United States v. Heppner – AI, Privilege, and Inequality in the Digital Age
Top 10 Opinions with Citations | Complete 115-Justice Summary Table
The Technology Blind Spot
On the morning of February 10, 2026, Bradley Heppner sat at the defense table in the Southern District of New York. On a seized laptop, federal agents had found 31 documents he had written himself using Anthropic’s Claude. He had typed his defense strategy into the tool. He had mapped his legal exposure. He had worked through the facts of a $150 million securities fraud investigation the way a careful defendant prepares for a consequential conversation with his lawyers. Then he had sent those documents to Quinn Emanuel Urquhart & Sullivan. He believed they were privileged.
Judge Jed Rakoff disposed of both privilege claims from the bench in nine words: ‘I’m not seeing remotely any basis for any claim of attorney-client privilege.’ The written opinion followed eight days later, on February 17, 2026. United States v. Heppner, No. 25-cr-00503-JSR (S.D.N.Y. Feb. 17, 2026). The doctrine Rakoff applied was not new. Anthropic’s consumer terms disclosed data collection, model training rights, and the right to share user inputs with governmental regulatory authorities. Communications lacking confidentiality at creation cannot acquire it by transmission to counsel. The AI element was a fact. It was not a variable.
What Rakoff’s opinion could not do, within the constraints of a single criminal case, was ask what the fullness of American legal thought would say about the structural conditions that produced Heppner’s loss. Not just whether the doctrine was correctly applied. Also: whether the doctrine is adequate for what technology has made possible, who bears the cost when it is not, and what no judge can fix from the bench.
This document examines how the justices who shaped American law would have ruled if they had heard the argument. Every one of them would have affirmed Rakoff’s result. Two would have written partial dissents on the work product element only. What follows are the ten opinions most analytically relevant to the questions Heppner raises, supported by the controlling authority each justice would have invoked, followed by a complete summary of all 115 justices.
#1 — Lewis F. Powell Jr.
Associate Justice, 1972-1987 | Burger Court
| AFFIRM — Most Doctrinally Important |
Powell wrote the opinion Heppner’s defense invoked and is the only justice required to grapple with his own prior work.
Controlling Authority:
Upjohn Co. v. United States, 449 U.S. 383 (1981). Powell wrote the unanimous opinion extending privilege to corporate employees throughout the hierarchy, rejecting the narrow control group test. The animating principle: ‘An uncertain privilege, or one which purports to be certain but results in widely varying applications by the courts, is little better than no privilege at all.’ Id. at 393. The extension rested on two structural requirements — the employees owed duties to the corporation, those duties were enforceable — not merely on the functional utility of the communication to the representation.
United States v. Kovel, 296 F.2d 918 (2d Cir. 1961). Judge Friendly extended privilege to accountants assisting attorneys, but only because attorneys engaged and directed those accountants. The third party owed confidentiality obligations through the attorney’s professional responsibility framework. Id. at 921-22.
The Opinion Powell Would Write:
‘We do not retreat from Upjohn’s functional purpose analysis. We apply it. The defense argues that Claude served a functional purpose within the representation — the same way corporate employees in Upjohn provided information attorneys needed. That argument misreads Upjohn. The extension in Upjohn rested on the human relationship and the enforceable confidentiality duty, not on functional utility alone. Upjohn, 449 U.S. at 395. Claude has no duty. Anthropic has no confidentiality obligation to Heppner. The terms it published expressly disclaimed one. A tool that has contractually eliminated confidentiality cannot be analogized to a Kovel third party regardless of the functional similarity in the client’s mind. Kovel, 296 F.2d at 921. Heppner’s expectation was not reasonable. His privilege was not uncertain. It was absent.’ Upjohn, 449 U.S. at 393, applied.
#2 — John G. Roberts Jr.
Chief Justice, 2005-Present | Roberts Court
| AFFIRM — Most Consequential Opinion |
Roberts’s digital-age jurisprudence most directly frames what Heppner decides and — more importantly — what it does not.
Controlling Authority:
Riley v. California, 573 U.S. 373, 393, 396 (2014). Roberts wrote the unanimous opinion requiring a warrant before searching a cell phone incident to arrest. Cell phones hold ‘the privacies of life.’ Id. at 403. The physical fact of the arrest does not transform the digital content of the phone. The physical/digital distinction is structural, not circumstantial.
Carpenter v. United States, 585 U.S. 296, 310 (2018). Roberts wrote the 5-4 opinion requiring a warrant for historical cell site location information. He acknowledged the third-party doctrine but held it required reconsideration for digital records: ‘The fact that the Government can compel a third party to disclose information does not mean the person sharing that information has no privacy interest in it.’ Id. The voluntary disclosure rationale operates with reduced force when third-party routing is a structural condition of communication rather than a deliberate choice.
The Opinion Roberts Would Write:
Roberts would affirm on the specific facts and write the most consequential separate analysis. Heppner voluntarily chose Claude. The government did not compel that choice. Heppner accepted non-confidentiality terms that expressly disclosed government access rights. Riley and Carpenter do not override voluntary disclosure of that kind. Heppner falls on the voluntary side of the line Carpenter drew. 585 U.S. at 310.
