WBUR News17%
Opponents knock Healey's latest pick to fill Parole Board seat 6%
By Ella Adams State House News Service46%
8/5/2026, 11:36:50 PM
Keywords: Healey, Parole Board, Kaitlyn Oleary, Governors Council, Prosecutor, Rehabilitation, Reentry, Criminal Justice
BS Summary: This article contains 13 faulty reasoning types, including Hasty Generalization, Bandwagon, and Composition/Division, with Framing Effect as the most egregious example at 5.8% saturation with 87 hits. Analysis detected 538 faulty-reasoning hits from 1,491 analyzed words, generating a BS Score of 15% and a BS Rank of 6% (27,636 of 29,339 articles). This article is better (less manipulative) than 94.20% of the article peer group.
Opponents of Gov.
Maura Healey's Parole Board nominee Kaitlyn O'Leary lined the Governor's Council chamber on Wednesday as the council heard testimony on Healey's second attempt to fill the open slot.
While three supporters honed in on O'Leary's work and reputation — attorney Michael Bergeron characterized her as "fair, reasonable and honorable" — over 10 people testified in opposition, calling on the council to reject the nomination and instead bring someone into the fold who has expertise in rehabilitation and reentry.
"I think sometimes historically we have amnesia," opponent Matt Hudson said, noting his familiarity with the board because of his time spent incarcerated.
"For decades, parole has been denied to eligible men and women because of prosecutorial prosecutors on the board, like Miss O'Leary.
This is not a judgment against her, but it talks about the mindset of a prosecutor.
She can't help herself.
And we should not put that burden on her."
Healey appealed to councilors ahead of the 1:15 p.m. hearing, touting O'Leary's understanding of the criminal justice system and telling them that the board "lacks representation from an attorney, a lawyer, a prosecutor who understands criminal law and also has experience — important experience — working directly with victims and survivors."
O'Leary, who began working for the board in November 2023 as an attorney and has also worked as an assistant district attorney in the Bristol and Plymouth County District Attorneys' offices, spoke extensively during her hearing about those experiences.
"I was here before.
I'm here again.
This is important to me.
This is important to Massachusetts," Healey said, referring to her appeal before the council in May in support of her first Parole Board nominee Vincent DeMore.
The council voted 4-3 to reject DeMore, after his nomination sparked backlash from advocates who said his work as a prosecutor doesn't reflect the "type of multidisciplinary, rehabilitative expertise" they said is needed on the board and that he may follow other board members who left the board to pursue judgeships.
Healey then nominated O'Leary, also was an assistant attorney general from 2019 to 2022 under Healey, who served as state attorney general from 2015 to 2023.
"You all have done a great job in saying, or at least pushing back and saying, 'We don't need a prosecutor at this time on the board.'
The governor's doubled down and said, 'We will get a prosecutor.
' And now I'm saying, are you going to listen to the people that you represent?
Or are you going to listen to the governor because you are afraid of political backlash?"
Hudson asked.
Licensed independent clinical social worker Olivia Dubois, who also testified in opposition Wednesday, said ahead of the hearing that more than 20 organizations and 200 constituents signed a letter in opposition to O'Leary's nomination, arguing that the board "lacks members who are experts in rehabilitation and reentry," and that her confirmation would make the board majority "law enforcement" with its makeup of "probation, parole and prosecutors."
Councilor Christopher Iannella pushed back at a couple of testifiers for how they categorized "law enforcement" members on the board, and Councilor Joseph Ferreira expressed frustration with those characterizations, as well.
Ferreira, issuing support for O'Leary, said, "I don't know anyone with more knowledge of the Parole Board than you."
"I do listen to the people in my town, in my district – 900,000 people.
Never once has anyone come up to me and said, "Hey, I want you to put people on the Parole Board to let more people out of jail.
I have never heard that in my 12 years that I've been here.
I have heard people that read the newspapers, when they go, ''Oh my God, how could the Parole Board let that person out?'
Ferreira said.
"I think that public safety has to be first.
I think that victims need to be notified and heard."
Republican candidate for governor Brian Shortsleeve and former gubernatorial candidate Michael Kennealy have criticized recent decisions of the board, arguing an overhaul is needed for public safety reasons.
