As the cold and dark winter gives way to the warm and lush days of spring, the Trinity-Pawling community finds itself in a familiar rhythm — one that inevitably leads to the culmination of another school year. For the Class of 2025, however, this transition is especially significant, as it marks both the conclusion of their high school journey and the beginning of a new chapter in their lives.
During the next several months, each senior will process his separation from Trinity-Pawling in his own way. In general, they are well-prepared for the next step by their hard work and steady growth. In other ways, however, they will be challenged by this process. Saying goodbye to close friends, who have shared in the same experiences of challenge and growth, can feel daunting. Many also come to realize they are leaving behind faculty members who know them well and care deeply about their success. Never again will the same people be together in the same place, and as this awareness settles in, it can magnify what is already an emotional experience.
This year’s seniors are an exceptional group of young men who have exemplified brotherhood and principled leadership. Over the coming months, they will experience a mix of emotions — pride in their achievements, excitement for the future, and the bittersweet realization that their time at Trinity-Pawling is coming to an end. As they prepare to say goodbye to close friends, dedicated faculty, and a school that has shaped them in countless ways, they will also embrace the opportunities that lie ahead.
Trinity-Pawling’s Commencement Weekend features several events, each designed to guide seniors through the transition from students to alumni. A key part of this experience is Senior Day. This special day allows the Class of 2025 to celebrate their bond as brothers while also shifting their perspective toward their new role as Trinity-Pawling alumni.
As we prepare to celebrate the accomplishments of our seniors, we look forward to the days ahead — days filled with learning, growth, and the lasting bonds of the Trinity-Pawling brotherhood.
On Tuesday, January 21, Head of School Bill Taylor announced that we have concluded the search process for the next Athletic Director for the 2025-26 school year. The career opportunity generated strong interest from applicants from around the country. Four semi-finalists were invited to interview on campus and met with an Advisory Committee that provided recommendations for the finalists. Two finalists were chosen, both possessing significant strengths that would have enabled either one to be a successful and effective leader in this important area of the Trinity-Pawling experience.
Please join us in congratulating Chris Gillman ’05 on his appointment as Trinity-Pawling’s next Athletic Director! (Effective July 1, 2025) Get to know a little more about him in this Q&A:
Tell us about your experience as a student-athlete at Trinity-Pawling.
My experience was quite enjoyable. One of the many reasons I chose to attend Trinity-Pawling was for the opportunity to compete at a high level, with terrific coaching and mentoring. I was thrilled to wear the Blue and Gold, and play for the Pride. My experience taught me much more about the game!
What were the most valuable lessons you learned from your athletic mentors — coaches or ADs?
I learned so much — it’s impossible for me to share all of them in this article. Perhaps the biggest: Lead by example. My predecessors — Miles Hubbard ‘57 and Brian Foster ‘79 — did not just talk about hard work, discipline, and integrity, but they embodied it. I have been so fortunate to garner so much advice and direction from Miles and Brian. While filling their shoes will be impossible, I feel confident that there is a strong foundation that we will continue to grow in the Athletics Program! It is important to be consistent and to have consistent expectations — my mentors emphasized the importance of setting a standard and sticking to it.
What other professional roles have you had at Trinity-Pawling and how have they prepared you for the role of AD?
I have been fortunate to hold many positions at Trinity-Pawling and help serve the community in a variety of capacities. I started my career in the Advancement Office. This gave me an opportunity to connect with alumni and talk about the School and its incredible impact on all of us. My passion was teaching, so when an opportunity came along to get in the classroom, I jumped at the chance. As time progressed, I had the incredible opportunity to take over our Center for Learning Achievement. This was an incredible experience and taught me a great deal about leadership. Being a classroom teacher and the Director of the CLA showed me how to manage expectations and hold students accountable while continuing to support them and help them grow. Currently, I am the assistant varsity hockey coach and lacrosse coach. This has taught me about sportsmanship and has helped shape my vision of how I want Trinity-Pawling to be represented as a school through our Athletics Program. I am also the Dean of the Senior Class, dorm parent, and advisor.
The tight-knit community is an important part of the Trinity-Pawling culture — what role does athletics play in keeping our community connected and building a sense of belonging?
Athletics plays a crucial role in strengthening our community. Trinity-Pawling Athletics is about more than competition — it’s a powerful tool that enhances the School’s culture by strengthening the values of sportsmanship, resilience, and community. It builds camaraderie within teams, fosters meaningful relationships, and deepens connections with families and alumni. All of which help define the Trinity-Pawling experience.