‘We note, however, that the question decided today is narrow. There is a distinction between a defendant who voluntarily accepts a ToS disclaiming confidentiality and an attorney who relies on enterprise-tier contractual protections while the government compels backend surveillance architecture that defeats those protections without notice to the client. Carpenter held that the third-party doctrine requires reconsideration when digital architecture makes third-party routing a structural condition of communication, not a deliberate choice. Id. Whether FISA Section 702 collection authority, exercised against platforms that have contractually promised confidentiality to enterprise clients, presents that question is not decided today. It is not outside the framework Riley and Carpenter established.’
#3 — Louis D. Brandeis
Associate Justice, 1916-1939 | White, Taft, and Hughes Courts
| AFFIRM — Structural Warning |
Brandeis understood, better than any justice before or since, that legal fictions dressed in the language of voluntary choice conceal structural realities that doctrine cannot pretend away indefinitely.
Controlling Authority:
Olmstead v. United States, 277 U.S. 438, 471-78 (1928) (Brandeis, J., dissenting). The Court held 5-4 that wiretapping a private telephone did not constitute a Fourth Amendment search because no physical trespass occurred. Brandeis dissented alone: ‘They conferred, as against the Government, the right to be let alone — the most comprehensive of rights, and the right most valued by civilized men.’ Id. at 478. The Court adopted his position thirty-nine years later. Katz v. United States, 389 U.S. 347 (1967).
Brandeis & Warren, ‘The Right to Privacy,’ 4 Harvard Law Review 193 (1890). The foundational text of American privacy law. Written sixteen years before Brandeis joined the Court.
Brandeis, Other People’s Money and How the Bankers Use It (1914). Brandeis’s analysis of how financial intermediaries exploit asymmetric information. His framework: wherever power asymmetries allow one party to impose terms on another under conditions not genuinely voluntary, the law should examine what ‘voluntary’ actually means.
The Opinion Brandeis Would Write:
Brandeis would affirm on the narrow question without difficulty — Heppner accepted the terms; the terms controlled — and then write the opinion no other justice would write. Anthropic’s consumer terms reserve the right to disclose user inputs to ‘governmental regulatory authorities.’ That is not hypothetical. It is the architecture of the waiver. A legal system that calls government access to privileged communications ‘voluntary’ because the client accepted a standard-form contract he could not negotiate has redefined ‘voluntary’ in the way the author of Other People’s Money recognized immediately: when one party holds all the drafting power and the other party holds only the option to accept or forgo the service, formal consent is not the same as genuine choice.
‘This case involves a voluntary disclosure and the result follows from that fact. The case where the government compels the conditions making disclosure functionally inevitable remains to be decided. That case will come. When it does, the word voluntary will require examination this opinion cannot supply. The right to be let alone is the most comprehensive of rights. It does not become less comprehensive because the mechanism of its defeat is a ToS rather than a wiretap.’ Olmstead, 277 U.S. at 478 (dissenting).
#4 — Robert H. Jackson
Associate Justice, 1941-1954 | Stone and Vinson Courts
| AFFIRM — Most Analytically Durable Framework |
Jackson’s Youngstown concurrence is the most-cited framework for organizing ambiguous authority questions. It translates to AI privilege doctrine with a precision that suggests Jackson would have recognized the structural parallel immediately.
Controlling Authority:
Youngstown Sheet & Tube Co. v. Sawyer, 343 U.S. 579, 635-38 (1952) (Jackson, J., concurring). Jackson organized presidential power into three zones: Zone 1 — acting with express or implied congressional authorization, maximum authority; Zone 2 — acting without congressional guidance, the zone of twilight; Zone 3 — acting against congressional authorization, lowest ebb. Id. The framework organized ambiguous authority questions that the majority’s direct holding could not reach and became the governing structure for every subsequent separation-of-powers case.
West Virginia Board of Education v. Barnette, 319 U.S. 624, 642 (1943). ‘If there is any fixed star in our constitutional constellation, it is that no official, high or petty, can prescribe what shall be orthodox.’ Id. Jackson’s model: establish structural principle first, apply it to specific facts second. Build the framework to outlast the case that generated it.
Brown v. Allen, 344 U.S. 443, 540 (1953) (Jackson, J., concurring). ‘We are not final because we are infallible, but we are infallible only because we are final.’ Institutional authority requires structural consistency. Doctrine must be organized so courts can apply it reliably, not because courts are always right, but because consistency is itself a component of legitimacy.
The Opinion Jackson Would Write:
Jackson would affirm Heppner and write the Zone framework for AI privilege that every subsequent court would use. Zone 1: The attorney directs AI use within the representation, controls the architecture through enterprise-tier confidentiality protections, and the AI operates as the functional equivalent of a Kovel third party under attorney direction. Privilege holds. Upjohn, 449 U.S. at 395; Kovel, 296 F.2d at 922. Zone 2: The client uses AI without attorney direction, the terms contain no express non-confidentiality disclosure, and the communication could be characterized as preparatory to the representation. Zone of twilight. Fact-intensive. No bright line. Zone 3: The client uses AI on express non-confidentiality terms, without attorney direction, and the AI actively disclaims providing legal advice. Heppner. Zone 3.
Heppner is Zone 3. He prepared 31 documents on a platform that told him his inputs were not confidential, without attorney direction, using a tool that disclaimed giving legal advice. Each element places him squarely in the zone where privilege is at its lowest ebb. ‘We affirm. We do so not because this case is difficult, but because the framework it requires is not. Zone 3 is Zone 3. The question courts will face is Zone 2. We leave them a structure.’ Youngstown, 343 U.S. at 635-38, applied.
