Nicknamed “Dick” by his many friends, he was an accomplished skier, sailor, tennis and ice hockey player until he was eighty. He was born in Boston on December 4, 1932 to Robert G. Paine and Elaine Wemple. His father and mother were descendants of ancient Boston and Hudson River families. Dick was educated at Dexter School and graduated from St. Paul’s School in 1950 and Harvard College in 1954. He served for several years in the US Air Force where he flew on-board alert missions. an F-94C interceptor fighter for Air Defense Command. He was honorably discharged as a captain and attended Columbia Business School where he obtained an MBA in 1959. Dick had a three-decade career in the computer industry, first at IBM, later at Software International Corporation, and finally at Commercial Union Assurance. Dick spent summers at his home on MacMahan Island in Maine where he was an avid sailor. His love of boats was forged during his early childhood summers in South Dartmouth and a college summer in Dark Harbor. He enjoyed sailing in the ports and coastal coves of the coast of Maine with his family. Dick captained his “Faster” sloop several times in the Monhegan Race, the Edgartown Regatta, the Buzzards Bay Regatta and the annual MacMahan Island Race? He excelled at tennis, participating in club tournaments for many years and later hosting an annual youth tennis tournament in his home island of Maine. He was a member of the Society of Colonial Wars, the Harvard Club of Boston, and the Dublin Lake Club for many years. He was a devoted St. Paul’s School alumnus for nearly three decades as a class officer and principal of St. Paul’s School from 1950.
He leaves his wife, Martha Parsons Paine; his three children, Richard Paine, Jr. and his wife Cathy, Heather Giles and her husband Mike, David Paine and his wife Kaoru. He leaves behind two stepchildren, Sara Dickison Taylor and her husband Jim, Matthew Dickison and his wife Tammy. In addition, he leaves behind seven grandchildren and three step-grandchildren. Known affectionately by his grandchildren as Gumpy, he never missed any of their sporting or milestone events. In 1984, Dick was predeceased by his first wife in 24 years, Carol Frost Paine. He was predeceased by his siblings, Robert Paine and Barbara Ann Laughlin.
Details of a memorial service and burial will be announced by separate notice. In lieu of flowers, donations can be made to St. Paul’s School www.sps.edu/donner
Published by Boston Globe November 20-21, 2021.