My brother and I grew up on the water and, for a brief time, learned to sail on the Long Island Sound. My skills never progressed much beyond a small Jayhawk, though I became a capable member of any crew. My brother, on the other hand, became an accomplished sailor and now spends his summers along the coast of Massachusetts aboard his wooden boat, Navajo.

While I lack his expertise, I often return to nautical imagery when thinking about schools. At this time of year, especially, I think about commencement — not as an ending, but in its truest sense: a beginning. A setting out from the harbor.

For those students who will graduate next month, commencement is precisely that moment. They are prepared to leave the safety of the harbor and embark on a journey that will demand resilience, adaptability, and purpose. A sailboat is not built for stillness. It requires wind and resistance to move forward. So too with their lives ahead — challenge should not impede their progress but enable it.

The path toward maturity, purpose, and character is marked by adjustments, recalibrations, and, at times, unexpected turns. As parents and educators, we may begin with a clear vision of where that path should lead. Yet, as boys grow into young men, it becomes essential that they begin to chart their own course — guided by our experience, but strengthened by their own decisions.

Growth is not linear. Sailing reminds us that the most direct route is rarely the right one. Progress requires tacking — adjusting course to move with the wind. Our students’ paths will not be linear, nor should they be. What matters is that, over time, they learn to take the tiller themselves, guided by the values and experiences that have shaped them thus far.

In time, their destination may not look exactly as we first imagined. But if they have learned to read the wind, to adapt, and to persevere, they will arrive somewhere meaningful — often not far from where they first set out, but shaped more deeply by the journey itself.

And so, as our graduates commence their next chapter, they will do so with confidence. The waters will change, as they always do. But they leave prepared — ready to navigate, to adjust, and to move forward with purpose. This beginning — this commencement — will become something far greater: not simply the end of high school, but the continued unfolding of lives shaped with purpose, courage, and care.

Onward!

by William Taylor, Head of School

During his three years at Trinity-Pawling, Arthur Figueiredo ’26 has made the most of every opportunity to get involved, lead, and create. A member of 15 clubs — his favorite being the Baking Club — and five teams, including varsity soccer and varsity baseball, Arty has built connections across campus while finding meaningful ways to support others.

His commitment to leadership became clear early on. When he first learned about opportunities to serve as a dorm proctor and later as a prefect, he knew he wanted to step into those roles. Now serving as Head Prefect, Arty helps set the tone for the student community by consistently showing up, supporting his peers, and modeling accountability. “Leadership truly is difficult,” he reflects, noting that making responsible decisions — especially when guiding friends — is one of the most important parts of the role.

Mentorship has also shaped his Trinity-Pawling experience. Encouraged by mentor Kweku Arthur-Mensah ’25 to be open and authentic, Arty now works to provide that same support to younger students. “Being away from home at this age is really hard,” he says. “Being able to have someone to look up to and talk to makes the Trinity-Pawling experience so much easier.”

In addition to his leadership roles, Arty has developed a growing passion for videography. After gaining experience in his TPSN class and creating content for the hockey team this season, as the team’s manager and videographer, he began working with the Office of Communications, producing videos for the School’s website and social media. Through this work, he’s building his portfolio and exploring future opportunities in film.

Whether supporting younger students as a leader or contributing creatively through his videography work, Arty has made his mark on the Trinity-Pawling community in meaningful ways. “Not only have I been able to find who I truly am, but I’ve been able to become more mature and accountable,” he says.

by Missy McCluskey

Congratulations to Dr. Andrew Burgess ’62, who was honored with the 2025 Orthopaedic Trauma Association (OTA) Lifetime Achievement Award. This award recognizes more than four decades of leadership, innovation, and mentorship that have helped shape the field of orthopaedic trauma. The award honors individuals whose career contributions have advanced orthopaedic trauma care through research, education, and service.

Over the course of his career, Dr. Burgess has played a significant role in advancing the treatment of complex musculoskeletal injuries and training generations of trauma surgeons. He spent more than 22 years at the University of Maryland’s R Adams Cowley Shock Trauma Center, where he helped develop the center into a global destination for trauma education and played a key role in organizing trauma care systems across Maryland. He also helped establish important research partnerships linking orthopaedic surgery with the Johns Hopkins School of Public Health, contributing to major research initiatives that shaped standards of care for musculoskeletal injury treatment worldwide.

