Case Summary and Outcome

The United States District Court for the District of Columbia held that an executive order imposing broad restrictions on a law firm’s security clearances, government contracting work, civil‑rights investigations, and access to federal facilities and employment was an unconstitutional act of retaliation in violation of the First Amendment of the U.S. Constitution. The firm challenged the order after it was targeted for its courtroom advocacy and pro bono representation, which the order deemed objectionable. The Court found that the punitive measures amounted to impermissible viewpoint discrimination, created a chilling effect on legal speech, and also infringed Fifth and Sixth Amendment protections of the right to counsel. Concluding that these core provisions could not be reconciled with established constitutional doctrine, the Court granted summary judgment in the firm’s favor and permanently enjoined enforcement of the operative sections, while declining to bar future actions based solely on the order’s preface statements, which it treated as protected government speech once stripped of any enforcement power.

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Facts

On March 25, 2025, American President Donald J. Trump issued Executive Order 14246 (EO 14246 or the Order) titled “Addressing Risks from Jenner & Block,” expressly identifying law firm Jenner & Block LLP (Jenner) as the target of regulatory and administrative restrictions. Jenner is a prominent American litigation firm with a workforce of around 900 attorneys and a national and international presence, including offices in London, U.K. Known for its extensive pro bono work, the firm has frequently been recognized as a leader in that space and maintains regular interaction with the federal government through litigation, contractual work, and appearances in federal buildings and courts.

The Order began with broad criticisms of law firms engaged in pro bono representation, asserting that such practices posed risks to public safety and national security, and harmed constitutional values and democratic integrity. Jenner was targeted for its alleged involvement in politically motivated litigation, its pro bono challenges to policies concerning transgender individuals and asylum seekers, and for having re-employed Andrew Weissmann, a former partner and ex-federal prosecutor who had previously served on the Special Counsel’s investigation into Russian election interference and had publicly expressed opposition to President Trump. Weissman’s professional and public conduct was characterized in the Order as indicative of Jenner’s allegedly problematic values. The Order also claimed that the firm had engaged in employment discrimination, pointing to its diversity policies and race-conscious hiring practices.

The Order’s operative provisions imposed a series of sweeping restrictions designed to isolate the firm from the federal government and its clients. Section 2 required that all security clearances held by firm employees be immediately suspended, subject to a review of whether continued access served what the Order referred to as the “national interest.” It also directed federal agencies to identify and cease the provision of government goods, property, and services provided for the firm’s benefit. Section 3 instructed contracting agencies to identify all associations with the firm, terminate any ongoing arrangements, and ensure that future contract-related funding decisions disfavored entities engaged with the firm, effectively pressuring third parties to disassociate. Section 4 placed the firm’s hiring and promotion practices under federal scrutiny, citing concerns about race-based employment targets and calling for review under Title VII of the Civil Rights Act of 1964. Section 5 barred the firm’s attorneys from entering federal buildings, discouraged engagement with federal officials, and prohibited federal agencies from hiring any firm employees without a formal waiver. Although Weissmann was not employed at Jenner at the time, he was named explicitly in this provision.

The issuance of EO 14246 had immediate effects. On April 3, 2025, government attorneys informed one of Jenner’s clients that their legal team could not participate in a scheduled meeting. That decision was later reversed through a court-issued temporary restraining order but by the time the reversal occurred the client had already retained alternative counsel. Around the same time, other clients voiced concerns over the firm’s ability to continue representation, indicating a likelihood of withdrawing or reassessing their engagements. These consequences were particularly serious given that approximately forty percent of Jenner’s revenue comes from its work with government contractors and affiliated entities.

The action against Jenner was not an isolated event but part of a wider governmental effort that had, in similar fashion, targeted multiple major law firms. Other firms, including Perkins Coie LLP, Covington & Burling, WilmerHale, Susman Godfrey, and Paul, Weiss, Rifkind and Garrison (Paul Weiss), were either directly subjected to executive orders or had preemptively entered negotiations with the administration. In one prominent example, Paul Weiss agreed to adjust its policies on client selection, attorney hiring, and internal advancement in favor of political neutrality and merit-based practices; in return, the government revoked the order issued against the firm. Similar settlements occurred with firms that had not been formally targeted, many of which pledged large-scale pro bono contributions toward causes favored by the administration.

