Ex-GWG Holdings Chair's Talks With AI Bot Lack Privilege

Federal judge rules conversations with generative AI not protected by attorney-client privilege.

Published on Feb. 22, 2026

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A federal judge ruled that communications between the former chair of GWG Holdings Inc. and a generative AI bot about his potential defense against securities fraud charges are not entitled to client-attorney privilege. The judge stated that the AI bot 'Claude' is not an attorney, and that no trusting human relationship exists between an AI user and a platform like Claude.

Why it matters

This ruling highlights the legal challenges around the use of generative AI tools and the limits of attorney-client privilege. As AI becomes more advanced and integrated into various aspects of business and personal life, the courts will likely continue to grapple with how to apply existing legal frameworks to these new technologies.

The details

The US District Court for the Southern District of New York ruled that the conversations between former GWG Holdings chair Bradley Heppner and the AI bot Claude do not contain communications between Heppner and his legal counsel. The judge stated that 'Claude is not an attorney' and that 'no such relationship exists, or could exist, between an AI user and a platform such as Claude.' Privileges like attorney-client privilege require a trusting human relationship, which the judge said does not exist in this case.

  • The ruling was issued on February 18, 2026.

The players

Bradley Heppner

The former chair of GWG Holdings Inc. who was communicating with the AI bot Claude about his potential defense against securities fraud charges.

Claude

A generative AI bot that Heppner was communicating with, which the judge ruled is 'not an attorney' and does not have the type of trusting human relationship required for attorney-client privilege.

Judge Jed S. Rakoff

The US District Court for the Southern District of New York judge who issued the ruling that Heppner's communications with the AI bot Claude are not protected by attorney-client privilege.

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The takeaway

This case highlights the legal complexities around the use of generative AI tools, particularly when it comes to established legal privileges like attorney-client confidentiality. As AI becomes more integrated into business and personal activities, the courts will likely continue to grapple with how to apply existing legal frameworks to these new technologies.