A Massachusetts Superior Court judge has ruled that AI-generated documents are not protected under the work product doctrine unless an attorney directed their creation, marking a decision of first impression in the state. The ruling in Shealy v. Seaside Investments, LLC exposes a growing risk for litigants who use AI tools without counsel's involvement: the output, and the prompts used to generate it, may be subject to discovery.
The dispute arose from a commercial investment relationship involving a purchase agreement and promissory note signed in January 2025. After receiving a default notice from Seaside in May 2025, Earl Wade Shealy Jr. sent the transaction documents to his romantic partner, Debbi Fields, who uploaded them to ChatGPT and asked the tool to prepare a response letter. Neither Shealy nor Fields consulted an attorney during the process, despite Shealy having counsel in the underlying transaction.
When litigation began, Shealy redacted communications between himself and Fields, claiming work product protection. Work product doctrine shields the mental impressions, conclusions, and legal theories that an attorney or representative prepares in anticipation of litigation. The court rejected that claim on multiple grounds.
Who counts as a "representative"
The court found that neither Fields nor ChatGPT qualified as Shealy's "representative" under the work product doctrine. Massachusetts does not recognize romantic partners as representatives for this purpose, and the court declined to extend the doctrine to cover them. The court also rejected the argument that ChatGPT itself could serve as a representative.
In doing so, the court distinguished recent federal rulings in Morgan v. V2X, Inc. and Warner v. Gilbarco, Inc., where courts in Colorado and Michigan extended work product protection to AI output used by pro se litigants. Those courts reasoned that the AI-generated material reflected the litigants' own mental impressions as they acted in the role of counsel. The Morgan court specifically cited a policy interest in leveling the playing field between represented and unrepresented parties.
Those cases did not apply here, the Massachusetts court said, because Shealy was represented by counsel at the time he used ChatGPT, and he acted without counsel's direction.
Why attorney direction matters
The court emphasized a critical distinction: "Nor does the output from ChatGPT constitute opinion work product. AI is a tool not a person. Nothing about what ChatGPT produces discloses the 'mental impressions, conclusions, opinions, or legal theories of an attorney or other representative of a party concerning the litigation.'"
Without attorney input or direction, the AI output reflected no lawyer's strategic thinking. The court analogized the case to United States v. Heppner, where a represented criminal defendant's independent use of an AI tool without counsel's direction fell outside privilege protection and was subject to disclosure.
What this means for legal professionals
The ruling signals that courts will apply traditional privilege doctrines to AI-generated materials without modification. The technology itself does not warrant departing from established frameworks. For legal professionals, the practical takeaway is direct: once litigation is anticipated, counsel must direct any analytical work, including AI-assisted work, to shield mental impressions and legal theories from discovery. Delegating AI queries to non-attorneys, or using AI tools without counsel's oversight, may forfeit protection entirely.
Legal teams working with AI tools in litigation contexts should also be aware of how these rulings affect day-to-day practice. For those looking to build skills around AI use in legal settings, resources like the AI Learning Path for Paralegals and broader AI for Legal training can help professionals understand both the practical mechanics and the boundaries of tools like ChatGPT in legal work.
The ruling is a cautionary example for anyone handling litigation-related documents: the tool itself does not create privilege. The lawyer's direction does.
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