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!