William Michael “Mike” O’Brien, 93, died peacefully on September 11, 2026.
Mike was born in Montpelier, Vt., on June 23, 1933, the eldest child of Madeline Massucco and Colonel William M. O’Brien (USMC).
Mike graduated from St. Michael’s High School in Montpelier and the University of Vermont and also served six years in the U.S. Army (active and reserve).
In 1959, after spending a day skiing on Stowe Mountain, Mike met Virginia Ann “Dee Dee” Ireland. They were married in September 1961 at St. Mark Church in Burlington, Vt. Together, they built their home and raised four children on Killarney Drive in the New North End. Killarney Drive was a special place of joy and pride for Mike, as it was developed by his father-in-law, Jack Ireland, and offered endless opportunities to take advantage of Lake Champlain and the adjacent green spaces of Rock Point and Leddy Park. Many a summer night included a picnic dinner on Killarney Beach.
In his professional life, Mike was employed by IBM for over 25 years, working as a manager in the procurement department. He often remarked how a big part of his job was “recognizing and pushing young talent along at IBM.” For decades, he carpooled with other IBMers from the North End. Upon taking early retirement, Mike began a second “career” as a guide for the Shelburne Museum. This became one of his greatest joys in his later life, sharing his vast knowledge of Vermont history with visitors from all over. The exhibit he loved most to talk about was the Ticonderoga. Each summer, Mike’s family would visit the Shelburne Museum. They took great pride in seeing their dad with arms draped over the steering wheel of the Ticonderoga, sharing the story of how that ship came to be.
Mike’s priorities for daily life focused on a few things: spending time with his beloved family, going to church at St. Mark with Dee Dee, offering himself in some volunteer capacity to his community, and being the biggest cheerleader for his 10 grandchildren through both their work opportunities and personal relationships. He was able to see his eldest grandchild get married last September.
Mike loved Christmas morning at 150 Killarney Drive, sharing a drink and dinner at camp on Coates Island, and relishing in his great fortune to have raised a happy and healthy family with Dee Dee.
Mike is survived by his wife, Dee Dee, of 65 years; his children and their spouses, Kathy (O’Brien) and David Houle, Mary (O’Brien) and Craig Brett, Sean and Nicole (Gilbert) O’Brien, and Chris and Jamie (Ha) O’Brien; and his grandchildren, Brian (Jen), Dan, Tommy (Annie) and Bridget Brett; Dylan and Jack Houle; Kiera and Finn O’Brien; and Lily and Ava O’Brien. He is also survived by his sister Patricia O’Brien Swanson and was predeceased by his sister Rosemary O’Brien Bennett.
Mike will be deeply missed, but that twinkle in his eye when he was having a good time and his incomparable smile will live on in his family’s hearts. His life was well lived and full of joy.
A Mass of Christian Burial will take place on Saturday September 19, 2026, 11 a.m., at St. Mark Church in Burlington. Burial will be held privately with the family. In lieu of flowers, please consider a donation to the Shelburne Museum in Mike’s name.
Arrangements have been entrusted to the care of Ready Funeral & Cremation Services. To share memories, photos and condolences with the family, please visit readyfuneral.com.