Press Release: 7/23/2026

Governor Healey Nominates Attorney Kaitlyn O’Leary to the Massachusetts Parole Board

 

FOR IMMEDIATE RELEASE:

7/22/2026

 

BOSTON — Governor Maura Healey today nominated Attorney Kaitlyn O’Leary to serve on the Massachusetts Parole Board. If confirmed by the Governor’s Council, O’Leary will fill the vacancy created when Tonomey Coleman was confirmed as an Associate Justice on the District Court. 

 "Kaitlyn O'Leary has dedicated her career to serving the people of Massachusetts and keeping our communities safe," said Governor Maura Healey. "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." 

 

“Attorney O’Leary brings extensive legal experience, sound judgment and a deep understanding of the parole process,” said Lieutenant Governor Kim Driscoll. “Her commitment to fairness, accountability and public service will strengthen the important work of the Parole Board on behalf of the people of Massachusetts.” 

The Massachusetts Parole Board promotes public safety through the supervised, conditional release of incarcerated individuals and supports successful reentry into the community. Board members conduct parole release hearings, notify and assist victims, supervise individuals on parole, and coordinate reentry services to those leaving custody without post-release supervision.   

About the Nominee:  

Kaitlyn O’Learycurrently 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. She also represents the agency in administrative and court proceedings and serves on the State Domestic Violence Fatality Review Team. 

Prior to joining the Parole Board, Attorney O’Leary served as an Assistant District Attorney in the Bristol and Plymouth County District Attorneys’ Offices, prosecuting serious criminal matters including homicides, firearm offenses, narcotics trafficking, sexual assaults, and domestic violence cases. She played a key role in public safety initiatives focused on reducing gang violence, illegal firearms activity, and narcotics-related offense through collaboration with law enforcement, community partners, and treatment providers.  

She also served as an Assistant Attorney General in the Massachusetts Attorney General’s Office for three years, where she handled complex investigations involving firearms, narcotics, and electronic surveillance.  

Attorney O’Leary earned a Bachelor of Arts, cum laude, from Brandeis University and a Juris Doctor, cum laude, from Suffolk University Law School. 

Statements of Support: 

Judith Lyons, former General Counsel of the Parole Board: 

“Kaitlyn O’Leary is a hardworking and thoughtful attorney who has dedicated herself to serving the people of the Commonwealth.  Her professional experience and her sincere desire to ensure public trust in the parole process will serve her well in balancing the concerns of victims, incarcerated individuals, and the people of the Commonwealth to support public safety, accountability, and safe community re-entry for incarcerated individuals.” 

Mike Bergeron, Criminal Defense Attorney: 

“I have known Kaitlyn for over a decade.  She is a smart, thoughtful, and fair-minded attorney.  Her reputation is beyond reproach, and she is more than qualified to make fair and reasonable parole decisions.” 

Allen McCarthy, Criminal Defense Attorney: 

“Kaitlyn is a great attorney, but more importantly, she will evaluate each case that comes before the Parole Board with responsibility, intellect, and integrity, and without bias.” 

###