Paul D. Pickard of Oak Bluffs died peacefully on Saturday, Sept. 7, 2024, after a decade of beating back blood cancer. He was 75.
Paul overcame childhood tragedy to become an accomplished educator, devoted husband and father, and loyal friend with a legendary sense of humor. He was born in Pittsburgh in May 1949, 10 years after his brother, Wesley. His mother died suddenly when Paul was 6; his father when Paul was 15. Paul went on to board at the Perkiomen School, outside Philadelphia, and to live with Wes in eastern Pennsylvania.
After graduating from Bucknell University, Paul moved to the Boston area, where he lived and worked as a teacher for the next 20 years. He spent the bulk of that time at Cardinal Cushing Central High School, an all-girls Catholic school in South Boston run by the Sisters of Notre Dame de Namur. Respected by all, he formed lasting friends with students, faculty, and nuns. Paul helped develop and pilot an innovative curriculum called “Facing History and Ourselves,” which uses lessons of history to challenge teachers and students to stand up to bigotry and hate.
Paul’s work in education reflected a deep commitment to progressivism. He was a longtime member of the ACLU, a charter subscriber to Mother Jones magazine, and a devotee of historians like Howard Zinn, who looked at the past from the bottom up. His interest in Latin America took him to study Spanish in the Guatemalan town of Huehuetenango.
Paul met his first wife, Gretchen Mayher, while both lived in Cambridge. In 1986, they moved to Martha’s Vineyard, and built their own home in Oak Bluffs. Their son, Duncan, was born in October 1987.
Paul was an active citizen in his new community. He resumed teaching, including at the Oak Bluffs West Tisbury schools, and the regional high school. He was elected to the board of health, volunteered as an EMT, and served as an assistant scoutmaster and youth basketball coach. He donated blood as often as he could.
Paul’s proudest accomplishment was his son. Duncan brought him tremendous joy from day one, particularly through Duncan’s high school and university years, marriage to Charlotte Bocage, and career in law.
Paul met his current wife, Anne Bennett, in 2001, and they were married at their home in Oak Bluffs in January 2007. They shared a deep love over their 24 years together, spanning many home-cooked meals (always including dessert), family visits, and trips to New Hampshire, Florida, Italy, France, the Netherlands, Mexico, Costa Rica, and beyond. They loved Rosie, their shih tzu–bichon frisé mix, and were regulars at the Trade Winds dog park.
Paul shifted careers in 1998, following in his father’s footsteps as a local banker. He worked for six years at the Edgartown National Bank, where he was a branch manager. He sold credit card services for Heartland Payment Systems before joining the Martha’s Vineyard Bank, from which he retired in January 2020. He later led tours of Martha’s Vineyard.
For colleagues, friends, and family, Paul was a constant source of lightheartedness. He delighted in spreading laughter through jokes, no matter the context, even when admittedly — or especially — ribald. One Christmas, he sported a printed T shirt depicting six-pack abs for customers at the bank’s Uncas Avenue branch.
Paul was a Pittsburgh and Boston sports junkie, with an encyclopedic knowledge of the NFL, MLB, and NBA. He also loved golfing at Farm Neck, though by his own admission he was a far better fan than player. At 52, he fulfilled his lifelong dream of running a marathon, completing Cape Cod in just over four hours. Other passions included music — especially blues, rock and roll, and showtunes — genealogy, and Irish whiskey.
Paul was diagnosed with chronic leukemia in 2014. He received excellent, cutting-edge care that kept the cancer at bay for many years, but the leukemia eventually transformed into an aggressive form of lymphoma. He was grateful for the compassionate support that he received from his providers at Martha’s Vineyard and Massachusetts General Hospitals, and from the Martha’s Vineyard Cancer Support Group.
Paul is survived by his wife, Anne Bennett; his brother, Wesley; his son, Duncan; Duncan’s wife, Charlotte Bocage; Duncan’s mother, Gretchen Mayher; his stepchildren, Laura Bennett and Greg Bennett; his stepsister-in-law, Frannie Rich; and many cousins, nieces, nephews, and friends. His grandson, Raphaël Paul Bocage-Pickard, is due in November.
A memorial service will be held at the Farm Neck Café in Oak Bluffs at 5:30 pm on Thursday, Sept. 26.
In lieu of flowers, please make donations in Paul’s memory to the Martha’s Vineyard Cancer Support Group, online at mvcancersupport.org/donate.
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