First Assistant Chief Probation Officer at the Brockton District Court Michelle Rawdon spoke about how O'Leary cares about those she interacts with, seeing them "as people and not just statistics" and approaching her job holistically.
But Louis D.
Brown Peace Institute Re-entry Services Director Milton Jones, who said he was formerly incarcerated and exonerated, told councilors he didn't believe a former prosecutor should serve on the board.
"The roles of prosecutor and parole decisionmakers are fundamentally different and create an appearance of bias that undermines public confidence," Jones said.
"The parole process is intended to focus on rehabilitation, institutional behavior, evidence-based risk assessment, and successful reintegration — not to retry original cases.
A prosecutor has often spent years building a case against defendants and advocating for lengthy incarceration.
Even if the prosecutor acts in good faith, which I'm sure she has, the public can reasonably question whether they can fully separate that professional identity."
Councilor Mara Dolan asked O'Leary about concerns that her work as a prosecutor means she'll continue thinking like a prosecutor and wrongfully deny parole, to which O'Leary said, "the aim of the board must be to strike the balance between second chances and public safety."
"It would be naive to think that no one who has been denied parole might not have gone on to recidivate, but I can tell you that I take the weight of this responsibility very seriously, and would evaluate each individual case on individual merits," O'Leary added.
Chief Empowerment Officer at THRIVE Communities of Massachusetts Kim Yeasir said, "It's clear that the governor wants to see someone who is victim-centered on the Parole Board, and I don't see any opposition to that.
I think there's many candidates who can hold that and people with lots of skills around supporting survivors."
She encouraged the council "to consider what that might look like outside of prosecution," alongside a number of different people from social and reentry organizations and others who said they'd been wrongfully imprisoned.
Iannella later asked O'Leary, "What do you say to these people?
They're not against you, they just think if you're on the Parole Board they're not gonna get a fair shake."
She replied that she "appreciate[d] their advocacy" and said she became a lawyer due to "a call to public service."
Iannella again asked her, "With all due respect, you really didn't answer my question."
"I hear these stories.
Thirty-three years in jail.
How do you sleep at night if you're on the Parole Board and you voted against this person's parole?"
Ianella said.
"Forget about all that experience here and there.
As a human being, tell me what you feel."
O'Leary replied: "Those stories are devastating.
Absolutely devastating."
In another line of questioning about how important it is to her that people show remorse when coming before the board, O'Leary said that taking responsibility "can be important evidence of personal growth" but that "it is not a prerequisite for a person to take responsibility as being necessary for a positive parole grant."
Councilor Tara Jacobs told O'Leary that "There's a lot I like about you, there's a lot I like about your values," but that "the type of experience I think would add diversity is not legal experience."
"We could benefit from someone with clinical psychology experience, with deep, deep reentry experience, rehabilitative experience, social work [experience] and the list goes on, just in terms of what we don't have," Jacobs said.
Councilor Tamisha Civil, who chaired the hearing, told the News Service her vote depends upon what her constituents want, and that "I believe that everyone has the opportunity to share their experience and what they've seen throughout the criminal justice system.
However, we are looking for balance.
If we look around our state of Massachusetts, there has been an increase of gun violence, there has been an increase of sexual violence."
"Once a prosecutor is not always a prosecutor.
Once a criminal is not always a criminal.
We all have an opportunity to evolve and learn from our experiences, but also do good to where we can in our criminal justice system," Civil continued.
Councilor Paul DePalo also questioned O'Leary on issues such as whether she thinks victims are being heard by the board and how she'd approach crafting conditions of parole.
He noted that he "personally could care less if there's a lawyer on the Parole Board" and drew in 2021-era conversations about structural racism in the parole process.
O'Leary said she does feel like victims are being heard by the board, expressing that she has worked through cases with victims in her role.
The Governor's Council at its 12 p.m. meeting voted 6-0 to confirm both Christopher Spring as an associate justice of the Superior Court and Lisa McCormack as an associate justice of the Probate and Family Court.
Speakers
9speakers52%attributed speech713writer words
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55%flagged-word coverageMilton Jones
87 attributed words11% of attributed speech32% writer coverage
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