Part 5 of 6
4. EO 14230 Violates the Fifth and Sixth Amendment Rights to Counsel of Plaintiff’s Clients.
The Sixth Amendment secures the right, “[i]n all criminal prosecutions,” for “the accused . . . to have the Assistance of Counsel for his defense.” U.S. CONST. amend. VI. Included in this Sixth Amendment guarantee is “the right to effective assistance of counsel,” Strickland v. Washington, 466 U.S. 668, 686 (1984) (quoting McMann v. Richardson, 397 U.S. 759, 771 n.14 (1970)), and a “right to choose one’s own counsel,” subject to some restrictions, Wheat v. United States, 486 U.S. 153, 159 (1988); see also supra n.1 (discussing briefly the historical context and purpose of the amendment). Relatedly, in the civil litigation context, the Fifth Amendment guarantees the right for parties to “the aid of counsel when desired and provided by the party asserting the right.” Powell, 287 U.S. at 68. Seeking to assert the rights of its criminal and civil clients, plaintiff contends, in Counts VIII and IX, that EO 14230 unconstitutionally interferes with both Fifth and Sixth Amendment constitutional protections by interfering with the ability of plaintiff to represent its clients. See Pl.’s Mem. at 29-31. Plaintiff is correct as to each claim.
Starting with the Sixth Amendment right to counsel in criminal matters, the instruction in EO 14230’s Section 5(a) for all agencies to “limit[] Government employees acting in their official capacity from engaging with [plaintiff’s] employees,” EO 14230 § 5(a), 90 Fed. Reg. at 11782, threatens to undermine plaintiff’s ability to provide effective assistance of counsel to clients in criminal cases, see 2nd Burman Decl. ¶ 20 (“Perkins Coie represents clients who have been indicted or are the targets of federal criminal investigations” and has “represented more than 80 individuals and companies who have been criminally investigated, charged, and/or prosecuted by federal authorities at the Department of Justice” in the “past five years”); TRO Hr’g Tr. at 26:23- 24 (plaintiff’s counsel confirming plaintiff has “clients who are indicted and federal targets”). For instance, “defense counsel have responsibilities in the plea bargain process . . . that must be met to render the adequate assistance of counsel that the Sixth Amendment requires.” Missouri v. Frye, 566 U.S. 134, 143-44 (2012); accord Lafler v. Cooper, 566 U.S. 156, 170 (2012). Obviously, the plea bargain process requires defense counsel to engage with federal prosecutors, through communicating with them in writing, speaking to them, or meeting in-person with them. The plain language of EO 14230 requiring any planned guidance to “limit[] Government employees acting in their official capacity from engaging with Perkins Coie employees” and further limiting plaintiff’s employees from entering federal buildings, EO 14230 § 5(a), 90 Fed. Reg. at 11782, poses an existential threat to that critical function. The immediacy of this threat is amply demonstrated by the fact that government officials cancelled two separate meetings in separate matters with plaintiff’s employees in the four business days between the issuance of EO 14230 and the Court’s TRO. See Pl.’s SMF ¶¶ 152, 162. Cancelled meetings and restricting plaintiff’s access to government officials with authority in matters affecting plaintiff’s clients in criminal matters, therefore, threatens to undermine plaintiff’s clients’ vital right to effective assistance of counsel.
Similarly, the Order impinges on “the right of a defendant who does not require appointed counsel to choose who will represent him.” United States v. Gonzalez-Lopez, 548 U.S. 140, 144 (2006). As the Supreme Court has explained, this right “to counsel of choice,” id. at 146, is “the root meaning of the constitutional guarantee” to counsel protected by the Sixth Amendment, id. at 147-48. In addition to impinging on the right to effective counsel by limiting access to federal government buildings and officials, as directed in Section 5(a), Section 3 undermines plaintiff’s ability to perform its professional duties in these representations, by requiring any client with a government contract, whether or not plaintiff’s representation of the client is related to that contract, to terminate the relationship with plaintiff or face the loss of all government contracts. EO 14230 § 3(a), (b), 90 Fed. Reg. at 11781-82. Though the Order does not explicitly ban government contractor clients from hiring plaintiff, the combination of limiting government building and officials access to Firm employees, directing termination of any government contract on which the Firm has provided services, and threatening termination of all government contracts held by contractors doing any business with the Firm, would effectively have that result. See Pl.’s SMF ¶¶ 151-61 (describing the clients who terminated and/or began to reconsider representations in the brief time between the issuance of the EO and the Court’s TRO and the resulting impacts on plaintiff); Pl.’s MSJ, Ex. 6, Expert Report of Robert E. Hirshon, former President, American Bar Association & former ethics and professional responsibility professor, Michigan Law School (“Hirshon Rep.”) ¶ 19, ECF No. 39-6 (“[T]he Executive Order, if upheld, would punish clients (through cancellation of their government contracts) for seeking advice or other legal services from their chosen lawyer, or from a law firm the President dislikes.”).
