After a rare rebuke, Governor’s Council approves Healey’s former prosecutor pick for Parole Board

Governor Maura Healey has spent the last several months pressing the council to approve an ex-prosecutor to the Parole Board.

For Governor Maura Healey, the second time’s the charm with the Governor’s Council.

The state panel on Wednesday approved Healey’s latest nominee to the Parole Board, former prosecutor Kaitlyn O’Leary, after rejecting the governor’s initial pick — who is also a former prosecutor — over concerns about packing the board with too many people with law enforcement résumés.

In brief remarks Wednesday before the council’s 6-2 vote, Councilor Tamisha Civil said the perspective of a former prosecutor is necessary on the Parole Board.

“Let’s be clear about what a prosecutor does. A prosecutor’s job is not simply to ask for people to be incarcerated. I should know that as a former victim witness advocate,” said Civil, a Stoughton Democrat. “Prosecutors are charged with seeking justice. 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.”

Prosecutors, Civil added, “see the impact of crime on victims.”

Healey has spent the last several months pressing the council to approve an ex-prosecutor to the Parole Board amid criticism from the state GOP and Republicans running against her about the board’s decisions. That intensified after a parolee allegedly shot and wounded motorists on Memorial Drive in May.

The board holds thousands of hearings each year, largely in state prisons and county jails, to consider the release of inmates.

In a statement after Wednesday’s vote, Healey said O’Leary will bring “deep experience” in the criminal justice system to her new role.

“Her years spent working as a prosecutor and with victims and survivors have given her a strong understanding of the responsibility to keep our communities safe while ensuring every case is considered fairly and carefully,” Healey said.

O’Leary has held multiple positions at the Parole Board since she joined in 2023. She is currently the deputy general counsel for the board and oversees its agreements with other states for supervising parolees.

Before joining the Parole Board, O’Leary worked as an assistant district attorney in the Bristol County and Plymouth County district attorneys’ offices, where Healey’s office said she prosecuted “serious criminal matters” such as homicides, firearm offenses, and narcotics trafficking.

O’Leary also spent three years as an assistant attorney general under Healey when she was the state’s attorney general. O’Leary earned a bachelor of arts from Brandeis University and a law degree from Suffolk University Law School.

Attorney Kaitlyn O’Leary.Governor Healey's Office

Councilor Paul DePalo, a Worcester Democrat who voted against O’Leary, said in a statement Wednesday that she lacked expertise in “rehabilitation and reintegration,” and that he wanted to keep the board “composed primarily of individuals whose professional training and experience directly align with the board’s work of protecting public safety and ensuring successful re-entry.”

Tara Jacobs, a North Adams Democrat who also voted against O’Leary’s nomination, did not respond to a request for comment on Wednesday.

In an interview last week with the Globe, Jacobs said she did not want someone on the board whose experience was “deeply rooted in the criminal justice system from the standpoint of looking at originating offenses and evidence and sentencing and all that.”

“That is not the kind of experience that I think benefits a Parole Board that has historically, and even now still, over-focused on original offenses in a way that relitigates original crimes,” Jacobs said.

Jacobs and DePalo also opposed Healey’s original pick for the vacancy on the Parole Board, Vincent J. DeMore III, a former prosecutor for the Suffolk County district attorney’s office.

DeMore faced a wave of opposition from advocates who argued he lacked the professional background to bring balance to the body. Even after Healey doubled down on DeMore’s nomination, the Governor’s Council rejected his nomination in a narrow vote in May.

It was a rare rebuke from the council to a sitting governor. The Governor’s Council, an eight-person panel of elected officials, infrequently rejects nominees to the Parole Board, the Globe previously reported.

Healey nominated O’Leary to the post two months after DeMore’s rejection, arguing the board should have someone who has handled difficult criminal cases and worked with victims.

During Wednesday’s hearing, Councilor Eunice Zeigler said the vacancy has caused delays, a “backlog of hearings, and put a strain on the institution of justice that is the Parole Board.”

Zeigler, a Methuen Democrat, said she was “sensitive” to those who did not want a prosecutor on the board.

“I want to acknowledge the opposition about the lack of lived experience and limited behavioral experience that this candidate holds,” she said. “This experience, I agree, would be invaluable to the board. However, it is not what’s before us.”