A significant number of amicus curiae submissions (filings by third parties seeking to offer the Court specialized legal arguments or broader viewpoints) were brought to the Court, including submissions by civil rights organizations, bar associations, media organizations and press freedom advocates, non-governmental organizations, law firms, academics, law students and student organizations, and former judges. The various amici curiae briefs articulate that President Trump’s EO targeting Jenner, along with similar executive actions, “pose a grave threat to our system of constitutional governance and to the rule of law itself.” Law Firms’ Amicus Brief p. 1] They reiterate that the impact of these orders is far-reaching, as these actions “take direct aim at several of the Nation’s leading law firms and seek to cow every other firm, large and small, into submission.” [Law Firms’ Amicus Brief p. 2]  The executive actions were also described as “unvarnished viewpoint discrimination against law firms [which] sends a clear message to Amici: Do not challenge the President or you will be next.” [NGOS’ Amicus Brief p. 6] Some amici described the consequences of these orders as a “naked attempt to instill fear in the legal profession and intimidate lawyers into submission.” [Bar Associations’ Amicus Brief p. 35]

In response to the issuance of EO 14246, Jenner initiated litigation, first filing a complaint on the grounds that the Order violated the First Amendment in six ways (as well as violations of the Fisth and Sixth Amendments, due process and the constitutional principle of the separation of powers), and then seeking a temporary restraining order (TRO) three days later.

The motion for the TRO sought to enjoin the enforcement of certain sections of the order, specifically those implicating client relationships, contractual activity, and staff access to federal spaces. The Court issued an order the same day, finding that Jenner had met the requirements for a temporary injunction – Jenner was likely to prevail on its claims that the Order violated the First Amendment (protecting freedom of speech and expression) through unlawful retaliation and viewpoint discrimination; the firm was facing “imminent and irreparable harm”; and the “public interest and balance of equities easily favored relied”. [p. 9] The Court noted that the Order’s constitutional “deficiencies” extended to the Fifth (guaranteeing due process and protection against self-incrimination) and Sixth Amendments (ensuring the right to counsel and a fair trial), particularly regarding the obstruction of legal representation and interference with the attorney-client relationship.

Consequently, the TRO barred enforcement of Sections 3 and 5 of the order and prohibited any punitive use of the statements set out in Section 1, including against Jenner’s clients or staff. By mutual agreement, the TRO remained in place pending final adjudication.

The government filed a motion to dismiss the case. Jenner countered with a motion for summary judgment (a request for the court to decide the case early because the facts and law clearly support one party) and a request for a permanent injunction (a court order prohibiting the government from enforcing the order in the future). Given the parties’ agreement that discovery was unnecessary and in light of the evidentiary materials submitted by both sides, the Court construed the government’s filing as a cross-motion for summary judgment.

A hearing on the motions was held on April 28, 2025.

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Decision Overview

Judge John D. Bates delivered the judgment of the United States District Court for the District of Columbia. The central issue before the Court was whether EO 14246 violated Jenner’s constitutional rights by targeting the firm for its advocacy, the clients it represents, and its prior association with a disfavored attorney, and whether its provisions concerning security clearances, government contracting, antidiscrimination enforcement, and restrictions on access to federal property and employment constituted unlawful retaliation in violation of the First Amendment and infringed protections guaranteed under the Fifth and Sixth Amendments.

Jenner challenged EO 14246 on the grounds that it amounted to unconstitutional retaliation for the firm’s protected speech, protected by the First Amendment. It argued that the Order was issued in response to its advocacy, particularly through courtroom litigation and pro bono representation on contentious matters such as immigration and transgender rights. The firm also pointed to its past employment of Weissmann, whose public criticisms of the President had drawn attention, submitting that the Order punished it for the firm’s connection to him and the views he had expressed. Jenner maintained that these actions amounted to blatant viewpoint discrimination, chilling its own expression and threatening the broader legal profession, and that they infringed Fifth and Sixth Amendment protections by interfering with clients’ rights to choose counsel and undermining the independence of the bar. On that basis, Jenner sought a permanent injunction and declaratory judgment (a court ruling that formally states the parties’ legal rights) invalidating the Order in its entirety, contending that its provisions were interdependent and could not stand in isolation.

