The oral arguments held on May 6, 2025, in Massachusetts, presided over by Chief Justice Blake and Justices Ditkoff and Brennan, focused on a complex real estate dispute involving the Hennessy family and Revolve Realty. The session was marked by a detailed examination of the claims surrounding the sale of a property and the alleged misrepresentations made during the transaction.

The proceedings began with a critical inquiry into the truthfulness of statements made regarding the closing of the property sale. Counsel for the Hennessys asserted that certain claims made by Revolve were false, particularly regarding the timing of the closing and the absence of a mortgage contingency. The argument emphasized that the Hennessys were not adequately informed about the status of the sale, particularly concerning a related marijuana business transaction that could have influenced their decision to proceed with the sale.

As the discussion progressed, the court examined the implications of these alleged misrepresentations. Counsel for the Hennessys argued that had Revolve Realty been aware of the complexities surrounding the marijuana business sale, they would not have entered into the purchase and sale agreement. This point was underscored by referencing multiple communications from the Hennessys expressing confusion about the closing timeline, which was initially set for January 19 but was delayed.

The justices probed deeper into the responsibilities of both parties, questioning whether Revolve Realty acted with due diligence in their dealings. Counsel for Revolve countered that the Hennessys bore the primary responsibility for understanding the terms of the agreement, suggesting that they had accepted the offer without sufficient investigation. This led to a discussion on the legal precedents regarding reliance on potentially fraudulent representations, with references to Massachusetts case law indicating that plaintiffs could recover damages even if they did not exercise due diligence.

The court also explored the concept of "unclean hands," questioning whether any misconduct by Revolve Realty would affect the case's outcome. Counsel for Revolve maintained that their client did not possess unclean hands, while also acknowledging that if they did, it could influence the court's equitable considerations.

In conclusion, the oral arguments highlighted significant issues regarding transparency and the responsibilities of parties in real estate transactions. The justices' inquiries revealed the complexities of the case, particularly the interplay between alleged misrepresentations and the expectations of both buyers and sellers. The court's decision will likely hinge on the interpretations of these discussions and the established legal precedents surrounding real estate transactions in Massachusetts. Further developments are anticipated as the court deliberates on the matter.