Charley Dey, A Lifetime of Finding Out

by Katie Jewett, Ph.D.

Charles Frederick Dey, a former head of Choate Rosemary Hall, passed away at home on April 16, 2020. His full obituary is posted on choate.edu.

As I stepped onto the snow-covered driveway of their home last December, carrying my iPad, a near-essential accessory at Choate Rosemary Hall that would not exist today without their early leadership, my heart was both light with anticipation and full of many stories of Charley and Phoebe’s graceful kindness. The school to which the three of us have devoted a combined total of nearly four decades is a place where Charley’s positivity and commitment to service are regularly invoked, and stories of Phoebe’s contributions to school life are as abundant as her beautiful watercolors, which decorate campus interiors.

Prior to that day, Charley and I had met only once or twice. Our initial connection was forged, mostly in written correspondence, through both our Choate ties and a shared interest in contributing to public education. Before I could worry that the connection we had established in letters might not transfer to this face-to-face December meeting, Charley was standing outside his front door, arms outstretched with a warm and welcoming grin on his face. Smiling back, I thought of the countless people at Choate who have told me that Charley always made you feel as if you were the only other person in the room.

After offering me a cup of tea and helping me get settled, it was Charley’s turn to reveal a schoolboy-like anticipation of our meeting. His home office was filled with family photographs, Phoebe’s watercolors, and framed evidence of his commitment to service. I was there at his behest (and as part of an 89 th birthday gift from his four adult children) to help him record his history, and he was excited to get started. During more than three hours together, we shared laughter, tears, and many stories, deepening our initial connection. I left that day with some notes, a hard drive full of video files from an oral history project begun with Charley’s son Tom, and a promise to return monthly, a pledge we kept up for two more visits until Charley fell ill in February.

Back on campus, watching the recorded interviews made it clear that there were two characteristics common to just about any conversation with Charley. The first is that he began with an affirming acknowledgement of his conversation partner, often a thank you. The second lies in the numerous references to his wife and life partner, Phoebe. Even in describing the most professional of situations, he was quick to point out that she was his North Star. There really was no him without her. Although I was in Walpole to interview Charley, crossing paths with Phoebe in their home was always a highlight and, in those last months of Charley’s life, some of the most inspirational moments I witnessed were when she made him laugh, when he went upstairs to kiss her before her nap, or when they held hands. They are a testament to the way the small things in life and love are actually the big ones.

The Dey family in the Philippines, where Charley was serving as an in-country director of Peace Corps volunteers.

My conversations with Charley revealed a compelling life story. Although the fullness of his contributions to the world cannot be reduced to numbers, Charley’s role in establishing the A Better Chance (ABC) program while a dean at Dartmouth led to opportunities and achievement for more than 14,000 (so far) young people of color in America. Moreover, it was at least in part his experience with ABC that led the boards of trustees of Choate and Rosemary Hall to choose Charley as the ideal person to combine their schools and move them forward. The roots of the progress that Choate Rosemary Hall has forged in the realm of equity and inclusion today were planted by Charley and Phoebe. Charley knew what a difference opportunity could make in part because he himself had been a first-generation college student at an Ivy League school. He brought with him a commitment to race and gender diversity and to introducing new voices at the leadership table. It was Charley who chose to call himself not by the gendered term “Headmaster,” but rather President and Principal. And it was Charley who worked with the School’s first (and thus far, sole) female Chair of the Board of Trustees, Beezie Brownell. Looking back now, it comes as no surprise that in 1989, toward the end of his tenure, Charley hired Director of Multicultural Affairs Connie Matthews, charging her with diversifying the school’s curriculum, faculty, and student body. These actions were of a piece with his tireless commitment to transforming lives through inclusivity, which had begun with his first job as a teacher.

In each of his professional roles, Charley worked to ensure that young people understood their responsibility to address what his own mentor, Dartmouth president John Sloan Dickey, called “the unfinished business of society.” To Charley that phrase meant taking responsibility for other human lives, not just doing something to make oneself feel a little better. It was a mantra to live by, and so upon leaving Choate, Charley addressed more of society’s unfinished business when he built the Start on Success (SOS) program, which made a difference in the lives of thousands of young people with disabilities by creating opportunities for them to join the work force.

The scope of his work demonstrates that while he was indeed a gift to us, and we at Choate Rosemary Hall like to claim him as our own, Charley Dey was not ours. He was a public servant through and through and ended his career as he wished, committed to the young people who needed his advocacy in the public sector.

Over the course of our meetings, it was not the titles or public accolades of Charley’s life that came to the fore. Rather, he conveyed a sense of humor and a spirit of adventure and love. He reminded me of Maya Angelou’s belief that “people will never forget how you made them feel.” In his humble, self-effacing way, Charley Dey ably created a spotlight for whoever stood before him, regardless of their rank or stature in the world.

Moreover, he left us with a common thread of brilliant advice woven through three wonderful anecdotes from his life. First, as Charley began his career in teaching at Phillips Academy Andover, he was assigned to teach Ancient History, which at the time he knew nothing about. When he mentioned this to Phoebe, she told him with great practicality, “Well, find out!” Later, in the early 1960s when Charley told Phoebe about the possibility of heading to the Philippines to oversee the newly established Peace Corps program, he mentioned that they probably couldn’t go because “What would it be like there with two small children?” To which Phoebe replied, “Let’s find out!” And finally, when Charley retired from Choate, his former Dartmouth roommate Alan Reich asked him to take on a leadership role at the National Organization on Disability. Charley responded, “But I don’t actually know much about the world of disability.” To that, Alan said with friendly exasperation, “Well, find out!”

Charley and Deval Patrick, former Governor of Massachusetts, an ABC graduate.

“Finding out” encapsulates in a single phrase the admirable resourcefulness and adventurous spirit shared by Charley and Phoebe Dey. How easily they seemed to reinvent themselves and venture into the unknown, always in service of a new community that needed their energy, spirit, and care. May they forever inspire us all at Choate Rosemary Hall and beyond to find out how to be of service and bring new voices to our table.