#5 — Potter Stewart
Associate Justice, 1958-1981 | Warren and Burger Courts
| AFFIRM — His Own Standard Disposes of the Case |
Stewart wrote the test whose language most cleanly and directly disposes of Heppner’s privilege claim — and would have recognized the irony that the standard he created to protect individuals from government surveillance now applies against a defendant who chose the non-confidential instrument himself.
Controlling Authority:
Katz v. United States, 389 U.S. 347, 351-52 (1967). Stewart wrote the majority overruling Olmstead: ‘What a person knowingly exposes to the public, even in his own home or office, is not a subject of Fourth Amendment protection. But what he seeks to preserve as private, even in an area accessible to the public, may be constitutionally protected.’ Id. Harlan’s concurrence formalized the reasonable expectation of privacy test. Id. at 360-61 (Harlan, J., concurring).
Berger v. New York, 388 U.S. 41 (1967). Stewart joined the majority striking down New York’s wiretapping statute, establishing procedural requirements for electronic surveillance that prefigured digital communications doctrine.
The Opinion Stewart Would Write:
Stewart would apply the Katz framework as doctrinal analogy, not constitutional holding — privilege analysis is common law, not Fourth Amendment. But the structure is identical. Heppner ‘knowingly exposed’ his communications to a commercial platform whose terms he accepted. He did not ‘seek to preserve’ those communications as private. He handed them to a service that told him, in terms he accepted, that they were not private. Katz, 389 U.S. at 351. He then transmitted them to counsel. The transmission added nothing. What lacked confidentiality at creation cannot acquire it by subsequent routing.
Stewart would note the irony without softening it: Katz adopted Brandeis’s Olmstead dissent thirty-nine years after Brandeis wrote it. Brandeis dissented in Olmstead to protect individuals from government surveillance. The standard that dissent produced now governs when the individual chose the non-confidential instrument himself. Both results follow from the same principle. What matters is what the disclosing party did with the confidentiality of the communication. Heppner chose. The Katz framework enforces that choice.
#6 — Oliver Wendell Holmes Jr.
Associate Justice, 1902-1932 | Fuller, White, and Taft Courts
| AFFIRM — Shortest Opinion, Harshest on Work Product |
Holmes wrote the most aphoristic prose in Court history. He would write the shortest opinion in this analysis. His contribution is not the length of the reasoning but the precision of the demolition — and his treatment of the work product claim would be the harshest of any justice here.
Controlling Authority:
The Common Law 1 (1881). ‘The life of the law has not been logic; it has been experience.’ The most cited sentence in American jurisprudence. Holmes would apply his own aphorism selectively: it describes how law develops, not how it applies once developed. The common law experience on third-party disclosure is settled. The novelty of the instrument adds nothing.
Olmstead v. United States, 277 U.S. 438, 469-70 (1928) (Holmes, J., dissenting). Holmes wrote separately, calling wiretapping ‘dirty business’ and arguing the government should not profit from conduct that would be criminal if done by a private party. Id. at 470. His narrower ground: governmental ethics, not constitutional privacy. His analytical method: state the principle, state the application, stop.
Hickman v. Taylor, 329 U.S. 495, 510-11 (1947). The foundational work product case. The doctrine exists to protect ‘the mental impressions, conclusions, opinions, or legal theories’ of attorneys in preparation for litigation. Id. at 511. Lawyer mental processes. Not client mental processes. Not client preparation for a conversation with a lawyer who has not yet given any direction. Lawyer mental processes.
The Opinion Holmes Would Write:
Two paragraphs. On privilege: the privilege requires confidentiality. The Common Law, at 1. The experience of the common law on third-party disclosure is settled. Anthropic’s terms disclosed non-confidentiality. Heppner accepted them. The privilege element fails. The novelty of the disclosing instrument adds nothing to an analysis whose inputs are not novel.
On work product: the doctrine protects lawyers’ mental processes. Hickman, 329 U.S. at 510-11. Documents written by a client, without a lawyer in the room, using a tool that disclaims giving legal advice, are not lawyers’ mental processes. They are not anyone’s lawyers’ mental processes. Extending work product to cover them is not extension. It is redefinition. A doctrine extended beyond its stated purpose does not acquire new content. It loses its old content. The work product claim is frivolous. Holmes would not use a gentler word.
#7 — Thurgood Marshall
Associate Justice, 1967-1991 | Warren, Burger, and Rehnquist Courts
| AFFIRM — Structural Equality + Equal Protection Call |
Marshall argued Brown v. Board of Education before joining the Court. His opinions consistently supplied the factual record the majority’s doctrinal analysis omitted. On Heppner, the omitted record is the one that determines who the ruling actually protects.
Controlling Authority:
Brown v. Board of Education, 347 U.S. 483, 495 (1954) (argued for NAACP by Marshall). ‘Separate educational facilities are inherently unequal.’ Id. Marshall’s oral argument in Brown established that formal legal equality can mask structural inequality. A doctrine that applies the same rule to parties whose circumstances are not equal without examining the structural conditions producing that inequality is not neutral. Its results are not neutral.
Regents of the University of California v. Bakke, 438 U.S. 265, 387-88 (1978) (Marshall, J., concurring in part). ‘It is because of a legacy of unequal treatment that we now must permit the institutions of this society to give consideration to race in making decisions about who will hold the positions of influence, affluence, and prestige in America.’ Id. Marshall’s method: ground the abstract doctrine in the specific factual record that gives it meaning.
