In Memoriam: Stephen B. O’Brien, Jr., 1928-2022

Mr. O’Brien was the owner of O’Brien’s Centerville Insurance

Stephen B. O’Brien, Jr of Centerville, passed away peacefully at home on 02/18/2022. A lifelong resident of Centerville, he was born at Cape Cod Hospital in Hyannis in 1928 and spent the first few years of his life in Osterville before the clan moved to the O’Brien “compound” in 1932. Steve’s wife Barbara (Drew) O’Brien preceded him in death in 2019 and he remained a loving and devoted husband to “Mema” for 68 years.

He placed the happiness and wellbeing of his family above all else in life and will forever be remembered as a kind, loving and patient man. His strong Catholic faith and love of Our Lady of Victory Church is part of his legacy with his family being one of the original families that started the church in Centerville. He and Barbara attended Mass regularly throughout their lives and their faith was both tested and unwavering. Steve loved his town and had a special affection for Barnstable High School where in his Senior year was named co-captain of the football team and voted best looking by his class. In later years he never missed listening to the Barnstable /Falmouth Thanksgiving Day game on his radio.

After graduation Steve enlisted in the Navy to serve our country in WW II and was part of the USS Briareus crew until the end of the war. Home safely, he enrolled in the first class of the newly founded Merrimack College, attending classes in Quonset huts, while taking room and board in town during the week. He loved to reminisce about a simpler time and that always included tales about the summer jobs he held as a youth. From unloading bicycles from the train station in Hyannis for transportation to the summer camps down cape to changing the movie marquee at the Hyannis East-End theater on Main St after closing. Working as a milkman for HP Hood he remembered delivering to Martin’s bakery on Main St and being greeted with a warm muffin every morning. Steve’s stories would fill a volume.

It was in 1948 that Steve was brought into the family insurance business, O’Brien’s Centerville Insurance started in the family home in 1939 by his mother and father which he successfully ran until his death. An avid golfer since youth, Steve spent many a day at his beloved Cummaquid Golf Course, as a lifelong member, past club President and member of the hole in one club – his love and support of the course, the members and the game never faded.

Steve also shared a love of Naples, FL. He and Barbara spent many winters at Fox Fire enjoying friends and hosting family yet always eager to get home to enjoy a family party at the compound, Cummaquid Golf Club, Craigville Beach, the Centerville Memorial Day Pancake Breakfast & Parade, Fourth of July fireworks, gathering with Cummaquid friends at Giardino’s and of course, happy hour with his one and only Barbara.

Family survivors include his daughter, Kathleen O’Brien Padova and her husband Joel D. Padova of Centerville, and his son Kevin R. O’Brien and his husband Brian J. Cabral of both Centerville and Provincetown. Steve was predeceased by his wife Barbara (Drew) O’Brien, his brothers Robert O’Brien, Joseph (Jay) O’Brien and sister Margot Carey, sons Stephen B. O’Brien III and Michael D. O’Brien. He leaves behind five grandchildren, Kaitlyn Beard and her husband Andrew of Centerville, Alexandra Riley and her husband Michael of Barnstable, Erin Hulme and her husband Jason of Marshfield, Conor O’Brien of Hyannis, and Griffin O’Brien of Hyannis, as well as his great grandchildren, Riley Beard, Cole Beard, Harrison Hulme, and Penelope Hulme along with his many nieces, nephews, and cousins.