Even if clients choose to maintain their relationship with plaintiff in the face of EO 14230’s threat of government contract termination, the Rules of Professional Conduct might force plaintiff to withdraw as counsel if government restrictions, particularly as agency guidance emerges, adversely impact plaintiff’s ability to conduct legal work effectively on behalf of the Firm’s clients. See, e.g., Pl.’s MSJ., Ex. 7, Expert Rep. of Prof. Roy D. Simon, Jr., Distinguished Professor of Legal Ethics Emeritus, Hofstra University’s Maurice A. Deane School of Law (“Simon Rep.”) ¶ 48, ECF No. 39-7 (“Clients and potential clients will be deprived of their choice of counsel if the Executive Order’s restrictions on Perkins Coie . . . interfere with Perkins Coie’s ability to represent a client competently, because in those instances the Rules of Professional Conduct will permit or require Perkins Coie to request a tribunal’s permission to withdraw from a pending matter.”). Either way, the fundamental rights of the clients would be adversely affected.
The law is well-settled that the government is not constitutionally permitted to interfere directly with the right of plaintiff’s clients in criminal matters to choose plaintiff to represent them. See Gonzalez-Lopez, 548 U.S. at 148 (“Deprivation of the right [to counsel of choice] is ‘complete’ when the defendant is erroneously prevented from being represented by the lawyer he wants, regardless of the quality of the representation he received.”). Nor may the government do indirectly what a government official “is barred from doing directly.” Vullo, 602 U.S. at 190. Yet, the record demonstrates this is exactly what has happened in this case. Since EO 14230 was issued, “[m]any clients” of plaintiff have “request[ed] frequent updates relating to the Order to assess whether Perkins Coie can continue to represent them.” Pl.’s SMF ¶ 158 (citing 2nd Burman Decl. ¶ 48). Whether due to fears that the government might retaliate against clients who hire plaintiff to represent them, such as by canceling any government contracts by firms that do business with plaintiff, see EO 14230 Fact Sheet (“[T]he Federal Government will prohibit funding contractors that use Perkins Coie LLP.”), or concern that plaintiff’s lawyers may not have access to federal buildings and officials, see Pl.’s SMF ¶ 152 (explaining that, after plaintiff’s lawyers were refused attendance at a scheduled meeting with a federal official on the day after EO 14230 was issued, the client, on which case plaintiff had already done over $1 million worth of work, “hired another law firm to represent it before the federal government and in related litigation” (citing 2nd Burman Decl. ¶ 44)), EO 14230 has already forced plaintiff’s clients to choose between using their chosen lawyers and facing potential consequences from the government due to who they have hired as counsel. Forcing plaintiff’s clients to make such a choice violates their Sixth Amendment rights. Plaintiff is therefore entitled to summary judgment on Count VIII.
For essentially the same reasons, EO 14230 also unconstitutionally invades the right to counsel in the civil context. In American Airways Charters, Inc. v. Regan, 746 F.2d 865, 866 (D.C. Cir. 1984), the D.C. Circuit considered the rights of a corporation designated as a “Cuban national” to “choose and retain counsel without obtaining in advance a government . . . license to do so”—in this case, from the Treasury Department’s Office of Foreign Assets Control (“OFAC”). In its decision, the Circuit discussed the potential danger of allowing “an executive agency that is, in significant respects, the adverse party” effectively to have veto power over the choice of an attorney. Id. at 872. In construing the statute in question to prevent OFAC from exercising power over the company’s choice of counsel, see id. at 873-74, the Circuit recognized the “invalidity of a governmental attempt to deny counsel to a civil litigant,” id. at 873 (citing Powell, 287 U.S. at 68-69, and collecting cases “elaborat[ing] on the same basic theme”); see also Muniz v. Meese, 115 F.R.D. 63, 66 n.11 (D.D.C. 1987) (noting “violation of civil liberties that is implied by a government intrusion into [citizens’] right to select and to be represented by counsel of their choice”).