Trinity-Pawling has a long history of athletic development, rooted in Dr. Gamage’s philosophy. Do you think those traditions are still relevant in today’s athletic /educational landscape?
While the landscape of education and athletics has changed over time, there are many values that remain relevant today. Character, discipline, and competition are all core principles that will help shape a successful athletic program. In my mind, the holistic athlete is extremely important. In today’s world, it is not just an athlete’s physical prowess or sportsmanship but their mental health and personal growth that means so much more. Athletics is an avenue for young men to handle adversity, work within a team, push themselves out of their comfort zones, and be vulnerable.
What is your vision for the future of Pride Athletics?
I want Trinity-Pawling Athletics to continue to evolve. Wins and losses are important, but they cannot overshadow the development of our athletes. I want our student-athletes to be PROUD to wear the Blue and Gold, to feel a sense of PRIDE when they are competing, and to be able to show CHARACTER when they are persevering.
What are your top priorities for the athletic program?
I want our athletes to be the best representation of the School — whether that means competing on the field, ice, or court, or supporting peers while they are competing. We will continue to grow as a program — with integrity! Athletics play a major role in growing school spirit and community engagement. I want every student at Trinity-Pawling to feel like there is an opportunity to belong to the Trinity-Pawling Pride team.
What goals are you hoping to accomplish in your first year as the new AD?
My first-year goal is simple — never stop learning. The best coaches and ADs are always evolving and seeking new knowledge. I plan to learn from others and ask questions. It is important that I remain loyal to the core values and principles of Trinity-Pawling Athletics, but find ways to adapt new strategies, technologies, and approaches.
You wear many hats at the School in addition to living on campus — how do you balance school life and family time?
This is, perhaps, the toughest part of the job — but the most important. The School demands can be high, and the days can be long. However, there is no better place/environment to raise a family. The cliche saying that “it takes a village” comes to life at Trinity-Pawling. The community is incredibly supportive! My two little boys — 5 and 3 — find incredible joy in being around the boys, whether in the dorm, dining hall, or on the fields/rink. They look up to the students as big brothers and role models and love chasing them around. None of this could happen without the support of my wife, Ariana. Ariana is incredibly supportive and remains my rock through busy days, long nights, and constant road trips. Short answer — having a family that enjoys their time on campus just as much as I do, helps balance school life and family time!
For his Senior Independent Project, Ryan Bellamy ’25 analyzed how Black people are represented in Spike Lee films. “Spike Lee’s portrayal of Black people differs from that of other Black producers because Spike Lee doesn’t show a lot of gun violence, drug use, and Black-on-Black crime,” Bellamy explained. “Spike Lee portrays Black people as intellectuals in his movies.”
Inspired by a previous Winter Project on Black stereotypes in television, Bellamy was guided by history teacher Jim McDougal to examine positive portrayals in Lee’s films. Through his research, Bellamy found that negative stereotypes of Black people in media are often what sells, while Lee’s films prove that successful movies can highlight Black excellence without relying on harmful themes. “I think it’s important for all races to be positively portrayed in film because negative portrayal of a race can translate to negative stereotypes,” he said. “I also think it’s important for young kids to see a positive portrayal of people who look like themselves in film.”
Bellamy presented his findings to the Board of Trustees during the Trustee weekend in January and received extremely positive feedback. “Eventually I would like something like my project and independent study to be available for the whole school as a class,” Bellamy stated. He also shared his research with the Black Student Union, leading a group discussion on He Got Game.
“Bellamy is a thoughtful young man, and I am pleased that he was able to find an opportunity to pursue an interest. It is important for all students to find a place where they can see themselves and have an opportunity to pursue a passion or question that they believe is important. Bellamy’s project reflected his desire to learn how people of color are represented in history and popular culture,” said Bellamy’s faculty advisor Jim McDougal.
While Bellamy plans to study economics in college, he hopes to continue examining the impact of media representation and storytelling.
by Missy McCluskey
Ryan Gift brings a wealth of experience and a dynamic background to his new role as Trinity-Pawling’s Director of Facilities. His career began in commercial construction, managing large-scale projects such as performing arts centers, hospitals, and sports arenas in Los Angeles and Houston. A shift in the industry led him to project management in the water and wastewater treatment sector, where he traveled extensively, overseeing equipment installations nationwide. Eventually, his career took him into corporate strategy and mergers and acquisitions, allowing him to work globally.
