Samuel Wiley Wakeman

Samuel Wiley Wakeman passed away peacefully in his home early on the morning of August 5, 2022 surrounded by family, watching one last sunrise over Minot’s Light.

Sam was born in Boston in 1943 to Frances McElwain Wakeman and Samuel Wiley Wakeman Sr. He grew up in Hingham and later made his home in Cohasset, which was where he learned to mess about on boats, as one would be inclined to do in with a family of sailors and shipbuilders. He was an engineer like his father and grandfather before him, attending Layfette as an undergraduate and getting his MBA at the Tuck School at Dartmouth. He was in the Navy in his uniformed career, the CEO of an insurance brokerage in his suited career, and later left insurance to buy Goodrich Lumber – a hardware store in Duxbury, MA – allowing a transition to a flannel shirt career he so thoroughly enjoyed.

Sam’s passion was sailing. Learning to sail with his parents, he had extensive ocean racing experience and was part of four America’s Cup Campaigns, defending the cup successfully in 1967 and 1974. Every effort was made to clear his calendar for a week in the summer to sail with close friends on the New York Yacht Club (NYYC) cruise. His expertise and wit were more recently commandeered by the NYYC Race Committee, which he chaired from 2012 to 2017. He readily admitted that his best accomplishment in sailing was in the relationships and friends he made from New England to New Zealand, those whose company he will undoubtedly miss. He also cherished childhood friendships that stood the test of time. His absence will be felt deeply by those who gather annually as part of “Camp Sammy” to reminisce over lifetime adventures in a weekend filled with banter, laughter and lobster.  

Sam supported various organizations including the Trustees of Reservation, Derby Academy, Governor’s Academy, the Town of Cohasset, the New York Yacht Club, and was a third-generation commodore of the Cohasset Yacht Club. He was known for exploring both sides of any argument and trying to maintain an even keel through discussions and disagreements. This balance was perhaps best evident when his family often asked him if it would rain (and they should bring a jacket), to which he would reply “Well, it may…or it may not.”

Sam is survived by his beloved wife of forty-three years Linda, daughter Neely (Peter), son Wiley (Lok Ting), stepchildren Heather and John, and his three loving sisters Nancy, Judy, Susie (who lived next door). He was the proud “Papa” to his granddaughters Mabel, Theodora, Wilhelmina, Madeline and Tilyard.

Sam’s life might best be exemplified in a statement from his mother Frannie, who once, upon learning of the birth of Sam’s first child, was said to have declared proudly, “Well done darling!”

In lieu of flowers, donations can be made to The Trustees of Reservation (thetrustees.org).

A memorial service is scheduled for September 16th at St. Stephens Church in Cohasset at 11am, with reception to follow at the Cohasset Yacht Club.

To send flowers to the family or plant a tree in memory of Samuel Wiley Wakeman, please visit our floral store.