

“Jay, Dad or Grampa” to his family, he was born in Woburn, Massachusetts to Florence and Joseph O’Brien, graduated from Woburn High School, and earned a bachelor’s degree in mathematics from Fitchburg State University while working steadily in his father’s paint and wallpaper store. While working full time, first as a teacher-principal in rural Vermont, and eventually as the youngest superintendent in Vermont, Jay received a Masters, CAGS, and then Doctorate in Education at BC, University of Vermont, and Boston University, respectively. He wrote his doctoral thesis on regional rural schools.
Fueled by his devotion to children (his retirement picture features him sitting “crisscross applesauce” reading to kindergarteners), Dr. O’Brien had a long career in public education. He served as superintendent of schools for the Bourne Public Schools from 1988 to 1998, and Superintendent in Northwest CT until his retirement in 2005, which coincided with the birth of his first three of eight beloved grandchildren. Jay spent numerous hours serving the town of Bourne on the Zoning Board of Appeals, the Capital Outlay Committee and the Police Station Committee for the Town of Bourne. He worked the polls every election.
An avid golfer, he played courses throughout New England and had five holes-in-one over his lifetime. Closer to home, he regularly played with men’s groups at the Falcon Golf Club on USCG Base Cape Cod. While not every grandchild has picked up golf, he passed his fierce competitiveness at cards on, enjoying family games of “pitch” at every holiday and family gathering.
He leaves his wife Joan Foley O’Brien of Pocasset; their children, Carolyn O’Brien and her husband Louis Jordano of Cambridge, Massachusetts, John O’Brien Jr. and his wife Cynthia of Arlington, Massachusetts and Steven O’Brien and his wife Cara of Castle Pines, Colorado. He was predeceased by his daughter Jane. He also leaves his eight grandchildren and many nieces and nephews.
He was predeceased by his four brothers, Joseph Jr., Hugh, Thomas and Edward O’Brien.
Visiting hours will take place on Tuesday, September 16, from 8:30 to 9:30 AM at the Nickerson-Bourne Funeral Home 40 MacArthur Blvd. Bourne, MA.
A Funeral Mass will take place at 10:00 AM on Tuesday, September 16, at St. John the Evangelist Catholic Church in Pocasset.
Burial will be private.
In lieu of flowers, please consideration a donation to Falmouth Hospital or St. John the Evangelist Church in Pocasset, MA. https://support.givetocapecodhealth.org/donate. https://www.wesharegiving.org/app/giving/WeShare-20000578?tab=home.
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