Press Release  Judges, Prosecutors, Defense Attorneys, Victim Advocates and Public Safety Leaders Endorse Former Prosecutor Kaitlyn O’Leary for Massachusetts Parole Board

BOSTON — Ahead of tomorrow’s hearing before the Governor’s Council, a broad coalition of judges, prosecutors, defense attorneys, victim advocates and public safety leaders are voicing their support for Kaitlyn O'Leary, who was recently nominated to the Massachusetts Parole Board by Governor Maura Healey. 

Supporters emphasized that O'Leary will bring fairness, thoughtfulness, integrity and sound judgment to the Parole Board, along with her deep commitment to justice and centering the voices of victims. They praise her ability to balance public safety with compassion, consider every case on its individual merits, listen to diverse perspectives, and make measured, impartial decisions informed by her extensive experience working in the criminal justice system.

O’Leary was nominated by Governor Healey in July to fill the vacancy created when Tonomey Coleman was confirmed as an Associate Justice on the District Court. Governor Healey has said that it is essential that the parole board include an experienced criminal attorney and someone with experience working closely with victims of crime. O’Leary currently serves as Deputy General Counsel and Interstate Compact Administrator for the Massachusetts Parole Board. Previously, she served as an Assistant District Attorney in Bristol and Plymouth counties and as an Assistant Attorney General, prosecuting serious crimes and leading complex investigations while working with law enforcement and community partners to advance public safety.

Statements of Support:

Angelo Gomez, Chair, Massachusetts Parole Board:

“Over the past several years I have had the opportunity to work closely with Kaitlyn at the Parole Board.  She is a smart, thoughtful attorney with a deep understanding of criminal law, and a history of balancing accountability and public safety with the rehabilitative needs of individuals.  She also has experience working closely with victims of crime and their families. Her knowledge and expertise in these areas will be a tremendous asset to the Board. I know she will hit the ground running and will make an immediate positive impact on the Board.”

Essex County District Attorney Paul F. Tucker: 

“Kaitlyn O’Leary is an outstanding nominee for the Parole Board. Her years of experience as a prosecutor, investigating and evaluating cases, working closely with victims and their families, and balancing public safety with meaningful opportunities for rehabilitation, will bring an important perspective to the Board. I urge the Governor’s Council to confirm her nomination.”

Massachusetts District Attorneys Association: 

“A prosecutorial viewpoint is fundamental to providing the Parole Board with the lived experience of evaluating complex evidence, understanding charging decisions along with trial and appellate procedures, considering risk and recidivism factors, and working directly with crime victims and the impact of trauma. A candidate with prosecutorial experience has responded to and investigated offenses, played a vital role in the court proceedings and the administration of justice in matters that come before the Parole Board, and worked alongside community service providers and stakeholders that absorb the impact of violence and crime. It is imperative that these experiences are reflected in parole decisions.”

Liam Lowney, Executive Director of the Massachusetts Office of Victim Assistance:

“It is important that candidates who possess deep professional experience working with survivors of crime or have personal lived experience with victimization are included on the Parole Board.  A trauma-informed perspective enables the Board to conduct a deeper analysis of a parole candidate’s readiness for reentry and potential impact on community safety.  Appointing a member who understands the full impact of trauma experienced by survivors ensures these values are reflected in every decision, providing the Board with the specialized expertise necessary to ensure fully informed parole decisions and successful outcomes for the Commonwealth.”

Hon. Julie J. Bernard (Ret.), Former Massachusetts District Court Judge and CEO, Flaschner Judicial Institute: 

“I worked closely with Attorney O’Leary when she was assigned as the prosecutor for the new Brockton Drug Court in the fall of 2014. Establishing this specialty court involved several months of collaboration with probation, prosecutors, defense attorneys, clinicians, and administrative staff. This also involved community meetings to discuss the benefits of intensive supervision of probation as an alternative to incarceration. I witnessed Attorney O’Leary’s openness to listen to the ideas of others, and her intellectual curiosity about substance use disorders as a disease. Attorney O’Leary is a fair-minded prosecutor that uses common sense, and treats people fairly.” 

