What does the special prosecutor mean for her retrial?

Criminality

“I think it will be interesting to see if he can not only win the case but also change the public perception of the case.”

In selecting Hank Brennan as the prosecutor in Karen Read’s retrial, Norfolk District Attorney Michael Morrissey emphasized the seasoned defense attorney’s respected reputation, decades of experience and familiarity with “complex law enforcement cases.”

Qualifications aside, legal analysts say the special counsel’s most valuable asset at this crucial juncture may be the fresh perspective he brings to the controversial Read murder case. In fact, two experts who spoke with Boston.com said Brennan’s nomination could signal some significant changes in Round 2.

“I think this case needs a real reassessment, a real thorough analysis of whether it’s worth the resources to go to another trial, given what happened before and all the evidence that could be favorable to Karen Read,” said Daniel Medwed, a criminal law professor at Northeastern University.

Read, 44, is accused of intentionally driving her SUV into her boyfriend, Boston police officer John O’Keefe, after a night of bar hopping in Canton in January 2022. While prosecutors say Read was driving drunk and left O’Keefe for dead in the snow, the Mansfield woman’s lawyers say she was framed in a cover-up by law enforcement. Read has pleaded not guilty to charges of second-degree murder, manslaughter while operating a motor vehicle while intoxicated and leaving the scene of a fatal crash.

The jury in her first trial ultimately could not reach an agreement, leading to a mistrial on July 1. Now, with the highly anticipated retrial set to begin on January 27, the prosecution team is undergoing a reorganization.

In January, Brennan — whose previous clients include the late mobster James “Whitey” Bulger — will lead the prosecution as a special assistant district attorney. Brennan, a former prosecutor in Essex and Suffolk counties, will work on the Read case alongside Norfolk District Attorneys Adam Lally, Laura McLaughlin and Caleb Schillinger.

“I’m definitely intrigued by this choice because I think it indicates the likelihood that the second trial will be conducted in a very different manner than the first,” Morrissey’s attorney Katherine Loftus said of the decision.

Although she hasn’t seen Brennan in action firsthand, Loftus said she “always found him to be someone who was willing to take on tough cases and take tough positions, and I think that will be reflected in his physical presentation of the case.”

Medwed also described Brennan as “someone who’s really well prepared to deal with what’s to come.”

“It’s a good choice from Morrissey’s perspective because he (Brennan) is an attorney, and that will send a good message to the public that Morrissey wants … that objective perspective, not just picking a prosecutor from a neighboring county or something like that,” he said. “But he’s also someone who’s been on both sides of the fence, so he understands the mission and the duty of the prosecutor.”

A fresh perspective

By selecting an outsider, the district attorney’s office also has the opportunity to counter some of its own biased views, Medwed explained.

“It’s very difficult to look at something with fresh eyes when you’ve been looking at it for ages,” he said. “And that’s the problem with the Norfolk County district attorney’s office, right? They’ve been looking at this for years. They probably have a pretty strong opinion, I imagine, about her guilt.”

According to Read, the case needs “someone who will really analyze the different theories without referring to previous decisions.”

Both he and Loftus noted Read’s second-degree murder charge, which Loftus has long considered a “stretch” for prosecutors. Medwed, meanwhile, noted that prosecutors’ theories of second-degree murder and manslaughter under the influence of alcohol or drugs appear to be “strained” when it comes to whether Read intended to kill O’Keefe.

Read’s attorneys appealed to the Supreme Court, hoping to have two charges thrown out, arguing that an allegedly undecided jury had informally agreed to acquit her of murder and leaving the scene of a fatal accident. As one juror reportedly told defense attorney David Yannetti after the mistrial, “Nobody thought she hit him on purpose or even knew she hit him.”

On Thursday, a single judge ruled that Read’s appeal would be heard by the full Supreme Court, with oral arguments expected tentatively in November.

While he said he wouldn’t be surprised if prosecutors ultimately decide to drop the murder charge, Medwed said he also sees the district attorney’s office keeping the charges intact, hoping a jury will return a conviction on the less serious manslaughter charge. Medwed compared it to restaurant patrons gravitating toward more moderately priced menu items, a behavior sometimes called middle-of-the-road bias or the “Goldilocks effect.”

What to Expect from Karen Read’s Retrial

Anyone joining the case from outside the district attorney’s office must “review the file thoroughly,” Loftus said. She predicts that prosecutors may decide to drop some witnesses the second time around who provided unnecessary testimony — such as the countless first responders called to the scene the morning O’Keefe died.

“It will probably be shortened, in some ways, and we may even have new witnesses who were not called,” Loftus said, adding: “Overall, I wouldn’t be surprised if we saw almost a different type of case presented at trial a second time.”

She noted that during Read’s first trial, many who followed the case found the prosecution’s presentation to be “a little bland.” In that respect, Brennan is prosecutors’ second chance to make a first impression.

“I think the district attorney’s office was looking for someone who could not only handle the case differently, but also present it differently to the public,” Loftus said. “Because whether we like it or not, … people are so invested in the outcome of this case. I think it will be interesting to see if he can not only win the case but also change the public’s perception.”

But prosecutors face a difficult task, especially when it comes to the testimony of the lead investigator in the case, Massachusetts State Police Trooper Michael Proctor. Proctor was fired and suspended without pay after Read’s first trial, during which he admitted sending vulgar text messages about the defendant to family, friends and co-workers.

“I’m sure there will be subtle differences in strategy, opening statements and the order of witnesses,” Medved said of the prosecution’s case. “They’ll have to deal with Proctor; they’ll have to deal with some of the fallout from the investigation.”

“We’ll see you in court”

In light of defense attorneys’ accusations of a law enforcement cover-up, Loftus said Brennan’s nomination makes it seem as if the district attorney’s office is distancing itself from the trial, which “may instill more confidence in the commonwealth’s case.”

“I think hiring someone who not only has a fresh perspective but also has a reputation for not being afraid to take on tough cases was the right decision, at least from a Commonwealth perspective,” she said.

Meanwhile, Read’s camp seemed unconcerned about the change in prosecutors.

“The news that Michael Morrissey has chosen to use taxpayer money to hire an outside attorney to handle this case speaks volumes about his confidence in his own team,” defense attorney Alan Jackson said in a statement. “They can put anyone they want on trial. We will defeat this unjust prosecution, just as we did last time.”

“As we said to Mr. Morrissey before, do your best,” he added. “We’ll see you in court.”