While the First Amendment’s free speech and association protections safeguard a client’s rights to hire and consult with an attorney, see supra Part III.B.2, separate constitutional problems are posed under the Fifth and Sixth Amendments when the government interferes with a client’s right to choose counsel. The government contracting compelled disclosure and termination instruction and government building and government official access bars in EO 14230’s Sections 3 and 5, respectively, would adversely impact both clients’ ability to choose plaintiff and plaintiff’s ability to provide representation to clients in criminal cases, and would adversely impact plaintiff’s representations of clients in civil matters involving the government. Plaintiff, therefore, is entitled to summary judgment on Count IX.33
5. EO 14230 Violates Plaintiff’s Procedural Right to Due Process of Law.
The Due Process Clause of the Fifth Amendment provides that no person “shall . . . be deprived of life, liberty, or property, without due process of law.” U.S. CONST. amend. V. Plaintiff claims, in Count II, that EO 14230 violates this protection by “vitiat[ing] the Firm’s right to petition the government,” without affording plaintiff proper process. Pl.’s Mem. at 21.34 Evaluating these procedural due process claims requires determining, first, whether a protected interest held by plaintiff in life, liberty, or property was deprived and, second, whether any process provided was adequate. See Reed v. Goertz, 598 U.S. 230, 236 (2023) (citing Zinermon v. Burch, 494 U.S. 113, 125 (1990)).35
Analysis of plaintiff’s claim that EO 14230 violates, without proper process, the Firm’s right to petition the government, which is an interest protected under the First Amendment, is straightforward. The Supreme Court has recognized that “[t]he very idea of government, republican in form, implies a right on the part of its citizens to . . . petition for a redress of grievances,” De Jonge v. State of Oregon, 299 U.S. 353, 364 (1937) (quoting United States v. Cruikshank, 92 U.S. 542, 552 (1875)), and that this right “is one that cannot be denied without violating those fundamental principles of liberty and justice which lie at the base of all civil and political institutions,” id. (citations omitted). See also BE & K Constr. Co. v. NLRB, 536 U.S. 516, 524 (2002) (“We have recognized [the] right to petition as one of ‘the most precious of the liberties safeguarded by the Bill of Rights.” (quoting Mine Workers, 389 U.S. at 222). This liberty interest in petitioning the government is so fundamental, therefore, that it is protected under the due process clauses of both the Fifth and Fourteenth Amendments. See De Jonge, 299 U.S. at 364 (citations omitted); Trentadue v. Integrity Comm., 501 F.3d 1215, 1236-37 (10th Cir. 2007) (recognizing that the Fifth Amendment’s due process clause applies to the “liberty interest in [the] First Amendment right to petition the government”).
The right to petition the government “extends to all departments of the Government” and, crucially, includes “[t]he right of access to the courts.” BE & K Constr. Co., 536 U.S. at 525 (quoting Calif. Motor Transp. Co. v. Trucking Unlimited, 404 U.S. 508, 510 (1972)); see also Borough of Duryea v. Guarnieri, 564 U.S. 379, 387 (2011) (“[T]he Petition Clause protects the right of individuals to appeal to courts and other forums established by the government for resolution of legal disputes.”). Moreover, retaliation based on the exercise of the right to petition the government via access to the courts violates that right, and the associated liberty interest, in the same way that retaliation based on protected speech violates the First Amendment. See Guarnieri, 564 U.S. at 387-93 (applying, in a case involving a public employee, the same test to retaliation for petition rights as is applied for retaliation based on speech). Since EO 14230’s retaliatory nature has already been determined, and that retaliation relied at least in part on lawsuits filed by plaintiff, see supra Part III.B.1, plaintiff’s liberty interest in petitioning the government was clearly implicated. In other words, the government’s retaliatory actions reflected in EO 14230, based in part on plaintiff’s filing of lawsuits on behalf of the Firm’s clients, deprived plaintiff of its liberty interest in petitioning the government.