After years of fast-paced corporate life and constant travel, Gift sought a change. He relocated to the Village of Pawling in August 2023, attracted by the town’s sense of community. When the opportunity at Trinity-Pawling School arose, he saw a chance to bring his career full circle back to construction management and leverage his leadership experience in a meaningful way.
Gift is eager to immerse himself in the school community. “The tight-knit environment was a big attraction for me,” he shares. “Trinity-Pawling’s mission to help students develop self-awareness in a safe environment is key to developing good men who will go out into the world and hopefully be positive forces for positive change.”
His top priority is understanding the School’s facilities and identifying areas for enhancement. Gift aims to preserve Trinity-Pawling’s historic charm while incorporating modern efficiencies that improve operations, sustainability, and learning environments. Listening to the faculty, staff, and students is key to his approach — ensuring that upgrades align with the School’s evolving needs. “I hope to help guide the development of capital projects that will improve functionality, keep TPS competitive with peer schools, and foster an environment where students and faculty can teach and learn successfully,” he shares.
Gift also values the experience and dedication of his facilities team. “Anyone in a leadership role is only successful when their team’s contributions are understood and appreciated,” he notes. He strives to create an environment where his team feels valued, empowered, and supported in their roles, fostering collaboration and open communication.
Beyond campus, Gift enjoys outdoor adventures on the Empire State Rail Trail and Appalachian Trail. He’s also diving into landscaping projects at home, inspired by Trinity-Pawling’s farm program. Most of all, he cherishes time with his partner, Ellie, and her two young children, Fiona and Rowan.
Gift’s leadership and vision will undoubtedly help shape the future of Trinity-Pawling’s campus, ensuring they support both tradition and progress.
by Judy Redder
On stage this weekend, the Trinity-Pawling Theater Department presents Lord of the Flies, a gripping adaptation of William Golding’s novel. Under the direction of Theater Arts Director Ricky Oliver, this production brings the story into the present day, making it more relatable for the cast and audience alike.
“In building out the theatergoing experience for the Trinity-Pawling community, I try my best to find titles that will excite, challenge, and inspire our students,” Oliver shared. “A play about prep school guys getting marooned on an island only to fall into savagery feels like a no-brainer to me.”
Unlike our past productions, Lord of the Flies is highly physical, using movement and stage pictures to tell the story. Oliver invited guest artist Kimiye Corwin to campus in January, to work with the students on Movement and Contact Improv to help them prepare for their roles. The dynamic set, designed by Mr. Garguilo, Mr. Moreno, and the TPS Stage Crew, transforms throughout the performance to reflect the island’s chaos.
The cast, the largest in recent history, includes students of all experience levels, two faculty members, and a faculty child. Oliver praised their growth: “Taking ownership of your work in a play is the greatest gift you can have as a young actor. It’s been amazing to see them go for it!”
Senior Luke Sansobrino ’25 echoed this sentiment: “Joining the play pushed me out of my comfort zone, and it’s been one of my best experiences at Trinity-Pawling.”
With its intense performances and innovative staging, Lord of the Flies promises to be an unforgettable theater experience. “You are not going to want to miss this one, folks!” Oliver said.
Mark your calendars! There will be two opportunities to witness this extraordinary production: Saturday, March 1, at 7:00 PM and Sunday, March 2, at 2:00 PM. Admission is free, so gather your friends and family and join us for an unforgettable night of theater!
by Missy McCluskey
Mark your calendars, Trinity-Pawling community — these are events you don’t want to miss!
April 8, 2025
Palm Beach Reception
6:00-8:00 PM
Palm Beach, FL
Graciously hosted by Dick Bauer ’70, Trustee
April 26, 2025
Mo Vaughn ’86 Baseball Field Rededication and Turf Celebration
Trinity-Pawling School
May 1, 2025
“For the Boys” Giving Day
Your support has the power to make a transformational difference!
June 11, 2025
Shenzhen Gathering
7:00-9:00 PM
Shenzhen, China
June 13, 2025
Shanghai Gathering
7:00-9:00 PM
Shanghai, China
June 14, 2025
Beijing Gathering
7:00-9:00 PM
Beijing, China
June 17, 2025
Tokyo Gathering
7:00-9:00 PM
Tokyo, Japan
June 19, 2025
Seoul Reception
8:00-10:00 PM
Seoul, South Korea
August 4, 2025
Cape Cod Reception
6:00-8:00 PM
Harwich Port, MA
Graciously hosted by Becca and Tom Ahrensfeld ’73, Trustee, and Chris Roux ’73, Trustee
October 3-4, 2025
Homecoming and Reunion Weekend
Trinity-Pawling School
More details and registration coming soon!