A founding member and past president of the Orthopaedic Trauma Association and a founding member of AO North America, Dr. Burgess helped guide the growth of orthopaedic trauma as a distinct subspecialty. His work included contributions to trauma system design, pelvic injury classification, and improved fracture management, as well as collaborations with engineers and the National Highway Traffic Safety Administration to better understand injury patterns in motor vehicle collisions — research that helped inform safety improvements in automobiles worldwide.

Earlier this year, he was also named a Distinguished Alumnus by Albany Medical College, an honor recognizing alumni who have earned national recognition for outstanding leadership in health care. Dr. Burgess currently serves as Professor and Vice Chair of the Department of Orthopaedic Surgery at McGovern Medical School at UTHealth Houston and is former Chief of Orthopaedic Trauma.

Together, these recognitions reflect a career defined by leadership, education, and lasting contributions to orthopaedic trauma care.

by Missy McCluskey

Slade Mead, Director of College Counseling, has announced his plans to retire at the end of this academic year. For the past 18 years, Mr. Mead has served the School, its students, and families with sagacity, professionalism, passion, and humor. During this tenure, he has forged a highly student-centered college counseling program and nurtured strong relationships with admissions offices at colleges and universities across the country and around the world.

Mr. Mead’s highly personalized approach to college counseling has been instrumental in allowing the often fraught and anxiety-producing college application process to also be a life-changing opportunity for greater self-awareness and personal growth for both students and parents. Simply, he is a master of his craft, and the legacy he will leave behind in the Office of College Counseling will continue to be a driving force in how Trinity-Pawling helps young men and their families navigate the college search and application process.

While Mr. Mead’s departure will certainly be felt by us all, the impact that he has made over these 18 years has resulted in a college counseling office that is extraordinary in its procedures and its work with boys.

It is my pleasure to inform you that Bill Dunham will step into the role of Director of College Counseling after Mr. Mead’s retirement in July. For the past three years, Mr. Dunham has been mentored by Mr. Mead, with the plan being a seamless transition of leadership when that time comes.

During this time of mentorship, Mr. Dunham has gained a comprehensive knowledge of the student-centered approach to college counseling at Trinity-Pawling; however, Mr. Dunham has had a much longer exposure to this work than just three years. For the past 16 years, he has chaired the Dunham Committee, a group of faculty writers who assist the Office of College Counseling in creating the distinctive Secondary School Reports (SSR) that provide a narrative of the students' strengths, gifts, talents, and accomplishments at Trinity-Pawling. These highly personalized narratives have been highlighted by admissions offices for years as clear indicators of how well students are known by the School, as well as of the depth of self-awareness among Trinity-Pawling students. Additionally, Mr. Dunham has been at Trinity-Pawling for 33 years and is an expert on many things at the School, including his deep knowledge and tutelage of “Trinity-Pawling Boys.” We are fortunate that, beginning next year, this expertise will extend to the Office of College Counseling's leadership.

I’m pleased to announce the appointment of Matthew Sweeney as Assistant Director of College Counseling. With more than 12 years of experience in recruitment, communication, and relationship-building, he brings a student-centered approach to guiding young men and their families through the college process. Known for his collaborative spirit and organizational strength, he will serve as a trusted mentor for Trinity-Pawling students — supporting them in identifying best-fit colleges and preparing them for success. Mr. Mead will work closely with Mr. Dunham and Mr. Sweeney to ensure a seamless transition. Furthermore, Mr. Mead will continue to be a resource for the School when such assistance is needed.

This transition has been anticipated for some time, though the exact timing was not known until recently. Nonetheless, the School is very well prepared for this transition, and I have every confidence that the excellence that has been the standard in the Office of College Counseling will continue to flourish under the leadership of Bill Dunham.

Please join me in congratulating Slade Mead on a job well done, and Bill Dunham and Matthew Sweeney on this next chapter in their careers of making a meaningful difference in the lives of young men and their families.

by William Taylor, Head of School

As one of the chaperones on our recent South African trip, I spent 14 days with 14 students traveling through a country I had never visited, ending in a three-day safari in Kruger National Park. While the experience was extraordinary from start to finish, what has stayed with me most was not the safari itself — it was the way our students learned to see it.

