Andy Chappell, Roxbury Latin’s Assistant Head for Program, has been elected the Head of School at The Derryfield School in Manchester, New Hampshire, a role he will begin on July 1, 2022.

Founded in 1964, The Derryfield School is a day school serving 400 students in Grades 6-12. Recognized as one of the top schools in the region, Derryfield attracts boys and girls from more than 50 different communities in New Hampshire and Massachusetts. Known for its ambitious academic standard and its effective outreach in the community, Derryfield represents an admirable example of aspiring independent education.

In his announcement of this news, Headmaster Kerry Brennan shared the following with the community: “Andy Chappell’s contributions to Roxbury Latin are peerless. Having come to RL in 1997 fresh out of the University of Virginia, he has gone on to fill virtually every role an adult can at Roxbury Latin. A fine teacher of Latin and Greek, Andy served a stint as an effective Chair of the Classics Department. He went on to become the Director of Admission, the Director of Studies and, for the past two years, the Assistant Head for Program. Andy has been an energetic, successful coach of baseball and soccer teams, and served as Class Dean over the years in Class V, Class III, and currently in Class II. He is a dedicated, loving advisor. Every evolutionary program we have launched over the past decade bears Andy’s distinctive fingerprints, from the junior class experience with RL@Work, to the imagining and building of the new athletic facilities, to systems for faculty assessment and curriculum development, to the expansion and deepening of our summer programs, to the establishment of RL’s Penn Fellows Program.

Andy is a bright, energetic, catalytic schoolman who has been dedicated to the realization of this old school’s distinctive mission. His leadership talent has been in evidence in all sorts of ways and in all sorts of places. He gives freely of his gifts and represents the very best combination of regard for tradition and eagerness for progress.

For me personally, Andy has been a reliable, inspiring partner eager to engage with new ideas, new projects, and new people in service to creating the finest school community we could imagine. I will miss him greatly, as all of us will. But I am convinced that he will be a brilliant head of school bringing a masterful sensibility to his new dignities and opportunities. Lucky Derryfield for having chosen Andy to lead their fine school. We have benefitted from having Andy with us for 25 years, and he and his wife, Kate, and son, Brady, have all contributed magnificently to our quality and dynamism. They and daughter Samantha will delight in moving to New Hampshire, to Derryfield, from which Kate graduated, and her father, Marcus Hurlbut, himself a former RL teacher and Dean of Students, served as Headmaster for 11 years.

Over the next several months, we will have plenty of opportunities to celebrate Andy, to thank him for all that he has meant to RL, and to wish him well. For now, though, please join me in offering him our congratulations.”

Long-time and beloved Roxbury Latin teacher Ken Conn died on Saturday, March 12. Ken taught at RL from 1973 until 2009, and though Ken principally taught French—and chaired the French Department, the inaugural holder of the Stanley Bernstein Professorship in Modern Languages—he was also an enthusiastic and iconoclastic teacher of English. During his years at the school, Ken dynamically coached varsity football and, for many years, coached our youngest boys in lacrosse. Ken was the longtime Class Dean for the junior class, and he served with good judgment and distinction as a member of the Admission Committee.

Credentials aside, Ken’s greatest contribution was to the boys of the school, whom he loved and served. Ken had a magnificent understanding of the teenage male psyche and generously offered counsel and support to everyone, but especially to those who were encountering difficult challenges, and those who were out of the mainstream. Ken’s room was a magnet for all kinds of kids and, over games of Boggle, boys came to know Ken and each other—coming to know “home” within a larger context. Ken advocated fiercely for those who deserved a second chance, and they loved him for it.

Ken represented an inspiring model of the teacher-coach and the fully invested schoolman throughout his time at RL. He was as respected by his colleagues as he was by the boys. Below is what Headmaster Kerry Brennan read to the community on the occasion of Ken’s retirement from RL in 2009:

“Great schools are the result of the work of great teachers. For some of those, their greatness is measured by brilliance, or by a consistently unreachable standard, or by the versatility of their contribution. For the greatest of the great, however, their impact is the result of doing that hard, but obvious thing well: loving the boys in their care. No one in my time at RL has so consistently and effectively loved the boys in his care as has Mr. Ken Conn. If our motto on the street is that we ‘know and love every boy,’ then Ken Conn ought to be on the poster advertising it.

Mr. Conn was hired in the spring of 1973. A graduate of Stoneham High School and Middlebury College, Mr. Conn came to RL after some seasoning as a teacher at Melrose High School and at the Lycee Albert Ier in Monaco, to which he went after a year of graduate studies at the University of Nice. Though he was principally a teacher of French, given his history degree from Middlebury and his love of literature, it was understandable that in his early years at Roxbury Latin Mr. Conn taught both history and English, as well.