December 8, 2025
New York City Holiday Reception
6:00-8:00 PM
Union Club of the City of New York
101 East 69th Street, New York, NY
Graciously hosted by Jean Doyen de Montaillou and Michael Kovner ’58, Trustee
More details and registration coming soon!
This year, the Entrepreneurship Institute at Trinity-Pawling has launched an Alumni/Parent Speaker Series, providing students with the opportunity to engage with entrepreneurs, startup founders, and business professionals. Driven by the seniors in the Institute, the series is also available for the Entrepreneurship Club members and other students who are interested in gaining insights from industry leaders.
The initiative stems from a pilot speaker program introduced last year, which received overwhelmingly positive feedback. Seniors who participated shared that hearing firsthand from alumni and parents in the business world helped deepen their understanding of entrepreneurship. Their feedback encouraged the Institute to expand the series into a permanent part of the program.
A key component of the Entrepreneurship Institute is hands-on learning. Seniors and club members are currently developing business projects, which include crafting business plans, initiating a minimum viable product, building websites, or solving real-world challenges within Trinity-Pawling or their own communities. Some students have already launched ventures and are refining their ideas through this process.
The goal of the Speaker Series is for students to gain experience, acquire knowledge, and develop the mindsets and skill sets essential to entrepreneurship. It also provides them with an opportunity to explore different business arenas, engage with experienced professionals, and ask questions. This experience aims to spark motivation, creativity, innovation, and strategic risk-taking, empowering students to bring their business ideas to life.
Rooted in innovation and leadership, the Entrepreneurship Speaker Series will be an invaluable addition to Trinity-Pawling’s program, equipping students with the tools and confidence to forge their own paths in the business world.
by Missy McCluskey
Trinity-Pawling School invites you to make your 2025 nominations for the Athletic Hall of Fame and the Arts Hall of Fame. The Athletic Hall of Fame will accept nominations for outstanding student-athletes, former coaches, and athletic teams. The Arts Hall of Fame will accept nominations for students and teachers who excelled in the arts. Please follow the links below to complete your nominations today! All 2025 Hall of Fame nominations are due by Wednesday, March 5, 2025.
Arts Hall of Fame Arts Eligibility Criteria
An alumna, alumnus, or alumni who participated and excelled in the arts while pursuing a Trinity-Pawling education and who completed their secondary school career at least ten years prior to the year of election, and whose personal or professional interests continue to include the pursuit of artistic expression. A teacher whose distinguished record or contribution to the Trinity-Pawling arts program for at least ten years. For a list of all current members, please visit the Arts Hall of Fame on our website. We look forward to receiving your nomination form!
Athletic Hall of Fame Athletic Eligibility Criteria
An alumna, alumnus, or alumni who participated and excelled in varsity athletic competition while pursuing a Trinity-Pawling diploma and who has completed his/her secondary school athletic career at least ten years prior to the year of election. A coach or athletic administrator whose distinguished record or contribution to the Trinity-Pawling athletic program for at least ten years. A team that has brought recognition and honor to Trinity-Pawling School by its significant achievement. For a list of all current members, please visit the Athletic Hall of Fame on our website. We look forward to receiving your nomination form!
Save the Date — Homecoming and Reunion Weekend 2025
We hope to see you at the Trinity-Pawling Arts Hall of Fame and Athletic Hall of Fame induction ceremonies at our upcoming Homecoming and Reunion Weekend, held on campus on October 3-4, 2025. Be sure to mark your calendars and stay tuned for more details!
Questions? If you have any questions about Hall of Fame nominations, please reach out to MJ Davenport in the Office of Advancement via email at mdavenport@trinitypawling.org
As we approach a well-deserved March break, that means the Winter Term of sports at Trinity-Pawling is coming to a close. Although it’s sad to see it go, it’s been a season to remember, certainly living up to the hype! The Winter Term consists of four sports: ice hockey, basketball, wrestling, and squash.
Varsity hockey has made major improvements this year. After coming off just a six-win season last year, the team has twelve already so far this season and is on track toward making large school playoffs! Their most recent game against Taft was a must-win, and after going down 4-0 heading into the third period, they came back to keep their season alive with a 5-4 overtime win! Standouts have been Liam Lefebvre ’25 and Andrew Migliore ’26 up front, as well as Andy Matousek ’25 backstopping the team in net.