Each day, we set out with a shared focus on observing the landscape and, if possible, encountering the “Big Five” — a term used to describe lion, leopard, elephant, rhinoceros, and Cape buffalo, originally coined to identify the most difficult animals to hunt on foot. Over time, the experience became less about what we might find and more about how carefully we were willing to look.

Elephants, zebras, and Cape buffalo appeared throughout the trip, and even a rare sighting of the elusive white rhino left a lasting impression — moments our guides noted as significant even by their standards. What stood out most was how the students responded: with patience, restraint, and growing attentiveness.

Photography became a central part of their experience. While many captured images casually, a few worked with real intention, waiting for composition, light, and timing. What they produced went beyond documentation; their photographs reflected an emerging artistic eye — thoughtful, composed, and at times worthy of exhibition.

As the days went on, I observed our students shift from excitement to focus. Conversations quieted, observation deepened, and even silence became part of the learning — rare within this group, and therefore especially meaningful.

We will be displaying their photographs in the Dann Building to share their perspective with our community — not simply what they saw, but how they learned to see it.

This trip also marked Mr. Mead’s final South African tour with Trinity-Pawling, giving the experience a deeper sense of culmination. I am grateful to have shared in it and to have witnessed our students developing, not just lasting memories, but a way of looking at the world with greater care and curiosity.

by Ricky Oliver, Director of Theater Arts

Cover Photo by Cole Lilley ’26

 

Watch the slideshow below featuring student photography from their trip to South Africa.

 

Trinity-Pawling School is excited to announce a new hands-on offering in its curriculum: Timber Framing.

As defined by North American standards, timber framing is the craft of building structures from timbers measuring at least 5” × 5”. In this immersive course, students will explore an ancient building tradition that has served humanity for thousands of years and is now experiencing a revival after being nearly replaced during the Industrial Revolution.

Each class will construct a structure that will serve a meaningful purpose on campus for decades to come. Using a simple set of hand tools typical of 17th- and 18th-century workshops, students will learn to read construction plans using the square rule method, lay out precise cut marks on timbers, and cut the joinery that brings each structure together. They will also hand-rive the wooden pegs used to secure each joint.

Once the timbers are prepared, the class will raise the frame, giving students the satisfaction of having crafted a beautiful, functional structure that will benefit the broader community. Timber Framing can be taken as a year-long or a trimester course.

This unique offering reflects Trinity-Pawling’s commitment to experiential learning, creativity, and the development of practical skills that connect students to enduring traditions. Students will leave the course not only with technical knowledge of timber framing, but also with the lasting experience of collaborating and contributing to a permanent structure on campus. Enrollment is now open for interested students seeking this hands-on experience at Trinity-Pawling School.

Teachers who understand boys, coaches who bring out their best, mentors who walk alongside them, and exploratory learning that keeps them engaged — these are among the transformational people and experiences your philanthropy sustains.

Just as importantly, it opens doors through scholarships and financial aid, strengthening the brotherhood that fosters belonging, resilience, and self-awareness.

Giving Day is an opportunity to invest in the people, programs, and places that help Trinity-Pawling students discover and pursue their distinctive gifts and talents.

Make your gift to help make a transformational difference FOR THE BOYS.

FOR THE BOYS GIVING DAY — MAY 5, 2026

Can’t wait to join in? Give today! We will still count your gift toward Giving Day.

www.trinitypawling.org/for-the-boys
Venmo: @TrinityPawlingSchool
Phone: 845-855-4830

We had an incredible evening reconnecting and reminiscing at our Palm Beach Reception on March 24, generously hosted by Trustee Dick Bauer ’70. It was a powerful reminder of the strength and spirit of the Trinity-Pawling community as alumni, current parents, grandparents, and faculty from across the generations came together. Head of School Bill Taylor shared an inspiring update on Trinity-Pawling’s momentum and vision, reinforcing the vital importance of boys’ schools and Trinity-Pawling in today’s world. It was a night filled with laughter, pride, and deep connection — a true celebration of our past, present, and future.

