Karen Read’s defense team has introduced new evidence about an altercation with her boyfriend, John O’Keefe, occurring the month before his alleged death in a drunken hit-and-run. Prosecutors argue that this evidence could suggest the incident was a “domestic violence homicide,” with Read unable to accept O’Keefe’s attempts to end their relationship, as revealed in a recent court filing.

Alan Jackson, one of Read’s attorneys, questioned Massachusetts State Police Sgt. Yuri Bukhenik about a series of text messages between Read and another potential romantic interest, ATF Agent Brian Higgins. Higgins was at the bar and after-party attended by Read and O’Keefe, a Boston police officer, before he was last seen alive.

“Where the defendant has introduced this evidence, it is crucial for the jury to recognize that it was the defendant who consistently refused to acknowledge the victim’s wish to end their relationship,” special prosecutor Hank Brennan stated. “The defendant made repeated hostile accusations that the victim was unfaithful, demonstrating a pattern of hostility in the days and weeks leading up to the murder.”

“This incident in Aruba seems to also be the turning point in the relationship as the defendant told Brian Higgins that her relationship with the victim was a ‘very f—ed up situation’ as she had observed the victim ‘all over [a] friend’s sister in the lobby of our hotel’ and accused the victim of ‘having hooked up with another girl.’”

Brennan said he plans to call four witnesses to the Aruba incident to testify.

Karen Read, front left, joins attorneys for a sidebar with Judge Beverly J. Cannone, right, during her murder retrial on May 12, 2025. (Pat Greenhouse/The Boston Globe via AP, Pool)

“In a domestic violence homicide, evidence such as prior disputes are relevant to show the ‘volatile nature of the relationship,’” Brennan wrote.

He added that he expected their testimony to show Read’s “intent and state of mind toward the victim.”

“Brennan is smart,” said Linda Kenney Baden, a high-profile defense attorney who squared off with Jackson in 2007 when he was the lead prosecutor in the murder trial of music producer Phil Spector. “You don’t get to represent Whitey Bulger for eight years if you’re not.”

Still, she said, Jackson may have been prepared for it.

“I think even if the judge allows him to bring it in, Jackson is ready for it,” she said. “That’s why he had the Aruba text read in the whole Higgins outline.”

Read has pleaded not guilty, and her attorneys deny she ever struck O’Keefe with her vehicle.

Four weeks into the trial, prosecutors have yet to show O’Keefe’s autopsy findings to the jury or allege specifically how she intended to kill him. 

“This feels desperate to get the intent,” said Grace Edwards, a Massachusetts defense attorney who has been following the case. “I don’t think the jury will care to hear more evidence that there were issues. No relationship is perfect.”