Jenner argued that Section 2’s bespoke process for suspending and reviewing its security clearances was justiciable as it singled the firm out without individualized assessment or procedural safeguards, resting on the tenuous rationale of the firm’s praise for and rehiring of Weissmann rather than any legitimate national security concern. It also objected to the denial of access to secure government facilities as similarly retaliatory. Under Section 3, Jenner argued that it had standing to bring the challenge based on the imminent economic harm arising from its dependence on government contractors and argued that coercing third parties to disassociate from the firm in order to secure federal funding violated the First Amendment and could not be excused by procurement authority or unsubstantiated claims of employment discrimination. In challenging Section 4, Jenner submitted that targeting it for an Equal Employment Opportunity Commission (EEOC) investigation in retaliation for its speech bypassed normal enforcement procedures and that its adoption of common diversity initiatives, like the Mansfield Rule, provided no legitimate basis for government scrutiny. Finally, Jenner argued that Section 5’s restrictions on access to federal buildings and personnel had already caused concrete harm to its representation of clients, violated the rights to counsel under the Fifth and Sixth Amendments, and that even the statements in the Order’s preface could give rise to further damaging actions that the Court should enjoin.

The government defended EO 14246 as a necessary response to what it viewed as troubling conduct by certain law firms, including concerns that their pro bono work and case selections threatened national security, public safety, and democratic integrity. It justified targeting the firm based on its involvement in politically sensitive litigation, its decision to rehire a former prosecutor who had publicly criticized the President, and allegations of discriminatory employment practices. The administration maintained that these non‑retaliatory policy considerations alone were enough to satisfy constitutional review, and that the presence of any legitimate government interest, however characterized, could insulate the Order from strict First Amendment scrutiny (US constitutional law’s highest level of scrutiny). The government argued that Section 2’s security‑clearance suspensions fell squarely within the President’s exclusive authority and involved predictive national security judgments that courts lack the expertise or jurisdiction to second‑guess. It attempted to connect the firm’s past praise for and rehiring of a controversial attorney to genuine security concerns. Under Section 3, the government contended that Jenner lacked standing because it held no direct government contracts, and any economic injury would depend on independent decisions of third‑party contractors and argued that government contracting decisions are discretionary and reflect the government acting like a private buyer in the marketplace rather than as a regulator or censor, and therefore do not implicate the First Amendment.

The government argued that the alleged employment‑discrimination concerns provided an additional non‑retaliatory rationale for contract actions. With respect to Section 4, the government downplayed the Order’s impact, framing it as a reiteration of existing civil‑rights enforcement rather than a novel directive, and noted that the firm was already subject to EEOC oversight. It argued that no special standing arose from this provision because the firm could not show any unique treatment. On Section 5, the government maintained that the challenge was premature, since the section required future agency guidance before any concrete restrictions would take effect.

The Court highlighted that EO 14246 “like the [other similar orders], seeks to chill legal representation the administration doesn’t like.” [p. 2] The Court analyzed the Order’s overall constitutional violations, provided a detailed examination of each contested section (Sections 2, 3, 4, and 5), and assessed the factors supporting an injunction.

The Court found that EO 14246 targeted Jenner for its past speech and aimed to suppress its future expression, which is inherently unconstitutional under the First Amendment. The Order’s offense is magnified by its viewpoint discrimination and its specific targeting of lawyers. The Court found that none of the Order’s sections could be salvaged by typical Executive Branch discretion in areas like national security, contracting, discrimination investigations, or employment.

The Court described Jenner’s “First Amendment retaliation claim” as “its most straightforward winner”. [p. 11] It applied the test outlined in Scahill v. District of Columbia for a First Amendment retaliation claim which stipulates that Jenner must prove: “(1) that it engaged in protected conduct, (2) that the government took some retaliatory action sufficient to deter a person of ordinary firmness in plaintiff’s position from speaking again, and (3) that there exists a causal link between the exercise of a constitutional right and the adverse action taken against him.” [p. 11]  On the first element, the Court found it plainly satisfied, emphasizing that the firm’s courtroom advocacy, including its partisan representations and pro bono litigation, fell squarely within core First Amendment protections, as did its past association with Weissmann. Turning to the second element, the Court concluded that the severity of the Order’s punitive measures, combined with evidence that other firms altered their conduct to avoid similar retaliation, made clear that the government’s action was sufficient to chill protected speech. In assessing the third element, the Court found a direct causal link between the firm’s speech and the issuance of the Order, noting that Section 1 expressly named the firm’s protected activities as the basis for governmental disapproval. The Court rejected the government’s argument that the Order was justified by non-retaliatory motives, stressing that the mere assertion of a content-neutral purpose cannot cure what is, at its core, viewpoint discrimination (a form of First Amendment limitation that courts particularly disfavor).