Here, deciding what process was due to plaintiff is unnecessary, because no process was provided. See TRO Hr’g Tr. at 11:12-20 (plaintiff’s counsel confirming no notice or process was given to plaintiff); see also id. at 17:20-18:4 (plaintiff’s counsel explaining that EO 14230 “does not provide any kind of notice with respect to the factual findings in Section 1” or “the restrictions that are placed only on this law firm,” since plaintiff “only learned about them contemporaneous with the release of the executive order”). Certainly, here, the text of EO 14230 does not satisfy the notice requirement because the retaliation, and thus the deprivation of the right, was completed at the time of issuance, regardless of whether guidance in some form remains pending. See TRO Hr’g Tr. at 17:5-19:11 (plaintiff’s counsel noting that plaintiff “only learned about” both the “factual findings in Section 1” and the “restrictions that are placed only on” plaintiff and not other law firms “contemporaneous with the release of” EO 14230, and further that, were guidance to be released in the future, “agencies are already told what the outcome of their analysis is, because they have been told in Section 1 that working with Perkins Coie is not consistent with the national interest and not consistent with the administration and policies of the administration”). Notably, even in cases involving legitimate national security interests, some level of due process is required before subjecting a person to the adverse consequences of government action. See, e.g., Ralls Corp. v. CFIUS, 758 F.3d 296, 318-19 (D.C. Cir. 2014) (finding a due process violation where a foreign-owned corporation was subject to an order preventing a merger without an opportunity to rebut the findings on which the order was based).36
In sum, plaintiff is entitled to summary judgment on its claim in Count II that EO 14230 violates the Firm’s procedural due process rights by severely impinging on the Firm’s protected liberty interest to petition the government by both retaliating against the Firm for exercising its right to petition the government and by restricting the Firm’s access to government facilities and officials, without any prior notice or opportunity to be heard.
6. EO 14230 is Impermissibly Vague.
Plaintiff claims, in Count III, that EO 14230 is impermissibly vague, in violation of the Fifth Amendment Due Process clause, because the Order “fails to provide adequate notice as to what are prohibited ‘diversity, equity, and inclusion’ policies,” Am. Compl. ¶ 109, but nevertheless directs government agencies to take multiple adverse actions against plaintiff based on this “vaguely defined” term, including “threatened investigation and enforcement action by the EEOC and [DOJ],” “threatened suspension of active security clearances,” “threatened termination of contracts or funding with Perkins Coie or entities doing business with Perkins Coie,” “threatened limitation of access to Federal property and engaging with government employees,” and threatened prevention of hiring of Perkins Coie employees for Federal positions,” id. ¶¶ 110-14. When asked about what precisely was wrong with “diversity, equity and inclusion,” the government provided little help, stating “diversity, in and of itself, isn’t the problem. The problem is stereotyping based off of these points.” Mots. Hr’g Tr. at 64:3-5. In defense of this due process challenge, the government avoids trying to define the terms “diversity, equity and inclusion” altogether and contends that the Order’s reference “to ‘categories prohibited by civil rights laws,’” Gov’t’s Mem. at 12 (quoting EO 14230 § 1, 90 Fed. Reg. at 11781), provides a sufficient “intelligible benchmark” to save the Order from plaintiff’s vagueness challenge, id. at 13. The government’s defense is not persuasive.