Gideon v. Wainwright, 372 U.S. 335, 344-45 (1963). The constitutional right to counsel for defendants who cannot afford an attorney. Id. The right is operationally dependent on the tools that make effective representation possible. Marshall would ask what Gideon’s guarantee means when the tools that preserve privilege in AI-assisted legal preparation are available only to defendants who can pay for enterprise licenses.
The Opinion Marshall Would Write:
Marshall would affirm and write about what Rakoff’s opinion never addresses: who bears the cost of the ruling in practice. Enterprise tier: confidentiality protected. Consumer tier: privilege destroyed. The defendant with Quinn Emanuel gets enterprise AI access and experienced counsel to explain which tier applies. The defendant who cannot afford Quinn Emanuel, who prepares for the public defender consultation on free consumer AI, loses privilege before the representation begins.
‘If AI-assisted legal preparation has become necessary for criminal defense, then equipping public defender offices with enterprise AI access is not a preference. It is an equal protection obligation. Gideon, 372 U.S. at 344, held that the Constitution requires counsel for defendants who cannot afford it. A constitutional right to counsel that is undermined in practice by resource disparities in the tools that make counsel effective is not a right. It is a procedure. This Court affirms the doctrine. Congress must address the disparity the doctrine reveals.’ Brown, 347 U.S. at 495, applied.
#8 — Antonin Scalia
Associate Justice, 1986-2016 | Rehnquist and Roberts Courts
| AFFIRM — Most Quotable Concurrence |
Scalia was the most combative and most quotable prose stylist on the modern Court. He would write the concurrence that demolished the defense’s best argument in a way that would be cited in law review articles about AI privilege for a generation.
Controlling Authority:
Morrison v. Olson, 487 U.S. 654, 699 (1988) (Scalia, J., dissenting). Scalia dissented alone: ‘Frequently an issue of this sort will come before the Court clad, so to speak, in sheep’s clothing: the potential of the asserted principle to effect important change in the equilibrium of power is not immediately evident… But this wolf comes as a wolf.’ Id. His method: identify the doctrinal move that appears narrow but isn’t, and name it.
King v. Burwell, 576 U.S. 473, 506 (2015) (Scalia, J., dissenting). ‘Words no longer have meaning if an Exchange that is not established by a State is established by the State… Under all the usual rules of interpretation, in short, the Government should lose this case.’ Id. On courts that bend doctrine to reach preferred outcomes: the method is as dangerous as the result.
Hickman v. Taylor, 329 U.S. 495, 510-11 (1947). Work product protects lawyers’ mental processes. Id. That is what the doctrine means. That is all it means.
The Opinion Scalia Would Write:
‘The novelty of the technology creates an appealing emotional argument. It creates no doctrinal argument. The privilege framework requires confidentiality. The document governing the communication informed the communicant that confidentiality did not exist. Counsel’s post-hoc characterization of the AI interaction as functionally equivalent to note-taking does not transform a disclosed communication into a confidential one. Courts do not apply functional equivalence doctrine as a general escape valve from privilege requirements. If they did, the requirements would cease to exist.’ Morrison, 487 U.S. at 699. ‘This wolf comes as a wolf.’ Id.
On work product: extending the doctrine to cover a client’s unilateral, unguided preparation is not extension. It is abandonment. Work product protects lawyer mental processes. Hickman, 329 U.S. at 510-11. That is what the doctrine means. That is all it means. Doctrines extended beyond their purpose do not acquire new content. They lose their old content. The Court would do well to remember that the next time a sympathetic set of facts invites doctrinal expansion that the doctrine’s text does not authorize.
#9 — William J. Brennan Jr.
Associate Justice, 1956-1990 | Warren, Burger, and Rehnquist Courts
| AFFIRM on privilege — PARTIAL DISSENT on work product |
Brennan is the only justice in this analysis to write a genuine partial dissent. He would affirm attorney-client privilege and challenge the work product holding — not as a close doctrinal question, but as a structural one with consequences for defendants who cannot yet afford counsel.
Controlling Authority:
New York Times Co. v. Sullivan, 376 U.S. 254 (1964). Brennan’s unanimous opinion built the constitutional doctrine from principle outward: the First Amendment requires breathing space for robust public debate; strict liability chills that speech; the actual malice standard balances protection for good-faith error. His method was always to identify the structural purpose of a doctrine before determining what specific facts required of it.
Hickman v. Taylor, 329 U.S. 495, 510-11 (1947). The work product doctrine exists to protect the adversarial system by ensuring lawyers’ strategic thinking is not discoverable. Id. The question Brennan would raise: whether that animating principle — protecting mental preparation for litigation — extends to a defendant who is preparing for litigation without an attorney who has yet given any direction.
Gideon v. Wainwright, 372 U.S. 335 (1963). The constitutional right to counsel for defendants who cannot afford an attorney. Brennan would ask: if preparation without counsel produces documents without work product protection, and if representation before arrest is the condition that would have changed the analysis, has the doctrine effectively penalized defendants for their own financial constraints?
The Opinion Brennan Would Write:
Brennan would affirm on attorney-client privilege. Voluntary disclosure to a non-confidential commercial platform is not a close question under any analytical framework he applied in thirty-four years on the Court. On work product, he would write separately and dissent in part.
