While runners prepare to chase glory on Marathon Monday, the Massachusetts legal system is preparing for a different kind of race: a retrial that has gripped the public imagination and split opinion across the state.
Karen Read, a financial analyst and former adjunct professor, is set to be retried for the alleged 2022 murder of her boyfriend, Boston police officer John O’Keefe. The first trial ended in a hung jury, and now prosecutors are making a second attempt at securing a conviction—though legal experts suggest the odds may not be in their favor.
Read is accused of hitting O’Keefe with her SUV after a night of drinking and leaving him to die in the snow outside the home of another police officer. The prosecution claims Read was intoxicated and acted in a rage following an argument. But the defense has offered a very different narrative, alleging that O’Keefe was assaulted inside the home and that Read is being scapegoated in a cover-up involving law enforcement.
Central to the defense’s strategy is undermining the credibility of lead investigator Michael Proctor, who was dismissed from the case after revelations of bias and mishandling evidence. Text messages presented in court showed Proctor making disparaging remarks about Read and appearing to coordinate with potential witnesses before statements were given. The defense argues that this points to a compromised investigation designed to protect police insiders.
The case has been further fueled by public interest, with a popular docuseries amplifying calls for justice and transparency. Supporters of Read have launched social media campaigns and raised substantial funds for her legal defense. Meanwhile, critics accuse her team of exploiting media sensationalism to sway public opinion.
The retrial is being led by Hank Brennan, known for his work on the defense team of notorious gangster Whitey Bulger. His presence adds even more intensity to an already dramatic courtroom showdown. Legal analysts say Brennan’s experience may help the prosecution, but note that the inconsistent forensic evidence and broader questions of institutional trust could work against them.
“The state has to present a much clearer and more consistent case this time around,” said attorney Maria Lopez, a former Massachusetts judge. “The defense has already planted serious doubt. Without new evidence, the prosecution is facing an uphill battle.”
A City of Contrasts and Character
Together, these two stories reflect the layered identity of Boston—a city where tradition meets transformation. Whether it’s elite athletes charging down Boylston Street or a courtroom grappling with justice and power, Boston continues to be a place where history is made and challenged in equal measure.
As the city prepares for the excitement of Marathon Monday and the tension of a closely watched trial, Bostonians are once again reminded of the passion, controversy, and resilience that define their hometown.
