PITTSFIELD — Richard A. Simons had a job that no one would call easy.

But he still loved every minute of it.

As first justice for Berkshire County’s Probate and Family Court, Simons has helped litigants work through some of the thorniest issues of their lives. Couples in the midst of divorce proceedings. Children caught up in custody battles. Family members at odds over how to divvy up an estate.

Calm and soft-spoken, Simons resisted the urge to match high-strung emotions in the courtroom.

Kadie Bragg is embraced by the Honorable Richard A. Simons during a graduation ceremony for the program, `Enhancing Families through Literature" at Berkshire Probate and Family Court in Pittsfield on May 30, 2017.

“I think I've been somewhat successful in just bringing down the temperature in the room, just by talking calmly about the issues,” he said.

As his longtime career in law comes to an end, Simons is grateful for the opportunity to have worked with so many families in pursuit of a better life for themselves and their children.

“I feel as though I had the privilege of a lifetime having this job,” he said.

Simons last took the bench on June 30. He will officially retire on Aug. 27.

Ahead of Simons’ departure, members of the city’s legal community are sad to say goodbye to a steadfast presence in the courtroom.

“It’s a loss,” said Elizabeth J. Quigley, a longtime Pittsfield lawyer. In addition to serving alongside Simons in his days as an attorney, she has tried many family-related cases in front of him over the years.

“Win, lose or draw, I felt that he was doing his best to be as fair and equitable and just as he could possibly be,” she said. “I know that was his guide, so to speak.”

As Chief Probation Officer Amy A. Koenig holds a certificate, at left, Trista Chandler is embraced by the Honorable Richard A. Simons during a graduation ceremony for the program, "Enhancing Families through Literature" at Berkshire Probate and Family Court in Pittsfield on May 30, 2017.

David Cianflone, another veteran lawyer, said Simons was child-centered and family-centered in his decisions, “always looking for the best possible result.”

“I think that one of the most important things for him was his ability to listen and try and understand the conflict, and try to come up with a resolution that was best for everyone,” he said.

A lifelong career in family law, first as an attorney and then as a judge, has convinced Simons of the general human inclination towards goodness. “What I have learned is that most people want to do the right thing in raising their children,” he said.

As for the people who pass through his courtroom, “You just see them going through a difficult time,” he said. “But you see all segments of society. And to me, it has been such an incredible privilege to represent a judicial system that is here to help parties navigate these incredibly intimate issues.”

Born and raised in Pittsfield, he became eager to leave the city as a teenager, intent on seeing what else was out there in the world. But living and working in Boston as a young man made him realize there’s no place quite like home, and he returned to Pittsfield to raise a family and work in family law. He and his wife have two daughters and three grandchildren.

Simons is a graduate of Union College and Boston University Law School. In 2008, then-Gov. Deval L. Patrick named Simons as a circuit judge to the Probate and Family Court.

Simons is especially proud of his role in co-creating the Enhancing Families Through Literature program, a 12-week court program in Berkshire County that helped parents improve their communication skills through targeted literacy education. It ran from 2014 until the start of the COVID-19 pandemic.

Now 67, Simons has spent a lifetime in the Berkshires. He is a lifelong member of Congregation Knesset Israel, according to Rabbi David Weiner, and previously served as president of the synagogue.

“He's a guy who really thinks about the big picture,” said Weiner. “He's also someone who's very invested in relationships. He knows how to listen to people, how to talk to them, how to set them at ease, and how to move a group forward. That combination is rare and very, very valuable.”

Now that Simons has shed his judicial robes for good, you can find him in a T-shirt and shorts as he trains for the Pan-Mass Challenge, an annual bike ride that takes participants across the state to raise money for cancer research and treatment. He participates in the memory of his wife’s former college roommate, who died of breast cancer.

Despite his love of working with the law, Simons said he knew the time to retire had finally come.

“I was very aware to not stay too long,” he said. “I wanted to end my career with the same level of enthusiasm that I had on the first day.”

Nicholas L. Parsenios, who has succeeded Simons as first justice for the county's Probate and Family Court, said he looks forward to continuing the legacy of excellence Simons is leaving behind.

"I can say he's left an indelible impact on this community and the court," he said of Simons. "He is going to be deeply missed."