Labor & Employment Law Daily Wrap Up, REMEDIES, DAMAGES—D.D.C.: Executive order issued against Jenner & Block permanently enjoined, (May 27, 2025)

By Kathleen Kapusta, J.D.

“This case arises from one of a series of executive orders targeting law firms that, in one way or another, did not bow to the current presidential administration’s political orthodoxy.”

Executive Order 14246, titled “Addressing Risks from Jenner & Block” and issued by President Trump on March 25, “targets Jenner for what it has said and thereby attempts to dampen what it might yet say,” a federal court in the District of Columbia concluded, finding this “unconstitutional under any view of the First Amendment.” Granting Jenner’s motion for summary judgment, the court also noted that the order’s viewpoint discrimination and its targeting of lawyers “magnify the offensiveness to the freedoms of the First Amendment guarantees.” Finding that none of the order’s sections could be salvaged, the court enjoined its operation (Jenner & Block LLP v. U.S. Department of Justice, No. 25-916 (JDB) (D.D.C. May 23, 2025)).

As a 900-person litigation-focused law firm with offices throughout the country and in London, Jenner & Block not only appears frequently in federal court and other federal buildings, it also has a large pro bono practice. According to Trump’s EO, Jenner undermines the country’s interests in three main ways: partisan case selection, pro bono representation, and past association with Andrew Weissman, an attorney and former partner at Jenner who served as a member of Special Counsel Robert Mueller’s team investigating Russian interference in the 2016 election.

EO. Among other things, the EO accuses the firm, through its pro bono representation, of supporting attacks on women and children based on its refusal to accept the biological reality of sex. It also accuses the firm of discriminating against employees based on race and other protected categories through the use of race-based “targets.”

Further, the EO instructs the Attorney General and other agency heads to immediately take steps to suspend any active security clearances held by individuals at Jenner pending a review of whether such clearances are consistent with the national interest, directs the Office of Management and Budget to “identify all Government goods, property, material, and services, including Sensitive Compartmented Information Facilities, provided for the benefit of Jenner,” and instructs agency heads to “expeditiously cease such provision.”

It also seeks to end all contractual and subcontractual relationships between Jenner and the federal government and appears to require a review by the EEOC of the firm’s compliance with civil rights laws. In addition, it instructs agency heads, “to the extent permitted by law, [to] provide guidance limiting official access [to]Federal Government buildings to employees of Jenner when such access would threaten the national security of or otherwise be inconsistent with the interests of the United States.”

TRO. Three days after the EO was issued, Jenner sued, seeking a TRO. Granting Jenner’s motion, the court restrained the defendants from enforcing three of the five sections of the order and from using statements in Section 1 to punish the firm.

The defendants then filed a motion to dismiss, which the court later construed as a motion for summary judgment, and Jenner filed a motion for summary judgment seeking a declaratory judgment and a permanent injunction.

First Amendment. Turning first to Jenner’s First Amendment retaliation claim, the court noted that Section 1’s accusation against Jenner of “engag[ing] in obvious partisan representations to achieve political ends” is “another way of saying courtroom advocacy on behalf of its chosen causes—that is, the very core of the First Amendment’s protection of ‘litigation as a vehicle for effective political expression and association.’” The same, said the court, goes for Jenner’s pro bono representation of transgender people and asylum-seekers. As for Jenner’s employment of Weismann, the court found his targeted activity “falls easily within the First Amendment’s muscular protection for ‘criticism of government and public officials.’”

This retaliation, the court stated, would also chill a speaker of ordinary firmness. Noting that the President issued a series of EOs targeting law firms, which “take extraordinary firmness to resist,” the court, pointing to one firm’s decision to adopt a policy of political neutrality, accept pro bono matters representing the full political spectrum, and dedicate $40 million in pro bono services to causes of which the President approves, explained that the end result of these EOs is the compromising of speech.

Lawyers. As to whether Jenner established that the speech was the but-for cause of the EO, the court turned to whether there were any nonretaliatory grounds for the EO’s adverse consequences. Pointing out that the EO has a prospective silencing effect, the court noted that “the administration has shown a repeated willingness to haggle, sending the message loud and clear that Jenner can spare itself—if it compromises its speech.” And because the EO deals with lawyers, the court observed that “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.”

Pointing further to the importance of lawyers in upholding our democracy, the court explained that “their independence is essential lest they shrink into ‘nothing more than parrots of the views of whatever group wields governmental power at the moment.’”