“A fundamental principle in our legal system is that laws which regulate persons or entities must give fair notice of conduct that is forbidden or required.” FCC v. Fox Television Stations, Inc., 567 U.S. 239, 253 (2012). Courts apply this doctrine to review both civil and criminal laws. See, e.g., Boutilier v. INS, 387 U.S. 118, 123 (1967) (“It is true that this Court has held the ‘void for vagueness’ doctrine applicable to civil as well as criminal actions.”); Gentile v. State Bar of Nev., 501 U.S. 1030, 1048-51 (1991) (finding a state Supreme Court rule governing attorney conduct void for vagueness); Keyishian v. Bd. of Regents, 385 U.S. 589, 603-04 (1967) (finding a restriction on government employee speech “wholly lacking in terms susceptible of objective measurement” (internal quotation marks, citation omitted)). In the civil context, an enactment is only void if it is “so vague and indefinite as really to be no rule or standard at all.” Boutilier, 387 U.S. at 123; see also Senior C.L. Ass’n, Inc. v. Kemp, 965 F.2d 1030, 1036 (11th Cir. 1992) (“To find a civil statute void for vagueness, the statute must be ‘so vague and indefinite as really to be no rule or standard at all.’” (quoting Boutilier, 387 U.S. at 123)). EO 14230 fails this test, as another Judge on this Court and other courts to review the Trump Administration’s use of these terms in various orders and agency rules have also concluded. See, e.g., NAACP v. U.S. Dep’t of Educ., --- F. Supp. 3d ---, 2025 WL 1196212, at *1-2, 6 (D.D.C. Apr. 24, 2025) (finding a certification requirement imposed on schools, which required compliance with a Dear Colleague Letter issued by the U.S. Department of Education (“DOE”) instructing “federally funded educational institutions to cease all racially discriminatory initiatives and unlawful DEI programs,” as further defined in a “follow-on ‘Frequently Asked Questions’ document,” was void for vagueness where the DOE documents “fail[ed] to provide an actionable definition of what constitutes ‘DEI’ or a ‘DEI’ practice, or delineate between a lawful DEI practice and an unlawful one”); Nat’l Educ. Ass’n v. U.S. Dep’t of Educ., --- F. Supp. 3d ---, 2025 WL 1188160, at *1, 18 (D.N.H. Apr. 24, 2025) (finding, in another case challenging the same DOE certification requirement and underlying documents, that the plaintiff was likely to succeed on its void for vagueness challenge, since the DOE Dear Colleague Letter “does not make clear . . . what the Department believes constitutes a DEI program, or the circumstances in which the Department believes DEI programs run afoul of Title VI, or “even define what a ‘DEI program’ is”); Nat’l Ass’n of Diversity Offs. in Higher Educ. v. Trump, --- F. Supp. 2d ---, 2025 WL 573764, at *1-2, 4, 19-20, 26 (D. Md. Feb. 21, 2025) (in considering two Executive Orders, Nos. 14151, 90 Fed. Reg. 8339 (Jan. 29, 2025), and 14173, 90 Fed. Reg. 8633 (Jan. 31, 2025), finding term “equity-related’ grants or contracts” void for vagueness, since “[t]he meaning of the word ‘equity’ is unclear to a degree that risks arbitrary and discriminatory enforcement” and “leaves current grant recipients and contractual counterparts unsure about what activities are prohibited,” and further finding direction to Attorney General to take steps to “deter DEI programs or principles . . . that constitute illegal discrimination or preferences” (quoting EO 14173, 90 Fed. Reg. at 8635), void for vagueness given lack of “guidance on what the new administration considers to constitute ‘illegal DEI discrimination and preferences,’ . . . or what types of ‘DEI programs or principles’ the new administration considers ‘illegal’ and is seeking to ‘deter’” (internal citations omitted)), stayed pending appeal, No. 25-1189, ECF No. 29 (4th Cir. Mar. 14, 2025).37
The Order and the accompanying fact sheet direct adverse agency actions against plaintiff due to the finding that plaintiff “racially discriminates against its own attorneys and staff, and against applicants” and engages in employment practices “on the basis of race and other categories prohibited by civil rights laws.” EO 14230 § 1, 90 Fed. Reg. at 11781; EO 14230 Fact Sheet (mentioning plaintiff’s “discriminatory actions”). While the government suggests that the Order’s reference to “categories prohibited by civil rights laws” provides clarity about what is prohibited, Gov’t’s Mem. at 12 (quoting EO 14230 § 1, 90 Fed. Reg. at 11781), neither the Order and fact sheet nor the record submitted in this case provides any actual evidence of illegal discrimination by plaintiff that would make clear what Firm employment policies or practices, in the government’s view, run afoul of the law. See also supra Part III.B.1(a).38
The Order goes on to mention the Administration’s goal of “ending discrimination under ‘diversity, equity, and inclusion’ policies,” EO 14230 § 1, 90 Fed. Reg. at 11781, leading to a possible inference that such policies, and not any concrete evidence of discrimination, are the problematic conduct that plaintiff should avoid. The terms diversity, equity, and inclusion, taken collectively or individually, however, could refer to a wide range of actions and programs, formal or informal, as well as basic thoughts and beliefs. The Order provides no definition or guidance as to what form of program possibly described by these terms is considered unlawful discrimination by the Trump Administration, leaving plaintiff to guess at what is and is not permissible in the government’s view, while already facing the threat of adverse actions during the guessing.
