Starting in late February, President Donald Trump began signing a series of unprecedented executive orders that imposed significant sanctions on prominent American law firms and lawyers: including Perkins Coie, WilmerHale, Paul Weiss, Covington & Burling, and Jenner & Block. The moves were in retaliation for the firms’ or lawyers’ prior legal work that the president characterized as personally harmful to him. The sweeping sanctions include suspension of security clearances, termination of government contracts, and restrictions preventing firm employees from accessing federal buildings. Notably, the executive orders specifically identify individual attorneys on the president’s so-called “enemies list.” These extraordinary actions against private lawyers conducting lawful legal representation have sparked significant constitutional concerns, and have been rightfully challenged in court as violations of the First, Fifth, and Sixth Amendments.
In an amicus brief filed on Apr. 8, 2025 in Perkins Coie LLP v. U.S. Department of Justice, 27 former senior government officials of both political parties, who served in the last seven presidential administrations, confirmed that they “have never before seen or condoned an ad hominem punitive, and retaliatory order of this kind, attacking and intimidating lawyers and a law firm on the basis of their lawful activities.” The authors of this piece helped author the brief. It expresses the shared view of amici and counsel that the president’s executive orders against Perkins Coie and other law firms were illegal not just because they violate constitutional rights, but because they offend the Constitution’s structure: the orders are “ultra vires, because they were based on no valid national security concern, issued without any colorable legal authority, and unconstitutionally interfere with the separation of powers.”
At the initial temporary restraining order (TRO) hearing for the Perkins Coie case, Judge Beryl Howell seized on this separation of powers challenge by asking whether “executive orders that . . . stand in for law . . . could be subject to a bill of attainder constitutional bar.” Executive orders are signed, written, and published presidential directives with the force of law that manage the operation of the executive branch. A bill of attainder is a law that imposes a punishment on a specific person or group of people without first going through a trial, something the Constitution explicitly forbids not once, but twice. Judge Howell’s simple question was: Are President Trump’s executive orders targeting specific law firms forbidden because they are essentially bills of attainder? The Trump administration’s lawyer responded that, “as a pure constitutional matter, . . . the bill of attainder restriction is only on Article I and not on Article II [of the Constitution], and so it doesn’t apply to the president.”
To be sure, Article I sets out the structures and powers of Congress, while Article II announces the powers of the president. But the government’s suggestion that the constitutional prohibition on attainder only applies to Article I represents a dangerous formalism that ignores separation of powers principles and contradicts clear historical practice. The original constitutional meaning of the Bill of Attainder clauses—as revealed by text, structure, and history—all show that the president cannot issue bills of attainder. Apart from their other constitutional defects, the unprecedented Trump orders targeting individuals and organizations plainly function as bills of attainder. On their face, they are prohibited by the Constitution and repugnant to its separation of powers.
A Limit on Kings Acting Alone
The Constitution’s prohibition on bills of attainder is rooted in British legal tradition. Several of the Constitution’s Framers, having been the targets of parliamentary attainders themselves, were determined to prevent this retaliatory tool from taking root in their new Republic. The Framers drew on a historical record to establish an important constitutional boundary: throughout British history Parliament and the king invariably acted in concert when issuing attainders. Even under the most tyrannical monarchs, the king never asserted unilateral authority to issue bills of attainder—a power the president now asserts for himself.
The bill of attainder first emerged in the early fourteenth century during the reign of Edward II (1307-1327). Initially, Parliament used such bills as counterweights to royal favoritism run amok. The first recognizable attainders were identified in 1308 and 1321, when Parliament intervened to exile royal favorites Piers Gaveston and later Hugh Despenser the Elder and Younger. Gaveston, whose rapid elevation and arrogance had enraged the nobility, was condemned by Parliament as “a traitor and robber of the people.” Similarly, the Despensers—father and son who had amassed enormous wealth and power through royal patronage—were exiled as “disheritors of the crown” after their influence over King Edward II became intolerable to the barons.
By Henry IV’s reign (1399-1413), the Crown had clearly come to accept the requirement that Parliament be involved in issuing bills of attainder. The King would issue a bill of attainder only on the “advice of his Lords Spiritual and Temporal in the said Parliament assembled” and “by the Authority of the said Parliament.” Even when faced with an open rebellion at Shrewsbury in 1403—treason so manifest it should have required no formal declaration—Henry IV was “particularly careful not to proceed unconstitutionally.” He therefore sought parliamentary action to declare forfeit the possessions of Henry Percy and his uncle Sir Thomas Percy.
