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McCandless preparing to start as principal at Great Barrington’s W.E.B. Du Bois Middle School July 1st

W.E.B. Du Bois Middle School in Great Barrington, Massachusetts.
Berkshire Hills Regional School District
W.E.B. Du Bois Middle School in Great Barrington, Massachusetts.

A well-known Berkshire County educator will soon become principal of a Great Barrington, Massachusetts middle school that was at the heart of a controversial police search.

Mount Greylock Regional School District Superintendent Jake McCandless has been tapped to replace the outgoing Miles Wheat as principal of W.E.B. Du Bois Middle School. Wheat announced in April that he had taken the position of principal at Chatham High School in New York starting in July.

“He's a thoughtful career educator who does a great job of building collaborative environments and listening to community members, and we couldn't be more excited to bring him on board to work with us," said Berkshire Hills Regional School District Superintendent Peter Dillon. “We had a 15-member search committee, and candidates went through two things, a set of fairly typical questions, there were about 15 of those, and then an inbox activity, which would be sort of the equivalent of having a teacher teach a model lesson, having a principal come to work on early morning in September and be confronted with 17 quite challenging circumstances, and then they had to go through them, put them in priority order and explain how they'd solve them. And Jake, with his background and experience, just really demonstrated his capacity to move work forward, to provide support for teachers and staff, students, and community members.”

McCandless, who previously served as superintendent of the Lee and Pittsfield school districts, began working at Mount Greylock in 2020. He’s signed a one-year deal with Berkshire Hills to work at W.E.B. Du Bois.

“It's been almost 20 years since I've been a principal," McCandless told WAMC. "You know, my final year as a principal was the 2004-2005 school year before I stepped into being a superintendent, and I want to make sure that I can adequately serve that group of students, that group of faculty and staff and their families and the community. And so I really was looking to, let's do a year, and I can see how I'm feeling about my work, and you can see how the community is feeling about my work, and then we can plan from there. I certainly would be very open to spending multiple years there, I think that best serves the school, but for now, I really want to make sure that this is a fit that works for all parties.”

He takes charge of the middle school after a controversial police investigation into the presence of Maia Kobabe’s graphic memoir “Gender Queer” in December 2023. An anonymous complaint from a since-fired staffer led to an officer entering W.E.B. Du Bois with the permission of Dillon and questioning a teacher associated with the award-winning book. The incident sparked outcry from the community and LQBTQIA+ groups, and Dillon and other officials have repeatedly apologized for the incident. He, the town, school district, and other officials are now the subject of a lawsuit from that teacher.

“I am much more interested in supporting the people that do the work than I am really anything else in the building, because they are the people that support children, and if they are not feeling safe, if they are not feeling heard, if they are not feeling respected and valued, then that cannot help but seep up to the children that we're all there to serve," said McCandless.

Dillon says the district is working to make McCandless’s entry as smooth as possible.

“We're going to use the summer to do some onboarding work to make space for him to build relationships with teachers and staff and, to some degree, students – though it's harder to do that with students in the summer – and with parents and families as well," he said. "As a school community, we've got some healing to do. There also continues to be lots of great work going on there, and he'll come up to speed on that and support it and push us to grow in other areas.”

McCandless tells WAMC that despite recent events, he’s confident in both Dillon’s leadership and the reputation of the Berkshire Hills Regional School District.

“What I owe the community first and foremost is to listen and to learn and to be there to support the fifth graders and the sixth graders and the seventh graders and the eighth graders and to support their families and to support the staff that go into that building and do the actual work in classrooms and cafeterias and hallways and make school happen," he told WAMC.

McCandless starts as principal of W.E.B. Du Bois Middle School July 1st.

Josh Landes has been WAMC's Berkshire Bureau Chief since February 2018, following stints at WBGO Newark and WFMU East Orange. A passionate advocate for Western Massachusetts, Landes was raised in Pittsfield and attended Hampshire College in Amherst, receiving his bachelor's in Ethnomusicology and Radio Production. His free time is spent with his cat Harry, experimental electronic music, and exploring the woods.
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