Are AI-Generated Materials Protected by the Work Product Doctrine?

Shealy v. Seaside Investments is one of the first Massachusetts decisions to address whether AI-generated materials are protected by the work product doctrine. Although its holding is narrow, it provides an early warning about the risks associated with clients’ independent use of generative AI.

In Shealy, upon receiving the defendants’ reservation of rights letter, the plaintiff emailed the letter and related documents to his girlfriend, who uploaded them to ChatGPT, a generative AI platform. Based on her prompt, ChatGPT generated a response letter and other materials, which she then emailed back to the plaintiff. No attorney participated in or directed this process. The defendants moved to compel production of the redacted email communications and attached documents, and the plaintiff asserted work product protection over those materials.

As the court explained, the work product doctrine protects (1) documents and tangible things, (2) prepared by or for a party or the party’s representative, (3) in anticipation of litigation or for trial. The court explained that the dispute centered on the second element: whether the AI-generated materials were prepared by or for the plaintiff’s representative.

The court first concluded that the plaintiff’s girlfriend was not the plaintiff’s representative for purposes of the work product doctrine. It then held that ChatGPT likewise did not qualify as the plaintiff’s representative. In reaching its conclusion, the court distinguished recent decisions out of the District of Colorado, Morgan v. V2X, Inc., and the Eastern District of Michigan, Warner v. Gilbarco. In both cases, the issue was the protection of materials prepared by pro se litigants. The court cited Morgan to explain that a pro se litigant is both the party and the advocate, and therefore, had better arguments for claiming work product protection in connection with their AI use.

Accordingly, the Shealy court concluded that neither the ChatGPT prompts nor the AI-generated output had been prepared by or for the plaintiff or a qualifying representative. Thus, because no attorney directed or participated in the AI use, the materials did not qualify for work product protection. The decision was also informed by the policy considerations underlying the work product doctrine. Under these circumstances, extending protection to the AI-generated materials would not advance the doctrine’s central purpose of safeguarding attorney preparation, mental impressions, and strategy.

Massachusetts is not alone in confronting this issue. In United States v. Heppner, a criminal case, the Southern District of New York held that materials generated through a defendant’s independent use of Anthropic’s Claude were not protected by the attorney client privilege or work product doctrine where the defendant acted on his own initiative.

These decisions serve as a reminder of the potential discovery risks associated with the independent use of generative AI in pending litigation. Litigants may assume that AI is simply another notetaking or brainstorming tool, but Shealy suggests that litigation-related AI use by parties may have consequences for whether resulting materials are discoverable. Although the decision leaves many questions unresolved, it counsels caution when litigants use AI for purposes related to pending litigation, particularly where that use occurs independently of counsel.

Fall 2026 Newsletter

Compliance Duties Don’t Cancel Whistleblower Rights

On January 27, 2026, the Massachusetts Supreme Judicial Court issued a significant decision in Thomas Galvin v. Roxbury Community College clarifying the scope of protection under the Massachusetts Whistleblower Act, G.L.c. 149, §185. The Court held that a public employee may engage in protected whistleblowing activity even if identifying legal violations falls within the employee’s job responsibilities and even if the employee may have been involved in the underlying compliance failures.

The decision provides important guidance for public employers, particularly educational institutions and other entities that rely on internal compliance officers or administrators to oversee regulatory obligations.

The plaintiff served as Roxbury Community College’s Director of Facilities and Public Safety and was the college’s primary campus security authority responsible for compliance with the federal Clery Act. Over a number of years, a student reported allegations of sexual assault to multiple senior administrators. Despite those reports, the college failed to disclose the allegations to the U.S. Department of Education as required by federal law. The plaintiff raised concerns internally, sought guidance from the Department of Education, disclosed the issue to the State Auditor’s Office, and later formally objected in writing to the board of trustees regarding the college’s failure to comply with its reporting obligations.

After external audits confirmed that Clery Act violations had occurred, the college terminated the plaintiff’s employment. The college asserted that the decision was based on performance deficiencies, including the plaintiff’s own failures to ensure regulatory compliance. The plaintiff sued, alleging that he was terminated in retaliation for whistleblowing in violation of the Massachusetts Whistleblower Act. A jury agreed and awarded substantial damages.

