A Chelsea District Court Stalwart Retires:Colleagues,Friends Honor Robert O’Leary

By Cary Shuman

George Cashman, Clerk Magistrate Kevin Murphy, and retiring First Assistant Clerk Magistrate Robert O’Leary, who was honored at a retirement celebration at the Knights of Columbus in Charlestown.

George Cashman, Clerk Magistrate Kevin Murphy, and retiring First Assistant Clerk Magistrate Robert O’Leary, who was honored at a retirement celebration at the Knights of Columbus in Charlestown.

Robert O’Leary, retired first assistant clerk magistrate of Chelsea District court, was honored at a celebration at the Knights of Columbus in Charlestown.

The room was filled with tremendous love and respect for a man who served with distinction in the Massachusetts court system for 43 years.

Professional court officials, friends, and family hailed his outstanding career, his warmth, and the assistance, knowledge, and guidance he provided to co-workers each day on the job.

He attended St. Francis School on the top of Bunker Hill Street in Charlestown, St. Benedict’s School, and Matignon High School.

A veteran of the Vietnam War, O’Leary attended Northeastern University and worked for the Teamsters as a truck driver for ten years.

In 1974, O’Leary began his service as an assistant clerk magistrate. He had previously been a summer intern at the court while a high school student. He was promoted to first assistant clerk magistrate at the Chelsea District Court in 1993.

He and his wife, Donna, have been married for 47 years. They have two daughters, Katie, a certified drug coach in the court system, and Bonnie, and five grandchildren.

Clerk Magistrate Kevin Murphy said O’Leary was not only an outstanding court official but a close friend as well.

“I came to Chelsea Court 21 years ago from Superior Court and Bobby and I not only struck up a nice employee relationship but we also struck up a good friendship,” said Murphy. “He’s been a big asset to the court. I miss him and the court’s going to miss him. You can see by the people who are here tonight how he was well liked by everyone.”

Edward O’Neil, assistant clerk magistrate, served as master of ceremonies. He was masterful in weaving humorous anecdotes and touching stories about O’Leary, his long-time colleague and friend.

“It’s nice to see such a blend of Chelsea and Charlestown in the same room,” said O’Neil.

State Rep. Dan Ryan presented a citation to O’Leary in recognition of his outstanding career.

“We’re celebrating a career but also a guy that’s helped out a lot of people,” said Ryan. “The court system is a place of advocacy. For people in Chelsea and Charlestown, the court has taken care of their neighbors and friends.  You’re looking for a friendly face and someone to help you out, and Bobby O’Leary embodied all of that. We thank you for your service.”

Governor’s Councilor Terrence Kennedy, who presented a citation on behalf of Gov. Charlie Baker, recalled O’Leary assisting him when he was a young attorney.

“Bob O’Leary has been very good to me over the past 34 years,” said Kennedy. “He was always helpful and accommodating, as he has been with everyone at the court.”

Presiding Justice Matthew Nestor said O’Leary “couldn’t have been more welcoming” upon his arrival at the court four years ago.

“The nice thing about Bobby being at the court for all those years is that he hasn’t changed – he is that face in the courthouse for the people who come in and are bewildered, are scared, and they’re looking for that friendly face,” said Nestor. “He has helped so many people over the years. It’s been an absolute pleasure. We’re going to miss you more than you know.”

Somerville District Court Clerk Magistrate Robert Tomasone spoke of O’Leary’s generous assistance to the children of the North End Athletic Association.

“He’s just a wonderful guy,” Tomasone told the gathering. “There are a lot of accolades and citations tonight but the truth of the matter is that when you leave here, the love of your family and friends will always be there and that’s the respect you have from all these fine people.”

Attorney Joseph Machera recalled O’Leary words of wisdom when he would come in to the courthouse. “He was unbelievable. He was great,” said Machera.

Machera added that he and O’Leary became friends and during vacations to Vermont through the years, he learned of his friend’s culinary talents.

“Bobby is an especially good cook,” said Machera. “We had some wonderful weekends.”

While lauding O’Leary dedication to his job, Machera said, “Bobby really took his job seriously. He really helped me out a lot.”

Katie O’Leary thanked her parents and noted how supportive and loving her mother has been of her father’s life and career.

She spoke with emotion about how proud she was of her father.

“How do you describe the most influential man in your life, the one who has shaped the woman you have become?” said Katie. “How you put so much love and support in to a couple of paragraphs?

“I could tell you all day that he’s a dedicated and loving husband, a devoted and supportive father, and a phenomenal grandfather – but that doesn’t him do him justice,” she said. “I would rather focus more on things he taught me over the years. There have been so many lessons and hardships along the way but so many blessings as well.

“His nature is altruistic in every sense of the word,” she said. “He never wanted to be recognized for the things he did. His work ethic is impeccable and speaks for itself. His character and integrity are unwavering and loyal to a fault. And his commitment to family and friends is something you cannot a price tag on.”

The loving embrace that father and daughter share before the guest of honor’s remarks spoke grandly about “the person that inspires me day in and day out.”

O’Leary received a warm standing ovation from the gathering.

“I want to thank everyone for being here tonight,” said O’Leary. “Thanks to everyone who I have worked with through the years – judges, attorneys, district attorneys, probation officers, court officers, security, custodial staff, especially the clerical staff – they’re the lifeblood of the system.”

He graciously thanked Carolyn Shannon for her efforts in organizing his retirement party. He then proudly introduced his family.

True to his nature, O’Leary left the audience with a witty story that was well received by the audience. A second standing ovation wrapped up a special tribute to a man who has obviously touched a lot of people’s lives in a positive way.

Echoing the wishes of the people in attendance, Kevin Murphy said, “I hope Bob O’Leary has a great retirement.”

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