11/04/2025
JOHN “JACK” J. FLANAGAN III – Ret. Arlington Police Dept., of Woburn, passed away suddenly at The VA Hospital in West Roxbury, Thursday, October 30th, 2025, with his beloved wife of 44 years, Diane M. (Murphy) Flanagan, by his side.
Born in Cambridge, Jack was the son of the late John and Anne Marie (Manley) Flanagan. He was raised in Arlington and graduated from Matignon High School in 1965. Jack was drafted into the United States Army, where he proudly served his country during the Vietnam War.
Stationed in Ft. Lewis, Washington, he served with the 1198th RA Unit. He attained the rank of First Lieutenant and was honorably discharged in 1970. For his service, he was awarded the Silver Star Medal, 5 Bronze Star Medals, one with Valor, Purple Heart, Air Medal, Army Commendation Medal, National Defense Service Medal, Vietnam Service Medal, and Vietnam Campaign Medal.
Upon his return, Jack began working as a manager of a bar, where his quick wit, and humor, made him a friend to all. This was also where Jack was introduced to Diane Murphy from Cambridge, whom he married, and journeyed over the next forty-four years together.
In 1977, Jack began a long, distinguished and dedicated career with the Arlington Police Department, serving his community with a great amount of pride and integrity during his tenure. A hardworking gentleman both in and out of uniform, Jack retired in 2002.
Bringing two sons into the world, they would often spend vacations and summers at their home in Alton, NH on Sunset Lake. This was the place to relax, enjoy, and share fun times with family and friends.
A lifelong sports fan, Jack especially loved football, and a good game of cribbage with his friends. Jack also had a passion for deep sea fishing. These adventures on the ocean, and ocean only, brought in a great number of fish, that would be filleted and given away to family and friends. Jack also loved to cook. When it came to holidays, Jack was always in the kitchen. Clams casino and homemade raviolis were a favorite.
Above all, Jack was a devoted husband, father, brother and “Grandpa”. His warmth, humor, and generosity touched everyone he met. Jack will long be remembered for his loyal heart, his love of family and friends, and the countless good times and laughter he created for those around him.
Jack was a proud member of the Elks, American Legion, VFW, Sons of Italy, and the Orient Heights Yacht Club.
Jack was predeceased by his parents, John and Anne Marie Flanagan.
In addition to his wife Diane, Jack is survived by his sons, John J. Flanagan IV, his wife Cora, of Leominster, and Michael L. Flanagan, U.S. Air Force, his wife Amber, of Las Vegas, NV. Cherished “grandpa” of Rosie, Camryn, John V, and Malachi. Beloved brother of Mary Nawn, her husband Ernest “Ernie,” and William “Bill” Flanagan, his wife Jeanne, all of Arlington. Also survived by many loving nieces, nephews, cousins, and friends.
A Funeral Service will be held in the Lynch-Cantillon Funeral Home, 263 Main Street, Woburn, on Friday, November 7th at 11 A.M. Relatives and friends are respectfully invited to Calling Hours, in the Funeral Home, PRIOR to the Service, from 9–11 a.m. Please, at the family’s request, in lieu of flowers, remembrances may be made in Jack’s honor to the Fisher House Foundation, PO Box 791598, Baltimore, MD 21279 or FisherHouse.org