On appeal, the college argued that the plaintiff could not qualify as a whistleblower because reporting Clery Act violations was part of his job and because he was himself implicated in the failures to report. The Supreme Judicial Court rejected those arguments and affirmed the verdict.

The Court held that when an employee objects to conduct that is undisputedly unlawful, the employee engages in protected activity as a matter of law. The statute requires only an objectively reasonable belief that a legal violation occurred, and that standard is automatically satisfied where the illegality is not in dispute. The Court further concluded that the Whistleblower Act does not exclude employees who had compliance responsibilities or who may have been involved in the misconduct they report.

Importantly, the Court drew a clear distinction between whistleblower status and cause for termination. While an employer remains free to discipline or terminate an employee for legitimate performance issues or misconduct, the employer may not do so because the employee objected to unlawful conduct. Determining whether the termination was motivated by whistleblowing or by performance failures is a fact-specific inquiry for the jury.

For public employers, this decision underscores the need for caution when responding to internal reports of regulatory violations, particularly when those reports come from compliance officers or administrators tasked with oversight. The ruling reinforces that the Whistleblower Act is intended to encourage the reporting of unlawful activity, not to penalize those closest to identifying it. Employers should ensure that adverse employment decisions are well documented, clearly grounded in legitimate performance concerns or other business needs unrelated to protected reporting activity, and carefully separated from any such activity. As regulatory scrutiny and enforcement continue to increase, this case serves as a reminder that an organization’s response to internal compliance concerns can have significant legal consequences.

Winter 2026 Newsletter

Tenant’s Termination Rights Upheld Despite Lender Consent Clause

In a decision clarifying the relationship between lease provisions and lender consent clauses, the Massachusetts Appeals Court recently upheld a trial court’s order in favor of the tenant, allowing the tenant to terminate a long-term lease and service agreement without first obtaining the mortgage lender’s written approval.

Hasseltine House, LLC (the landlord) leased a Newton residential facility to Jewish Family and Children’s Services, Inc. (the tenant) under a sixteen-year lease and a companion service agreement. The agreements between the landlord and the tenant provided “special termination rights,” permitting the tenant to end the tenancy if five of the facility’s fourteen residents gave notice of intent to vacate. Weeks later, the landlord, tenant, and Brookline Bank executed a Subordination, Non-Disturbance, and Attornment Agreement (SNDA) in connection with the landlord’s $2.6 million mortgage. The SNDA subordinated the lease to the bank’s mortgage and prohibited termination without the bank’s prior written consent, though such consent could not be unreasonably withheld.

Between May and August 2017, five residents gave notice to leave to the tenant. After notifying the landlord, the tenant formally invoked its termination rights in January 2018. The landlord sued, alleging that termination without Brookline Bank’s consent breached both the lease and service agreement and violated the implied covenant of good faith and fair dealing.

After motion practice, the trial judge entered judgment in the tenant’s favor. The Appeals Court agreed, holding that the SNDA did not override or limit the tenant’s termination rights clearly established in the lease and service agreement between the landlord and the tenant. The court reasoned that those agreements, executed together, defined the essential terms of the tenancy – including the special termination clause – and that the later SNDA could not “render illusory” the rights the tenant had already secured with the landlord.

The court emphasized that all three documents must be read together to discern the parties’ intent. Because the SNDA expressly preserved the tenant’s rights under the lease, the absence of written lender consent did not amount to a contractual breach between landlord and tenant – even if it might have violated obligations owed to the bank.

The landlord also claimed the tenant failed to “promptly” report residents’ notices to vacate, as required under the service agreement, and acted in bad faith by waiting until enough notices accumulated to justify termination. But the court found no evidence that the landlord suffered harm from any delay or that earlier notice would have changed the outcome. Exercising an expressly negotiated right, the court concluded, cannot constitute bad faith.

This case reinforces that:

  • Contract integration matters – when multiple agreements form a single transaction, courts interpret them together to preserve the original bargain.
  • Lender consent clauses in SNDAs do not automatically supersede negotiated lease rights unless the parties clearly intend that result.

By upholding the tenant’s right to terminate, the Appeals Court underscored the importance of clear contractual language, especially when sophisticated parties structure multi-agreement real estate transactions.

