By Bill Hartzer · Published · Updated · How this site is researched
What happened
Bradley Heppner, a financial services executive, was indicted in the Southern District of New York in October 2025 on securities fraud, wire fraud and related charges arising from his roles at GWG Holdings and affiliated companies. Before the indictment, after he had received a grand jury subpoena and knew he was a target of the investigation, he used Claude, the publicly available AI assistant made by Anthropic, to work through his situation. According to the court, he entered information he had learned from his lawyers and produced reports that outlined his anticipated charges and possible defense strategy.
FBI agents seized about 31 documents memorializing those exchanges when they arrested him and searched his home in November 2025. Mr. Heppner had shared their contents with his defense counsel, and counsel asserted privilege over them. Counsel also conceded that they had not directed him to use the system. The government moved for a ruling that the documents were not protected.
What the court did
Judge Jed S. Rakoff granted the government's motion from the bench on February 10, 2026, and explained the ruling in a written memorandum filed February 17, 2026. On attorney-client privilege, the memorandum states: "Because Claude is not an attorney, that alone disposes of Heppner's claim of privilege." The court also found that he had no reasonable expectation of confidentiality in the exchanges, pointing to the provider's written privacy policy, which describes collecting user inputs and outputs and reserves the right to disclose data to third parties, including government authorities. Sharing the documents with counsel afterward did not make them privileged.
On work product, the court found that the documents were not prepared by or at the direction of counsel, and that the fact that they later influenced counsel's strategy did not mean they reflected it. The memorandum noted that the analysis might be different if counsel had directed the use.
Where it stands
The case went to trial before Judge Rakoff. On May 5 the court denied the defense Rule 29 motion as to counts 1, 3 and 4 and granted it as to count 5. On May 7 the jury returned a verdict of guilty as to all counts submitted to it, and the verdict form was docketed a week later.
On June 22 the defense moved under Rules 29 and 33 for a judgment of acquittal or a new trial. Opposition was filed July 24 and the reply on August 7. That motion is fully briefed and undecided. Sentencing, originally set for October 7, was adjourned at a September 11 status conference to October 21 at 4:00 p.m. No appellate ruling on the privilege question was located.
The privilege holding itself no longer stands alone, and it has not fared well. Two state trial courts have expressly declined to follow it. In Assini v. Hayward, the Supreme Court of New York, Nassau County, quashed a subpoena to OpenAI for a litigant's account records, reasoning that the contents resemble the kind of confidential, strategy-laden iterative work that New York protects, and noting this court's contrary conclusion. In Tate Group Automotive v. Legacy Automotive Capital, the Business Court of Texas sustained work-product protection over a non-lawyer's ChatGPT conversations and said in terms that it disagreed with this decision.
So there are three trial-level answers to the same question and no appellate authority anywhere in the United States. An expert should not assume that any one of them travels, and should certainly not assume the most protective one does.
This decision is now the most-argued-against of its kind. Morgan v. V2X, decided six weeks earlier, had held that a self-represented litigant's AI use falls within work product because such a party is simultaneously party and advocate, and Warner v. Gilbarco had held that using a system is not itself a waiver. Tate Group Automotive v. Legacy Automotive Capital expressly disagreed with this court, reasoning that the Texas rule protects material prepared by or for a party rather than only by counsel. Assini v. Hayward expressly considered this decision and declined to follow it, one day later, in quashing a subpoena served on the provider. Tym v. Cerno adopted Morgan. On the other side, Shealy v. Seaside Investments reached a compatible result where the prompting was done by a party's partner and no attorney had directed it. No federal court of appeals has resolved the question.
Update, October 21. Sentencing did not go forward as scheduled. According to the Kansas Reflector, the defense team withdrew, citing a "complete breakdown in communications," and Judge Rakoff approved the withdrawal; new counsel appeared the day before the scheduled hearing. No new sentencing date and no ruling on the pending Rule 29 and Rule 33 motion were located as of October 21, 2026. The report states that Heppner plans to appeal; the privilege ruling would be reviewable only in such an appeal.
The obligation it engaged
Mr. Heppner was a defendant, not an expert, but the ruling reaches anyone who puts sensitive material into a consumer AI system and assumes the exchange stays private. It illustrates Clause 6, custody and confidentiality. The Standard asks the expert to establish, before submitting anything, what leaves the expert's environment and who retains it. Here the court looked to the provider's own terms to decide whether confidentiality could be expected at all.
It also bears on Clause 7, contemporaneous record, and Clause 8, disclosure. A record of AI use exists whether or not its author organizes it, and it may be obtained by someone else. An expert who assumes that a session is producible, keeps it within the engagement's agreed accounts, and records its purpose is in a better position than one who learns what the platform retained when an opponent asks for it. Whether expert work done at counsel's direction on a business-tier account would be treated differently is a question this ruling did not decide.
Sources
- U.S. District Court, S.D.N.Y. (copy hosted by Akin Gump) · February 17, 2026
Memorandum, United States v. Heppner, ECF 27 (Feb. 17, 2026) - Harvard Law Review (blog) · March 2026
United States v. Heppner - O'Melveny & Myers · February 2026
S.D.N.Y. First-of-its-Kind Ruling: AI-Generated Documents Are Not Privileged - Kansas Reflector · May 7, 2026
Former Beneficient executive with Kansas political ties guilty of fraud in $150M scheme - Kansas Reflector · October 21, 2026
Lawyers for convicted felon who led Kansas venture withdraw
What could not be confirmed
Only the sentence beginning "Because Claude is not an attorney" is quoted from the memorandum; the court's other reasoning is paraphrased because the renderings available differed slightly in wording. The docket activity in this entry is taken from the public docket; the Rule 29/33 papers were not opened. No appeal of the privilege ruling was located as of September 17, 2026.
About this entry
This entry was checked against the primary document listed in the sources. The entry for United States v. Heppner records conduct and what the tribunal did. It does not characterize a holding and it is not legal advice. Last checked October 21, 2026. More matters like this one are collected under the AI evidence matters. If something here is out of date, write to [email protected].