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Gov. Healey declares new Parole Board pick after her last nominee was rejected 11%
By Katie Castellani19% State House News Service34%
7/22/2026, 11:29:12 PM
BS Summary: This article contains 7 faulty reasoning types, including Halo Effect, Begging the Question, and Recency Bias, with Framing Effect as the most egregious example at 12% saturation with 57 hits. Analysis detected 219 faulty-reasoning hits from 476 analyzed words, generating a BS Score of 27.2% and a BS Rank of 11% (19,683 of 21,887 articles). This article is better (less manipulative) than 89.90% of the article peer group.
Gov.
Maura Healey announced a new Parole Board nominee with prosecutorial experience on Wednesday, months after the Governor's Council rejected her previous nominee who garnered criticism for their background as a prosecutor.
Healey nominated Kaitlyn O'Leary, who is the board's deputy general counsel and deputy interstate compact administrator — a position she's held since June, according to O'Leary's resume.
O'Leary began working for the Parole Board in November 2023 as an attorney.
O'Leary has also worked as an assistant district attorney in the Bristol and Plymouth County district attorneys' offices.
In those roles, O'Leary prosecuted homicides, firearm offenses, narcotics trafficking, sexual assaults and domestic violence cases, according to Healey's office.
She also was an assistant attorney general from 2019 to 2022 under Healey, who was the state attorney general from 2015 to 2023.
In that role, O'Leary handled investigations involving firearms, narcotics and electronic surveillance, according to Healey's office.
"Kaitlyn O'Leary has dedicated her career to serving the people of Massachusetts and keeping our communities safe," Healey said in a press release.
"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.
I know she'll be a tremendous asset to the Board."
In May, the council voted 4-3 to reject Vincent DeMore's nomination to the Parole Board.
The vote came after Healey wrote a letter to the council and made an unusual appearance before the group where she implored members to support her nominee.
DeMore's nomination had sparked backlash from those who said his work as a prosecutor doesn't reflect the “type of multidisciplinary, rehabilitative expertise” needed on the board.
At an April hearing, opponents also said DeMore might follow other board members who departed to pursue judgeships.
DeMore has worked as defense counsel in state and federal courts and worked in the Suffolk County district attorney's office for 11 years beginning in 2007.
Councilors said during a meeting on Wednesday that they plan to hold a hearing on O'Leary's nomination on Aug.
12.
If confirmed, O'Leary would would fill the vacancy left when Tonomey Coleman was confirmed as a judge on the District Court.
Healey also unveiled other judicial nominees: Christopher Spring as an associate justice of the Superior Court; Connie Wong as an associate justice of the Boston Municipal Court; Lisa McCormack as an associate justice of the Probate and Family Court; Lynn Feigenbaum as an associate justice of the Superior Court; and Keith Nicholson as an associate justice of the Boston Municipal Court
Councilors unanimously voted to confirm Raquel Webster as an associate justice of the District Court.
Councilors also voted 7-1 to confirm Thomas Johnson as an associate justice of the District Court.
Councilor Tara Jacobs voted against Johnson's nomination.
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