Principal Jake McCandless Announces Retirement Amid Contract Extension

BREAKING NEWS: W.E.B. Du Bois Regional Middle School Principal Jake McCandless has just announced his retirement, effective at the end of the school year in June 2025. This surprising decision comes only a day after the Berkshire Hills Regional School District extended his contract through June 2028.

During a district meeting on January 15, 2025, McCandless revealed his intent to step down after just two years in the role. He previously transitioned to this position in the summer of 2024 after former principal Miles Wheat took a new role at Chatham High School in New York.

With an impressive 33 years in education, McCandless has held various significant roles, including principal at Lee Middle and High School and superintendent for multiple districts, including the Lee School District and the Pittsfield School District. He has been a pivotal figure in the educational landscape of Berkshire County.

In a poignant statement, McCandless expressed deep gratitude for his time at Du Bois, stating, “My heart will very much be with Du Bois [Middle School]. As you can tell from watching me walk up to the [meeting] table and back again, my hips and knees are on a different planet, and the rigors of keeping up with 330 middle schoolers are just about more than I can do on some days.”

Superintendent Peter Dillon praised McCandless’s contributions, saying, “I think the world of Jake. He stepped into the [principal] role from being a superintendent. He put his heart into Du Bois [Middle School], and he stabilized it and still has a smile on his face. It’s way too early to say goodbye because we have another five months left with his skillful leadership.”

The announcement has sent shockwaves through the community, as parents, students, and staff reflect on the impact McCandless has had during his short tenure. His focus on supporting teachers and maintaining a positive environment has been widely recognized and appreciated.

Looking ahead, the school district will be tasked with finding a successor who can continue McCandless’s legacy and uphold the standards he set. As the school prepares for the transition, the community is encouraged to celebrate McCandless’s contributions and support the students during this period of change.

Stay tuned for more updates as the situation develops.