The Court described this case as “no run-of-the-mill retaliation case” and highlighted that the greatest danger of retaliation lies in its “prospective silencing effect”, describing the administration’s approach as an impermissible scheme of informal censorship. [p. 15] It noted that because the Trump administration’s bargaining demonstrates that Jenner can avoid sanction “if it compromises its speech” the retaliation is ongoing in this situation. It compared this to the “scheme of informal censorship as discussed in the NRA v. Vullo case and that this “especially harmful sort of retaliation” is analogous to a prior restraint, described in Nebraska Press Association v. Stuart as “the ‘most serious and least tolerable’ of all First Amendment violations”. [p. 16] The Court  noted that targeting lawyers poses an even greater constitutional threat, implicating the Fifth and Sixth Amendments by interfering with the right to counsel. It added that threatening lawyers’ independence also threatened judicial independence and so “the ability of a coequal branch of government to function”. [p. 18] The independence of the legal profession is critical for judicial oversight, and the EO undermines this by forcing firms to choose between loyalty to clients and government appeasement. Section 5, by restricting access to government facilities, obstructs representation and clients’ right to choose counsel. The Court also emphasized that the Order’s focus on Jenner’s “specific views” was a blatant instance of viewpoint discrimination – the “egregious form of content discrimination” as described in Rosenberger v. Rector & Visitors of University of Virginia.

Accordingly, the Court concluded that the Order punishes and seeks to silence speech at the heart of the First Amendment, shields government action from scrutiny, and violates foundational constitutional protections. However, it then examined whether the “order – or any of its sections – can nevertheless survive”. [p. 19]

The Court accepted that Jenner’s challenge to Section 2 was justiciable, despite the traditional deference to Executive Branch decisions involving national security as this case raised legal rather than political questions, as it targeted Jenner with a bespoke process lacking individualized review. It added that this process was clearly implemented “in retaliation for Jenner’s speech”. [p. 23] Blanket suspensions of this nature, the Court warned, could justify discriminatory actions against entire groups without recourse. Although the Court accepted that “discriminating on the basis of speech and belief, verboten almost everywhere else, is routine in the security-clearance context”, it held that Jenner had cleared this procedural hurdle as the Court found no genuine national security concern, dismissing the rationale of public praise for Weissmann as insufficient. [p. 23] It found that the vague invocation of the national interest did not shield the Order, particularly when the true motive, as shown in Section 1, was political disapproval, noting that “Section 2, in other words, is about using another lever in the President’s arsenal to extinguish speech he dislikes.” [p. 25] The Court, in reference to the earlier Paul Weiss example, where the firm avoided sanctions by compromising its speech, held that: “[w]hat it took to escape that process – denouncing a former partner, changing client selection and hiring practices, and pledging pro bono work to the President’s liking – had not even a glancing relationship to national security[,]” highlighting that Section 2 was aimed at changing speech. [p. 25] Section 2(b), which restricted access to federal resources, failed for the same reasons, as it also functioned to suppress expression.

The Court found Jenner had standing to challenge this Section 3. Beyond monetary loss (approximately 40% of its revenue depended on government contractors, and client responses to the Order made the economic harm both imminent and traceable), the Court observed the Order’s chilling effect on Jenner’s speech independently supported standing, reiterating that “the injury to Jenner’s constitutional right to express itself without fear of government reprisal itself confers standing. […] [A]s made clear by other firms’ negotiations (and capitulations) – the mere existence of the order chills Jenner’s expression. Jenner has standing to challenge the order casting that chill.” [p. 29] The Court relied on Vullo to conclude that Section 3 used “coercion against a third party to achieve the suppression of disfavored speech.” [p. 30] It rejected the government’s claim that the government was acting merely as a private contractor, noting that the First Amendment binds the government in all roles, including as an “employer.” It emphasized that indirect discouragements can be as coercive as direct penalties, and discretion used to retaliate against speech is unconstitutional. The Court referenced Vullo in concluding that “the government may regulate but it may not regulate in retaliation for speech.” [p. 31] The government’s justification based on alleged discriminatory practices was unsupported by fact or law. Participation in diversity, equity and inclusion (DEI) programs like the Mansfield Rule was widespread and not illegal. The Court held that the government was attempting to enforce a “novel legal theory” without due process. [p. 33] Drawing from Bantam Books v. Sullivan and Vullo, the Court condemned this as a scheme of state censorship via extralegal means. Jenner, it concluded, was entitled to due process before being blacklisted from contracts. The Court further observed that the Order lacked any notice or hearing and imposed extensive sanctions and explained that although the government can restrict speech of some government employees, government funding does not give license to suppress independent speech, especially when the entity involved is a private law firm with indirect government ties. Much of Jenner’s work positioned it in adversarial relation to the government, and the Court noted that “Section 3, then, employs retaliatory means against lawyers engaged in litigation opposing the government” making the procurement-based retaliation especially offensive. [p. 37]

