John E. O'Brien

John (Jack) E. O’Brien, 70, passed away at his New Hampshire home on Monday, March 30th, 2026. He was born on May 26, 1955 in Boston, Massachusetts to the late Ed and Dot O’Brien. Jack spent much of retirement residing in his New Hampshire home with his wife, Jolanta, where he was surrounded by the quiet beauty of nature and the untamed spirit of the wilderness he so deeply loved.

He was the heart of his family- a steady, loving presence who made everyone feel safe, supported, and valued. As a husband, he was a true partner and best friend, sharing a bond that was built on respect and unwavering love. As a father he led with patience, kindness and wisdom- always present, always listening, and always believing in those he loved. His patience shaped the lives of his family in immeasurable ways, leaving a legacy that will continue to live on through them.

Perhaps his greatest joy in life was being “Grandpa." He adored his four grandchildren and found endless happiness in their laughter, stories, and milestones. Whether sharing his wisdom, offering advice, or simply being present, he created lasting memories that they will carry with them forever.

He was raised in Rockland and attended Rockland High School, graduating in 1973 after spending many years playing sports. He later attended the University of Massachusetts- Amherst, graduating with a Bachelor of Science in 1977, Magna Cum Laude. He worked alongside his father-in-law at Alice’s Bakery in South Boston creating relationships in the community. His passion was coaching and teaching. He coached the Acton-Boxborough lacrosse team 16-0 winning the state championship in 1987, earning Coach of the Year and placing him and his team in the Hall of Fame in 2011.

Jack spent almost 20 years of his career at Prospect Hill Academy in Cambridge, MA as a physical education teacher, basketball coach, cheerleading coach and athletic director. He created the Massachusetts Charter School Athletic Organization (MCSAO). Jack will be remembered as far more than a physical education teacher—he was a mentor, a coach, and a tireless builder of opportunities for others. Over the course of his career, he dedicated himself not only to educating students in the classroom, but to shaping their character, confidence, and sense of belonging.

Jack is survived by his loving wife of 45 years, Jolanta, his children, Kyle O’Brien and wife Jennifer of Braintree, Lukasz O’Brien and fiance Taryn of Quincy, and his sister, Kathy of Rockland and his cherished grandchildren, Jackson, Raelyn, Cooper and Abigail. Additionally, he is survived by his sister-in-law, Mary Gunzy and husband Brian, nieces, cousins and many loving friends and extended family. He also leaves behind his devoted four-legged companion, Bruski. Predeceased by his parents, Ed and Dot O’Brien, in-laws Jan and Wanda Wieckowski and brother-in-law, Mark.

He will be remembered for his generous spirit, his attentive heart, and his ability to make everyone around him feel loved and valued. Though his passing leaves an unfillable void, the love he gave so freely will remain a constant source of comfort and strength for those who he loved. A life so beautifully lived leaves a lasting imprint. He will forever be in our hearts.

At Jack’s request there will be no services. A Celebration of Life will be planned for a later date.