Editor’s note: Richard C. Gregory died on May 31, 2023, at the age of 90. Read his obituary here. This article originally appeared in the Fall 2012 Bulletin.

When Richard C. Gregory first arrived at Williston Academy, the now fully grown maples on campus were saplings. So was he, in a manner of speaking. He was 29, and had already completed six years of English and drama at Yale, and served in Guam with the navy, but he looked 18—just like the boys he was suddenly in charge of in the dorms and classrooms.

Some 50 years later, Gregory sat down in the Dodge Room, under a plaque bearing his name. This is the same acoustically rich, wood-paneled room where he so fondly remembers rehearsing with the a cappella groups he started, the Caterwaulers and the Widdigers. Eight years after his retirement from the Williston Northampton School, Gregory’s voice filled the room once again, this time with a chat about art, life, and teaching.

“When I came to Williston in 1961, I expected to spend a year before going on to some other school because Williston actually had no reputation, good or bad,” Gregory said. “But once I met a few people here I realized it was a place I’d like to spend my life. I thought there were things I could do that the school needed.”

Those things were many, indeed. Born in Providence in 1931, Gregory attended Episcopal choir schools, where he learned to sing and compose. At Choat—and then at Yale—he studied directing and was a famed Whiffenpoof. (The Whiffenpoofs, or “Whiffs,” are renowned, not only for their musical talent, but for being the longest running collegiate a cappella group in the world.) While serving in the military, Gregory also wrote an opera. With this wealth of musical experience, he took on Williston as his next challenge.

“Probably the most significant thing I did here in my years, aside from running Ford Hall for 25 years, was to found the Fine Arts Department,” Gregory said. “The headmaster, Phillips Stevens, asked me to start an academic department in the early ’70s. It’s the first such program that we know of in any prep school in America. Now practically every prep school and every high school in America has one—but we were probably the first. We had very, very fine people.”

At Williston, Gregory became the successor of Henry Teller, the head of the music department at the time and the father of curretn archivist Richard Teller ’70. To craft a new department, he worked closely with art teacher Barry Moser and theater director Ellis Baker. Gregory also credits Headmaster Phillips Stevens, “a tall, brawny, deep-voiced leader of men” and Associate Headmaster Karen O’Neill as making a big difference in helping usher the school into a new era of music.

At the time, the area colleges would send students to see the theatrical shows at Williston. Recalling the first show he directed, “Cyrano de Bergerac,” Gregory said he remembered thinking that the last performance would be sparsely attended.

“A whole lot of people came from the University of Massachusetts because their professor had told them they’d better see it because they’d never see this ‘Cyrano de Bergerac’ again,” he said. “I had 60 people on stage at one time…that was starting big and we’ve been big ever since.”

Excellent work. High standards. That’s what he thinks a “giant” of teaching engenders in students. Anyone who, like Gregory, wears so many hats over 40 years is a tall figure: he taught English; created sets, designed, and even sewed costumes—fabulous hats included—for theater productions; directed plays; guided all those boys in the dorm; formed the Caterwaulers, Widdigers, and the Glee Club; directed the Teller Choir; composed operas and chamber music; arranged choral music. And started the Fine Arts Department. He even led tours of the campus and worked in the Admission Office. He stopped just shy of mowing the vast lawns by himself.

But the Fine Arts Department was Gregory’s pride and joy, his opportunity to help students ‘appreciate what the human spirit can do.”

“We don’t always teach you how to do it, though we teach you to dance and sign and play the piano,” Gregory said. “I think one of the great joys we’ve all had in the fine arts is to discover talent that’s nascent, that hasn’t shown itself before.”

To encourage students to reach beyond what they thought they were capable of, Gregory combed the dining halls and playing fields, personally inviting potential singers or actors to tryouts, even if they themselves didn’t think they had the right stuff. Many football captains and hockey players found themselves equally at home in the Dodge Room or the theater—thanks to Gregory.

Both teaching styles and students changed a good bit during his tenure, but Gregory kept pace. One key to his success: he believed in students’ potential.

“Over the years, especially as the school became co-ed, I and our lucky other teachers learned to treat people as adults-in-the-making, not just intelligent children,” Gregory said. “I think in some ways the secondary school years are the most teachable because the kids are open to ideas. Almost all students who come to secondary school are intelligent enough to take in difficult concepts yet are still receptive—and that’s why I never thought of teaching in college.”

Like any working artist, however, Gregory does occasionally feel dismay over what might have been, noting that he could have been more musically productive or he could have sold more music and directed more plays. At this moment, music director and teacher Ben Demerath pops into the Dodge Room and reminds Gregory that he has written a lot of music, and has given immesurable gifts to this community.

“I’ve given art to a lot of people, both of us have…and they’ve turned it into thousands now,” Gregory agrees, leaning forward in his chair. He may have retired from teaching, bugt even Gregory knows that he’s still a familiar part of campus—and will continue to be hailed by each new class in the fall.

“So many of the kids, I don’t even know their faces, know who I am,” Gregory says, adding with a chuckle, “I’m becoming sort of a fixture here.”

Richard C. Gregory Faculty Chair established

A chair may just seem like a nice place to rest for a moment, but on Friday, Sept. 14, it meant a great deal more to an esteemed member of the Williston Northampton School community. The Richard C. Gregory Faculty Chair was established and mainly funded by Chuck Tauck ’72 and Jack. G. Tatelman ’73. The chair was presented to Gregory at a reception just prior to the 172nd Convocation, where it would be awarded to English teacher Greg Tuleja. Tauck, a former president of the Board of Trustees, said alumni were constantly asking after Gregory, and reflecting on his influence on their time at Williston, and that was where the idea for the chair game from. A faculty member from 1961 to 2004, Gregory was a cornerstone in Williston Northampton’s Fine Arts Department. “We had a long run together,” said longtime colleague and former faculty member Ellis Baker. Calling Gregory “the Renaissance man of the arts at Williston,” Baker recollected that Gregory had donned every hat the theater department had to offer, literally. “He loved designing period hats,” said Mr. Baker, “and we always argued because they were so good that we couldn’t see the faces for the shadows.”