vagueness concerns."

Trump's instructions to his underlings are also alarmingly vague, Leon says. 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,'" he writes. "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!"

WilmerHale also cited the Sixth Amendment, which guarantees criminal defendants the right to "have the assistance of counsel." Leon says WilmerHale "has alleged and shown that the Order 'infringes the Sixth Amendment right to counsel of [its] clients' by 'eviscerat[ing] the Firm's ability to provide effective representation and advocacy.'"

Since WilmerHale's criminal defense work "requires entering federal buildings and engaging with federal employees," Leon notes, the order "effectively prevents the firm's attorneys from representing their clients in criminal matters." It also "coerces WilmerHale's federal contractor clients to choose between their contracts and their engagements—including engagements on criminal matters—with WilmerHale."

Those restrictions "may thus cause the firm's criminal defendant clients to abandon the firm and seek alternate counsel," and "some clients have already begun to do so," Leon notes. Although the order "does not directly prohibit criminal defendants from hiring WilmerHale as their counsel," he says, "it certainly has that effect!" According to the Supreme Court, he notes, "indirect infringements on the right to counsel of choice can violate the Sixth Amendment," and "the indirect infringement on the right to counsel here is severe."

Finally, Leon concludes that Trump's order "violates the separation of powers by usurping judicial authority to identify and sanction abuses of the judicial process." Even if "each section could be grounded in Executive power, the directives set out in each section clearly exceed that power!" he says. "The President, by issuing the Order, is wielding his authority to punish a law firm for engaging in litigation conduct the President personally disfavors. Thus, to the extent the President does have the power to limit access to federal buildings, suspend and revoke security clearances, dictate federal hiring, and manage federal contracts, the Order surpasses that authority and in fact usurps the Judiciary's authority to resolve cases and sanction parties that come before the courts!"

Federal judges have reached similar conclusions in response to lawsuits filed by Perkins Coie, which obtained a permanent injunction on May 2; Jenner & Block, which obtained a permanent injunction on May 23; and Susman Godfrey, which last month obtained a temporary restraining order and is now seeking a permanent injunction. This string of successes makes the capitulations by firms such as Paul Weiss, Skadden, and Latham & Watkins, which sought to assuage the president's wrath by changing their policies and practices, look unwise as well as cowardly.

Among other things, those firms agreed to abandon DEI programs and devote huge amounts of pro bono resources to Trump-favored clients and causes. Trump has "hinted" that he views those promised services as "a legal war chest to be used as he wishes," The New York Times reported last month. Citing "two people briefed on the matter," the Times said the options include "sending the lawyers to help Elon Musk's Department of Government Efficiency," "deploying them to aid the Justice Department," or even assigning them to represent "Mr. Trump or his allies if they [become] ensnared in investigations."

In an April 28 executive order, Trump mentioned another use for the legal services obtained through these shakedowns. He ordered "the use of private-sector pro bono assistance" to defend "law enforcement officers who unjustly incur expenses and liabilities for actions taken during the performance of their official duties."