Former assistant district attorney in Bristol and Plymouth County confirmed as new member of Massachusetts Parole Board

Katie Castellani

STATE HOUSE, BOSTON – After rejecting her initial choice, the Governor’s Council voted 6-2 on Wednesday to confirm Gov. Maura Healey’s controversial nomination of Kaitlyn O’Leary to the Parole Board.

Opponents to O’Leary’s nomination raised concerns about her prosecutorial background and lack of experience with reentry and rehabilitation of individuals who were incarcerated. Similar concerns were raised over Vincent DeMore, a Healey nominee who was rejected by the council on a 4-3 vote in May.

Councilors Joseph Ferreira, Tamisha Civil, Mara Dolan, Eunice Ziegler, Terrence Kennedy and Christopher Iannella voted in favor of O’Leary’s nomination. Councilors Tara Jacobs and Paul DePalo voted against both O’Leary’s and DeMore’s nominations. Iannella voted against DeMore’s nomination in May. Ziegler was unable to attend the meeting when the council voted on the DeMore nomination but told the News Service later that she would have voted no if she had been there.

Asked about why he voted in favor of O’Leary and not DeMore, Iannella told reporters that he spoke with Parole Board member Charlene Bonner about O’Leary’s nomination. Iannella said Bonner told him that she’s worked closely with O’Leary – who began working for the Parole Board in November 2023 as an attorney – and that the nominee would be a good addition to the board.

“That was a big factor to me. Yeah, she’s a prosecutor. I don’t really like prosecutors on the board, but this has been vacant for a long time,” Iannella said.

Civil spoke in favor of O’Leary’s nomination Wednesday.

“Prosecutors are charged with seeking justice,” Civil said. “That can mean incarceration, but it can also mean diversion, treatment, mental health services, substance use treatment, rehabilitation and other resources when those options serve justice. And most importantly, prosecutors see the impact of crime on victims. That perspective matters.”

Civil said that O’Leary has worked closely with those seeking parole and has firsthand knowledge of the process including reentry, rehabilitation and resources available to those who are incarcerated. Civil also said the board currently has three former probation officers, a defense attorney, a social worker and a psychologist and that she supports having those perspectives on the board. However, to ensure balance, there needs to be members who can consider victims’ perspectives.

“Who is bringing the perspective of accountability and the impact of offense into these decisions? A former prosecutor can bring a perspective while still understanding rehabilitation and reentry,” Civil said. “Voting yes does not mean ignoring rehabilitation. Voting yes does not mean denying second chances. Voting yes does not mean automatically opposing parole. It means adding another perspective to the conversation.”

Ziegler also spoke in favor of O’Leary’s nomination, saying the board has had an opening for five months and that vacancy has strained the board and caused a backlog of hearings. Ziegler said she did not take her vote lightly and that it was in favor of “no further delays to justice.” The councilor agreed with advocates that a candidate with lived experience of going through the parole process or someone who has worked in behavioral health would be helpful to the board.

“However, it is not what’s before us,” Ziegler said. “Nevertheless, I do find it valuable. And moving forward, I welcome the opportunity to work with members of the community to address the statute, to look at ways to ensure that we have a more comprehensive makeup of the of the board that creates a true balance that will focus more on professional experience in behavioral health, forensic psychology, law enforcement, and lawyers, as I believe this balance of experience would lead to upholding justice.”

Olivia DuBois, a licensed independent clinical social worker who testified against the DeMore and O’Leary nominations, said she is disappointed in the council’s decision.

“My experience working with people seeking parole and working in the criminal legal system for over a decade, is just that the experience should be different,” DuBois said. “We need a Parole Board member who has a really deep understanding of reentry.”

DuBois said her opposition wasn’t solely based on the nominees’ prosecutorial backgrounds. DuBois said she’d like to see a candidate who has worked in reentry services or who has lived experience of going through the process – experiences a prosecutor usually doesn’t have, she said.

DePalo agreed.

“A Parole Board member’s work is essentially about psychology and human behavior,” DePalo said in a statement to the News Service. “That’s why people like myself and many members of the Massachusetts’ legislature’s Criminal Justice Reform Caucus have sought Board members who have deep expertise in rehabilitation and reintegration through direct work with impacted populations. Today’s nominee is a talented and dedicated public servant who lacks this deep and direct experience.”

Before working for the Parole Board, O’Leary worked as an assistant district attorney in the Bristol and Plymouth County District Attorneys’ offices. She was an assistant attorney general from 2019 to 2022 under Healey, who was the state attorney general from 2015 to 2023.

Healey took the unusual step of appearing before the council to vouch for both Parole Board nominees.

While speaking last week to councilors in favor of her nomination, Healey said that “for years” the board was criticized for its prosecutorial lens, which is why she has worked to “build a board with expertise spanning mental health, reentry, juvenile justice, restorative justice and parole supervision.”

“Yet 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,” Healey said.

Councilors also voted unanimously to confirm both Keith Nicholson as an associate justice of the Boston Municipal Court and Lynn Feigenbaum as an associate justice of the Superior Court.

[Ella Adams contributed reporting.]

Katie Castellani is a reporter for State House News Service and State Affairs Pro reach her at kcastellani@statehousenews.com