Fall 2025 Newsletter

Court Clarifies Boundaries of Post-Employment Restrictions

On June 13, 2025, the Massachusetts Supreme Judicial Court (SJC) issued a decision in Miele v. Foundation Medicine, Inc. that reinforces the distinction between noncompetition and nonsolicitation agreements under the Massachusetts Noncompetition Agreement Act, G.L. c. 149, § 24L (the “Act”). The court concluded that a forfeiture clause triggered by a former employee’s breach of a nonsolicitation agreement does not convert that agreement into a “forfeiture for competition agreement” subject to the Act’s strict requirements.

This ruling offers some welcome clarity for Massachusetts employers who include post-employment restrictive covenants in severance or transition agreements, particularly those concerned about how to enforce nonsolicitation provisions without running afoul of the Act.

Susan Miele, a former executive at Foundation Medicine, Inc. (FMI), had entered into both a restrictive covenant agreement at the outset of her employment and a transition agreement upon her separation in 2020. The restrictive covenant included a standard employee nonsolicitation clause, which prohibited her from recruiting FMI employees for one year after her departure. The later transition agreement incorporated that nonsolicitation clause and added a forfeiture provision: if Miele breached any agreement with FMI, she would forfeit remaining severance payments and be required to return those already made. FMI ultimately paid Miele approximately $1.2 million.

After leaving FMI, Miele joined Ginkgo Bioworks and allegedly solicited several FMI employees. FMI ceased her severance payments and demanded repayment. Miele sued FMI for breach of contract and argued that the forfeiture clause violated the Noncompetition Agreement Act because it imposed financial penalties based on post-employment conduct.

The Superior Court initially sided with Miele in part, holding that the forfeiture provision rendered the nonsolicitation clause a “forfeiture for competition agreement” — a type of post-employment restriction covered by the Act. Under that reasoning, FMI’s forfeiture clause would be unenforceable because it did not meet the Act’s strict procedural and substantive standards for noncompete agreements.

FMI sought direct appellate review, arguing that the Legislature expressly excluded nonsolicitation agreements from the scope of the Act and that attaching a forfeiture clause does not change that characterization.

The SJC agreed with FMI and reversed the Superior Court’s partial grant of judgment in Miele’s favor. The court emphasized that the Act expressly excludes nonsolicitation agreements from the definition of noncompetition agreements. Since forfeiture for competition agreements are a subset of noncompetition agreements, the court reasoned, they too must exclude nonsolicitation provisions. Allowing a forfeiture clause to change the character of the underlying agreement would, in the court’s view, effectively undermine the Legislature’s clear exclusion of such provisions from the Act’s coverage.

The court also rejected Miele’s attempt to reinterpret “competitive activities” in a way that would sweep solicitation back into the Act’s coverage. To do so, the court said, would contradict the plain language and would render the statute internally inconsistent.

For employers, this decision reinforces the legal distinction between noncompetition and nonsolicitation agreements in Massachusetts. While the two types of provisions may serve similar business interests, they are treated differently under the statutory framework. Employers incorporating nonsolicitation clauses into severance or other post-employment agreements may find some reassurance in the court’s conclusion that doing so, even with an accompanying forfeiture mechanism, does not implicate the Act.

At the same time, the case serves as an important reminder of the scrutiny that restrictive covenants can invite, especially where severance pay or other post-employment benefits are conditioned on continued compliance. Companies reviewing or updating such agreements should consider how these provisions are structured, what remedies they contemplate, and whether the agreements are likely to withstand legal challenge in light of evolving interpretations of the statute.

Summer 2025 Newsletter

Independent Contractor Label Notwithstanding, MCAD Holds Small Business Liable For Employment Discrimination

Earlier this year, the Massachusetts Commission Against Discrimination (MCAD) confirmed that small businesses may be subject to the anti-discrimination provision of Chapter 151B, even if the business claims to only hire independent contractors because it is the nature of the employment relationship that determines the MCAD’s jurisdiction and not the label chosen by the business. The commission confirmed that the anti-discrimination law applies to all businesses in Massachusetts with six or more employees even if the business happens to call them independent contractors.

