Shealy v. Seaside Investments

What happened

After receiving a default letter, Earl Wade Shealy, Jr. emailed the letter, the Note and the Purchase Agreement to his romantic partner, Debbi Fields. She uploaded them to ChatGPT with prompts and returned an AI-generated response letter and other documents. No attorney was involved at any point in that exchange.

When the emails were produced in the litigation, the plaintiffs redacted the ChatGPT material. The defendants moved to compel the unredacted versions.

What the court did

The court allowed the motion to compel and ordered the plaintiffs to produce, within five business days and by June 23, 2026, unredacted versions of the exhibits at issue together with all documents concerning the attempts to prepay the Note and the financial ability to do so.

The reasoning was direct. Neither the queries of AI programs for legal assistance by a party's romantic partner nor the AI output are protected from disclosure under the work product doctrine unless performed at the direction of counsel. And, echoing Warner v. Gilbarco on the nature of the system: AI is a tool not a person, and nothing about what ChatGPT produces discloses the mental impressions, conclusions, opinions or legal theories of an attorney.

The case is therefore not a counter-example to the protective line so much as a boundary marker on it. Morgan v. V2X protected a self-represented litigant because he was simultaneously party and advocate. Nobody here occupied that position.

Where it stands

Production was ordered by June 23, 2026. No later ruling was located as of September 28, 2026.

Read with United States v. Heppner, where a represented defendant's own Claude documents were held neither privileged nor work product, the shape of the doctrine becomes visible: what matters is who did the prompting and whether counsel directed it, not which system was used.

The obligation it engaged

The matter engages Clause 6, custody and confidentiality, at the point where most exposure is actually created. Material left one person's control, went to another person, and then to a provider, before any question of protection arose. Each step was a decision nobody recorded at the time.

It also engages Clause 2, non-delegation, in a setting outside expert work. A drafted response came back from a system and was treated as usable. The doctrine then asked whose work it was, and there was no answer that placed it with a lawyer.

Sources

• AI Discovery Database (Damien Charlotin) · September 28, 2026
  Shealy v. Seaside Investments, LLC

What could not be confirmed

The exact decision date could not be fixed: the document's date line reads "June ___, 2026" and the database gives June 1, 2026. The June 23, 2026 compliance deadline is used here as the anchor. The entry date has not been confirmed against the docket.