What the special prosecutor means for her retrial

Crime

“I think it will be interesting to see if he’s able to not only win the case, but whether he’s able to change public perception.”

In tapping Hank Brennan to lead prosecutors’ upcoming retrial of Karen Read, Norfolk District Attorney Michael Morrissey touted the veteran defense attorney’s esteemed reputation, decades of experience, and familiarity with “complex law enforcement matters.”

Credentials aside, though, legal analysts say the special prosecutor’s most valuable asset at this crucial juncture may be the fresh perspective he brings to Read’s controversial murder case. In fact, two experts who spoke with Boston.com said Brennan’s appointment could mean some notable changes for Round 2.

“What this case needs, I think, is truly a reevaluation, a sort of soup to nuts reevaluation of, ‘Is it worth expending resources on another trial, given what happened before and given all of the evidence that might be favorable to Karen Read ,’” said Daniel Medwed, a criminal law professor at Northeastern University.

Read, 44, is accused of intentionally backing her SUV into her boyfriend, Boston Police Officer John O’Keefe, following a night of bar-hopping in Canton in January 2022. While prosecutors allege Read was driving drunk and left O’Keefe to die in the snow, lawyers for the Mansfield woman argue she was framed in a law enforcement coverup. Read has guilt not guilty to charges of second-degree murder, manslaughter while operating a motor vehicle under the influence, and leaving the scene of a fatal accident.

Jurors in her first trial ultimately returned deadlocked, resulting in a mistrial July 1. Now, with the highly anticipated retrial slated to begin Jan. 27, the prosecutorial team is getting a shakeup.

Come January, Brennan — whose past clients include the late gangster James “Whitey” Bulger — will lead the prosecution as special assistant district attorney. A former prosecutor in Essex and Suffolk counties, Brennan will work the Read case alongside Norfolk ADAs Adam Lally, Laura McLaughlin, and Caleb Schillinger.

“I’m definitely intrigued by the choice, because I think it indicates the likelihood of the second trial being presented in a fairly different manner than the first trial was,” attorney Katherine Loftus said of Morrissey’s decision.

While she hasn’t seen Brennan in action firsthand, Loftus said her “Understanding of him has always been that he’s somebody that is willing to take on difficult cases and difficult positions, and I think that will likely reflect in his physical presentation of the case “

Medwed likewise described Brennan as “someone who’s really well-equipped to grapple with what’s to come.”

“It’s a nice choice from Morrissey’s perspective, because he (Brennan) is a defense lawyer, and that’s going to send a nice signal to the public that Morrissey wants … this objective look, not just tapping a prosecutor from the next county or something like “that,” he said. “But it’s also somebody who has been on both sides of the fence, and so he understands the prosecutorial mission and duty.”

A fresh look

By choosing an outsider, the DA’s office also has an opportunity to counter some of its confirmation bias, Medwed explained.

“It’s very hard to take a fresh look at something when you’ve been staring at it for ages,” he said. “And that’s the problem with the Norfolk County DA’s office, right? They’ve been looking at this for years. They probably have a pretty fixed opinion, I imagine, of her guilt.”

What Read’s case needs, he said, is “someone who will really scrutinize the different theories without the backdrop of prior decisions.”

Both he and Loftus also pointed to Read’s second-degree murder charge, which Loftus said she’s long felt was a “stretch” for prosecutors. Medwed, meanwhile, pointed out that prosecutors’ theories of second-degree murder and OUI manslaughter seem to be “in tension” when it comes down to whether or not Read intended to kill O’Keefe.

Read’s lawyers have appealed to the Supreme Judicial Court in hopes of dismissing two of the charges, alleging the purportedly deadlocked jury informally agreed to acquit her of murder and leaving the scene of a fatal accident. As one juror allegedly told defense attorney David Yannetti following the mistrial, “No one thought she hit him on purpose or even knew that she had hit him.”

On Thursday, a single justice ruled that Read’s appeal will be heard by the full panel of the Supreme Judicial Court, with oral arguments tentatively scheduled for November.

While he said he wouldn’t be surprised if prosecutors ultimately decided to drop the murder charge, Medwed said he could also see the DA’s office keeping the charges as-is in hopes that a jury would convict on the less-serious manslaughter charge. Medwed liked this to restaurant diners gravitating toward more moderately priced menu items, behavior sometimes called middle option bias or the “Goldilocks Effect.”

What to expect from Karen Read’s retrial

Anyone joining the case from outside the DA’s office is bound to “go through the file with a fine-tooth comb,” Loftus explained. She anticipates the second time around, prosecutors may decide not to call some of the witnesses who offered redundant testimony — for example, the myriad first responders called to the scene the morning O’Keefe died.

“It’ll probably be shortened, in some sense, and we might even have new witnesses that weren’t called,” Loftus said, adding, “Overall, I would not be surprised if we see almost a different type of case presented at trial the second time.”

She noted that during Read’s first trial, many who followed the case found the prosecution’s presentation “a little bit lackluster.” In that regard, Brennan is prosecutors’ second chance at a first impression.

“I think the DA’s office was looking for somebody not only who can try the case in a different way, but also present the case to the public in a different way,” Loftus said. “Because whether we like it or not, … people are so intricately involved in the outcome of this case. I think it will be interesting to see if he’s able to not only win the case, but whether he’s able to change public perception.”

But prosecutors face an uphill battle, particularly when it comes to testimony from the case’s lead investigator, Massachusetts State Police Trooper Michael Proctor. Proctor was relieved of duty and suspended without pay following Read’s first trial, during which he admitted to sending vulgar texts about the defendant to family, friends, and coworkers.

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

‘We’ll see you in court’

In light of the defense team’s accusations of a law enforcement coverup, Loftus said Brennan’s appointment gives the impression of distancing the DA’s office from the trial somewhat, which “may instill some more confidence in the commonwealth’s case.”

“I think bringing in someone else who not only has fresh eyes on it, but has a reputation for someone who’s unafraid to sort of take on tough cases, was the right thing to do, at least from the commonwealth’s perspective,” she said.

Read’s camp, meanwhile, seemed undecided by prosecutors’ change in lineup.

“The news that Michael Morrissey has decided to use taxpayer funds to hire an outside lawyer to prosecute this case speaks volumes about his confidence in his own team,” defense attorney Alan Jackson said in a statement. “They can bring anyone they want to court. We will beat this unjust prosecution, just like we did the last time.

“Like we’ve said to Mr. Morrissey previously, do your worst,” he added. “We’ll see you in court.”