‘Heppner prepared these documents specifically because he was a criminal target who anticipated prosecution. That is precisely the scenario the work product doctrine was designed to protect. Hickman, 329 U.S. at 510. The defense conceded the documents were prepared without attorney direction, and current doctrine treats that concession as fatal. I would not. A defendant who prepares documents in genuine anticipation of criminal defense should receive some protection for his mental processes even without direct attorney direction, because the alternative penalizes defendants for preparing their own defense before they can afford or retain counsel. Gideon, 372 U.S. at 344, guaranteed the right to counsel. It did not guarantee that preparation before counsel is retained would be protected. That gap is real. I would close it.’
Brennan would not carry the Court. His partial dissent would be the opinion practitioners in public defense work cited first, because it names the operational reality Rakoff’s clean doctrinal analysis produces: preparation without counsel destroys privilege; preparation with consumer AI destroys privilege; the defendant who does both compounds a loss neither doctrine was designed specifically to create.
#10 — Ketanji Brown Jackson
Associate Justice, 2022-Present | Roberts Court
| AFFIRM — Structural Equality + Legislative Call |
Jackson brings the historical analysis Harlan I identified in 1896 and Marshall advanced in 1967 into the specific vocabulary of 2026. Her contribution is precision: she names the resource asymmetry, its cause, and its remedy specifically enough that the analysis might reach a congressional record.
Controlling Authority:
Allen v. Milligan, 599 U.S. 1, 69-70 (2023) (Jackson, J., concurring). Jackson’s concurrence deployed detailed historical analysis of Reconstruction-era legislation to establish that the Fourteenth and Fifteenth Amendments were designed to produce a multiracial democracy, not merely eliminate formal legal discrimination. Id. Her method: supply the historical record the majority’s doctrinal analysis requires but does not always explicitly engage.
Gideon v. Wainwright, 372 U.S. 335, 344-45 (1963). The right to counsel is a constitutional guarantee for defendants who cannot afford an attorney. Id. Jackson would build her argument on Gideon: the guarantee is operationally dependent on the tools that make effective representation possible. If AI-assisted legal preparation has become functionally necessary for effective criminal defense, and if the tools that preserve privilege in that preparation are available only to defendants who can pay for enterprise licenses, Gideon’s guarantee requires examination.
Loper Bright Enterprises v. Raimondo, 603 U.S. ___ (2024) (Jackson, J., dissenting). Jackson dissented from the elimination of Chevron deference, arguing the administrative expertise rationale served a structural function the replacement framework did not capture. Id. Her dissents in institutional structure cases show a justice who takes seriously the consequences of doctrinal shifts for the institutions that must implement them — including chronically underfunded public defender offices.
The Opinion Jackson Would Write:
Jackson would affirm and write the opinion most likely to reach a congressional record. Enterprise tier: confidentiality protected. Consumer tier: privilege destroyed. The line between them is a subscription fee. Chronic underfunding of public defender offices creates conditions where privilege-protected AI-assisted legal preparation is available to defendants with resources and unavailable to defendants without. Gideon, 372 U.S. at 344.
‘Courts cannot correct the resource asymmetry this ruling reveals. The privilege doctrine the Court applies today is formally neutral. Its practical operation is not. Allen, 599 U.S. at 69. Congress and state legislatures have funded public defender offices at levels that make effective representation structurally difficult before AI introduced a new resource variable. AI has added a new tier to an inequality that existed before it. The remedy is the same Gideon required at the level of counsel: public funding for the tools that make the constitutional right operational. The defendant with Quinn Emanuel will not face this problem again. His lawyers will now give the briefing Heppner needed before this case began. The defendant without Quinn Emanuel, preparing on consumer AI because the enterprise tier costs money his public defender’s office does not have, has no equivalent protection. That is not this Court’s failure to correct. It is Congress’s failure to prevent.’
Summary Table: All 115 Justices
Every justice affirms the attorney-client privilege result. Douglas and Brennan write partial dissents on work product only. Column 4 = privilege ruling. Column 5 = work product ruling.
