Longtime school superintendent passes away

A longtime Martha’s Vineyard superintendent has passed away after a hard-fought battle with leukemia. 

Jim Weiss, 78, passed away on Sunday afternoon at Massachusetts General Hospital in Boston. He is survived by his sister, Susan Filler, in Florida, nephew, Alan Miller, in New York, and daughter-in-law, Nicole Weiss of New Hampshire.

Jim Weiss spent nearly a half-century in education, and spent the last decade of his 26 years as a superintendent on Martha’s Vineyard. He started his education career with the National Teacher Corps in 1969, teaching in Mississippi and later Connecticut. Before arriving on-Island in 2005, Weiss was superintendent of the Sanborn Regional School District in New Hampshire. 

Islanders remember Weiss as a dedicated educator who truly embraced the Vineyard, and cited his kindness and generosity. 

“We were hoping for a recovery,” said Richie Smith, current Martha’s Vineyard superintendent. “It’s still shocking.” 

Smith, who considered Weiss his mentor, called Weiss a “child-centric superintendent,” and highlighted his launching of various partnerships for student programming as well as pushes for children with special needs. Smith reminisced about how Weiss was always active with school activities like sports and fundraisers, even recalling how Weiss would sometimes wear “silly costumes,” such as a turkey or Cookie Monster. 

“He embraced the Island so much, and the Island embraced him,” Smith said.

Weiss was superintendent when Smith was hired as principal of the Tisbury School, and he eventually recommended Smith to the Vineyard’s highest seat in education leadership. Even after Weiss retired, Smith said, he sought his advice. “He walked the walk [as superintendent],” Smith said. 

Edith Rousseau, who worked under Weiss as an administrative assistant, said in an email to The Times, “You could not ask for a better boss.

“He was fair, and worked tirelessly for the community, especially the children,” Rousseau said. “Even after he retired, he attended sporting events and plays at the PAC [Performing Arts Center]. I was fortunate to call Jim my best friend. He became part of my family, and after he retired, we would go to my grandchildren’s games together. They loved him as much as I did. He will be greatly missed.”

Weiss also served on the Cape Cod Community College graduate board, and was a board trustee with the Tower Foundation. Cindy Doyle, one of the owners of the foundation, highlighted Weiss’ work to get funding for Island schools and initiatives.

“It’s a huge loss for us … he’ll never be able to be replaced,” she said. 

For many who knew Weiss, they are also losing a dear friend. West Tisbury resident Susan Silk reminisced about how she and her sister, Barbara, would play Rummikub weekly with Weiss, and their many travels together, from Tanglewood to Greece. To the Silk sisters, his was one of their longest-lasting friendships on the Vineyard.

“He was very generous of spirit, and kind,” Silk said. 

A funeral is planned for Thursday at 2 pm at Chapman Funerals in Oak Bluffs. The funeral will be officiated by Rabbi Todd Zinn of Falmouth Jewish Congregation, where Weiss was a member. Those interested in attending can contact Chapman Funerals for more information.