In his Commencement Address to the Class of 2026, Head of School Bill Taylor reflected on the enduring connection between people, memories, and the spaces that shape them. Welcoming graduates, families, faculty, staff, and alumni to Trinity-Pawling’s 119th Commencement Exercises, Taylor reminded the seniors that while graduation marks the end of one chapter, Commencement signals the beginning of another. “Today’s event celebrates their graduation from Trinity-Pawling,” he said. “Yet, as a ceremony, it is a Commencement, a beginning of the next chapter of their lives.”

Throughout his remarks, Taylor returned to the idea that the places students inhabit during their formative years become deeply tied to the friendships, experiences, and memories that define them. Drawing on conversations with alumni during a recent trip to Asia, he shared how graduates from different decades — despite having attended Trinity-Pawling years apart — found themselves reminiscing about many of the same experiences, from the Effort System (now called the Effort Challenge) to meals in Scully Dining Hall and, perhaps most passionately, the pizza shop in the village.

“Why, you may rightly ask, am I talking about pizza?” Taylor said. “Because it’s not about the pizza — it’s the space.”

He explained that places like Village Pizza had become lasting symbols of friendship, belonging, and shared experience for generations of Trinity-Pawling students. “It's the space where they went on their own, during their free time, and enjoyed time together,” he said. “It’s the space where the friendships of adolescence are captured and eternalized for a lifetime. The pizza was always the reason to go to the space, but it's the space where the memories live.”

Taylor reinforced this theme through the words of educator and social commentator Hamilton Wilson: “People leave spaces, but the spaces retain the memories and the youth of those who have left them.”

Later in the address, Taylor shared the story of Henry Ernst Obermanns, the valedictorian of the Pawling School Class of 1926, whose son recently sent Taylor a collection of his father’s memoirs from his time at the School 100 years ago. Though Obermanns would go on to Yale University, earn a PhD in Engineering, and build a successful career, Taylor noted that his memories of Pawling were still described through the eyes of a teenage boy — recalling friendships, challenges, dorm life in Cluett, and the teachers who shaped his life.

“Though these memories were written down in 1971 and were formed in the mid-1920s, they are not that far removed from the memories that many of you seniors will take away with you,” Taylor said.

In closing, Taylor challenged the graduates to remain connected to one another and to Trinity-Pawling long after leaving campus. “Stay connected to one another. Stay connected as a class. And, stay connected to this space,” he said. “Your lives will be richer as a result, I promise you.”

by Missy McCluskey

Watch Bill Taylor’s full Commencement Address.

Luca Fugo, the Valedictorian of the Class of 2026, is, by definition, an excellent student. But as Head of School Bill Taylor shared in his introduction, what sets Luca apart is not simply his academic achievement, but his genuine love of learning and the way he embraces challenge and discovery. Taylor compared Luca’s approach to learning to that of a rock climber — focused not on recognition at the top, but on the process of the climb itself. Quoting Cervantes, Taylor remarked, “The journey is always more memorable than the Inn,” adding that Luca appreciates the pursuit of growth more than the award itself.

Over his three years at Trinity-Pawling, Luca completed 11 AP courses, four Honors courses, and a Senior Independent Project with Distinction, which resulted in the creation of a robot tennis ball launcher. Taylor also praised Luca for his thoughtful nature, self-awareness, and ability to reflect deeply on both learning and life before introducing him to deliver his address to the Class of 2026.

In his address to the Class of 2026, Luca reflected on the uncertainty that comes with leaving Trinity-Pawling and stepping into a new chapter of life. Admitting that he still does not have life “figured out,” he reassured his classmates that uncertainty is not something to fear.

To explain this idea, Luca described life as “a hallway filled with doors.” Some doors, he said, are wide open, while others are locked — but the most meaningful opportunities are often the doors left slightly ajar, where the outcome remains unknown. “Navigating uncertainty is choosing to open those doors,” he said, “not knowing exactly what awaits, but trusting that beyond them is your next step forward.”

Reflecting on his transfer to Trinity-Pawling midway through sophomore year, Luca shared how difficult it initially was to feel like he belonged. Over time, however, he realized that growth required him to stop looking backward and instead embrace discomfort, uncertainty, and change.

“If you want to reach your full potential and beyond,” he said, referencing the School’s longtime motto, “you too must realize that growth belongs to those willing to become comfortable being uncomfortable.”

Throughout the speech, Luca emphasized the importance of faith, support systems, and extending grace to yourself during moments of uncertainty. He encouraged his classmates to lean on the people around them — family, friends, mentors, and the broader Trinity-Pawling community — reminding them that growth is rarely something accomplished alone. He also reflected on the importance of taking risks while surrounded by people who believe in and support you, noting that “you can only go up from here” when you are grounded by a strong foundation.