Parliament’s role in issuing bills of attainder was again re-enforced when, in 1488, Henry VII (1485-1509) sought to pass a bill of attainder without the assent of the House of Commons. The entry in the year books of Henry VII is clear: the “opinion of the Judges, contrary to that of the king, [is] that the participation of the Commons is necessary to an Act of Attainder.” From 1489 onwards, the law was settled: even where a bill of attainder was introduced on the king’s behalf, the Executive could not issue the bill alone: “the consent of both branches of Parliament was requisite.”
The tumultuous reign of Henry VIII (1509-1547) provides the most compelling evidence of this constitutional constraint on unilateral executive action. Acts of attainder were the “favourite weapon” of Henry VIII. Yet even the mercurial king who broke with Rome, dissolved monasteries, executed two of his queens, and ruled with unprecedented personal authority conceded that he could not issue a bill of attainder without Parliament’s consent. For each of the approximately 130 attainders issued during his reign, Henry VIII observed the requirement for parliamentary approval. If Parliament’s assent was not forthcoming, Henry VIII acknowledged that he was powerless to act. So, when Henry VIII famously sought to attain a list of alleged traitors, and the House of Lords refused to proceed until Sir Thomas More was removed from the bill, it was Henry VIII that relented. This was only one of several instances in Henry VIII’s reign where Parliament made their will known and “complied with the [King’s] wishes only after adding provisos.”
The history books are littered with examples of English kings using bills of attainder to target their political enemies, cursorily blessed by the approval of more compliant parliaments. From Jack Cade of Kent (1450), to Thomas Cromwell (1540), to the Earl of Strafford (1641), many famous enemies of the Crown were condemned by attainder. But even if legislative approval merely gave the kingly act “political cover,” no king dared to dispense with it entirely. In short, for the 300 years leading up to the American Revolution, no British monarch acted without the “consent of lords and commons.” As far as we can tell, unilateral action was never even proposed.
Throughout English history, bills of attainder were invariably a joint exercise—the weapon of both king and parliament working in concert. When the Framers drafted the Constitution’s prohibitions against bills of attainder, they did so with this complete historical picture in mind. The attainder was the king’s instrument as much as Parliament’s, and the Framers understood it as an abuse of governmental power broadly conceived, not merely a legislative excess. Thus, America’s president, with powers “much inferior to” those of the British Crown, cannot claim a power even the king did not possess.
Early Professional Purges
In keeping with this history, bills of attainder became “the most expeditious way of condemning political opponents” in the colonies during the Revolutionary era. These instruments of oppression were “dreaded” for their violation of fair judicial procedure. State legislatures weaponized attainder to strip political opponents of profession, property, and liberty without trial. Each of the 13 colonies enacted attainder legislation to confiscate and sell British loyalists’ property. For example, New York’s Act of Attainder of October 22, 1779 named 59 individuals who were declared “ipso facto, convicted and attainted,” stripping them of property worth an estimated $3,600,000—an enormous sum for the time.
Early American attainders frequently targeted the legal profession. Lawyers, then as now, were penalized for upholding the principle that even the most reviled deserve representation. As Revolutionary fervor swept through the colonies, attorneys associated with loyalist interests found themselves particularly vulnerable. Everyone understood that the surest way to curtail loyalist power was to limit their access to legal representation. As Shakespeare had put it, speaking through Dick the Butcher in Henry VI, Part II, “the first thing we do is, let’s kill all the lawyers.” Accordingly, New Jersey closed its courts to Loyalist attorneys. Pennsylvania extended bills of pains and penalties to lawyers and other professionals, effectively destroying their livelihoods without judicial process. New York suspended Tory lawyers’ right to practice their profession.
Fortunately, use of bills of attainder in the new American states was short-lived. Between 1784 and 1787, as the Constitutional Convention approached, states moved away from such extreme measures. But like the historical weaponization of attainder in England, the early abuse of attainder in the states —including the targeting of the legal profession— had a lasting effect on the Framers.
