This article is a part of 12-piece series for The Times’ 2025 “Year in Review.” Click here for the print version.
The Island lost a beloved icon in April of this year: Captain Robert (“Bob”) Douglas, a beloved waterfront legend who sailed Vineyard seas aboard his tall ship and founded the Black Dog Tavern. Originally from Chicago, he developed a fascination with sailing during his summers on the Island. After his time in the United States Air Force, Dougles worked as a deckhand in Maine, where he later constructed the topsail schooner Shenandoah, and sailed to the Vineyard in 1964.
Douglas is widely credited for making Vineyard Haven’s working waterfront into the world’s wooden-boat mecca, with the Shenandoah standing tall to greet those who enter the harbor. But he is also remembered for his mentorship of young Islanders, leading many to have cherished summertime memories of being aboard the Shenandoah in fifth grade. Family and friends gathered in September to remember the irreplaceable member of the community with a final sendoff for Douglas.
Words can never perfectly capture the intricate lives led by the many memorable souls who depart the Vineyard, and this year is no exception. Sam Feldman, a visionary Island philanthropist and entrepreneur who helped bring various beloved institutions like the Martha’s Vineyard Public Charter School and the Martha’s Vineyard Film Center, died in January. Dr. Michael Jacobs, who brought laughs to patients and was adamant on having a dedicated health center on the Vineyard, died in August. Peter and Cora Weiss, who led inspiring lives of service to others in a mission for peace, died in November and December, respectively.
Other headlines:
Sam Feldman, Island visionary and philanthropist, dies at 95
Capt. Robert Douglas, waterfront legend, dies at 93
Dr. Michael Jacobs, Island renaissance man, dies at 85
Longtime school superintendent passes away
Sending off Capt. Robert Douglas