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James J. Reynolds Jr.

February 26, 2022


Mr. James J. “Jimmy” Reynolds, Jr., 88, of Milford, MA, died Saturday February 26, 2022, at home with his family after a period of declining health. Jim was the beloved husband of Elaine (Sullivan) Reynolds.


Jim was born in Milford, MA, the son of the late James and the late Angelina (Pinardi) Reynolds. He graduated in 1950 from Milford High School and attended Tilton Preparatory Academy before graduating from Boston College in 1955. He was a US Marine, serving active duty and earning the rank of Lieutenant Colonel before retiring from the USMC Reserves with 20+ years of service. Jim went on to earn a master’s degree in Education from Worcester State University and completed postgraduate coursework at Boston University.


After joining Ashland Public Schools in 1957, Jim became a German teacher and a football coach, also serving as the head of the high school’s Foreign Language Department. In 1968, he assumed the role of Assistant Principal, cherishing the honor to guide students and faculty. During this time, Jim earned grants from Hofstra University and Dartmouth College to teach in their German summer programs. Jim then advanced as Principal, a perennial fixture at all hours in Ashland High’s classrooms, gymnasium, lunchroom, and hallways before his retirement in 1993. Mr. Reynolds was known for his commanding voice and ardent support for all youth involved in the arts, academics, and athletics.


After “retiring,” Jim became a certified tutor at the Goethe Institut, where he was renowned for displaying the highest mastery of the German language, typically achieved only by native speakers. He performed translations for local police and the US Senate and German Consulate and consulted on technical assignments for execs and corporations like Timex and Siemens.


Following a joyful stint at Hopedale High as a part-time German, Italian and Latin teacher, Jim was one of 15 U.S. educators selected to teach in Cologne, Germany in 1999. The exchange program was sponsored by the Fulbright Society with support from the German Parliament and American Congress to promote cultural awareness in education.


Jim was also a lifelong member of the Plains Reunion, the NASSP, and The Ashland James O. Carey American Legion. He was proud to be a member of the MIAA, Valencia Council First Degree and Edward McSweeney Fourth Degree Knights of Columbus, and a parishioner of St. Mary’s in Milford.


Apart from his love for his family, the Marine Corps, and his students, Jim enjoyed classical and country music. He was often found outside on sunny days working in his yard, enjoying a cigar and eager to chat with neighbors and friends. Jimmy will forever be known for his quick smile, hearty laugh, and his gentle and patient manner.


Along with his cherished wife of 59 years, Jim is survived by his loving daughter, Tara Reynolds and her husband, Jeffrey McCorkindale and Jeff’s daughters, Jordyn and Emma; his dear cousins, MaryEllen Ianzito of Manchester, NH; Michael Ianzito and wife Andrea and children Elena and Kika of Atlanta, GA; Edward Pinardi and wife Josette of Clarkston, MI; a sister-in-law, Ann Marie Sullivan of Spartanburg, SC; a niece and nephew, Elizabeth Draper and Richard Draper Jr of Greer, SC; also, many treasured friends, neighbors and caregivers who brightened his days.


Jim’s funeral will be held Friday (March 4th) from the Edwards Memorial Funeral Home, 44 Congress Street, Milford MA followed by a Mass of Christian Burial at 12 Noon in St. Mary of the Assumption Church, 19 Winter Street, Milford MA, preceded by calling honors (10:30am-11:30am) at the Edwards Memorial Funeral Home. Burial, with Military Honors, will follow in St. Mary’s Cemetery, Milford MA. Visit www.edwardsmemorialfuneralhome.com for condolence book.


Due to COVID-19 concerns the use of face masks will be requested for all facets of the funeral services.


In lieu of flowers, the family gratefully encourages donations in Jim’s memory to either:


The Ashland Scholarship Foundation, 87 West Union St, Ashland MA 01721, or


The Oliva Cancer Comfort Fund, c/o the Milford Regional Healthcare Foundation, 14 Prospect Street, Milford MA 01757.

















To send flowers to the family or plant a tree in memory of James J. Reynolds Jr., please visit our floral store.


March 4, 2022

10:30 AM to 11:30 AM
Edwards Memorial Funeral Home, Inc.
44 Congress Street
Milford, MA 01757

Mass of Christian Burial
March 4, 2022

12:00 PM
St. Mary of the Assumption Church
19 Winter Street
Milford, MA 01757

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