It is with great sadness that I write to inform you of the death of Phillips Smith P’79, the fifth Headmaster of Trinity-Pawling School. Phil passed away the evening of Saturday, April 22, after a brief illness. He would have turned 92 next month. His wife, Holly, and son, Mark ’79, were with him when he passed away.
Phil served the School from 1970 until his retirement in 1990. He began his tenure at Trinity-Pawling in the summer of 1970, when the School was in the midst of enrollment and financial distress. The late 1960s and 1970s were challenging times for boarding schools. Rapidly shifting cultural norms and a poor economy combined to create tremendous headwinds for a traditional boarding school like Trinity-Pawling. In 1974-75, trustees of Trinity Episcopal School Corporation considered closing Trinity-Pawling. Phil’s steadfast leadership brought the School back from this brink and toward an upward arc of success. Nearly 2,000 young men graduated under his tutelage.
Phil’s tenure as Headmaster is distinguished by his courageous and creative leadership. While honoring the importance of structure and tradition central to the boarding school experience, Phil implemented an extensive re-evaluation of the academic and extracurricular life of the School. Elective and term courses were added to the curriculum, complementing the foundation of yearlong required courses. In 1975, the Language Retraining Program, created by Ted and Carol Kneeland, was initiated to meet the learning needs of students with language-based learning differences. This program evolved to the current Center for Learning Achievement that exists at Trinity-Pawling today. Phil also created the Effort System at Trinity-Pawling which forged a systematic approach to recognizing and rewarding students for their effort in addition to their achievement. It has long been a distinguishing characteristic of the Trinity-Pawling experience for both students and faculty.
In 1978, Phil oversaw the formal separation of Trinity-Pawling School from the Trinity Episcopal School Corporation and worked closely with the first Board of Trustees of Trinity-Pawling School, creating an independent institution that retained historical and traditional ties to both The Pawling School (1907-1942) and Trinity-Pawling School (as part of Trinity School: 1946-1978). Indeed, the continuity of the School’s mission and focus is, in large measure, the result of Phil’s leadership as Headmaster. It was during Phil’s leadership that important strides were made in alumni relations, including building a bridge so that the Pawling School alumni and the Trinity-Pawling School alumni were equally acknowledged.
Once he was able to stabilize and create a permanent foundation for the future of Trinity-Pawling School, Phil turned his attention to strengthening the foundation and building the School for the future. He created the Development Office and the Annual Fund. When he began his tenure as Headmaster, the School’s endowment was $35,000. When he retired in 1990, this endowment had grown to $4M. He launched the first capital campaign in school history, raising over $6M. This campaign led, in part, to the creation of Starr Hall in 1984 and its expansion in 1989. He also led an effort to strengthen faculty and staff salaries, which quadrupled during a fifteen-year period during his tenure.
Of course, Phil was not the sole force of leadership during his tenure as Headmaster. Phil’s dedication to the life of the School’s community was matched stride-by-stride by Holly’s commitment and love for the School. The beautification of the School’s campus was augmented significantly under her tireless efforts. Additionally, Holly’s commitment to the School and local communities was pervasive and several traditions were born from this commitment. Students and faculty were welcomed into Gamage House for regular evening coffee gatherings; the campus was adorned in festive beauty during the Christmas season, particularly with freshly and artistically created wreaths; faculty children gathered each year for an Easter Egg Hunt at Gamage House which culminated in a magic show; and the annual lobster dinner became a highlight of the spring term. Moreover, Holly served on numerous boards and as a volunteer in the larger community. Together, Phil and Holly worked tirelessly to create a vibrant and healthy relationship with the larger Pawling community, a legacy that continues to thrive to this day.
Phil was devoted to creating a transformational learning experience for the students, which for many of his years as Headmaster included young women who were day students at the School. It was critically important to him that every student learn the value of hard work, character development, respect, compassion, and the importance of giving back.
Phil was also an incredible mentor to the faculty whom he hired. As a leader, he modeled critical components of effective and transformative leadership: hard work, purpose, dignity, servant leadership, and compassion. He also worked to cultivate leadership in others. Of those whom he hired at Trinity-Pawling, ten went on to serve schools as Heads. Remarkably, Phil hired both the future sixth and seventh Headmaster of Trinity-Pawling School.
On a personal note, Phil had a tremendous impact on my professional life and instilled within me a profound respect and love for the mission of Trinity-Pawling School. I was blessed to work with him for the first two years of my career and then have the good fortune to work closely with Arch Smith for the next eleven years before I left for a leadership position at another school. I learned what an honor it is to be able to be a part of a school that makes a transformational difference in the lives of young people. I learned the impact of earnest striving as a leadership skill and that hard work, discipline, and dedication are incomplete leadership characteristics if they are not complemented by compassion, faith, and kindness.
While I join so many others who are saddened by the passing of Phil Smith, this sadness is paled in comparison to the depth of my gratitude for having known him and had the gift of being able to work with him serving Trinity-Pawling School. The heartfelt love and gratitude of the Trinity-Pawling community are extended to his wife Holly, sons Ted and Mark ’79, grandchildren, and extended family.
Phil once said, “We shall continue to strive to make [Trinity-Pawling] an even better place for students who come here to learn, to grow, and to mature.” What a legacy of continuity he left to the School, one that leaves me with a simple response.
Onward!
Well done, thou Good and Faithful Servant.
by William W. Taylor
A Celebration of Life will be held on May 20, 2023 at 2:00 PM at St. Columba’s Episcopal Church, Boothbay Harbor, Maine.
The family has asked that donations, in lieu of flowers, be donated to Trinity-Pawling School or to the Boothbay Region YMCA, where Phil was active on the board for many years.