For that reason, the court also found the EO implicated the Fifth and Sixth Amendment guarantees of the “right to choose counsel without interference by officialdom.” Specifically, said the court, Section 5 of the EO, with its threatened bar of Jenner employees from negotiating with federal prosecutors and agencies and even entering federal courthouses, could hamstring its ability to represent its clients, and thus its clients’ right to choose Jenner without interference.

Security clearance review. Finding that the EO punishes and seeks to silence speech protected by the First Amendment, the court turned to whether any of the sections could survive, including Section 2(a)’s requirement that the Attorney General take steps to suspend security clearances held by individuals at Jenner. Although courts may not second-guess an Executive Branch decision to deny or revoke a security clearance, they may hear claims arising from the clearance revocation process.

Here, said the court, the EO’s immediate revocation of all clearances without individualized explanation, consideration, or opportunity to be heard “raises none of the concerns that make individual security-clearance determinations nonjusticiable.” Noting further that Jenner requests only that the court question the special suspend-then-review process the order imposed on a categorical basis, the court pointed out that refusing “to do so would equally bless blanket security-clearance suspensions for all Muslims, Catholics, or disabled people,” and the “Constitution does not tolerate such judicial abdication.”

As far a national security justification, the defendants argued that Jenner’s “public praise for” and rehiring of Weismann after his “role in the Mueller investigation” showed a national security nexus. But this, said the court, “doesn’t even feign at national security” and the defendants did not articulate a cogent argument otherwise. Accordingly, the court found Jenner’s challenge to Section 2 was justiciable.

Contracting. Regarding Section 3’s attempt to end all contractual and subcontractual relationships between Jenner and the federal government, the court noted that approximately 40 percent of the firm’s revenue comes from representing government contractors. According to the firm, as a result of the EO, contractors, in an effort to keep their government business, will jettison their ties with Jenner. Finding the threat to Jenner posed by Section 3 clear and imminent, the court noted that many of the firm’s clients must decide shortly “whether to keep their contracts and lose Jenner or keep Jenner and risk losing their contracts.” The court also found it predictable that they would choose keeping their contracts.

In addition to economic injury, the court noted that the mere existence of the order chills Jenner’s expression. Accordingly, said the court, Jenner has standing to “challenge the order casting the chill.”

Discrimination. Turning to Section 4, which the court explained means “The practices of Jenner will be reviewed under Title VII to ensure compliance with civil rights law,” the court found the defendants failed to offer any reason that would justify singling Jenner out for investigation aside from its speech. While the defendants pointed to Jenner’s “adoption of the ‘Mansfield Rule,’” a certification process that seeks to “diversify the power structure of law firms and legal departments, more than 360 other firms earned the Mansfield Certification in 2023-24 and thus, said the court, Jenner, in this sense, was entirely unremarkable. Further, the court observed, “the President may not evade the ‘extensive regulation’ governing EEOC proceedings, and single out Jenner for investigation in retaliation for its speech.”

Personnel. Finally, as to Section 5’s attempt to limit Jenner personnel access to federal buildings, among other things, the court found not only was the claim ripe as “the mere existence of the Order” harms Jenner, on the merits, “Section 5 is inexplicable by anything other than a pure desire to inflict pain on Jenner.” Section 5, said the court, “which directs an astonishingly broad range of actions against Jenner employees past, current, and future, has no plausible legitimate rationale and thus cannot stand.”

Irreparable harm. After determining that Jenner prevails on the merits and is entitled to summary judgment, the court, turning to the remaining factors for a permanent injunction, found that the EO would cause Jenner irreparable harm not compensable at law. “Absent court intervention, the order puts Jenner to a choice the Constitution protects it from having to make: change its speech or suffer a serious injury to its livelihood.”

As to the balance of equities and public interest, the defendants, said the court, offered nothing on their side of the equities scale and Jenner’s side was much weightier. The EO, the court observed, “casts a chill over the whole of the legal profession, leaving lawyers around the country weighing the necessity of vigorous representation against the peril of crossing the federal government.”

Scope of injunction. Addressing, finally, the scope of the injunction, the court found that the United States was a proper defendant. While Jenner must eventually list the individual federal officers it seeks to enjoin, it is not required to do so in the caption of the complaint. Moreover, it attached to its proposed injunction a lengthy list of agencies and agency heads subject to the executive order. Accordingly, the court enjoined any actions taken pursuant to the order’s operative sections, Sections 2 through 5. It refused, however, to enjoin future actions taken pursuant to Section 1.

The case is No. 25-916 (JDB).

Judge: Bates, J.

Attorneys: David E. Mills (Cooley) for Jenner & Block LLP. Richard Lawson, U.S. Department of Justice, for U.S. Department of Justice.

Companies: Jenner & Block LLP

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