Trinity-Pawling School Class of 2023


The excitement of Trinity-Pawling’s 116th Commencement Weekend was felt across campus on Saturday, May 27, 2023. The sun was shining, the blue and gold Trinity-Pawling banner hung proudly on Cluett, and hundreds of family members and friends filled the tent on the quad to celebrate the graduating class.

Donning their blue blazers, the graduates of the Class of 2023 sat alongside each other in All Saints’ Chapel and on the quad one last time — looking back on their years of accomplishments and memories at Trinity-Pawling and looking ahead at their next great adventures.

In the days leading up to this milestone, we asked members of the Class of 2023 a series of three questions about their time in the Pride. In celebration of their graduation, we are pleased to share some of their answers with the Trinity-Pawling community.

What is one word you would use to describe your senior year at Trinity-Pawling?

Popular answers included:


What will you miss most about Trinity-Pawling?

The Top 10 responses:

10. The Phoenix
9. Faculty dogs
8. The pond
7. Softball on the quad/Coratti Field
6. Chapel Talks
5. Head’s Holidays
4. Dorm life
3. Competing in the Founders League
2. The teachers, faculty, and staff
1. The close-knit community

Now that you are graduating, what is your BEST piece of advice for underclassmen to make the most of their time at Trinity-Pawling?

Here’s what the graduates had to say:

“Get involved.”

“Do the right thing, always.”

“Meet people outside of your friend group.”

“Just get in the action…don’t stand back and watch.”

“Work hard and make friends.”

“If there is something you want to do in life, use the tools and resources you’ll find here because this is the best place to start.”

“Always put your brothers first.”

“Be where your feet are.”

“Waste no more time arguing what a good man should be. Be one.” – Marcus Aurelius

“Be yourself.”

“Do the work and go to Chapel.”

“Make the most of your time here, because in the blink of an eye it will all be gone. Use this place to become the best version of yourself. Everything you need to become successful is available to you.”

“Give a Chapel Talk.”

“Meet everyone on campus.”

“Keep working until you reach your goals.”

“Find a mentor, and take advantage of the different things T-P has to offer (like a new sport or club).”

“Work hard in every facet of life at Trinity-Pawling.”

“Don’t blink and don’t waste a minute with the fellas.”

“Be a good person, it’s that simple.”


On behalf of the entire School community, we extend one more heartfelt congratulations to the Class of 2023! We know you will continue to leave your mark on the world, just as you left it on Trinity-Pawling School.

by Emma Quigley

Head of School Bill Tatlor addressing the Class of 2023 at Trinity-Pawling School


Message to the Class of 2023:

In a real sense, you have been Pioneers on this journey. As I have said before, you represent ½ of 1 percent of the American school-age population who have had the opportunity to attend a prep school such as Trinity-Pawling. You are in a distinct minority of students who have had this opportunity and this type of experience. And, it has not all been easy.

There have been days of triumph and days of defeat. Days of joy and days of sorrow. But, through it all, you have pressed ONWARD. You have pioneered your way ahead and you stand on the precipice of your new, adult life. Indeed, you will be pioneering your way into this new stage of your life.

Like Pioneers, you will be leaving what has become familiar to you and venturing out into a wilderness of new challenges and new opportunities.

Like Pioneers, you will need to pack for the journey. You can’t take everything from your current life for the journey ahead, but there is room for some things to pack with you before you depart. Here are some suggestions for your packing list — consider packing:

