George O'Brien

George O'Brien, born 4 September 1926 in Arlington, MA, died Sunday, September 14, 2025, in Winchester, MA; more affectionately known as Uncle George to all four (4) generations of not just his family, but even close friends. His journey on this earth was a shining light of hope, joy and the "good stuff" of life that truly matters. His unwavering faith in the Great Creator, our God from which he formed the very foundation and path of his life was an encouraging witness to all of us who knew him. He had a strong appreciation of the arts, and it was this love of music and theater that brought so much joy to himself and his lovely belated bride and the love of his life for over 72 years, Olga O'Brien and in addition to exposing all his nieces and nephews to the amazing world of the arts.
George was born in an era that many are too young today to remember, because in 1926 the world was very much a different place. During Georges 20's and 30's America was a strong nation of great men and women in a time known as the Greatest Generation. George joined the Navy in service to his country at the age of 17, a WWII Veteran, serving onboard the USS PRENTISS during the war. George and men like him were revered because of their belief in what maintained a great Nation and the true values of life. Until his final day, George maintained his love of country.
George was lucky to be able to have a job he loved in the career of travel. As an agent for Island Holidays, he was able to continuously share his love of the Hawaiian Islands, the Hawaiian people, and their culture for over 50 years as he shared this interest and culture with many of his family and close friends.
George attended Boston English High School and then after his military service he went on to attend Boston Clerical School and Bryant & Stratton Community Business School.
George's positive outlook on life, regardless of almost any situation would inspire even those of the most negative mindsets. He often would greet you with a simple, "Good Morning" regardless of the time of the day almost as if he was encouraging one to look forward, with a fresh start and to renew their thoughts despite the circumstances. When talking with someone he made them feel like the most important person in the room! George's love of life was an infectious and contagious quality that will never be forgotten, especially by those he inspired and those who loved him. We ask you to remember George not from the way his life on earth ended, but for the way he lived and for the profound impact his life had to so many that spanned over ten decades and four generations!
George was the Beloved son of the late William and the late Helen O'Brien of Dorchester, and was preceded in death by his siblings William O'Brien, Helen O'Brien, John O'Brien, Rita Quinn, Joseph O'Brien and Robert O'Brien. He is survived by his sister Mary Cooey (Julius) of Steinhatchee, Florida. In addition, he is survived by an incredible number of adoring nieces, nephews, great nieces, and great nephews who will forever be enriched and blessed to have had Uncle George as part of their lives.
Relatives and friends are welcome to gather for visitation at Costello Funeral Home, 177 Washington St., Winchester, on Saturday, October 4th from 9-10:30AM followed by a Mass of Christian Burial in St. Mary's Church, 155 Washington St., Winchester, at 11AM. Interment will follow in Calvary Cemetery, Winchester. In lieu of flowers donations in his memory may be made to St. Jude Children's Research Hospital, 501 St. Jude’s Place, Memphis, TN, 38105 or to the Wounded Warrior Project .