Some teachers are lifers. Jack Pidgeon is one. He is and was my headmaster at The Kiski School, a private boys’ preparatory boarding school for students in grades 9-12 in the rolling hills of western Pennsylvania, near Pittsburgh.
Now in his 42nd year, Jack is believed to be the longest serving “head master,” as he likes to pronounce the word, in the United States--a remarkable durability, considering the average tenure of a headmaster at private preparatory schools today is three years.
“You know the word ‘principal,’ if you think about it, is an adjective. It’s the principal teacher,” Jack explained to me in an interview not too long ago as he described his love for teaching. “For many principals, the teacher part has dropped off over the years,” he said. “I have never felt that way. I wanted to be a head master. I wanted to be the super teacher.”
“I have always wanted to create a community of boys where academics was the thing that held it together. I wanted to have boys who were some of the brightest in the country and boys who were just able to make it.”
In the years since he has been headmaster, Kiski has attracted both, as well as boys who were so rich they could fly to Europe on their family’s plane on the weekend and those boys--black and white--who were so poor that the school has to buy clothes for them. Jack made sure that intolerance and elitism in a social, economic, or intellectual way didn’t keep people apart at his school.
“What I have been trying to do is to build humility and tolerance by throwing all kinds of boys together,” said Jack. “Running a private boarding school that shapes character,” he explained, “is much like operating a stone-polisher. Boys with different ability levels, intellectual and athletic, rub off on each other. Over four years, they study, compete on sports teams, and eat together. On their way to maturity, they learn to interact, be polite and considerate, and to gain humility and tolerance.”
Another concept that Jack has tried to teach is self-knowledge, getting boys to not only ask who they are but to introspectively find out and objectively come to terms with their personas.
“You have probably known adults who never found out who they were. They always were somebody else,” Jack added. “They have been playing a role for 40 or 50 years. This has been a real passion of mine to get kids to understand. They only do it by trying, by finding out their weaknesses, by failing, by rubbing up against somebody who is better than they are at something.”
My memory of Jack, as a Kiski student 36 years ago, was his upright football player’s gait when he crossed the campus--all 6 feet 2 inches and 190 pounds. Often, he wore a bow tie that was a little askew. Other clothing staples included his button-down, blue-lined shirts, blue-and-brown tweed blazers, gray wool pants, and cordovan wingtips from his New England roots.
Today, at 74, he’s spry. His blue eyes sparkle. The warmth of his winning smile still glints like sunlight on his open face. Only a few wisps of wheat-colored hair cling to his now lined, cue ball head.
Jack’s values were forged in a different era. He began life as an Irish boy from a slum in Lawrence, Mass. His parents were union laborers in a woolen mill. He went on to Phillips Academy at Andover, Mass., where he played on the baseball team with George Bush and was a classmate of Jack Lemmon. A scholarship student, he waited tables and always ate in the kitchen with other scholarship boys. He graduated from Bowdoin College, also on scholarship.
Teaching Latin and English appealed because it offered an opportunity to shape character. Hired at Deerfield Academy in Deerfield, Mass., he served as an instructor for eight years on Frank Boyden’s teaching team. Mr. Boyden, Deerfield’s headmaster for 66 years, was known for training teachers who became headmasters.
Kiski’s headmaster since 1957, Jack has been the school’s educational, emotional, and administrative keel, as well as its chief fund-raiser. He took the school, founded in 1888, and its then-negative endowment and built it to $30 million while expanding facilities. The 350-acre campus includes a golf course, tennis courts, all-weather track, indoor and outdoor swimming pools, and a variety of playing fields.
He attributes his success to his love of pedagogy. Like all good teachers, he’s memorable because he challenges and inspires. He’s demanding when assigning papers on Emerson and Thoreau and when he is coaching football, track, baseball, and swimming.
“I think it’s bred in me,” said Jack. “As far back as I can remember, I have been fascinated by the opportunity to teach people younger than me whatever I knew. When I was 12 years old, I played sandlot football with my peers. When I came home, I would have a bunch of 8-year-olds and I would coach them.
“I said to somebody the other day that I have been going to practice every day since 1935 at 3 p.m. I love to teach in the classroom. I love to watch boys’ eyes pop open wide when an idea hits them that they haven’t thought of before,” Jack said.
When many people are on their third or fourth jobs by the 42nd year of their careers, Jack continues in the same job to pursue his dream each fall, welcoming a new class of freshmen and playing a part in the lives of 250 boys.
As the head “schoolman,” a word he uses to describe the ideal boarding school teacher who is involved in all aspects of a boy’s life--from the classroom to the dormitory, to athletics, to extracurricular activities, to the dining room--Jack’s will still prevails on a campus wired for the Internet.
I found Jack that day still largely the same man I remembered from 36 years before. It seemed like only a few minutes that we had been talking, but actually it had been two hours. When I arrived in the doorway to his commodious office, I surveyed the walls filled with student photographs, oversized leather and wooden chairs, and school memorabilia on tables and bookshelves--artifacts of a lifetime teacher.
Jack had risen from behind his desk to greet me. In a flashback, how clearly I remembered that stance from when I was a student. Then, Jack had greeted me the same way each time I came to hear his personal report of my grades. Jack’s personal audiences, three times a year, were a tradition which every Kiski student endured, usually with some trepidation.
Now, as I stood before him, his still-rangy frame was a bit stooped with age. His hands were jammed into his dungarees and his collar lapels rolled onto the neck of his gray Kiski sweatshirt. When he flourished his arm and motioned me to a chair, he interrupted my flashback reverie about my student days.
One more personal audience with Jack began. “When I was a little kid, I used to coach ‘littler’ kids in baseball,” he said. “I always wanted to play a part in a boy’s life. This has always been an obsession of mine.”
This is why I call Jack a lifer. Some day he won’t be there as that rigorous and caring schoolman--that super teacher. What Jack Pidgeon the “head master” has wrought on his Kiski boys, though, will continue into the new millennium.
Bryant Mason is a senior fellow at the Phelps-Stokes Fund, a nonprofit educational foundation in New York City.
A version of this article appeared in the December 02, 1998 edition of Education Week as Tribute to a ‘Head Master’