

Born in Quincy, Massachusetts, he was the son of the late James and Elizabeth (Moss) O’Brien.
Father of his three children, Kerry McNamara and her husband Patrick McNamara of Scituate, Erin O’Brien of Quincy, and Holly Ambrose and her husband Tom Ambrose of Scituate.
He was the proud Poppy (grandfather) of Grace, Aidan, Katie McNamara and Madelyn and Owen Ambrose.
Stephen, more commonly known as “OB”, was an avid sports fan and spent many nights in his youth playing basketball at the Quincy YMCA. Later, he would witness Larry Bird and the Celtics clinch THE ’84 and ’86 championships. However, his favorite basketball to watch happened at Scituate High School, where he never missed a game for his three oldest grandchildren.
OB would delight dinner time with exciting stories that had occurred during his time at Boston Coach. Some colorful stories included the likes of Julia Childs, Charles Barkley, and even a tire change with Dennis “DJ” Johnson.
Most will remember OB for his quick wit and that legendary head of hair. He had a remarkable gift for making people laugh—often coining an incredibly accurate and hilarious nickname that would stick for life. He praised our history makers with his knowledge of history books and most importantly, was a man that made the room better as soon as he entered. His gift of gab could only be rivaled by his beloved wife, Donna.
A visitation will be held from 3:00-7:00 PM on Thursday, July 31, 2025, at Richardson-Gaffey Funeral Home, 382 First Parish Road, Scituate, Massachusetts. Funeral Mass at 10:30 AM on Friday, August 1, 2025, at St. Mary of the Nativity Church, 1 Kent Street, Scituate Harbor. Relatives and friends are respectfully invited to attend.
In lieu of flowers, donations in Stephen’s memory can be made to Tunnel to Towers Foundation.
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