Judith M. Lyons, Former General Counsel, Massachusetts Parole Board: 

“Attorney O’Leary’s work as a Legal Counsel for the Parole Board provides her with an understanding of the needs of the Parole Board. Her knowledge of the policies and practices will be of immeasurable value to the Board’s decision-making. Her experiences will inform her ability to conduct fair and impartial parole hearings, balance the equities of a situation, apply the law, and exercise sound judgement with compassion.”

Michael A. Bergeron, Criminal Defense Attorney, Law Office of Michael A. Bergeron: 

“I know Kaitlyn’s reputation from all sides within the legal community. Whether it be judges, prosecutors, or defense attorneys, all respect Kaitlyn’s ability as a professional, and as a person. Kaitlyn’s reputation is beyond reproach and she is more than qualified to make reasonable and fair parole decisions.” 

Amy McNamee, Criminal Defense Attorney and Former Suffolk County Assistant District Attorney: 

“Kaitlyn was committed to ensuring that if she was to make sentencing concessions, that the safety of the community would not be jeopardized. This attention and commitment led to a fair and just outcome. I have rarely seen that kind of commitment to a case by an assistant district attorney who was balancing quite a few serious cases. Kaitlyn cared about justice; she cared about how she did her job and was the ultimate professional.”

Allen J. McCarthy, Criminal Defense Attorney, Law Offices of Allen J. McCarthy: 

“In my humble opinion, the necessary qualities to be a member of the critically important Parole Board include integrity, intellect, and a commitment to justice. Without any hesitation or doubt, I can say that Kaitlyn O’Leary possesses these qualities and is precisely the type of person that we want sitting on the Parole Board.”

Gregory M. Longo, Former Assistant District Attorney, Plymouth County District Attorney’s Office and Criminal Defense Attorney: 

“Working on cases with Kaitlyn, this time on opposing sides of the law, only increased my respect and admiration for her. Her offers of resolution were always fair, again weighing on what was best for all parties involved, which is a unique skill not all attorneys have. Kaitlyn was always available to discuss a case and was happy to listen and try to look at things from all perspectives.”

Jason A. Guida, Criminal Defense Attorney: 

“Based on my direct experience with her, I believe Ms. O’Leary possess the sound judgement, fairness and thoughtful attention to individual circumstances that the Massachusetts Parole Board requires. She has demonstrated a genuine and consistent ability to weigh mitigating factors, such as a defendant’s personal history, family circumstances, and capacity for rehabilitation, against the interests of justice and public safety, and to arrive at balanced, reasonable outcomes as a result. I believe the Board would benefit greatly from her extensive experience, professionalism, and this capacity for measured, individualized decision-making.”

Deborah M. Almeida, Victim Witness Associate, Massachusetts Superior Court: 

“Ms. O’Leary was an incredible asset in our office who prosecuted her cases with passion and compassion. She patiently listened attentively to victim survivors’ input and requests and took them into consideration while considering a fair and just outcome. She was very detailed, kind and logical.” 

Christian T. McCloskey, Career Specialist, MassHire Bristol Workforce Board; Former Youth Services Coordinator, City of Fall River: 

“Kaitlyn is capable of making important and thoughtful decisions with a view towards evaluating the long-term consequences. In my experience, she was always thinking about the participants and sought to ensure that the individuals that we were working with were held accountable as appropriate but would also receive appropriate services to prepare them for returning to the community.”

Gina Masotta, Former Division Chief, Massachusetts Attorney General's Office: 

“As a former prosecutor, Kaitlyn has a deep understanding of the criminal justice system and how it impacts the lives of those involved in it. She has worked closely with crime victims, witnesses, law enforcement, defense attorneys, and community stakeholders across Massachusetts.”

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