Basketball finished off their season yesterday with an 87-71 win at Suffield, giving them a 10-13 record. Despite not making playoffs, they finished on a high note with a dominant 68-51 victory on Senior Night against Kent prior to their win at Suffield! Some of the top performers from the year included the captains, Beni Maly ’25, Jaice Martabano ’25, and Ryan Bellamy ’25. On top of them, Mikey Malachi ’26, as well as Aaden and Anthony Walters ’28 proved to be strong contributors despite their young age.
Varsity squash ended their year with a cumulative team record of 7-5. The team was packed with standout performers. Special shoutouts go to Tanner Braden ’27, Nick Brandmeyer ’25, Yassin Elmoutasem ’27, Michael Huang ’27, Teddy Kempner ’25, Solomon Rossi ’26, James Tesei ’28, and Corey Van Etten ’26, all of which made it to the NEPSAC Championship weekend in Middletown, Rhode Island!
Varsity wrestling had an especially strong season as always. They finished with a whopping 13-2 record, advancing many wrestlers to WNEISWA, then New England’s, then even a select few to Nationals (Kweku Arthur-Mensah ’25, Axel Caramico ’26, Tyler Fromm ’25, Avi Meltzer ’26, Maxx Miller ’25!) Kweku and Tyler were each one match away from placing.
As we wrap up the Winter Term at Trinity-Pawling, let’s be sure to cheer on our remaining athletes and look forward to an exciting spring season!
by Ian Arnott ’25
Our Pride Perspectives webinar series continues through the academic year! We hope you’ll tune in for our next presentation:
The Resilient Boy: Fostering Healthy Masculinity, Emotional Intelligence, and Mental Well-Being
Trinity-Pawling fosters health and wellness in every aspect of student life. Faculty and staff members, dorm parents, and coaches work with our Health and Wellness Center team to ensure that all students feel healthy, safe, and cared for during their time on campus. Our Health and Wellness faculty help students adapt to boarding school life and develop strategies for dealing with stress and the challenges of adolescence.
Join Head of School Bill Taylor and members of the Trinity-Pawling faculty to learn more about how boys benefit from a Trinity-Pawling education.
Thursday, March 6, 2025
7:00 PM (EST)
For the full list of webinars in our Pride Perspectives series, please visit our website. If you have any questions, please reach out: info@trinitypawling.org
Join us on May 1 for Trinity-Pawling’s “For the Boys” Giving Day
Trinity-Pawling School is designed for boys — we embrace their strengths, nurture their self-awareness, and ignite their love of learning. While many schools rely on restrictive, test-driven models that leave boys behind, we provide the freedom to take healthy risks through hands-on, experiential learning, fostering their creativity and building their confidence in and out of the classroom. Guided by mentors who instill our core values — Excellence, Character, Community, and Curiosity — we empower boys to discover their distinctive gifts and talents. Trinity-Pawling is the next-generation school for boys.
Your gift to Trinity-Pawling supports:
Scholarships and Financial Aid
Expand access to a Trinity-Pawling education, ensuring that more boys benefit from a school built for their growth, success, and transformation.
Faculty and Staff Excellence
Honor the mentors who guide our students — not only as teachers and coaches but as role models who shape their confidence, leadership, and values.
Academics
Strengthening innovative and experiential learning opportunities and active discovery — preparing boys to think critically, collaborate, and engage with the world.
Arts
Inspire creativity and self-expression, helping boys build confidence, embrace different perspectives, and find their voice in an increasingly complex world.
Athletics
Develop character, teamwork, and resilience through competition and camaraderie, teaching boys the value of effort, discipline, and integrity.
Student Life
Enrich campus experiences that foster self-awareness, independence, and a deep sense of belonging, ensuring that every boy feels seen, supported, and empowered.
Special Projects and Innovations
Support bold ideas such as our Institutes of Active Learning and Practicum for Civic Leadership that keep Trinity-Pawling at the forefront of boys’ education.
Together, we can make an extraordinary difference For the Boys.
Ways to Contribute:
● Online: www.trinitypawling.org/for-the-boys
● Phone: 845-855-4833
● Venmo: @TrinityPawlingSchool
● Check: Trinity-Pawling School, Office of Advancement, 700 Route 22, Pawling, NY 12564
Can’t wait to join in? Give today! We will still count your gift towards the Giving Day.
Thank you!