In examining Section 4, the Court referred to the prior EO 14230 against Perkins Coie LLP, and identified that this section aimed to subject Jenner to EEOC review for compliance with civil rights laws. The accompanying fact sheet clarified that Jenner’s practices would be reviewed for potential racial bias. The Court rejected the argument that Jenner lacked standing and held that the firm was being uniquely targeted due to its speech, not simply subjected to standard EEOC oversight and that the injury was both traceable to the Order and redressable through an injunction. The Court found no legitimate justification for targeting Jenner as the only cited basis was Jenner’s use of the Mansfield Rule, a widespread diversity policy. The Court concluded that the primary unifying factor among the firms targeted for investigation was speech disliked by President Trump. It noted that “Jenner is among more than 360 law firms that earned the Mansfield Certification in 2023–24. […] In this sense, Jenner is entirely unremarkable. What is remarkable is the shared characteristic of the firms now threatened with EEOC investigations: speech the President dislikes” [p. 38], citing Perkins Coie v. Department of Justice, which catalogs other firms targeted by President Trump. It ruled that the President could not direct EEOC investigations in retaliation for protected expression, bypassing established procedures requiring specific charges.

The Court noted that the Order’s hiring ban in Section 5 was immediately effective, and the requirement for agencies to develop guidance necessarily implied that access would be restricted and that harm was already occurring, as DOJ officials had barred Jenner counsel from a meeting, forcing the client to find new representation. This interfered with both Jenner’s advocacy and clients’ rights to choose their lawyers. The Court also found that Section 5 violated the First Amendment and threatened the Fifth and Sixth Amendments. It described the provision as “inexplicable by anything other than a pure desire to inflict pain on Jenner.” [p. 41] While the rights to counsel are qualified, they cannot be arbitrarily denied. The Court found that by blocking access to agencies and courts, the Order impaired Jenner’s ability to function as counsel, it held that: “[a] lawyer without the ability to negotiate with federal agencies, appear in court, and the like is hardly a lawyer at all.” [p. 42] It observed that other sections of the Order imposed similar constraints, collectively undermining the ability of clients to retain the lawyers of their choice. Although the Court’s decision rested on First Amendment grounds, it warned that the Order risked expanding into broader constitutional violations.

Having ruled for Jenner on the merits, the Court evaluated whether a permanent injunction was warranted. The Court relied on the standard established in Zukerman v. USPS requiring that Jenner show: “(1) irreparable injury that it will suffer absent injunctive relief; (2) no available remedy at law, such as monetary damages, adequate to compensate its injury; and (3) an upper hand considering the balance of hardships and the public interest.” [p. 10]

The Court found that Jenner faced irreparable harm not compensable by legal remedies. The Order forced the firm to choose between altering its speech or facing serious economic and reputational damage. The threat to First Amendment freedoms alone met the irreparable harm threshold. Financial losses, though typically not irreparable, were unrecoverable here due to sovereign immunity, leaving Jenner without a damages remedy. The Court stressed that only a permanent injunction could prevent these harms. The equities and public interest weighed overwhelmingly in favor of relief. The enforcement of an unconstitutional order was inherently contrary to public interest. The impact extended beyond Jenner, threatening the entire legal profession. Other law firms had already been targeted, and the orders created a chilling effect on vigorous advocacy and pro bono representation.

The manipulation of pro bono work, forcing firms to align with the President’s political agenda, was especially harmful to the public, and the Court noted that “[t]he orders strongarm firms into redirecting their uncompensated services to work the President prefers—or even perhaps to work for the President himself.” [p. 46] The Court cautioned that this chilling effect could spread to other institutions, including the press and civil society, undermining the balance of the constitutional system.

In conclusion, the Court held that EO 14246 was an unconstitutional act of retaliation that violated Jenner’s First Amendment rights through viewpoint discrimination and a severe chilling effect on legal advocacy. It found the Order unlawful under settled First Amendment principles, without needing to address broader or novel claims. The decision also highlighted serious risks to the Fifth and Sixth Amendments, particularly the right to counsel. Citing irreparable harm and the public’s interest in protecting constitutional freedoms and an independent legal profession, the Court granted summary judgment for Jenner, denied the government’s motion, and permanently enjoined enforcement of Sections 2 through 5. However, it declined to enjoin future actions based solely on the statements in Section 1, treating them as protected government speech absent operative effect.

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