Skowhegan – William "Bill" Joseph O'Brien, age 88, of Skowhegan, ME, formerly of Homosassa, FL, passed away peacefully on January 30, 2024, surrounded by the love of his family. Bill was born on October 25, 1935, in Somerville, MA, son of Helen (Kearsey) and William A. O'Brien. As a teenager Bill was highly active in sports, playing hockey and baseball, which continued into his adult years. He became an avid golfer and belonged to the Needham Golf Club working his way up to President of the club in 1975. He was also an active member of the Elks and a Lifetime Member of the Knights of Columbus. He met the love of his life in 1954 in Harvard Square while working as a soda jerk at Howard Johnsons, she had come in with her friends for a soda. Two years later, in 1956, they married at ages 18 and 19. He joined the Army National Guard in 1958 and for 6 years he worked in Field and Radio Communications, from there he became a Senior Electronic Technician for Damon. He eventually went on to purchase the Needham Dairy in the 70's and then in the 80's started up his own advertising agency. He owned TAWE Communications up until his retirement. Bill and Anne moved to Sugarmill Woods, Florida, in 2000, where golf and traveling became his new pastime along with enjoying retirement. Bill was preceded in death by both his parents and the love of his life and wife of 66 years Anne S. O'Brien. Bill is survived by his daughters Theresa Weaver with her husband Gary of Skowhegan, ME, and Elizabeth Ralston with her husband Tom of Uxbridge, MA; beloved grandchildren Lisa Leenhouts of Groton, CT, Christopher O'Malley of Glen, NH, James O'Malley and Sean O'Malley of Orlando, FL, Katherine Leenhouts of Woonsocket, RI, Jonathan Weaver of Reno, NV, and Joshua Weaver Glendale, AZ; great-grandchildren Christopher O'Malley, Jr., Allison Woodworth, Ethan Woodworth, Leighana Boutiette and Aliyah Boutiette; brother-in-law Phillip Carrara with his wife Emma of Brandon, VT, along with nieces and a nephew in VT. Internment will be this spring at Mt. Auburn Cemetery, in Cambridge, MA.