Retired Mass. Housing Court Judge Anne Kenney Chaplin died suddenly at her Truro home on July 21, 2025. The cause is unknown, pending an autopsy. She was 75.
“She was generous; she was faithful,” said Mary Cole, her former colleague and friend of 40 years who spoke to her on the phone nightly.
Born in Boston on Dec. 6, 1949, Anne was adopted at birth by the late Joseph and Mary Kenney, a firefighter and homemaker, and raised in Belmont. She attended Catholic school, Boston College, and the University of Virginia Law School, graduating in 1978 and going on to practice at several Boston firms — LeBouef, Lamb, Lieby and MacRae; McCullough, Stievater & Polvere; and Chaplin & Chaplin. She focused on landlord-tenant disputes.
In 2000, she was nominated to the Housing Court bench by Gov. Paul Cellucci and served as a justice at courts in New Bedford, Taunton, and Fall River until she retired in 2019.
“Her reputation was that she was thorough, listened to both sides, and rarely said anything from the bench,” said Marylou Muirhead, a fellow judge who met Anne 40 years ago. “While she’d occasionally ask a question, there was no way you could tell what was going on in her head.
“As a friend,” she added, “she was a lot of fun.”
She was also a spirited and devoted grandmother, said her stepdaughter Meg Chaplin, a psychiatrist whose father, the late Ansel B. Chaplin, married fellow attorney Anne in 1995 after a long friendship. He introduced her to life on the Cape at the Truro house that had been in his family for generations.
Anne became a “bonus grandmother” for Ansel’s grandchildren and an important figure in his children’s lives, said Meg. In 2023, Anne officiated the wedding of Meg’s son at the Truro house.
“She and I hated that term, ‘stepmom,’ ” Meg added. “She’d always say, ‘My husband’s daughter,’ and in a lot of ways she was more like an older sister to us, especially when my dad died. She meant a lot to us.”
The family came to know her as a fun-loving woman with many interests: She was a Beatles aficionado, a guitarist (a passion starting in high school, said her friend Alice Churella), a fierce lover of board games, an avid Wordle and sudoku player, and a Lego enthusiast who displayed the models she built — including of the Notre-Dame cathedral and the Fab Four — around her house. She was a trivia nut who appeared as a contestant on Jeopardy! in 2011. And she traveled to Panama, Liverpool (for a Beatles tour), and Ireland, to honor her Irish birth parents.
She was a Red Sox and Patriots fan. “She told us that her childhood dream was to play left field for the Red Sox, but when that didn’t work out, she aspired to be a judge,” said Meg. And when she achieved that goal, she “wasn’t the least bit pretentious” about it. For Halloween, Meg said, Anne and Ansel dressed as Harry Potter characters in her court robes and witch hats. “That was probably the biggest impact on our family of her becoming a judge,” she said.
Chief Justice Diana Horan met Anne when they were two of the first three women to be appointed to the Housing Court. Anne was humble about her appointment.
“She was a judge’s judge,” Diana said. “She was genuine and very level-headed, and she was very good at simply doing the job and not making the job about her.”
Off the bench, she added, “she was full of spirit and laughter.” Often, Anne would invite friends to Truro for the weekend, and they would make many plans but wind up barely leaving the house. “We would sit down and start talking and we wouldn’t stop.”
After retiring, Anne continued to serve the court as a recall judge, filling in because of a shortage of sitting justices. “Whenever I picked up the phone and said, ‘Anne, I need you here,’ she never said no,” said Diana.
Anne is survived by her sister, Mary O’Connell, and husband Mark of Chelmsford; nephew Brian O’Connell and wife Meg of Sudbury; nephew Kevin O’Connell of Billerica; and niece Meghan O’Connell of Nashua, N.H. She also leaves Ansel’s children, Rawson Chaplin of Cummings, Ga., Margaret Chaplin of West Hartford, Conn., and Jane Chaplin of Middlebury, Vt.; and grandchildren Rachel, Max, Miles, Sam, and Ben and wife Alyssa.
She was predeceased by her husband, Ansel Chaplin, and by Meg’s husband, Michael Aronow.
Anne’s funeral took place on Aug. 6 at Newton Cemetery.
Editor’s note: An earlier version of this article, published in print on Aug. 7, incorrectly reported that Ansel Chaplin had three daughters. He had two daughters and one son, Rawson. That report also misstated the year that Anne and Ansel married. It was 1995, not 1992.
