South Portland School Department’s interim superintendent takes over amid turbulence
A week into the job, George Entwistle talks delegation and strategic planning.
Published August 12, 2025 by Dana Richie, Portland Press Herald.
Taking the reins of the South Portland School Department, interim Superintendent George H. Entwistle plans to lead with big-picture planning and clear delegation, guided by the question: “Is this in the best interest of kids?”
“My feeling is we need to take a deep breath and assess how we are delivering on our promise to give every kid a good, strong education,” he said. “The sky is not falling.”
Entwistle is inheriting a turbulent school district. Within the past six months, two school board members and the previous superintendent resigned.
Former School Board member Jennifer Ryan resigned in March, citing mental health concerns. Tim Matheney, the prior superintendent, announced his resignation in June, writing in an email to parents that “the board should have the opportunity to identify a new leader who is more aligned with them.”
In late June, Molly Schen, the chair of the school board, submitted her resignation, effective immediately. She said that she did not see eye-to-eye with other board members, writing that they were “micromanaging matters best left to our educational leaders,” obscuring their job of working through big-picture challenges facing the district. Her term was due to expire in December of 2027, and the seat will be left vacant until the election in November.
Entwistle remains optimistic about the future of the district.
He has worked in and around schools for more than three decades, serving as the superintendent in Falmouth and Scarborough before moving abroad to work as the head of campus for the Shanghai American School.
While raising his three children in Cape Elizabeth, Entwistle served on the school board for seven years and was chair for four. That experience guides the way he thinks about the dynamic between a school board and a superintendent.
“We knew how to differentiate who was responsible for what,” he said. “When everyone knows their roles and performs their roles in the right way, things work well.”
In his eyes, the board is responsible for making sure finances are in order, examining and setting policy and hiring and retaining a qualified superintendent.
“The day-to-day and overarching responsibility for the safety and performance of this school district as a whole is the responsibility of the superintendent,” he added.
And Entwistle is a proponent of strategic plans. To him, they don’t have to be long or complicated. They don’t need to have a five- or 10-year timeline. They can even be one page.
“You can’t do 15 things great,” he said. “You can do five things really well.”
“Some schools try to do 50 things,” he said. “It’s just a constant cycle of frustration because they are trying way too hard to do way too many things. There’s got to be priorities.”
Entwistle is already working with stakeholders to identify these top priorities. With a background working in mental healthcare for this first third of his career, student mental health is top of mind. Part of the district’s strategic planning should include a needs assessment, he said.
He will serve as superintendent for a year as the district searches for a permanent superintendent. Tandy Ratliff, the acting board chair, said that the district has yet to launch its search.