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John Francis Caulfield Jr.

September 14, 1928 ~ September 30, 2023 (age 95) 95 Years Old

John Caulfield Jr. Obituary

John Francis Caulfield Jr., a loving patriarch, dedicated public servant, and steadfast friend, passed away peacefully on September 30, 2023, in Milton, MA. Born on September 14, 1928, in Boston, MA, John was known for his loving, kind, and gentle nature, leaving a legacy of warmth and compassion that touched everyone he knew.

John was a proud graduate of Roslindale High School. Following his education, he devoted himself to serving his community as a Boston Police Officer for 42 years. His dedication to public service was a testament to his deep-rooted love for his city and the people within it. He was a man of honor and integrity, respected by his peers and deeply valued for his contributions to his community.

John's life was a testament to love and devotion. He was the beloved husband of 72 years to the late Phyllis J. (Squeglia), a love story that inspired all who knew them. He was also a devoted father to John F. III (MSP) and his wife Colleen of Franklin, Dennis M. and his wife Mary Lisa of Canton, Dorinda Smyth of Milton, Kevin J. and his wife Kathleen of Hyde Park, Ralph W. (BPD) and his wife Maria of Canton, William E. and his wife Kathy of Hingham, and Marcia A. Wetterberg of Weymouth. His family was his pride and joy, and he cherished every moment spent with them.

Known affectionately as "Grandpa," John was the cherished grandfather of 20 grandchildren and 30 great-grandchildren. His love for his family was boundless, and he took great delight in attending his grandchildren's sporting events. He was their biggest cheerleader, always there to offer words of encouragement and celebrate their victories, both big and small.

John was also a beloved uncle, survived by many loving nieces, nephews, and friends. His home was always open, his heart always willing to listen, and his hands always ready to help. He was a pillar of strength, a beacon of love, and a source of joy to all who knew him.

The loss of John Francis Caulfield Jr. is deeply felt by all who knew him. His life was a living testament to the power of love, kindness, and gentleness. His legacy will continue to inspire and guide all those who were privileged to know him. He will be fondly remembered and deeply missed by his family, friends, and community. As we mourn his passing, we also celebrate a life well-lived, honoring a man who gave so much of himself to others.


Visiting hours will be held Friday morning from 9-10:30 AM at the Carroll-Thomas Funeral Home, 22 Oak Street, Hyde Park. A Mass of Christian Burial will be celebrated Friday at 11 AM at Most Precious Blood Church, Hyde Park. Interment at Milton Cemetery. Relatives and friends are invited.  In lieu of flowers, donations in memory of John may be made to St. Jude Children’s Research Hospital at

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Visiting Hours
October 6, 2023

9:00 AM to 10:30 AM
Carroll-Thomas Funeral Home
22 Oak Street
Hyde Park, MA 02136

Mass of Christian Burial
October 6, 2023

11:00 AM
Most Precious Blood Church
25 Maple Street
Hyde Park, MA 02136

October 6, 2023

Milton Cemetery
211 Centre Street
Milton, MA 02186


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