In late 2025, Bradley Heppner, former CEO and board chairman of GWG Holdings, Inc., was indicted on multiple federal counts, including securities fraud, wire fraud and conspiracy. The Government alleged a massive scheme wherein Heppner defrauded investors of over $150 million through complex, undisclosed and self-serving transactions involving entities under his control.
Following the indictment, the Federal Bureau of Investigation (FBI) executed a search warrant at the defendant’s residence. The FBI seized digital devices and physical documents—31 of which memorialized extensive, verbatim “written exchanges” between Heppner and the AI platform “Claude,” an advanced large language model (LLM) operated by Anthropic.
On Feb. 10, 2026, Judge Jed Rakoff of the Southern District of New York held in United States v. Heppner that a criminal defendant’s extensive conversations with a consumer-grade AI chatbot were neither privileged under the attorney-client privilege nor protected under the work-product doctrine. The ruling establishes a limiting precedent: Conversations and documents generated through AI, even those a client subjectively intends to keep private for the specific purpose of legal strategy, are freely discoverable by the government or opposing counsel.
A magna cum laude graduate of Cornell University, Christopher P. Woehrle earned his JD and LLM (Taxation) from the Widger School of Law at Villanova University, where he also is a member of the Graduate Tax Program Advisory Board. Chris is a member of the Pennsylvania Bar and teaches charitable gift planning and principles of wealth management in the LLM taxation program at the Widger School of Law. You can connect with Chris by email.
