A legal battle over an inadvertently sent email has intensified the ongoing wrongful death lawsuit against Karen Read, raising complex questions about attorney-client privilege in the digital age. Read's legal team is seeking to compel the destruction of a message she accidentally copied to opposing counsel, while lawyers representing the family of her late boyfriend, Boston Police Officer John O'Keefe, argue the communication contains statements that undermine her previous sworn testimony.
The controversy centers on a December 16, 2025, email that Read sent using the "reply all" function. According to court filings, Read's attorneys had initially sent a message to the O'Keefe family's legal representatives, and Read, intending to respond only to her own lawyers, instead distributed her reply to everyone on the original thread. Her legal team quickly recognized the error and requested that the opposing counsel delete the message within an hour of its transmission.
Attorney-client privilege forms the cornerstone of Read's position. Her lawyers contend that the email constitutes a protected communication between a client and her legal representatives. In a court filing, attorney Damon Seligson argued that this single mistake in operating her email should not constitute a waiver of this fundamental legal protection. He emphasized that this was reportedly the first and only instance where Read had been blind copied on correspondence between her counsel and the opposing side.
However, the O'Keefe family's legal team, led by attorney Marc Diller, has taken a firm stance against this request. They characterize the message as a "bell that cannot be unrung," suggesting that the information has already entered the legal record and cannot be simply erased. More significantly, they assert that the email contains statements that are "inconsistent with her previous under oath positions" regarding the circumstances of O'Keefe's death.
The case itself stems from the tragic events of January 29, 2022, when Officer John O'Keefe was found dead in the snow outside a fellow officer's home in Canton. The O'Keefe family alleges that Read, after an evening of heavy drinking, struck him with her SUV and left him to die. These accusations mirror the criminal charges Read previously faced—and was acquitted of—in a highly publicized trial.
Read continues to maintain her innocence through an affirmative defense, a strategy she employed during her criminal proceedings. She alleges that individuals inside the home conspired with law enforcement officials to frame her for the crime. This defense has extended beyond the civil case; Read has filed a separate federal lawsuit alleging civil rights violations by those present at the scene and the investigating officers.
The email dispute has emerged amid ongoing interrogatories—formal written questions requiring sworn responses—that the O'Keefe family has served upon Read. These interrogatories specifically demanded all information supporting her theory that a third party was responsible for O'Keefe's death. The family previously filed a motion to compel more comprehensive answers, which Read's team claims she has now provided.
In her most recent sworn responses, Read stated that "as a result of the destruction and concealment of key evidence, the truth about what happened to Mr. O'Keefe has been deliberately obscured." She directed attention to specific testimony from her criminal trials, including data suggesting O'Keefe had traveled up and down stairs in the hours before his death, which she argues supports her theory of the case.
Seligson maintains that comparing Read's interrogatory answers with the privileged email reveals no unique impeachment material. In other words, he argues that the email does not provide additional ammunition to challenge her credibility beyond what is already available in her sworn statements. This assertion directly counters the O'Keefe family's position that the email contains damaging inconsistencies.
The legal principle at stake extends beyond this individual case. Courts have long grappled with how to handle inadvertent disclosure of privileged information in an era where electronic communication dominates legal practice. The "reply all" error represents a common pitfall that can have significant consequences in high-stakes litigation. While some jurisdictions have adopted rules that protect against waiver when reasonable precautions are taken, the specific circumstances of each case often determine the outcome.
The O'Keefe family's resistance to deleting the email suggests they believe it holds strategic value. In civil litigation, any statement that appears to contradict prior sworn testimony can be used for impeachment purposes, potentially undermining a witness's credibility before a jury. The family's lawyers have not publicly specified the exact nature of the alleged inconsistencies, as neither side has attached the actual email to their court filings, leaving the specific content subject to speculation.
This development adds another layer of complexity to an already convoluted legal saga. Read's acquittal in criminal court did not shield her from civil liability, as the burden of proof in civil cases is substantially lower than the "beyond a reasonable doubt" standard required for criminal conviction. The wrongful death lawsuit seeks monetary damages rather than criminal punishment, but the stakes remain high for both parties.
The separate federal civil rights lawsuit filed by Read further complicates the landscape, creating a web of interconnected legal actions that span both state and federal courts. This multi-jurisdictional approach suggests Read is pursuing an aggressive counter-narrative, attempting to shift focus from her own actions to alleged misconduct by investigators and witnesses.
As the dispute over the email continues, legal observers note that the outcome could set important precedents for how courts handle similar situations. The tension between protecting privileged communications and ensuring transparency in litigation reflects broader debates about fairness and efficiency in the justice system. For now, the question remains whether a single click of the "reply all" button will provide the O'Keefe family with a tactical advantage or whether Read's legal team can successfully contain the damage from this digital misstep.
The court's eventual ruling on whether the email must be destroyed will likely consider several factors: the nature of the privilege claimed, the circumstances of the disclosure, the promptness of the effort to rectify the error, and the potential prejudice to either party. Until then, the inadvertent message remains a point of contention, illustrating how modern technology continues to create new challenges for age-old legal principles.