HEBRON – Friends of longtime Hebron Academy teacher Jay Woolsey were mourning his death Saturday, a man respected as much for his contributions to his community as for his excellence in the classroom.

“Talking with alums who had Jay, they all seem to speak reverently of him, of what they learned here … not just in the classroom, but in the larger context of their lives and their places in their communities,” said Jack Leyden, associate head of school who worked with Woolsey from 1982 until his retirement in 1997. “He was a class act.”

Woolsey lived what he taught. His long career at the private boarding school started in 1965 as a language teacher, moving to head of the Language Department, college counselor and director of studies, as well as various coaching positions and Outing Club advisor. After his retirement, he continued to serve as a trustee until his death Wednesday, the result of a January bike accident in Arizona.

“He was always such a fit man, always energetic and healthy,” said Roina Berube, a former selectman who learned CPR from Woolsey during her time on the town’s volunteer rescue squad. “For this to happen to him is so sad.”

Woolsey was severely injured when he was hit during a 20-mile bike ride in Tucson. He had been in serious condition at University Medical Center since the accident.

A trained emergency medical technician, Woolsey co-founded the town’s volunteer rescue squad in the 1970s. He volunteered in many other ways, such as driving senior citizens to medical appointments and leading outdoor trips. An avowed naturalist, Woolsey cared passionately for the outdoors.

“He was a very strong environmentalist, long before environmentalists got a capital E’,” said Leyden. “He was a huge lover and defender of the outdoors.”

Richard Davidson, former headmaster of the school and close friend of Woolsey, said he had a tremendous impact on the lives of his students. A man with an ironic, wry sense of humor and a taskmaster in the classroom, he earned the admiration of his students.

“Kids unfailingly think of him as one of the greatest people and influences in their lives,” said Davidson. “He was a great teacher in that he combined sympathy and empathy with students and a faithfulness to academic demands.”

Leyden said he was unaware of any special commemoration activities planned at the school. He said Woolsey was very clear in his wishes that there be no memorial services for him.

“We will abide by his wishes and his family’s wishes,” said Leyden.

Although he never married or had children of his own, Woolsey’s influence was felt among hundreds of students’ lives. Leyden said his own father, John Leyden, headmaster from 1977 to 1985, called Woolsey “his ace.”

“He knew what was important,” said Leyden, listing service to community and others at the top. “The world needs a lot more Jay Woolseys.”


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