Two months after a state panel rejected her nomination of a former prosecutor to the Parole Board, Governor Maura Healey on Wednesday put forward a new candidate — who is also a former prosecutor.
Attorney Kaitlyn O’Leary is deputy general counsel for the Parole Board, one of several roles she’s held since joining the agency in 2023, Healey’s office said. She also oversees the board’s agreements with other states for supervising parolees.
O’Leary previously worked as a prosecutor in Bristol and Plymouth counties and as an assistant attorney general under Healey, who led that Attorney General’s office for eight years before becoming governor.
The Governor’s Council, the elected panel that must vote on her nomination, scheduled a hearing to question O’Leary for Aug. 12. O’Leary was not available Wednesday for an interview, Healey’s office said.
By nominating another former prosecutor, Healey signaled she remains committed to adding that perspective to the Parole Board after the Governor’s Council in May rejected her last nominee, Vincent J. DeMore III, a former Suffolk County assistant district attorney turned defense lawyer.
Healey wants the seven-person board to include a lawyer who has handled complex criminal cases and worked with victims — experience she says is missing from the panel, her office said Wednesday.
In a statement, Healey praised O’Leary for dedicating her career to state government service and public safety.
“As both a leader at the Parole Board and a former prosecutor, she understands the importance of making thoughtful, fair decisions that protect public safety while supporting successful reentry,” Healey said. “I know she’ll be a tremendous asset to the Board.”
O’Leary’s nomination must be approved by the Governor’s Council, a relatively obscure group of elected officials who represent eight districts from across the state.

The body rejected DeMore’s nomination by a 4-3 vote after some council members said they wanted a candidate with more experience evaluating prisoners’ fitness for integrating back into society.
Some criminal justice reform advocates also argued that adding DeMore would give the Parole Board a majority of members with a law enforcement background, given three others previously worked in probation and parole services. One councilor, Eunice D. Zeigler, didn’t attend the meeting when the vote was taken.
About a week before the vote on DeMore, a parolee allegedly shot and wounded motorists on Memorial Drive in Cambridge, generating fresh scrutiny of the Parole Board. But the incident didn’t shift opinions enough among councilors to secure his nomination.
On Wednesday, two opponents of DeMore’s nomination criticized Healey for tapping another former prosecutor.
“Why is Governor Healey doing this? Why does she think it’s OK to put a former DA on the board?” asked Stacey Borden, founder of New Beginnings Reentry Services in Roxbury and a former Governor’s Council candidate.
Borden said she prefers a nominee with a background in psychology or social work, or a person who was previously incarcerated.
“Maura Healey is not hearing the community,” she said.
Olivia Dubois, a social worker with a background working with public defenders, said she was also disappointed with Healey’s nomination.
“The Governor’s Council made it pretty clear they wanted a Parole Board member who had a deep understanding of reentry, mental health, substance abuse, and trauma,” she said.
A former prosecutor hasn’t served on the Parole Board since 2022 when Gloriann Moroney — who had been nominated to the board by Healey’s Republican predecessor, Charlie Baker — resigned to become a District Court judge. If confirmed, O’Leary would fill a vacancy left by Tonomey Coleman, who was nominated last year by Healey, and approved by the Governor’s Council, for a District Court judgeship.
O’Leary on Wednesday drew praise from others, including Julie J. Bernard, chief executive of the Flaschner Judicial Institute, who said O’Leary in 2014 helped to establish a drug court in Brockton District Court.
O’Leary was open to alternatives in incarceration and sentencing, said Bernard, who was the presiding justice in Brockton District Court when she met O’Leary.
“She’s fair-minded, reasonable, and I think she’d be an excellent choice for the Parole Board,” Bernard said Wednesday.
Criminal defense lawyer Michael A. Bergeron said O’Leary has a “unique ability to listen and look at the other side’s perspective and evaluate what was appropriate for each defendant.”
“She is more than qualified to make reasonable and fair parole decisions,” said Bergeron, a former supervising attorney for Pilgrim Advocates, Inc., a nonprofit organization that provides lawyers to indigent defendants.
Robert Sheketoff, a criminal defense attorney who has faced O’Leary in court, said she is smart, detail-oriented, and was attuned to his clients’ circumstances.
The Parole Board holds thousands of hearings annually, mostly in state prisons and county jails, and parole officers supervised nearly 3,000 people in 2024, according to data released by the panel in May.
Four people have joined the Parole Board under Healey, with three getting unanimous votes: Rafael Ortiz and Edith J. Alexander, both former probation officers; and Sarah B. Coughlin, a licensed clinical social worker.
The fourth, Angelo Gomez Jr., a former parole supervisor, was confirmed on a 6-1 vote. He took charge as chairperson of the board in October.
Healey also renominated Charlene Bonner, a forensic psychologist who joined the board in 2011 and was confirmed for a fourth term in 2023. Her credentials satisfy a state requirement adopted by the Legislature in 2014 that the board have at least one member with “experience in forensic psychology.”
Laura Crimaldi can be reached at laura.crimaldi@globe.com. Follow her @lauracrimaldi.