| Justice | Tenure | Court Era | Privilege | Work Product | Key Contribution |
| John Jay | 1789-1795 | Founding | AFFIRM | AFFIRM | Institutional clarity; mechanism irrelevant |
| John Rutledge | 1790-1795 | Founding | AFFIRM | AFFIRM | Plain facts dispose of the case |
| William Cushing | 1790-1810 | Founding | AFFIRM | AFFIRM | Methodical application of settled rule |
| James Wilson | 1789-1798 | Founding | AFFIRM | AFFIRM | Privilege’s purpose defeated by prior disclosure |
| John Blair Jr. | 1790-1796 | Founding | AFFIRM | AFFIRM | Joins majority; no separate writing |
| James Iredell | 1790-1799 | Founding | AFFIRM | AFFIRM | Common law third-party doctrine governs |
| Thomas Johnson | 1792-1793 | Founding | AFFIRM | AFFIRM | Brief tenure; would affirm |
| William Paterson | 1793-1806 | Founding | AFFIRM | AFFIRM | Contract terms accepted; contract terms control |
| Samuel Chase | 1796-1811 | Founding | AFFIRM | AFFIRM | Combative; resists functional equivalence exception |
| Oliver Ellsworth | 1796-1800 | Founding | AFFIRM | AFFIRM | Clear rule required; functional equiv. destroys it |
| Bushrod Washington | 1799-1829 | Marshall | AFFIRM | AFFIRM | Joins Marshall; no separate writing |
| Alfred Moore | 1800-1804 | Marshall | AFFIRM | AFFIRM | One opinion on record; would affirm |
| John Marshall | 1801-1835 | Marshall | AFFIRM | AFFIRM | Mechanism irrelevant; doctrine stable and clear |
| William Johnson | 1804-1834 | Marshall | AFFIRM | AFFIRM | First justice to note resource implications |
| H.B. Livingston | 1807-1823 | Marshall | AFFIRM | AFFIRM | Commercial terms govern; contract controls |
| Thomas Todd | 1807-1826 | Marshall | AFFIRM | AFFIRM | Follows Marshall; no separate writing |
| Joseph Story | 1811-1845 | Marshall | AFFIRM | AFFIRM | Treatise-length opinion; common law origins |
| Gabriel Duvall | 1811-1835 | Marshall | AFFIRM | AFFIRM | Rarely wrote; joins majority |
| Smith Thompson | 1823-1843 | Marshall | AFFIRM | AFFIRM | NY common law privilege doctrine supports result |
| Roger B. Taney | 1836-1864 | Taney | AFFIRM | AFFIRM | Contract formalism; Dred Scott context noted |
| John McLean | 1830-1861 | Taney | AFFIRM | AFFIRM | Raises structural access question separately |
| Henry Baldwin | 1830-1844 | Taney | AFFIRM | AFFIRM | AI = cloud storage on confidentiality analysis |
| James M. Wayne | 1835-1867 | Taney | AFFIRM | AFFIRM | Doctrine applies consistently regardless of novelty |
| Philip Barbour | 1836-1841 | Taney | AFFIRM | AFFIRM | Brief tenure; follows established doctrine |
| John Catron | 1837-1865 | Taney | AFFIRM | AFFIRM | Commercial entity = non-privileged; result clear |
| John McKinley | 1838-1852 | Taney | AFFIRM | AFFIRM | Limited record; would affirm |
| Peter V. Daniel | 1842-1860 | Taney | AFFIRM | AFFIRM | Affirms; warns on corporate power over information |
| Samuel Nelson | 1845-1872 | Taney/Chase | AFFIRM | AFFIRM | Reliable centrist; follows established doctrine |
| Levi Woodbury | 1845-1851 | Taney | AFFIRM | AFFIRM | Brief tenure; would affirm |
| Robert C. Grier | 1846-1870 | Taney/Chase | AFFIRM | AFFIRM | Plain facts; impatient with extended analysis |
| Benjamin R. Curtis | 1851-1857 | Taney | AFFIRM | AFFIRM | Strongest consent opinion of the era |
| John A. Campbell | 1853-1861 | Taney | AFFIRM | AFFIRM | Resigned to Confederacy; limited post-record |
| Nathan Clifford | 1858-1881 | Multiple | AFFIRM | AFFIRM | Correct result reached on page 47 |
| Noah H. Swayne | 1862-1881 | Chase/Waite | AFFIRM | AFFIRM | Lincoln appointee; solid; no distinctive contribution |
| Samuel F. Miller | 1862-1890 | Chase/Waite | AFFIRM | AFFIRM | Commercial AI as institutional threat to privilege |
| David Davis | 1862-1877 | Chase/Waite | AFFIRM | AFFIRM | Notes govt-compelled access question obliquely |
| Stephen J. Field | 1863-1897 | Multiple | AFFIRM | AFFIRM | Long separate opinion on adhesion contracts |
| Salmon P. Chase | 1864-1873 | Chase | AFFIRM | AFFIRM | Clean procedural opinion; no doctrinal innovation |
| William Strong | 1870-1880 | Waite | AFFIRM | AFFIRM | Follows established doctrine |
| Joseph P. Bradley | 1870-1892 | Waite | AFFIRM | AFFIRM | Contract terms govern confidentiality status |
| Ward Hunt | 1873-1882 | Waite | AFFIRM | AFFIRM | Would affirm |
| Morrison R. Waite | 1874-1888 | Waite | AFFIRM | AFFIRM | Workmanlike opinion; no notable contribution |
| John M. Harlan I | 1877-1911 | Multiple | AFFIRM | AFFIRM | Enterprise/consumer divide = class privilege; prescient |
| William B. Woods | 1881-1887 | Waite | AFFIRM | AFFIRM | Brief tenure; follows established doctrine |
| Stanley Matthews | 1881-1889 | Waite | AFFIRM | AFFIRM | Facially neutral doctrine; unequal practical effect |
| Horace Gray | 1882-1902 | Waite/Fuller | AFFIRM | AFFIRM | Historical survey of privilege’s confidentiality req. |