The government’s own briefing reflects this uncertainty. While repeatedly accusing plaintiff of engaging in racial discrimination, see Gov’t’s Mem. at 2, 8-10, 17, 19, 21, 23; Gov’t’s Opp’n at 13, 14; Gov’t’s Reply at 3, 4, the government at various times also states that (1) plaintiff should be investigated by the EEOC to determine “whether [they] are violating the civil rights laws,” Gov’t’s Mem. at 2 (emphasis supplied); (2) the government is merely trying to advance “valid social policies regarding discrimination,” rather than enforcing any legal prohibitions, Gov’t’s Mem. at 3; see also Gov’t’s Opp’n at 3, 4; (3) “[d]iversity initiatives” are “legally suspect,” and thus plaintiff’s practices “provide ample basis for review,” Gov’t’s Mem. at 11 (emphasis supplied); see also Gov’t’s Opp’n at 16; (4) the government is merely “rais[ing] legitimate legal issues of just how far DEI policies and programs can go and whether such policies cross the line into illegal discrimination,” Gov’t’s Mem. at 27 (emphasis supplied); (5) plaintiff engaged in “aggressive DEI practices,” Gov’t’s Reply at 1; and (6) plaintiff “appears to have” engaged in what the government characterizes as discrimination, Gov’t’s Opp’n at 17-19 (emphasis supplied). When even the government cannot decide what exactly the grounds for its actions were, plaintiff is truly left unable to know what conduct to avoid.
In short, EO 14230 fails to set a coherent standard for plaintiff to follow. For that reason, plaintiff is entitled to summary judgment on Count III.
C. Permanent Injunction Factors
Plaintiff has amply demonstrated entitlement to summary judgment on its claims that EO 14230 violates the First, Fifth and Sixth Amendments. Given this determination, EO 14230 cannot be “implemented consistent with applicable law,” EO 14230 § 6(b), 90 Fed. Reg. at 11782, as required by the embedded terms of the Order, which is thus is null and void. Both parties agree that, notwithstanding the effect of Section 6(b), plaintiff’s request for injunctive relief must still be addressed. Mots. Hr’g Tr. at 15:3-17:20 (government counsel discussing Section 6(b) and urging that “the application of the factors to each section that was being enjoined would still need to be undertaken”); id. at 91:17-92:23 (plaintiff’s counsel urging same to ensure future “enforceability”).
To obtain the permanent injunctive relief sought, plaintiff “must demonstrate: (1) that it has suffered an irreparable injury; (2) that remedies available at law, such as monetary damages, are inadequate to compensate for that injury; (3) that, considering the balance of hardships between the plaintiff and defendant, a remedy in equity is warranted; and (4) that the public interest would not be disserved by a permanent injunction.” Monsanto Co. v. Geertson Seed Farms, 561 U.S. 139, 156-57 (2010) (quoting eBay Inc. v. MercExchange, L.L.C., 547 U.S. 388, 391 (2006)). The final two factors “merge” into one when “the Government is the opposing party,” Nken v. Holder, 556 U.S. 418, 435 (2009) (applying merged factors in stay context), because “the government’s interest is the public interest,” Pursuing America’s Greatness v. FEC, 831 F.3d 500, 511 (D.C. Cir. 2016) (emphasis in original) (applying merged factors in preliminary injunction context); see also Anatol Zukerman & Charles Krause Reporting, LLC v. U.S. Postal Serv., 64 F.4th 1354, 1364 (D.C. Cir. 2023) (applying the merged factors in permanent injunction context). Plaintiff succeeds on each showing.