In MCAD and Pavlov v. Happy Floors, Inc., a female worker alleged that her employer discriminated against her on the basis of sex and pregnancy in violation of Mass. Gen. Laws c. 151B, § 4(1). The flooring company maintained that it was not subject to MCAD’s jurisdiction because its workers were independent contractors, not employees. The Hearing Commissioner took evidence at a public hearing and determined, basedon an in-depth analysis of the nature of employment relationship, that the workers were in fact employees and not independent contractors.

In making that determination, the Hearing Commissioner focused on “the extent to which the employer has the right to exercise control over the employee’s work, not only to specify the final result, but also to supervise and direct the details and the means by which the result is achieved.” The Commissioner also considered (a) whether the work is of a type done under supervision or by a specialist working independently; (b) the skill required; (c) whether the employer furnishes the equipment and workplace, and bears the costs of operation; (d) whether payment is wages or salary for the time worked rather than profit or a set contractual fee on production of a final product or service; and (e) whether the parties have an ongoing relationship which may be terminated without notice or explanation by either party.

On appeal, the full commission also considered the independent contractor statute, Mass. Gen. Laws ch. 149, § 148B, which states that a worker is an employee unless all the following factors are met: (1) the worker is free from control and direction in connection with performing services; (2) the worker’s services are performed outside of the usual course of business of the recipient of the services; and (3) the worker is customarily engaged in an independently established trade, occupation, profession, or business of the same nature as that involved in the service performed. Under the second prong of this test, for example, a drywall installer working for a drywall company performing drywall installations cannot be properly classified as an independent contractor.

Construing the law liberally, the Hearing Commissioner found that Happy Floors employed flooring installers to do flooring installations, the company had a right to control the workers’ individual performance, the company provided tools and materials to the workers if they did not have their own tools, and the company required workers to wear company-branded tee shirts while on the job. On appeal, the full commission recognized that the Hearing Commissioner weighed the credibility of the testifying witnesses and conducted an in-depth analysis of the evidence, and thus affirmed the findings in their entirety.

This opinion from the MCAD is particularly instructive for small businesses in Massachusetts that employ six or fewer workers because they may be subject to employment-related claims before the MCAD despite only hiring (what they consider are) independent contractors.

Spring 2025 Newsletter

To Infinity and Beyond: When a Business Contract is Incomplete

Parties who decide to do business with each other must be very careful to ensure that the agreement between them contains all the important terms, especially the duration of the contract over which the parties expect to be in business with each other. A recent case from the Massachusetts Appeals Court confirms that in situations where a contract does not have an express duration term, the parties’ intent and circumstances dictate the reasonable duration of the contract, and one party cannot terminate the contract at-will.

Fall 2024 Newsletter

Navigating Joint Employer Liability in Massachusetts

The Massachusetts Appeals Court recently affirmed that a management company providing comprehensive services to a car dealership qualifies as a “joint employer,” subject to potential liability for Wage Act violations. This ruling in Tran v. Jennings Road Management Corp., et al. sets a significant precedent for how joint employer status is determined under Massachusetts law.

Summer 2024 Newsletter

Splitting up in Massachusetts: Who Keeps the Pet?

Who gets custody of “Teddy Bear”? That question was answered in recent decision of the Massachusetts Appeals Court regarding the ownership of Teddy Bear, a Pomeranian dog. Lyman v. Lanser, 103 Mass. App. Ct. 787 (2024). In its ruling, which granted joint custody of Teddy Bear to an unmarried couple who had split up, the court relied upon important principles of contract law which extend far beyond the specific facts of the case.

Spring 2024 Newsletter

The Wedding is Off, and Who is at Fault? Let the Court Decide!

In the case of a broken engagement, who gets to keep the rings? This was the question the Massachusetts Appeals Court recently addressed in Johnson v. Settino, 103 Mass. App. Ct. 291 (2023).

In Johnson, the plaintiff had given his fiancé a $70,000 engagement ring and purchased two wedding bands. After he broke off the engagement, and his now ex-fiancé refused to return the rings, he filed a lawsuit to get them back.

Fall 2023 Newsletter

Real Estate Brokers May Get A Commission Even Without A Written Contract

The Massachusetts Supreme Judicial Court recently ruled that a real estate broker could obtain damages stemming from a breach of contract of an oral agreement, even where the broker did not produce the final closing.

Spring 2023 Newsletter