Luca also spoke about the power of laughter and connection, describing laughter as one of the ways people remain present during uncertain times. Rather than becoming consumed by fear or overthinking the future, he encouraged his classmates to find joy in shared moments and use laughter as a way to move forward together through life’s challenges.

As he concluded, Luca reminded his classmates that they do not need to have every answer before moving forward. “Maybe the goal is simply to take this last step forward together,” he said, “even before we know where the road leads.”

Luca will attend the University of Colorado Boulder in the fall, where he is pursuing Aerospace Engineering.

by Missy McCluskey

Watch Luca’s full address to the Class of 2026 here.

Introduced by Head of School Bill Taylor as a servant-leader whose “thoughtfulness, care, and deep love for the School and the brotherhood of the students” strengthened the community, Head Prefect Arthur Figueiredo’s address to the Class of 2026 reflected on the small moments, relationships, and experiences that define life at Trinity-Pawling.

Taylor praised Artie’s compassionate and empathetic leadership style, sharing that “when Arthur Figueiredo speaks, people listen.” He highlighted the impact Artie had on younger students throughout the year, noting his ability to make others feel heard, welcomed, and supported. Presenting him with the McCollum Award, Taylor encouraged Artie to continue developing the qualities that have shaped his leadership: “compassion, thoughtfulness, empathy, and integrity.”

Opening his remarks, Artie admitted that ever since hearing last year’s Head Prefect speech, he had been trying to figure out how to explain what Trinity-Pawling truly is. “You can describe the campus, talk about the sports, the classes, the traditions, the opportunities,” he said. “But none of those things really capture what this place is.”

Instead, Artie explained, Trinity-Pawling is defined by “a million small things” — the moments and experiences students often do not realize they will miss until it is time to leave.

He reflected on the energy and “loudness” of life at an all-boys school, sharing memories from the dorms, the quad, Dorm Olympics, and the Rising Senior Leadership Program’s memorable boat-building competition. He spoke about the friendships formed through dorm life, the support of dorm parents and faculty members, and the comfort of being surrounded by a community that consistently shows up for one another.

Throughout the speech, Artie returned to the idea of growth — something he said nearly every teacher described as the most rewarding part of teaching at Trinity-Pawling. He highlighted classmates whose journeys reflected that transformation, including students who overcame academic struggles, injuries, personal challenges, and self-doubt.

Sharing his own experience as a new student, Artie reflected on learning to stop worrying about what others thought and instead focus on being authentic. “Just be yourself,” he said. “You never know when your last day will be, so wake up every day with the mindset of ‘it’s a great day to be alive.’”

He credited Trinity-Pawling with helping him discover interests beyond athletics, including videography and editing through Ms. Rafferty’s Trinity-Pawling Sports Nation class, which inspired him to pursue videography in college and beyond.

As he concluded, Artie encouraged younger students to take advantage of every opportunity available to them and reminded his classmates to appreciate the time they shared together. “One day you will realize what this place truly did for you and how special it truly is,” he said.

Quoting the closing words from a recent chapel talk, Artie left the Class of 2026 with one final message: “Go and make the world a better place. I know you will.”

by Missy McCluskey

Watch Arthur’s full address to the Class of 2026 here.

After 37 years of tending every boiler on campus, keeping the roads clear of snow during storms, repairing water leaks or busted pipes, responding to every fire alarm and power outage, and making sure the Zamboni and hockey rink function smoothly, Ron Gallagher is retiring from his role as Trinity-Pawling’s Buildings and Grounds Supervisor, a position he has held since 2007.

If there’s one person who knows every square inch (visible and far behind – or under – the scenes) of our 230-acre campus, it’s Ron Gallagher. Over nearly four decades, he has amassed the knowledge and skills to fix or find a solution to every imaginable glitch that might crop up, invariably at the most inopportune times of day or night.

“My job is to keep the campus safe for 250 students, 50 families, all the staff, and visitors. I’m constantly thinking, What could happen, what could go wrong, and find ways to prevent unfortunate situations.”

Reflecting on his career, Ron says he appreciates the myriad opportunities he had to expand his knowledge. “Ed Hauser, the former physical plant director who brought me on board, had impressive foresight. In the early 1990s, he knew we had some major construction projects in the works, namely the Cluett renovation and enclosing the hockey rink, so he sent me to New York State building code school so I could assist the project on that level. I also went to asbestos abatement training, and I earned both federal and state certification licenses so I could serve as an official project monitor.”