1. Plaintiff Has Demonstrated Irreparable Injury Will Occur Absent an Injunction, With No Adequate Remedy at Law.
“It has long been established that the loss of constitutional freedoms, ‘for even minimal periods of time, unquestionably constitutes irreparable injury.’” Mills v. District of Columbia, 571 F.3d 1304, 1312 (D.C. Cir. 2009) (quoting Elrod, 427 U.S. at 373); see also Roman Cath. Diocese of Brooklyn v. Cuomo, 592 U.S. 14, 19 (2020) (“The loss of First Amendment freedoms, for even minimal periods of time, unquestionably constitutes irreparable injury.” (quoting Elrod, 427 U.S. at 373); Karem v. Trump, 960 F.3d 656, 668 (D.C. Cir. 2020) (“[A] violation of Fifth Amendment due process rights . . . support[s] injunctive relief.”). Here, plaintiff has demonstrated that EO 14230 violates the Firm’s rights under the First, Fifth, and Sixth Amendments, as well as its clients’ rights under the Fifth and Sixth Amendments. See supra Parts III.B.1-6. These violations were ongoing until Sections 1, 3 and 5 were temporarily enjoined and would continue were the injunction lifted, meaning they are sufficient, by themselves, to establish irreparable harm. Furthermore, these injuries are irreparable “because [they] cannot be fully compensated by later damages,” Christian Knights of the Ku Klux Klan Invisible Empire, Inc. v. District of Columbia, 751 F. Supp. 218, 224 (D.D.C. 1990) (collecting cases); see also, e.g., Book People, Inc. v. Wong, 91 F.4th 318, 340 (5th Cir. 2024) (“An irreparable harm is one for which there is no adequate remedy at law.” (citation and internal quotation marks omitted))—a reality reinforced in this scenario by the existence of sovereign immunity.
Plaintiff has also shown monetary harm sufficient to establish irreparable harm. Where, as here, sovereign immunity limits plaintiff to seeking nonmonetary equitable relief and thus renders unrecoverable plaintiff’s monetary damages, courts have recognized these losses “can . . . constitute irreparable harm.” Xiaomi Corp. v. Dep’t of Def., No. 21-cv-280 (RC), 2021 WL 950144, at *10 (D.D.C. Mar. 12, 2021) (citations omitted); see also California v. Azar, 911 F.3d 558, 581 (9th Cir. 2018) (stating that economic harm caused by federal agencies protected by sovereign immunity “is irreparable . . . because the states will not be able to recover monetary damages”); Chamber of Com. v. Edmondson, 594 F.3d 742, 770-71 (10th Cir. 2010) (“Imposition of monetary damages that cannot later be recovered for reasons such as sovereign immunity constitutes irreparable injury.”); Iowa Utilities Bd. v. FCC, 109 F.3d 418, 426 (8th Cir. 1996) (“The threat of unrecoverable economic loss, however, does qualify as irreparable harm.”); TRO Hr’g Tr. at 26:11-15 (plaintiff’s counsel recognizing sovereign immunity bars monetary recovery in this case). Even where unrecoverable economic harm exists, courts in this district have required the economic harm faced to be “serious in terms of its effect on the plaintiff,” Gulf Oil Corp. v. Dep’t of Energy, 514 F. Supp. 1019, 1026 (D.D.C. 1981), “significant,” Air Trans. Ass’n v. Exp.-Imp. Bank, 840 F. Supp. 2d 327, 335 (D.D.C. 2012); Cal. Ass’n of Priv. Postsecondary Schs. v. DeVos, 344 F. Supp. 3d 158, 170 (D.D.C. 2018) (quoting Air Trans., 840 F. Supp. 2d at 335), or “sufficiently severe,” Save Jobs USA v. U.S. Dep’t of Homeland Sec., 105 F. Supp. 3d 108, 115 (D.D.C. 2015).
