On Aug. 12, the Massachusetts Governor’s Council will vote to confirm or deny Parole Board nominee Kaitlyn O’Leary. It is Gov. Maura Healey’s second attempt to fill the empty board slot with a prosecutor.
The oft-maligned eight-member council, which votes on the governor’s judicial and other nominees, rejected her first pick, Attorney Vincent DeMore, on May 20 in a 4-3 vote. Advocates had circulated a letter signed by more than 400 individuals and organizations, stating that the former prosecutor’s background and expertise did not qualify him for the board.
Gov. Healey made a rare appearance at the council’s weekly assembly in May to argue in support of DeMore, and she did so again on Aug. 5 for her new nominee. According to a media release, “O’Leary currently serves as the Deputy General Counsel and Interstate Compact Administrator for the Massachusetts Parole Board, where she conducts parole hearings, advises agency leadership, oversees legal operations, manages interstate compact matters, and develops policies and procedures to support the Board’s mission.”
“I was here before. I’m here again.” The governor’s statement came ahead of the public hearing later that day. When Healey was attorney general, she hired O’Leary as an assistant attorney general. She added that her nominee’s prosecutorial background and work with “victims and survivors” would help “balance the board.”
“This is important to me,” Healey said. “This is important to Massachusetts.”
How the parole system actually works
As we have shown in prior reporting, the parole system is often ignored, misunderstood, and misrepresented. In reality, it is the earned and conditional release of prisoners to the free world where they live under strict supervision for the remainder of their sentence.
Parole requires a prisoner to prove to a parole board that they are no longer a risk to society. The Prison Policy Initiative (PPI), a nonprofit think tank, analyzed 35 states that grant parole and found that “most parole boards are politically appointed [by the governor] and aren’t required to have diverse perspectives or experiential knowledge.”
Often, state legislatures vote on a governor’s nominee, although there are some states where no second look is required. New Hampshire is the only state besides Massachusetts where a council independently evaluates the picks. Terms of board members nationwide vary from two to seven years, but in Massachusetts, members serve five years and can be reappointed without term limits.
Some states favor those with criminal legal system experience to serve on these bodies, while none call for a member who has lived experience with probation, parole, or prison. Some parole boards around the country require attorneys, but they don’t specify what kind of attorney. And many states, like Massachusetts, allow members to have a variety of backgrounds. They look for recruits who enforce the law as well as members who have expertise in areas like substance use, mental health, reentry, and juvenile justice.
According to Massachusetts General Law, there are seven board members: “one must at all times have experience in forensic psychology,” and a nominee must be a graduate of a four-year college with five years of experience in one or more of the following: “parole, probation, corrections, law, law enforcement, psychology, psychiatry, sociology, social work.”
Speaking for this article, PPI spokesperson Wanda Bertram said “the public welfare is no better represented by law enforcement than by community supervision workers and social workers, all of whom are present on the Massachusetts Parole Board.”
Currently, the Mass Parole Board has six members: Charlene Bonner, a forensic psychologist; Edith Alexander and Rafael Ortiz, who come from a probation background; Sarah Coughlin, a clinical social worker; James Kelcourse, an attorney and former state representative; and Chair Angelo Gomez, who was a corrections and parole officer, and then served as the chief parole supervisor for field services at the Parole Board. There is one vacancy.
The controversy over a prosecutor
Defense attorney Michael Bergeron, one of three witnesses who testified for O’Leary, said that “one may wonder whether an attorney with a former prosecutorial background can make reasonable and fair decisions regarding the parole of incarcerated defendants.” Adding that the nominee’s “background should be of no concern. Quite the opposite. Kaitlyn’s background should provide confidence.”
Kate Malone, a civil litigator from Springfield, echoed Bergeron. Saying O’Leary has the “courage to make decisions,” Malone cited how “as an assistant attorney general, she prosecuted Springfield police officers in relation to an incident which deeply eroded public trust.”
On the other side, 14 people testified against O’Leary, countering the view that her background would be an asset. Some discussed what PPI calls an “ingrained law-and-order background that creates a structural bias toward punishment.” Others simply said that the addition of a prosecutor could undermine the board’s duty to evaluate rehabilitation and reentry.
Exoneree Edward Wright, who spent four decades in prison and testified on Zoom, said he helped many people with parole petitions while he was behind bars. “Prosecutors opposed every person,” he said, “even in cases where they knew that a person was possibly innocent.”
Milton Jones, director of reentry services at the Louis D. Brown Peace Institute, clarified how his background gave him a unique platform. “I am formerly incarcerated, fully exonerated … and I am a survivor of homicide, having lost a son.”
Jones said a “prosecutor’s responsibility is to secure convictions and advocate for public safety through criminal prosecution,” while a “Parole Board member … must objectively evaluate whether an individual has changed, accepted responsibility, and can safely return to the community.” He emphasized, “Those are distinct functions requiring different perspectives.”