Ron is proud of the significant changes the School has made to the physical plant over his 37 years. “Trinity-Pawling always looks to the future and finds thoughtful ways to improve the quality of life for students, faculty, and staff. Everyone works hard here, and it’s important for morale that the campus is clean and well-managed. My staff pays attention to keeping the buildings and grounds neat, safe, and orderly, and the faculty do their part to make sure the curriculum, dorms, and programs run smoothly as well. This approach makes me proud to be part of this community.”

How will life change when he retires on June 30? “I’m looking forward to spending more time with my wife, Debbie, and our 10-year-old twin grandsons, Noah and Aiden, who live nearby. We’ll be doing some camping this summer and watching a lot of baseball games.”

We sincerely thank Ron Gallagher for his years of selfless dedication to Trinity-Pawling and wish him much health and happiness as he enjoys the next phase of life.

*A more in-depth profile celebrating Ron Gallagher and his 37 years of service will appear in the fall edition of Trinity-Pawling Magazine.

by Maria Buteux Reade

At this year’s Commencement Exercises, the Trinity-Pawling community honored Chris Gillman ’05 with the Dunbar Award for Service — an award presented annually to recognize steadfast devotion to the School and named in honor of Bill and Helene Dunbar, who dedicated more than 30 years of service to Trinity-Pawling.

In presenting the award, Head of School Bill Taylor reflected on Gillman’s growth as a leader and the impact he has made on the community over the past 22 years.

“This year’s recipient invests significantly into the lifeblood of the School so that the lives of students and colleagues will be enriched,” Taylor shared. “This is a person who, in many ways, discovered their distinctive gifts and talents while at Trinity-Pawling. Over the past 22 years, this discovery has been accompanied with a growth in voice, self-actualization, and leadership.”

“This is a person with very high emotional intelligence and, like many great leaders, their leadership is grounded in empathy and a concern for others,” he said. Drawing a connection between Gillman and Bill Dunbar himself, Taylor noted that alumni often described Dunbar’s leadership as being rooted in “humility, endless energy, and quiet confidence,” adding that the same through-line could be seen in Gillman’s leadership and service to the School.

Taylor also acknowledged the challenges Gillman faced this year as he stepped into a new leadership role on campus. “Yet, he approached the challenges of change with a quiet determination that day-by-day strengthened his confidence, his voice, his leadership, and his impact on the community,” Taylor said.

“It is my pleasure to present this year’s Dunbar Award for Service to a member of the Class of 2005, Chris Gillman.”

Congratulations, Chris, and thank you for your continued dedication and service to Trinity-Pawling.

by Missy McCluskey

After 17 years of guiding Trinity-Pawling students through one of the most formative periods of their lives, Edward “Slade” Mead delivered this year’s Commencement Address to the Class of 2026 with the same energy, humor, and student-centered perspective that have defined his time at the School.

Introducing Mead, Head of School Bill Taylor reflected on the tremendous impact he has had on both students and the broader Trinity-Pawling community since arriving in 2009 as Director of College Counseling. Taylor described Mead as “dynamic and creative,” praising the way he helps students develop a deeper understanding of their own gifts and talents while guiding them toward opportunities they may never have otherwise considered.

Taylor also credited Mead as one of the driving forces behind Trinity-Pawling’s Practicum for Civic Leadership program, explaining how conversations between the two eventually led to the creation of the Senior Independent Project, which later evolved into one of the School’s signature project-based learning experiences.

In his address, Mead reflected on the importance of learning how to “pivot” — to reinvent yourself, change direction, and embrace unexpected opportunities. “Your life will not be a straight line,” he told the graduates. “It will be a series of pivots.”

Using humor throughout the speech, Mead joked about struggling to decide on a Commencement topic after ruling out recycled speeches and chapel talks for fear of being called out by students and colleagues alike. But beneath the humor was a deeply personal message rooted in his own life experiences.

Reflecting on his career path, Mead shared how he moved from teaching history to law school, to representing professional athletes, including tennis star Andy Roddick, before eventually serving in the Arizona State Senate, advocating for education initiatives and special-needs students. After losing reelection and later another statewide race, Mead admitted he felt devastated and uncertain about what would come next. That uncertainty, however, eventually led him to Trinity-Pawling. What he originally thought would be a temporary stop became a calling. “One of the greatest blessings of my life may have been the thing I once considered one of my greatest failures,” he said.

Throughout the speech, Mead encouraged the Class of 2026 not to fear moments when life changes direction unexpectedly. Resumes, he explained, may appear linear, but life itself rarely is. “Life twists. Life surprises. Life humbles. Life redirects,” he said. “And sometimes the moments that feel like endings are actually beginnings in disguise.”

