Bob Moore , at the podium during the October celebration in his honor, is remembered for his dedication to education. —Nicholas Vukota

Perhaps nobody was more instrumental in establishing the community of Martha’s Vineyard Public Charter School than Bob Moore. 

Moore, who passed away last month, was the first director of the Charter School. He was remembered by Islanders for his years of service to education, and positively impacting hundreds of community members. 

“He was our light,” Pete Steedman, the current Charter School director, told The Times. “He was instrumental in creating the educational vision for this school.” 

Moore is being remembered for his adventurous spirit, and his firm belief that anyone could be taught, which transcended the Charter School. He also led an effort at the Vineyard’s house of corrections that positively influenced numerous inmates, Dukes County Sheriff Robert Ogden said. 

“God, was he not the right influence?” Ogden said. “I can’t say enough for what he did for us … There’s a large hole that’ll never be filled at our department.”

Much of Moore’s career was in education. He steered the school for 20 years, taking the helm in 1998. He established many elements that are now fixtures of the school’s education, such as the morning meetings, personalizing education, and “six pillars” of cooperation, democracy, freedom, respect, responsibility, and trust. 

Moore also excelled at building community, Steedman said. He had a “real skill” to hire exceptional people who were not only great educators, but also communicated and connected well with students and their families. 

“Just thinking about the impact he has had on so many lives on this Island, it’s really immeasurable,” Steedman said.

“He was a listener, and compassionate to the needs of students. The need of students always came first to him,” Jonah Maidoff, who retired as a teacher in August after nearly 30 years at the Charter School, said. 

Maidoff, who’d been teaching at the school since its 1996 inception, said a search committee for a full-time director didn’t happen until the following year.

“He was a very wise choice,” Maidoff said of the school hiring Moore. 

Maidoff reminisced about Moore accompanying students on field trips, like skiing and hiking at Mount Greylock. Some of the students’ trips had to overcome obstacles first. Maidoff said there was uncertainty about a trip to Italy after the 9/11 terrorist attacks in 2001. But, after surveying the sentiments of parents, Moore was willing to allow the first Charter School flight to Italy, which took place in April 2002. That’s now become a regular part of the eighth grade experience at the school. 

“He continued until the very end,” Maidoff said. “His life was a dedication to learning.” 

Moore retired as the Charter School director in 2018, but his educational legacy didn’t end there. In “typical Bob Moore fashion,” as Steedman put it, Moore looked for other ways he could help people. That led him to become director of inmate education at Dukes County House of Corrections. 

Sheriff Ogden said he first met Moore in the early 2000s, long before his tenure at the county jail. Ogden was trying to create the Ropes Challenge Course, located in the Martha’s Vineyard Airport Business Park. 

“He had this glint in his eye, and said ‘I’m in,’” Ogden said. 

Moore was actually applying to be a 911 dispatcher in 2018, to find a way to help in his retirement. Upon seeing Moore’s application, Ogden called him to instead pitch the position of inmate education division director. 

“He did it with such vigor,” Ogden said, saying Moore helped around 150 inmates. 

With the rehabilitative education philosophy called the “five keys of success” — consisting of a stable family, secure housing, a job, good physical and mental health, and education — and his experience from the Charter School, Moore established various programs for inmates. These included book clubs, college courses, bringing in speakers to talk about inmates’ struggles, and improvement initiatives, like the Nurturing Fathers program that taught men how to have better family dynamics and be better fathers. 

Ogden said Moore’s passionate drive to personalize the educational journey of each inmate was a driving force behind the success of released individuals, who opened up to the director. 

“I always thought it was so great that he’d bring the inmate into the office and ask, ‘What do you want to do with your life from here?’” Ogden said. 

Even as he was in the hospital, Ogden said, Moore would keep returning to the inmate education division. 

And Moore’s passion for education was felt by those he reached. Ogden said some inmates reached out to ask if they could send cards of condolence to Moore’s family after he died. 

A month before his passing, Moore’s generosity as an educator was recognized in October. The Charter School honored Moore by ceremoniously naming a planned school building in his honor, the Bob Moore Learning Center

“I’m moved by it all, because many people contributed to the success of this school; great teachers, supportive parents, and wonderful students have made the school successful, and I feel very fortunate for that,” Moore said in October after the ceremony. “What’s important to me, and has always been, is creating an environment where students and teachers can come together and work in a positive way.”

Beth O’Connor, who helped plan the celebration, and called Moore a family friend, said the former director had taken a “multitude of children … under his wing.” 

One of those kids was her son, who was struggling socially when they were still living in New York. After seeing Moore’s way of compassionately making kids “feel very much at home,” O’Connor decided to enroll her son at the Charter School. 

“He’s probably the reason we moved to the Island,” she said. 

O’Connor saw “an incredible alteration” in her son, who thrived on the Island thanks to Moore and the team of teachers he put together. She said her son is now in law school. 

After Moore’s passing, O’Connor hosted a small gathering at her Edgartown home to honor him. Around 50 people gathered, and “everyone had a story about him,” O’Connor said, remembering former students saying Moore focused on listening to and guiding how a student can improve, rather than just disciplining them. 

“He actually altered the trajectory of a lot of kids on this Island … he taught kids that they could do things,” she said. “He believed in them.”