In a memorandum opinion that every trial lawyer should read, Judge Jed S. Rakoff of the United States District Court for the Southern District of New York has ruled that a criminal defendant’s written exchanges with the generative AI platform Claude are protected by neither the attorney-client privilege nor the work product doctrine. The decision appears to be the first of its kind nationwide, and its reasoning carries significant implications for how lawyers counsel clients — and for how clients use AI tools — in the shadow of litigation.
The Facts
In United States v. Heppner, No. 25 Cr. 503 (S.D.N.Y. Feb. 17, 2026), Bradley Heppner was indicted in October 2025 on charges of securities fraud, wire fraud, conspiracy, making false statements to auditors, and falsifying corporate records arising from his alleged conduct as an executive of GWG Holdings, Inc. Following his arrest, FBI agents executed a search warrant at his home and seized, among other materials, approximately thirty-one documents memorializing communications Heppner had with Claude, the AI platform operated by Anthropic. These exchanges — which Heppner’s counsel described as “reports” outlining potential defense strategy and legal arguments — were prepared by Heppner on his own initiative, after he had received a grand jury subpoena and it was clear he was a target of the investigation. Counsel conceded, critically, that they had not directed Heppner to use Claude.