Under any formulation of this standard, plaintiff succeeds in showing irreparable monetary harm. The undisputed facts in this case show that plaintiff suffered significant losses in the week between the issuance of EO 14230 and entry of the TRO as a direct result of the Order. One client who had used the Firm for seven years and was represented by the Firm in seven open matters said, “within hours of the Order’s release, that due to the Order, [plaintiff] cannot represent that client in any litigation or before the relevant federal agency.” 2nd Burman Decl. ¶ 48.a (emphasis supplied); see also Pl.’s SMF ¶ 151 (referencing this client); Gov’t’s Resp. to Pl.’s SMF at 5 (noting the facts of ¶ 151 are undisputed). Another client, who had used the Firm for 35 years, reassigned two matters to other law firms the day after EO 14230 was released. Pl.’s SMF ¶ 153. Yet another client, with the Firm since 2018, “withdrew all work from [plaintiff] as a result of the Order,” as of the day after the Order’s issuance. 2nd Burman Decl. ¶ 48.c (emphasis supplied); see also Pl.’s SMF ¶ 154. A coalition of four clients similarly withdrew “all coalition work from [plaintiff] as of March 7, 2025 due to the need of the clients to engage with various federal agencies—including the DEA, DOJ, and HHS—by the nature of their business.” 2nd Burman Decl. ¶ 48.d; see also Pl.’s SMF ¶ 155. “The abrupt loss of so many longstanding and significant clients across a variety of business types of practice disciplines in a one-week period is exceptional and abnormal” for plaintiff, 2nd Burman Decl. ¶ 49, and the revenue loss from terminated clients alone was “significant,” id. ¶ 50, in the short time period EO 14230 was in effect—a statement readily supported by the facts.
Moreover, without an injunction, these losses are almost certain to continue. On March 7, 2025, a major client with fifteen open matters with plaintiff “informed the firm . . . that it is reconsidering its engagements with [plaintiff] unless something changes in terms of the Order’s requirements.” 2nd Burman Decl. ¶ 48.e. Another long-time client “that had increased its work five-fold over the past three years and had 30 open matters started to reconsider whether to terminate every engagement with [plaintiff].” Id. ¶ 48.g. Finally, “[ b]ecause of the uncertainty created by the Order, and even after the entry of the TRO, many clients have begun requesting frequent updates relating to the Order in order to assess whether [plaintiff] can continue to represent them,” id. ¶ 48.h., providing strong evidence that, were the current temporary injunction lifted and implementation and enforcement of EO 14230 allowed to proceed, plaintiff would continue to suffer serious, or significant, or severe revenue losses. Therefore, plaintiff additionally succeeds in showing irreparable injury based on monetary harms. Again, because sovereign immunity bars recovery of money damages, these losses could not be adequately compensated by legal remedies.
2. Balance of equities/public interest
The balance of the equities and the public interest also favor the issuance of an injunction for a simple reason: “enforcement of an unconstitutional law is always contrary to the public interest.” Karem, 960 F.3d at 668 (quoting Gordon v. Holder, 721 F.3d 638, 653 (D.C. Cir. 2013)). Plaintiff has demonstrated that EO 14230 is unconstitutional in all its action items, from findings to instructions to federal agencies, and therefore the government should have no interest in the Order’s continued enforcement. Plaintiff, meanwhile, has demonstrated the strong interests of the Firm, its employees, and clients, as well as the American legal system and the public more broadly, in issuance of an injunction to protect the independence of counsel to represent their clients vigorously and zealously, without fear of retribution from the government simply for doing the job of a lawyer.
Plaintiff, therefore, is entitled to a permanent injunction barring enforcement of any portion of EO 14230 by any Executive branch agency or entity subject to EO 14230.
IV. CONCLUSION
The U.S. Constitution affords critical protections against Executive action like that ordered in EO 14230. Government officials, including the President, may not “subject[] individuals to ‘retaliatory actions’ after the fact for having engaged in protected speech.” Hous. Cmty. Coll. Sys., 595 U.S. at 474 (quoting Nieves, 587 U.S. at 398). They may neither “use the power of the State to punish or suppress disfavored expression,” Vullo, 602 U.S. at 188, nor engage in the use of “purely personal and arbitrary power,” Yick Wo, 118 U.S. at 370. In this case, these and other foundational protections were violated by EO 14230. On that basis, this Court has found that EO 14230 violates the Constitution and is thus null and void. For the reasons explained, plaintiff is entitled to summary judgment and declaratory and permanent injunctive relief on Counts II through IX of the Amended Complaint. The government’s motion to dismiss is denied.
An order consistent with this Memorandum Opinion will be entered contemporaneously.
Date: May 2, 2025
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BERYL A. HOWELL
United States District Judge