| Samuel Blatchford | 1882-1893 | Waite/Fuller | AFFIRM | AFFIRM | Commercial agreements enforced as written |
| L.Q.C. Lamar | 1888-1893 | Fuller | AFFIRM | AFFIRM | Brief tenure; would affirm |
| Melville W. Fuller | 1888-1910 | Fuller | AFFIRM | AFFIRM | Formalist; rules are rules; applies them |
| David J. Brewer | 1890-1910 | Fuller | AFFIRM | AFFIRM | Commercial novelty doesn’t transform the transaction |
| Henry B. Brown | 1891-1906 | Fuller | AFFIRM | AFFIRM | Completeness only (Plessy author) |
| George Shiras Jr. | 1892-1903 | Fuller | AFFIRM | AFFIRM | Would affirm |
| Howell E. Jackson | 1893-1895 | Fuller | AFFIRM | AFFIRM | Brief tenure; would affirm |
| Edward D. White | 1894-1921 | Multiple | AFFIRM | AFFIRM | Rule of reason analog; terms unreasonably disclaim priv. |
| Rufus W. Peckham | 1896-1909 | Fuller | AFFIRM | AFFIRM | Freedom of contract cuts both ways; Heppner chose |
| Joseph McKenna | 1898-1925 | Multiple | AFFIRM | AFFIRM | Long tenure; unremarkable; would affirm |
| Oliver Wendell Holmes | 1902-1932 | Multiple | AFFIRM | AFFIRM (strict) | Novelty adds nothing; 2-paragraph opinion; work product = lawyers only |
| William R. Day | 1903-1922 | Fuller/White | AFFIRM | AFFIRM | Exclusionary rule structural parallel |
| William H. Moody | 1906-1910 | Fuller | AFFIRM | AFFIRM | Brief tenure; would affirm |
| Horace H. Lurton | 1910-1914 | White | AFFIRM | AFFIRM | Brief tenure; would affirm |
| Charles Evans Hughes | 1910-1941 | Multiple | AFFIRM | AFFIRM | Courts apply; Congress expands; institutional division |
| Willis Van Devanter | 1911-1937 | Multiple | AFFIRM | AFFIRM | Strict formalist; elements fail; result follows |
| Joseph R. Lamar | 1911-1916 | White | AFFIRM | AFFIRM | Brief tenure; would affirm |
| Mahlon Pitney | 1912-1922 | White | AFFIRM | AFFIRM | Contract terms control; would affirm |
| James C. McReynolds | 1914-1941 | Multiple | AFFIRM | AFFIRM | Completeness only (antisemitic; not quotable) |
| Louis D. Brandeis | 1916-1939 | Multiple | AFFIRM | AFFIRM | ‘Voluntary’ in adhesion ToS is a legal fiction |
| John H. Clarke | 1916-1922 | White | AFFIRM | AFFIRM | Resigned to pursue world peace; would affirm |
| George Sutherland | 1922-1938 | Taft/Hughes | AFFIRM | AFFIRM | Govt cannot benefit from commercial conditions it designs |
| Pierce Butler | 1923-1939 | Taft/Hughes | AFFIRM | AFFIRM | Four Horsemen formalist; strict application |
| Edward T. Sanford | 1923-1930 | Taft | AFFIRM | AFFIRM | Would affirm |
| Harlan Fiske Stone | 1925-1946 | Multiple | AFFIRM | AFFIRM | Formally neutral; practically unequal protection |
| Owen J. Roberts | 1930-1945 | Hughes/Stone | AFFIRM | AFFIRM | Facts too clear for doctrinal evolution in defense favor |
| Benjamin N. Cardozo | 1932-1938 | Hughes | AFFIRM | AFFIRM | Functional equiv. destroys privilege’s purpose; Upjohn anticipated |
| Hugo L. Black | 1937-1971 | Multiple | AFFIRM | AFFIRM (strictest) | Textualist absolutist; checklist fails; work product = lawyers only |
| Stanley F. Reed | 1938-1957 | Multiple | AFFIRM | AFFIRM | Reliable centrist; joins majority; no notable writing |
| Felix Frankfurter | 1939-1962 | Multiple | AFFIRM | AFFIRM | Narrowest opinion; leave structural questions to legislatures |
| William O. Douglas | 1939-1975 | Multiple | AFFIRM | PARTIAL DISSENT | Sixth Amendment structural impairment; surveillance warning |
| Frank Murphy | 1940-1949 | Multiple | AFFIRM | AFFIRM | System morally compromised when govt benefits by design |
| James F. Byrnes | 1941-1942 | Stone | AFFIRM | AFFIRM | Resigned after one year; limited record |
| Robert H. Jackson | 1941-1954 | Multiple | AFFIRM | AFFIRM | Three-zone Youngstown framework; most analytically durable |
| Wiley B. Rutledge | 1943-1949 | Multiple | AFFIRM | AFFIRM | Neutrality must be genuine; doctrine applies to defendants |
| Harold H. Burton | 1945-1958 | Multiple | AFFIRM | AFFIRM | Centrist; joins majority; no notable writing |
| Fred M. Vinson | 1946-1953 | Vinson | AFFIRM | AFFIRM | Administrative; workmanlike; weak Chief |
| Tom C. Clark | 1949-1967 | Multiple | AFFIRM | AFFIRM | Mapp exclusionary rule parallel; structural concern |
| Sherman Minton | 1949-1956 | Vinson/Warren | AFFIRM | AFFIRM | Conservative deference; would affirm |
| Earl Warren | 1953-1969 | Warren | AFFIRM | AFFIRM | Rule 1.1 attorney duty; Quinn Emanuel briefing failure |
| John M. Harlan II | 1955-1971 | Warren/Burger | AFFIRM | AFFIRM | Federalism; courts apply settled doctrine; Congress modifies |
| William J. Brennan | 1956-1990 | Multiple | AFFIRM | PARTIAL DISSENT | Work product for anticipation-of-prosecution defendants |
| Charles E. Whittaker | 1957-1962 | Warren | AFFIRM | AFFIRM | Resigned due to illness; limited record |
| Potter Stewart | 1958-1981 | Warren/Burger | AFFIRM | AFFIRM | His own Katz standard (‘knowingly exposes’) disposes of case |
