Doane Beal & Ames


The Family invites you to join them for a light lunch at Our Lady of the Cape Parish Center after the burial.

William A. Winn Jr.

July 20, 1920November 4, 2021

William Arthur Winn, Jr., was born at home July 20, 1920, in Medford, Massachusetts. The third of eight children of Theresa (Dooley) Winn and William Arthur Winn, he was the oldest boy, and his life, character and legacy in many ways were shaped by the expectations and attention that position often confers and places on a child, notably one who comes of age during a great depression and a world war. Bill worked hard and took responsibility from an early age because he had to. When hardship seemed to be pressing all around his and other families as the thirties wore on, he and his sister Teresa, the eldest, used their earnings as an usher and waitress at Symphony Hall to help their family. The partnership and respect he had for her was foundational to the deepest and most treasured of his life—that with his wife of 62 years, Gertrude Marie O’Brien Winn, whom he married in 1949 and would go on to have six children, William III (Elaine Delaney), Robert (Leilla Dutcher), Peter (Katherine Schoettmer), Charles (Evelyn Plant), Mary (Craig Huzway) and George (Dorothea Kiplock). Together, they were said to be the ones who brought the “fairy dust” to the gatherings of the many friends and seemingly endless family members they counted and loved. Their love was enduring and timeless and propelled Bill to continue to grow and care for Gerta at an age when most of his peers were increasingly dependent. Bill, though, was independent and giving until his last weeks, when giving carried him to thank and bless those who took care of him.

His love for family sustained him. It began with care for his siblings, all of whom predeceased him, and included his other older sister, Mary, younger brothers, Ed, Bobby, Jack and Bart, and his younger sister, Barbara. Firing up the coal furnace in the morning and tamping it before going to bed was simply one part of his day from boyhood--until he would one-day gift an “oil burner” to his family with savings from his first full-time job. After graduating Boston Latin School in 1937 at the top of the class, he was appointed to the Naval Academy only to be told he could not matriculate owing to “malocclusion of the back teeth”—news that broke his heart at the time but did not break him. He would go on to work at New England Telephone and AT&T after studying engineering at the Lowell Institute and appointment to the RADAR school established at MIT in the lead up to WWII. His service in the war would take him to Bermuda, England and eventually Normandy and Paris as a member of the Army Signal Corps, whose view of his brain eclipsed any concern the Navy had for his bite. Indeed, Bill was among the last appointments to officer in the European theater after a former MIT professor, walking the Champs-Élysées, spotted him at the corner of Avenue Georges V. After inquiring with Bill as to his duties, the professor turned to the general accompanying him and admonished him to “send this young man, whom the US government had invested greatly in, directly to Officers Training School.” The order was waiting for him when he got back to his barracks. He would return to the phone company and AT&T’s Bell labs after the war only to be called up again during the Korean Conflict. His orders however, confidential at the time, were to Austria and West Germany, where he helped lay down the communication infrastructure the west would rely on as the cold war set in and Eastern Europe faced isolation.

His expansive view of the world and people was his legacy to his children. In a Cape Cod neighborhood rife with many wonderfully social families on a hill in Brewster, he was tagged “the mayor.” He simply greeted everyone, and the future, with a smile. Every day. That optimism and tolerance and the sense of possibility they grew up with was grounded in his experience and education. The product of the oldest public school in the country, also one of its best, Bill made sure his children had a similar opportunity in the Belmont schools. It was simply his and Gerta’s unspoken priority. The “space-age stainless” kitchen would stay as-is through the half century they lived there, long enough to come back in style and sturdy enough to see all six children to college and beyond. He enjoyed skiing and sailing, teaching them all at an early age, and his golf game probably reflected as much. But polishing the latter would have taken him away from his children when they were young. His commitment to and pride in them was direct and unabashed, rivaled only by the pride and ridiculous joy he took in his ten grandchildren, Benjamin Delaney-Winn (Aidan), Adam Delaney-Winn (Ariel), Jonathan Winn (Julie), Joseph Huzway, Tucker Delaney-Winn (Blair), Samuel Winn, Haley Winn Ruch (Tyler), Catherine Winn, William Arthur Winn IV and Elizabeth Winn, and eight great grandchildren, Keira, Liam, Jack, Jonah, Luke, Ruby, Hadley and Miriam Winn. If Bill and his love, Gerta, spread joy, any gathering with the two aforementioned newest generations would tell anyone that his legacy lives on. And so may we all be channels of his living lesson of faith, optimism and love—spreading the magic dust, as he did, until we return to it ourselves. Bill wouldn’t have it any other way.

Instead of flowers, the family requests a donation to one of the charities below, or to a charity of your choice.

Addresses provided for those who prefer to donate by mail.


1. Doctors Without Borders USA

PO Box 5030 Hagerstown, MD 21741-5030

Online donation:

Very easy to navigate and they have an In Memorium box to write a name.


2. Macular Degeneration Research

22512 Gateway Center Drive Clarksburg, MD 20871

Online donation:


3. Alzheimer's Association Mass/New Hampshire Chapter

309 Waverley Oaks Road Waltham, Mass 02452

Online donations:


  • Family and Friends Gathering

    Monday, November 8, 2021

  • Funeral Mass

    Monday, November 8, 2021

  • Burial with Military Honors

    Monday, November 8, 2021


William A. Winn Jr.

have a memory or condolence to add?

Carrie Kane

November 11, 2021

I'm so sorry and saddened to hear of Bill's passing. I worked for several years at Epoch and Wingate / Brewster and served Bill his Breakfast, Lunch and Dinner each day. He was always a joy to be around. He always had a smile , a jovial personality and kind word . He will be missed!

Lynn Laurie

November 6, 2021

With sympathy to the Winn family, as you go through your grieving process, I hope that you find comfort from shared memories and your own personal memories. They are treasures that you will always have.

Keith Bissonnette

November 5, 2021

Sincerest condolences to the entire Winn family for the loss of your patriarch. Stephen and I grieve with you.