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Deer Isle, Isle au Haut and Stonington, Maine.
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by Jessica Brophy
On Tuesday, October 16, Gary Webb died from cancer.
Webb taught health and physical education from 1970 to 1997 on the Island, first at the Stonington High School and then at the consolidated Deer Isle-Stonington High School. He and his wife, Elaine, raised a daughter and lived in Sunset.
Clare Grindal attended elementary and high school with Webb in Stonington, and also worked with him as a teacher and counted him as a “friend that was there from 1949 onward.”
“He was the epitome of kindness and loyalty,” said Grindal. “He had time for each and every person he knew. He didn’t judge anyone—except maybe the occasional ref.”
Webb helped lead the Stonington Rockets to two state championships in basketball, one in 1961 and one in 1962, the year Webb graduated from high school.
“He was an even-tempered, good-natured, steady and dependable guy,” said Bill Flagg, who taught science at the high school for many years. Flagg also noted Webb’s integrity and commitment to his students.
Charlie Johnson, who also taught at the school for many years with Webb, recalled the “quiet and strong” voice of Webb. “In faculty meetings, he hardly spoke, but when he did speak, people listened. He always considered what he had to say carefully.”
Mary Rees-Nutter, middle school social studies teacher, remembers observing him teaching health in her classroom. She appreciated his dry sense of humor and his witty jokes, many of which went right over students’ heads.
Webb taught more than one generation of students, many of whom remember him fondly. Tim Thompson, a 1991 graduate who is now a second-grade teacher in Greene, remembers Webb as a summer basketball camp coach and then later as a teacher.
“He was one of the kindest men I ever knew,” Thompson said via email. “But he was persistent and earnest about everything he did. This blend of consideration and tenacity was unique to coaching and teaching.” Thompson also remembers Webb’s ability to create “engaging games to present content and review concepts,” such as “Health Bingo.”
“The kindness, focus and creativity he put into his work as a teacher each day were guideposts for me as I fashioned myself into a leader in a classroom of my very own,” said Thompson.