Those who have been privileged to study French with Mr. Conn know well what kind of teacher he is. Utterly engaged by the language and the culture, he is gently ferocious in his insistence that all who enter his welcoming classroom become similarly excited. Under his leadership as a model teacher, supportive colleague, and attentive department head, the French program became one of the most respected in the school. During an era in which teachers of modern language have been encouraged to move away from the reading and writing emphasis that had marked the curriculum in the past to one in which communication was paramount, Mr. Conn has led the charge enabling his French students to express themselves beautifully and often to have the wherewithal not just to study French in college but to tackle other languages as well. Given his effectiveness and commitment, it was only logical that, in 2004, Mr. Conn would be named the inaugural Stanley Bernstein Professor of French. 

For the better part of his time at RL, Mr. Conn also served as the Class II master. In that capacity he guided hundreds of boys through the rough shoals of junior year with their dignity, academic standing, and emotional stability intact. A gentle, persistent advocate, Mr. Conn had the rare capacity to make every single person feel respected and cared for. On behalf of countless junior classes, he helped them to grow more cohesive, even as he was quick to celebrate the individual gifts and quirks of its members. While an affectionate mentor to many, Mr. Conn has a special devotion to those who were experiencing tough times, or those who might not be noticed as easily. Mr. Conn was an especially good listener, and, in his capacity as a loving advisor, he has provided space and time and counsel for boys to be themselves, to betray insecurities, to grow into men. When Ken Conn wraps that big paw around your arm, you know that you are safe; you know that you are cared for.

While not a lacrosse player himself, Mr. Conn helmed the junior lacrosse program for more than thirty years. While he had different coaching partners in this enterprise, Mr. Conn’s formula has always been the same: ensure that RL’s players know what they’re doing, that they try hard, that they are supportive as teammates, and that they have fun. Along the way, Mr. Conn’s lax squads consistently dominated their opponents earning him the respect and puzzlement of countless coaches on the circuit.

Mr. Conn’s most prodigious output as a coach, however, came as a result of his role for 36 years as the coach of the RL varsity football line. Everyone knows that the linemen are the workhorses of any football team—unheralded but absolutely essential. Mr. Conn’s success in motivating all those RL linemen over all those years is because he is one of them. I don’t mean that he was one of them because he did his duty on behalf of his own high school line or the ferocious forces at Middlebury. I say that because that is Mr. Conn’s approach to life. One of RL’s greatest schoolboy athletes put it this way: ‘Mr. Conn used to remind all of us linemen that the fans would always view the quarterback as the hero and star of any football team. Linemen would never get the same attention or fame that the quarterback would, even though a quarterback’s success depended wholly on his linemen’s protection and support. He encouraged us to take pride in the role that we played on our team, as it was a most important one. He never allowed us to forget how special we were, nor how little we needed any outside recognition of this fact. A true lineman did his job to the best of his ability while only seeking the satisfaction of achieving the team’s goal: a victory on the playing field. To him we were all stars.’ Like his linemen, Mr. Conn eschewed the spotlight, conceding it gracefully to others. And, like his linemen, Mr. Conn has during his time here endured a few solid hits and the occasional broken play. No one, however, in the RL of which we are so proud, has done more to support individual boys, to champion the underdog, to imagine a happier ending when all signs signaled otherwise.  

In his 36 years at RL, Ken Conn has given himself, heart and soul, to the simple mission of caring about kids and inspiring them to care about ideas, about the world, about each other, about pursuing their better, more ranging, more fulfilling selves. Mr. Conn is a great, optimistic, loving bear of a mentor who has changed the lives of hundreds and saved the lives of many. We will always be grateful for his steadfast commitment to all that is right and good about this work; for the model of his devotion to the lucky boys in his orbit; and for the friendship that he has extended so freely and selflessly to so many of us over so many years.”

Ken is survived by his wife, Peg. He was predeceased by his son Tim, Roxbury Latin Class of 1999. We will share the family’s plans for remembering Ken when we know them.

Thank you for helping to make Roxbury Latin’s fourth annual Giving Day a resounding success. With your help, we raised more than $695,000 for the Annual Fund—including $150,000 in challenge money from generous alumni and trustee donors—with 1,258 gifts, in 24 hours. Every dollar raised yesterday will go directly toward supporting our students, faculty, and distinctive mission. Your generous support—in dollars and in words of love for teachers, advisors, friends, classmates, coaches, mentors, family, and friends—went above and beyond our expectations for the day. Your gifts will preserve the school’s core values, while ensuring that students are equipped to lead and serve, taught by a talented, passionate, and dedicated faculty, who are committed to the boys in their care. For your excitement, for your generosity—for your love of, and belief in, this school—we are deeply grateful. Thank you for marching forth with us this Exelauno Day.