Dick Gregory

Beloved Teacher & Musical Mentor

On May 31, 2023, beloved Williston Northampton educator Richard C. “Dick” Gregory died at the age of 90. Gregory, who started his career at Williston Northampton when it was still Williston Academy, touched the lives of countless students that stepped foot on campus. Whether it was through his work leading the Caterwaulers or Widdigers, being the dorm head at iconic Ford Hall, starting the Fine Arts Department, or teaching students the rules of English and grammar, Gregory’s fingerprints were all over the school that he worked at for over four decades.

“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 in a 2012 Bulletin interview, discussing students’ potential at Williston. “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.”

The evidence of Gregory’s impact is apparent when talking to one of his former pupils. Williston alumni have also shown their affection for Gregory through song, video interview, and newspaper articles. To celebrate the life and legacy of Dick Gregory, we’ve compiled everything from our archives to highlight just how much of Williston’s fabric was sewn by Gregory’s guiding hands.

To read his obituary and to view remembrances from former students, click here. If you have any memories of Dick Gregory you would like to share, you can comment on our Facebook page or email

Dick Gregory and Greg Tuleja

A Scholar and True Gentleman

On Sunday, June 11, 2023, Williston held a Service of Remembrance as part of Reunion weekend. During this ceremony, retired Academic Dean and faculty member Greg Tuleja recounted his memories of a Mr. Gregory, a man who influenced his teaching and with whom he shared a deep love of music. In his honor, Tuleja performed a stirring rendition of “Londonderry Air (Danny Boy)” to close the ceremony. His remarks about Mr. Gregory are below.

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    I met Dick in the summer of 1983, when I first visited Williston to interview for a part-time music teaching position.  In contrast to the then Head of School, who greeted me in his office in shorts and bare feet, Dick gave me an extensive tour of the campus, in 85 degree heat, dressed professionally in sharply pleated trousers, shined loafers, jacket and tie (he would have called it a “necktie”).  Dick was gracious and engaging, and took a great interest in me, as he would continue to do for decades after.  Karin O’Neil and Bob St. George decided to take a chance on a completely green young musician, fresh out of grad school, and I was hired.

    Later that week back in New Jersey, I received from Dick a five-page handwritten letter of congratulations, in his beautiful penmanship and impeccable prose.  The letter was an introduction to the musical life of the school, intelligent, funny, and encouraging, characteristics that would become reliable features of a long friendship with him.  I was nervous and uncertain about my new job, but after reading that letter (three times), I knew that there was at least one person at Williston who would be in my corner, a seasoned, well-regarded veteran who was eager to help me get started.  I was yet to learn of Dick Gregory’s brilliant talents as a musician.

    Dick’s extraordinary ability as a composer, arranger, and performer (piano, violin, viola, and yes, tuba) were well known at Williston, and an absolute revelation to me when I arrived.   One of Joseph Haydn’s string quartets had been appropriated by the school as the Williston hymn, and at some point during my first few years, Dick and I were asked to put together a student group to perform the piece for an alumni function.  We did not happen to have two violins, a viola, or a cello, so we were faced with the task of rewriting the quartet for the forces that we did have – flutes, clarinet and French horn, as I remember.  My plan was to work from the score and transcribe Haydn’s string parts, making the necessary adjustments for keys and ranges.  Dick’s strategy was more direct.  As I watched him, in some amazement, he simply sat down at his desk in the music classroom, took out some blank sheet music and started writing out the score, using only his memory of Haydn’s original melodies and harmonies, and I could see that he would not need to have the original music in front of him at all.  In about half an hour, all four parts of the 32-measure piece were written out, transposed for our wind quartet. By the way, he did this, not with a pencil, but with a black non-erasable marker (we would, much later, call them Sharpies). I would discover the next day at rehearsal that in the several pages of four-part writing, there were no errors.  Dick would be surprised, I think, that I still remember that incident 40 years later. That musical feat, and so many others like it, although spectacular to me, was for him, routine.

    Dick was an unfailing advocate, advisor, and friend to me.  I sometimes wondered how he could do such a good job propping up a brand new teacher, while he was also busy teaching art history and English classes, and running three choral groups, including the already legendary Caterwaulers, and the newer but also impressive Widdigers. He was also designing costumes for theater productions (he was very skilled in drawing and adept behind a sewing machine).  Dick was also busy directing school plays, writing original plays, and serving as the renown and beloved dorm head in Ford Hall.  Through our many years together at the school, first when I was part of the music program and later when I was not, Dick was a constant source of knowledge and inspiration to me.

    For some years after his retirement, Dick used to meet his fellow retirees and contemporaries Bob Couch, Ray Brown, and Al Shaler for weekly Friday morning coffee in the Williston Stubop.  Somehow, I got a standing invitation to join them, which I often did, for fifteen or twenty minutes, when Heads of School Brian Wright or Bob Hill no doubt expected me to be hard at work in my office in the Schoolhouse.  But seeing Dick again, even briefly, was worth the trip across campus.  He was, in the most authentic sense, a scholar and a true gentleman, and I feel grateful to have known him and worked so closely with him for so many years.  Dick helped me to unravel the mysteries to be found in that wonderful and bewildering species known as “the teenager,” and I know that many hundreds of former students and singers who once populated these paths and these buildings, will remember Dick as I do, with great affection, admiration, and respect.

Tributes and Videos

Honorary Diploma

Dick Gregory received honorary diploma at Commencement 2004.

A Lively Tribute

Dick Gregory was honored at Reunion 2004 where Ellis Baker spoke during dinner and alumni entertained the crowd.

Personal Reflections

One evening at Reunion 2004, alumni gathered in the Dodge Room to sing a few songs and share their reflections on the great Dick Gregory.

The Twelve Days of Christmas

The Caterwaulers reunited at The Williston Northampton School’s 2009 Reunion to sing Dick Gregory’s unique, playful, and masterful arrangement of “The Twelve Days of Christmas.”

Singers in Seoul

“Sammy” and “Down in the Old Cherry Orchard” sung by alumni in Seoul, Korea, featuring: Alex Park ’81; Michael Ko ’94; Wookie Kim ’08; Kevin Jung ’10; and Charlie Park ’11.

From the Bulletin Archives

In September 2012, the Richard C. Gregory Faculty Chair was established by some of his former pupils. To commemorate the occasion, the Bulletin included a feature article about Gregory titled “Giant on Campus: Dick Gregory Reflects on His More Than Four Decades on Campus.” Read the article here.