He concluded by reminding students that Trinity-Pawling has always been a place rooted in transformation — one that recognizes students as “works in progress, not finished products.”

“Sometimes the detour becomes the destination,” Mead said. “Sometimes the pivot becomes the path.”

by Missy McCluskey

Watch Slade Mead’s full address to the Class of 2026 here.

Congratulations to William Han ’28 on earning international recognition at the global finals of the China Thinks Big (CTB) competition, held at Harvard University this spring.

William and his team competed against students from around the world and were awarded High Distinction — Second Place in Social Behavior and Economics . The group was also named Global Finalists and received the Outstanding Teamwork Award during the competition’s Hackathon component.

Their project focused on how behavioral “nudges” can help teenagers develop stronger saving habits. Through their research, the team explored how interactive support systems, combined with financial education, can encourage young people to make more thoughtful, long-term financial decisions. The project highlighted the growing role that psychology and behavioral economics can play in helping students build positive habits and financial confidence at an early age.

China Thinks Big, co-hosted by Harvard’s Undergraduate Association for U.S. Cross-Cultural Relations and Tsinghua University in Beijing, brings together student teams from across the globe to research real-world issues and present their findings through academic defense sessions. The program aims to inspire high school students to tackle complex global and local challenges through academic research and social innovation while fostering cross-cultural exchange, project-based learning, and future leadership development.

William’s recognition reflects not only academic excellence but also creativity, collaboration, and a commitment to meaningful research. Congratulations to William on this outstanding achievement and for representing Trinity-Pawling on an international stage.

by Missy McCluskey

At this year’s Senior-Parent Dinner, the Class of 2026 and their families were honored to hear from Trinity-Pawling alumnus Dr. Richard Hoefer ’68, whose career in medicine, military service, and surgical oncology reflected a lifetime of perseverance, collaboration, and purpose.

At the start of his remarks, Dr. Hoefer reflected on his own graduation from Trinity-Pawling in 1968 before sharing four lessons that shaped his journey: find your gift; to be a success you need to persevere with grit; the path to realizing your dream is never a straight line; and collaborators, mentors, and friends are essential for you to succeed.

Dr. Hoefer spoke about his experiences as a student at Trinity-Pawling, where he participated in choir, band, football, and lacrosse, while also learning the study habits and discipline that would guide him through Gettysburg College, medical school, and a distinguished career in surgery. Along the way, mentors, including Dr. C. Everett Koop and Dr. Morey Ziegler, encouraged him toward a career in surgical oncology and research.

Throughout his remarks, Dr. Hoefer emphasized that success is rarely a predictable path. His path took him from Pennsylvania to Texas, California, Kentucky, Iraq, and Virginia, including service as Chief of Surgery for the 159th MASH unit during the Gulf War and nearly three decades practicing surgical oncology in Virginia.

Reflecting on both the challenges and rewards of his career, Dr. Hoefer reminded students that perseverance matters more than talent alone and that meaningful accomplishments are built alongside others.

Closing his talk, he encouraged the Class of 2026 to move forward with confidence, remain open to unexpected opportunities, and continue seeking out the gifts and passions that will shape their futures.

“You are ready,” he told the class. “Not because you have all the answers — but because you have the foundation to find them.”

Through stories of service, resilience, mentorship, and leadership, Dr. Hoefer left the Class of 2026 with a reminder that the Trinity-Pawling experience can serve as the foundation for a meaningful and impactful life.

by Missy McCluskey

We had an incredible evening reconnecting and reminiscing at our Washington, D.C. Reception yesterday, June 4, which was graciously hosted by Kathy and Erik K. Olstein ’86, P’11,’14,’17; Ryan E. Olstein ’11; Kathryn and Kenneth B. Weeman, Jr. ’59, P’91, GP’27; and Carter A. Weeman ’91. It was a wonderful reminder of the strength of the School community as alumni, current parents, grandparents, and faculty from across the generations came together to share the spirit of Trinity-Pawling.

SAVE THE DATES FOR OUR UPCOMING RECEPTIONS:

June 15, 2026
Cape Cod Reception and Golf Outing
Golf Outing - 10:00 AM
Reception - 5:00 - 8:00 PM
Cape Cod, MA
Register Now: https://www.trinitypawling.org/events

December 7, 2026
New York City Holiday Reception
6:00-8:00 PM
The Union Club of the City of New York

December 10, 2026
Boston Holiday Reception
6:00-8:00 PM
Harvard Club of Boston