John Jay, New York’s chief justice, lamented that his state was “disgraced by injustice too palpable to admit even of palliation.” Alexander Hamilton warned that if the legislature “may banish at discretion all those whom particular circumstances render obnoxious, without hearing or trial, no man can be safe, nor know when he may be the innocent victim of a prevailing faction.” Later Chief Justice John Marshall questioned whether the American people can “pretend to the enjoyment of political freedom or security when [they] are told that a man has been, by an act of Assembly, struck out of existence without being confronted with his accusers and witnesses, without the benefits of the law of the land.” In the words of one scholar: “the experience of watching loyalist property at the mercy of popular assemblies helped convince the Framers no legislature could be entrusted with such a terrible power at any time.”
Having witnessed the legal profession being subjected to punishment without trial and barred from practicing simply for representing unpopular clients, the Framers viscerally understood the dangers of circumventing judicial process. Thus, Article I, section 9 of the Constitution flatly states that “[n]o Bill of Attainder or ex post facto law shall be passed,” without distinguishing between statutes and executive orders. Article I, section 10 goes on to bar the states from “pass[ing] any Bill of Attainder.” The proscription against bills of attainder was so universally accepted that the two constitutional prohibitions “were adopted by the Constitutional Convention unanimously, and without debate.” The Framers’ decision to prohibit bills of attainder twice in the Constitution stemmed directly from their firsthand experience with these professional purges. The historical record speaks with unmistakable clarity: measures to deprive lawyers of professional standing through political fiat, rather than judicial determination, represent the very tyranny that the attainder clauses were designed to prevent.
The Article I Fallacy
In sum, the prohibition on bills of attainder reflects the Framer’s profound concern with preventing the government from “singling out disfavored persons and meting out summary punishment for past conduct.” As Judge Howell recognized during the Perkins Coie TRO hearing, when executive orders function as de facto legislation targeting specific individuals for punishment, they trigger the same constitutional concerns as legislative bills of attainder. This constitutional safeguard must therefore apply whether punishment comes through legislative act or executive order, particularly when targeting lawyers for representing unpopular clients.
The Bill of Attainder clauses in the Constitution do not just protect against governmental abuse; they safeguard the separation of powers. America’s constitutional order reserves to the judicial branch alone the power to determine guilt and impose punishment following due process. Executive orders that bypass this structure threaten not just the legal profession, but the very separation of powers that shields every citizen from the arbitrary exercise of authority the Framers so deeply feared. As the Supreme Court recently noted in SEC v. Jarkesy, the Framers took pains not to concentrate “the roles of prosecutor, judge, and jury in the hands of the Executive Branch.” But the recent Trump executive orders unconstitutionally install the president in all three roles, levying retaliatory punishment against individuals and institutions who have been neither charged with nor found guilty of any crime.
To be sure, the Constitution places the bill of attainder prohibitions in Article I, which governs legislative power. However, legislation only becomes law when signed by the president pursuant to Article I’s presentment requirement. How could a president alone have the authority to issue by executive order what would be unconstitutional if enacted with his signature and congressional approval? Unleashing executive bills of attainder would also threaten the residents of every state. Could ambitious state governors seeking political advantage, at their whim, similarly claim power to launch performative punitive orders targeting disfavored groups within their state? As the Supreme Court emphasized in Cummings v. Missouri, the “inhibition [on bills of attainder is] levelled at the thing, not the name”—“what cannot be done directly cannot be done indirectly.”
The Trump administration’s claim that the president alone can issue what would be forbidden bills of attainder if enacted by legislation represents a dangerous misreading of the Constitution’s history. The very Framers who suffered under bills of attainder never intended to grant their new president a unilateral power to punish perceived enemies that even three centuries of English kings did not possess. As amici say in closing their brief:
“When [we] served in the United States government, executive orders of this nature would have been viewed as unthinkable violations of [our] constitutional oath. Yet the repeated issuance in recent weeks of punitive executive orders against specific lawyers and law firms, with perhaps more to come, makes clear that this Administration will continue to levy such sanctions unless enjoined by the courts.”
For a court to accept that claim would disregard centuries of Anglo-American legal tradition and undermine one of our most fundamental safeguards against arbitrary power. Using formalism to validate the president’s retaliatory orders would distort the original historical meaning of the Constitution and undermine one of its most fundamental purposes: to “establish Justice, . . . and secure the Blessings of Liberty.”
Editor’s note: This piece is part of the Collection: Just Security’s Coverage of the Trump Administration’s Executive Actions