Dr. James Weiss was the superintendent of Vineyard schools from 2005 to 2015.
Ivy Ashe

James Weiss, Former Superintendent of Schools, Dies

Dr. James Weiss died on August 10 at the age of 78. He spent 10 of his 46 years in education serving the Island.

Dr. James Weiss, former superintendent of Vineyard schools, died on August 10 at the age of 78 after a battle with leukemia. He spent 10 of his 46 years in education serving the Island.

Mr. Weiss was born in Connecticut in 1947. He started his educational career as a teacher and principal before becoming a superintendent in New Hampshire. He became superintendent of the Vineyard school system in 2005 and served until his retirment in 2015.

The Island community remembered him as an affable problem-solver who led with a steady hand.

Richie Smith, the current school superintendent, said that Mr. Weiss brought a new level of professionalism and accountability to the job and was a stalwart mentor.

“He is the measuring stick for leadership,” Mr. Smith said.

John Custer, the principal of the Tisbury School, echoed Mr. Smith’s remarks. Mr. Custer was appointed principal in 2011 by Mr. Weiss, but said he was at first reluctant to take on the role until Mr. Weiss convinced him he could do it.

“During that summer, he and I had many heart-to-heart conversations that made me consider him a father figure,” Mr. Custer said.

Sandy Joyce served as co-president of the teachers union during Mr. Weiss’ tenure. She said that he provided unwavering support for everyone involved in the school system, including the teachers, maintenance staff and other workers. He was also involved in the lives of students.

“He supported the student body. You would see him out and about at almost anything you would go to in terms of the students, he was there cheering them on,” Ms. Joyce said. “He was just this true, deep down into his bones educator.”

One of Mr. Weiss’ lasting impacts was helping to develop support programming for disabled students across the Island. Mr. Smith said that the work Mr. Weiss and others did meant that students could access the resources they needed on the Vineyard.

“We’re able to do that for children on the Island without having to send them to day programs off Island,” he said. “He was a lynchpin in getting that done for us.”

Dan Seklecki, former director of special education services, worked with Mr. Weiss to expand services across the Island. Mr. Seklecki said that Mr. Weiss held the department to a high standard and helped communicate the need for increased services to school committees and select boards.

“He was the point person to run and lead those initiatives,” Mr. Seklecki said. “He was a good boss. His standards were the best service to our students.”

Many of Mr. Weiss’ colleagues said that a large part of what made him a successful superintendent was his ability to navigate the different cultures and environments of the Island schools.

Susan Mercier served on the Edgartown school committee for 12 years. She said that in addition to being a friend and mentor to herself and others working on school committees, he was a strong presence in students’ lives.

“I never met anybody who could create relationships like him and sustain them,” she said.

He would even go to various schools on Halloween wearing different costumes, and he ran the Turkey Trot dressed as a turkey, she said.

“For his retirement party, I had a friend of ours get him out of his house and went into his basement and took some of his Halloween costumes,” Ms. Mercier said. She then had students dress up in Mr. Weiss’s old costumes while serving appetizers. Guests also wore colorful ties, a nod to Mr. Weiss’ sense of style.

After retirement, Mr. Weiss remained active in the community, taking part in nonprofit work across the Island. Mr. Seklecki said that in addition to attending school events, Mr. Weiss could be found taking walks and reading on the beach.

“It was an enjoyment to see him enjoying himself so much,” Mr. Seklecki said.

Mr. Weiss also traveled in his retirement. Sue and Barbara Silk were frequent companions on trips around the world.

“It didn’t matter where we went, he always said ‘I’m in,’” Barbara Silk said. “He was a great companion. He would always put in his time, his energy, his money to make something worthwhile.”

Sue Silk agreed, saying that Mr. Weiss found joy in being together.

“It was the going together that was what he liked. It was going with us, laughing, having a good time, getting out in the world,” she said.

Mr. Weiss is survived by his sister, Susan Miller, daughter-in-law, Nicole, and his nephew, Alan Miller. He was predeceased by his son, Joel.

Mr. Miller remembered his uncle as someone who was committed to serving his community wherever he was.

“His sense of service was like a gravitational pull, one he embraced wholeheartedly and encouraged in others,” he wrote in a statement to the Gazette.

A funeral service will be held on Thursday, August 14 at 2 p.m. at Chapman Funerals and Cremations located on Edgartown Road in Oak Bluffs, officiated by Rabbi Zinn.

Donations can be made in his name to the Martha’s Vineyard Community Foundation Scholarship Fund.

 

Comments

Submitted by Anonymous (not verified) on Thu, 08/14/2025 - 10:47

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Julia Rappaport Newton and Chilmark

I am so sorry to hear about this loss. Jim made such an impact on our island. More personally, he was close with my dad, and now both of them are gone - two wonderful men. Our hearts are with Jim's family, may his memory be a blessing.

Submitted by Anonymous (not verified) on Thu, 08/14/2025 - 11:21

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Rob Kosienski Oak Bluffs/ Meriden CT

Dr. Weiss was a principal here in Meriden CT for a few years at Casmir Pulaski School. He made an impact on the school community and the entire Meriden Community. He was a strong leader with a vast knowledge of Education and a true role-model to our students and families. We met up again on the Vineyard while he was Supt of Schools on island when I was working here full time. It was fun talking to him over an Ice Cream at Mad Martha's or a chat at the bench at the Post Office. He fell in love w/ the Vineyard. The island certainly made him complete. My condolences to his family, and on behalf of the Meriden Board of Education, we salute his service to thousands of students and staff over his lifetime of love for the education community.

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