SAVE THE DATES FOR OUR UPCOMING RECEPTIONS:

June 4, 2026
Washington, D.C. Reception
6:00 - 8:00 PM
University Club
Register Now: https://www.trinitypawling.org/events

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

Trinity-Pawling is proud to announce the expansion of our faculty and coaching staff, with the addition of Coach Danny Green, who will lead Pride baseball starting in the 2026-2027 school year.

No stranger to boarding school and NEPSAC baseball, Coach Green will bring coaching experience, passion, and energy to the Trinity-Pawling baseball program. Coach Green grew up playing baseball throughout the New England AAU and showcase circuit, competing alongside many of the region's top players. He attended the University of South Carolina, where he graduated with a degree in Business in 2020. He then spent some time with the South Carolina Gamecocks as a bullpen catcher. It was during this time at South Carolina that Coach Green really found his passion for coaching. He spent the summers helping his coach with his dad’s American Legion Baseball Team. Immediately following his graduation, Coach Green began a career in coaching AAU programs before transitioning into the prep school setting.

In 2023, Coach Green was a teacher and coach at The Rivers School in Weston, MA, and contributed to one of the program’s most successful seasons in recent years. It was during his time at Rivers that Coach Green fell in love with the New England Prep School, and “the perfect blend between holistic student-athlete experience of high school sports and the more competitive, detail-oriented nature of the college game.” Coach Green has most recently taken over as Head Baseball Coach at Hillside School, a junior boarding school in Marlborough, MA.  During his time at The Rivers School and Hillside, Coach Green has learned and built relationships with some of the most respected coaches in New England. In addition to his coaching responsibilities, Coach Green is a Learning Specialist and provides additional academic support for students with language-based learning differences.

Throughout his career, Coach Green has emphasized player development in a collegiate-level training environment while building genuine, meaningful relationships with his players. Coach Green believes, “Trust is the basis for development, both on and off the field, without sacrificing character, leadership, or academic engagement. Practices will be structured, intentional, and designed to maximize development for each individual, while also strengthening the collective identity of the team.” Recruitment will be essential to his work, and he understands the importance of identifying student-athletes who are a strong fit for Trinity-Pawling’s culture and values. I am excited about Coach Green’s passion and hunger to continue growing Trinity-Pawling’s baseball program.

Trinity-Pawling has a tremendous foundation, in large part due to the great work of Coach Cody Doyle over the past five years. I cannot thank Coach Doyle enough for his leadership, vision, and level of care for our student-athletes, as he worked closely with them daily. Mike Webber, Josh Collins ’95, and Alex Steele will remain on staff to help with the transition.

We are thrilled to welcome Coach Green to our faculty and coaching staff.  From the very first conversation, it was clear that he brings a passion for student-athlete development, a commitment to excellence, and a vision for building something special within our program. We are excited to see not only the immediate impact on our baseball program, but the long-term growth and success he will help foster.

“I have had the pleasure of having Coach Green on my staff, and he is the real deal. Baseball is in his blood, which shows in his deep understanding of the game. What impressed me most was his ability to connect with the players. He speaks their language and earns their respect effortlessly. He brought innovative drills and concepts to our program that I still use today. Any program would be lucky to have him leading young men.” - Coach Darren Sullivan, The Rivers School

“Coach Green squeezed every ounce of talent out of me, developing me as a pitcher, a leader, and a man. He made baseball fun every day and played a massive role in our team’s success, as well as my step up to the Division 1 level. He is truly a players' coach that wants his guys to develop and succeed in baseball and beyond.”  - Coley Schaefer, Villanova 2028

“I played for Coach Green at The Rivers School. Instantly, I could sense his love and passion for the game. The energy he brought every day created a positive, rewarding environment that made you want to show up and compete. His care and desire to win were genuine, which was appreciated and mirrored by his players.”  - Carter Bentley, Northeastern 2028

Coach Green will officially move to campus this summer with his fiancée, Ashley. We encourage you to reach out to Coach Green to introduce yourself or with any questions. Coach Green can be reached at dgreen@trinitypawling.org.

Roll Pride!

by Chris Gillman ’05, Athletic Director