| Byron R. White | 1962-1993 | Multiple | AFFIRM | AFFIRM | Terse; the answer is the answer |
| Arthur J. Goldberg | 1962-1965 | Warren | AFFIRM | AFFIRM | Ninth Amendment; unenumerated right to effective preparation |
| Abe Fortas | 1965-1969 | Warren | AFFIRM | AFFIRM | Attorney obligation; resigned under ethics cloud |
| Thurgood Marshall | 1967-1991 | Multiple | AFFIRM | AFFIRM | Enterprise/consumer divide = equal protection obligation |
| Warren E. Burger | 1969-1986 | Burger | AFFIRM | AFFIRM | Bar association guidance needed; workmanlike opinion |
| Harry A. Blackmun | 1970-1994 | Burger/Rehnquist | AFFIRM | AFFIRM | Doctrine has not kept pace; courts cannot close the gap |
| Lewis F. Powell Jr. | 1972-1987 | Burger | AFFIRM | AFFIRM | Wrote Upjohn; most doctrinally important; Kovel analogy fails |
| William H. Rehnquist | 1972-2005 | Burger/Rehnquist | AFFIRM | AFFIRM | Give the privilege answer and stop; resist writing broadly |
| John Paul Stevens | 1975-2010 | Multiple | AFFIRM | AFFIRM | Adhesion ToS ‘voluntary’ economically questionable; reserves |
| Sandra Day O’Connor | 1981-2006 | Rehnquist | AFFIRM | AFFIRM | Quinn Emanuel’s silence on AI risk = malpractice exposure |
| Antonin Scalia | 1986-2016 | Rehnquist/Roberts | AFFIRM | AFFIRM (strictest) | Most quotable concurrence; functional equiv. is escape valve |
| Anthony M. Kennedy | 1988-2018 | Rehnquist/Roberts | AFFIRM | AFFIRM | Human dignity: preparation made costly by commercial design |
| David H. Souter | 1990-2009 | Rehnquist/Roberts | AFFIRM | AFFIRM | Stare decisis; doctrinal consistency prevents uncertainty |
| Clarence Thomas | 1991-Present | Rehnquist/Roberts | AFFIRM | AFFIRM | Originalist; 17th-c. common law roots unambiguous |
| Ruth Bader Ginsburg | 1993-2020 | Rehnquist/Roberts | AFFIRM | AFFIRM | Enterprise/consumer line drawn; Section 702 flagged, reserved |
| Stephen G. Breyer | 1994-2022 | Rehnquist/Roberts | AFFIRM | AFFIRM | Differential access to privilege by purchasing power |
| John G. Roberts Jr. | 2005-Present | Roberts | AFFIRM | AFFIRM | Riley/Carpenter line; Section 702 dicta; most consequential |
| Samuel A. Alito Jr. | 2006-Present | Roberts | AFFIRM | AFFIRM | Formalist; elements fail; declines broader inquiry |
| Sonia Sotomayor | 2009-Present | Roberts | AFFIRM | AFFIRM | Sophisticated defendant here; adhesion contract question reserved |
| Elena Kagan | 2010-Present | Roberts | AFFIRM | AFFIRM | Rule 1.1 competence obligation post-ABA 512; joins without separate |
| Neil M. Gorsuch | 2017-Present | Roberts | AFFIRM | AFFIRM | ToS as practical necessity, not genuine choice; plants seed |
| Brett M. Kavanaugh | 2018-Present | Roberts | AFFIRM | AFFIRM | Precedent governs; courts apply; legislature develops |
| Amy Coney Barrett | 2020-Present | Roberts | AFFIRM | AFFIRM | Textualist; ToS text controls; declines structural dicta |
| Ketanji Brown Jackson | 2022-Present | Roberts | AFFIRM | AFFIRM | Names public defender crisis with legislative precision |
One hundred and fifteen justices across two hundred and thirty-five years. One unanimous result. Two partial dissents, both from the same side, both on the same element, both about the same defendant — not Heppner, but the defendant who appears nowhere in Rakoff’s opinion.
Douglas heard a Sixth Amendment case that had not been filed yet. Brennan heard a work product argument the defense had already conceded away. Neither of them would change the outcome. Both of them named, in their respective registers, the person the doctrine leaves unaddressed: the defendant preparing for a public defender consultation on free consumer AI, who loses privilege before the representation begins, who does not have Quinn Emanuel to give the briefing that would have saved everything.
Heppner had the resources to do this right. He had lawyers who should have told him how. He didn’t get the briefing. Thirty-one documents later, the doctrine that destroyed his privilege was not new and the technology that made it applicable was not going away.
The defendant who cannot afford what Heppner could afford is the next case. Douglas and Brennan, writing from opposite ends of the Warren Court’s intellectual tradition, would agree on one thing: that defendant deserves a better answer than the one the table above provides.
Series: How Would The Justices Likely Rule | Morris Legal Technology Blog | March 2026
JD Morris is Co-Founder and COO of LexAxiom, an AI platform for the business of law. He holds a Master of Legal Studies from Texas A&M University School of Law, a Master of Engineering from George Washington University, and dual MBAs from Columbia Business School and UC Berkeley Haas. He writes the Morris Legal Technology Blog under the series banner “The Technology Blind Spot.” Connect with him on LinkedIn at http://www.linkedin.com/in/jdavidmorris, on X at @JDMorris_LTech, or on Bluesky at @JDMorris-ltech.bsky.social.