Mac Hudson, formerly incarcerated for 33 years, is now a community liaison and paralegal for Prisoners’ Legal Services of Massachusetts. Speaking out against prosecutors on the Parole Board, he challenged members of the Governor’s Council.
“The governor doubled down and said we will get a prosecutor,” Hudson said. “And now I’m saying, Are you going to listen to the people that you represent? Are you going to listen to the governor because you’re afraid of political backlash? This is the real question facing this Governor’s Council.”
What does it mean to have a ‘law enforcement background’?
When it came his turn to ask questions of Kaitlyn O’Leary, Councilor Joseph Ferreira first responded to Hudson.
“I do listen to the people in my town, in my district. I represent 900,000 people. … And never once has anyone come up to me and said, Hey, I want you to put people on a parole board to let more people out of jail. I have never heard that in my 12 years that I’ve been here.”
Ferreira told O’Leary that she would “make a fantastic member of the board,” and said she would be “the first and only prosecutor or law enforcement type, however you want to call it, on there.” The councilor added, “I was in law enforcement for 30 years. There’s no one on the Parole Board that’s in law enforcement. I can tell you that for a fact.” Ferreira didn’t ask O’Leary any questions.
Criminal defense attorney Patty Garin, director of the Northeastern Law School Prisoners’ Rights Clinic, disputed that characterization of “law enforcement.” In her testimony against O’Leary, Garin explained to the council that Parole Board members Alexander, Ortiz, and Gomez represent law enforcement.
Councilor Christopher Iannella previously stated at a hearing (for Angelo Gomez): “I’ve always been a strong supporter that we should have fewer members of law enforcement and more members on the Parole Board with the social science background.” He challenged Garin, questioning if she really considered these members “law enforcement.”
In a follow-up phone interview, Garin said, “I’m afraid some councilors were redefining what law enforcement is in order to justify their votes. Law enforcement describes persons who are employed to make sure people follow the law. This is exactly what correctional officers, probation officers, and parole officers do. If confirmed, Kaitlyn O’Leary would be the fourth member of the board from law enforcement.”
Later at the hearing, Councilor Paul DePalo said that he took issue with Healey’s characterization that the Parole Board does not listen enough to victims. He asked O’Leary to validate his understanding that the board is “very respectful of victims,” which she did by saying that the agency’s “victims’ services unit works very strongly, consistent with our statutory obligations but much more than that.” The nominee further detailed how important it is for her to hear the voices of victims.
DePalo also noted a letter the legislature’s Criminal Justice Reform Caucus sent to the governor on July 31. While it did not mention O’Leary by name, the coalition of lawmakers asked for “a board member with deep expertise in rehabilitation and reintegration through direct work with incarcerated and formerly incarcerated individuals.”
Councilor Tara Jacobs told O’Leary, “There’s a lot of positives to be said about the work that you’ve done.” However, she added, “the type of experience that would add diversity is not legal experience.”
Jacobs emphasized the same sentiment reflected in an open opposition letter launched by members of the public. As of this writing, it has 275 signatures.
“We could benefit from someone with clinical psychology experience, deep deep reentry experience, rehabilitative experience … and the list goes on,” Jacobs said.
The upcoming vote
As we previously reported, Councilors DePalo, Mara Dolan, Iannella, and Jacobs voted “no” on Vincent DeMore, while Councilors Tamisha Civil, Ferreira, and Terrence Kennedy voted yes. Councilor Eunice Zeigler was not in attendance for that vote.
Councilor Iannella, who voted against DeMore, said at his hearing, “If the Parole Board’s going to change, if we’re going to have more people with social science background, we have to take a stand.”
This time, pressures on the council to confirm O’Leary are mounting. In addition to her speech to the body, the governor issued a press release with the title: “Judges, Prosecutors, Defense Attorneys, Victim Advocates and Public Safety Leaders Endorse Former Prosecutor Kaitlyn O’Leary for Massachusetts Parole Board.”
Meanwhile, news outlets like the Boston Herald have mounted criticism that Healey and her Parole Board are “releasing murderers,” publishing headlines such as, “Massachusetts murderer who killed bouncer at Boston nightclub has been granted parole.” The tabloid has attacked the Governor’s Council as well, namely Councilor Dolan’s concern that a nominee must not only assure public safety, but also assure opportunities for parole. According to the Herald, “councilors rejected her [the governor’s] last ‘law and order’ candidate over fears he would ‘go too far in ensuring public safety.’”
At the end of her testimony, Patty Garin told the councilors that their “constituents do not want another law enforcement person on the board.” Referring to the pressures they may face, she said, “I don’t know what’s going on with these nominations. … I’ve heard people threaten from [the governor’s] office, If you don’t do this, we’ll just nominate another prosecutor.
“That’s not the point of government. Stand up to this nomination.”