  • You, at your best — we all have better days than others. We all have days when we are at our best and then there are days when we are not really at our best. Know what the difference is between the two days and pack you, on your best days.
  • Consider packing effort — you have learned at Trinity-Pawling that effort leads to achievement. Never lose sight of this simple equation. On the journey ahead, you will run into many people who will achieve. Some will have been given the gifts to achieve without much effort. I would suggest that such people have not yet learned the critical nature of this simple equation. And, if they didn’t learn it when they were younger, they may never be able to learn it. You have learned this equation and you have mastered it. Now, you can apply it in the real world. But, just remember that this equation will no longer be equated with more free time, more weekend privileges, and special treats. The reality is that this equation of effort leading to achievement will now, more often than not, also mean that more effort will be rewarded with more work, more responsibilities, and greater accountability. Yet, it will also lead to greater satisfaction, stronger confidence, and the happiness of knowing that you did your best.
  • Consider packing a joyful perspective — wherever the journey ahead takes you, there will be challenges, hardships, and setbacks. You have faced this reality here. Out there, however, this reality can have more of an impact on how you look at life, yourself, and others — if you let it. Take a joyful perspective with you because this will allow you to process challenges, hardships, and setbacks in a healthy way. This doesn’t mean that you have to try to find joy in challenges, hardships, and setbacks as such an approach can actually be unhealthy. Rather, it means that you have the choice each day to see aspects of joy in each day. You have had these moments here, many of them. You have shared these moments with one another. Make sure you stay in touch with one another, especially during times of challenges, hardships, and setbacks. There is joy in the relationships that you have forged with your brothers. Allow this joy to always be a part of your life and journey.

As much as you have been Pioneers and as much as you will be Pioneers for the coming journey away from Trinity-Pawling, you must always remember that every Pioneer eventually becomes a Settler.

So, at some point on the journey ahead you, too, will become a Settler. You will settle down and plant some roots. You will likely do this several times ahead. You may become a Pioneer again, choosing to leave a career in order to find the next chapter in your life. But, you will settle. You have learned how to do this here, too — how to settle.

On the journey ahead, while you are pioneering forward, be thinking about where and how you might like to settle. But, remember that the choice of settling well or settling poorly will be yours, just as it has been here.

The trick to settling in life is to know how to settle well. So, when you are packing your bag for your pioneering journey, I would suggest you pack a separate bag that is your settling bag.

Here are some items that you might want to consider adding to this bag — consider packing:

  • Your integrity — often the difference between settling well in life and settling poorly in life is whether or not you have settled with your integrity. Character matters in life. Choose to take it with you on any journey and make sure it is in the bag you have with you when you settle. If it is not, then you will settle for anything. Slowly, choice by choice, you will lose yourself when you settle for anything. When you settle with integrity you will always be where you are.
  • Consider packing your compass. When you settle, you will always want to check to see if you are still pointed in the right direction. Make certain you pack a compass for this purpose. Now, the compass can be anything in your life that will be able to check your direction to see if you are still heading where you want to go. This can be your family, it can be your close friends, and it can be times in your life when you can be quiet and still, so that you can reflect on who you are, who you want to become, and how you are going to get there. If you find yourself settled without a compass, then you may discover that you have grown so accustomed to the act of settling you will have forgotten why you settled there to begin with.
  • Consider packing anything that reminds you of the you that you were before you started the journey. Keep your pictures of times spent in this place. Stay in touch with one another. Stay in touch with that part of you that will always be 18 or 19 years old. Often, when we settle in life, we can lose sight of that version of ourselves if we do not bring that part of us along when we settle.

You all are continuing on a journey that started before you arrived at Trinity-Pawling. It is a journey of self-discovery and self-awareness. It is a journey of figuring out your way in the world. It is a journey of determining your role in this world and the opportunities that exist for you to contribute positively and productively to it.

The fact of the matter of this journey is this. It is a journey of both pioneering and settling. Often this is happening at the same time. Whether or not you are packing bags for your pioneering journey or your settling journey, the important thing to remember is that you are on a journey and you get to decide what you take with you as you go. I hope that, in one way or another, in large ways and in small ways, your journey at Trinity-Pawling will always be a part of the longer journey on which you will shortly embark.

And, my last word before you embark on this journey is, of course: ONWARD!

by William W. Taylor

Watch Head of School Taylor’s full Commencement Address here.

Visit our Commencement 2023 website page to read about the Class of 2023 achievements.

Eric Drath ’88 speaking to the Trinity-Pawling Class of 2023


Address to the Class of 2023:

Thank you, Headmaster [Head of School] Bill Taylor, your predecessors Arch Smith and the late Phil Smith, the trustees, faculty, and everyone from the T-P community. And hello to the graduating Class of 2023, your proud families, and friends.

When I received the email asking if I was available to speak today, I had to read it twice — I figured opportunities like this were left for guys like Mo Vaughn, former NY Met and Boston Major League Baseball star — my former teammate and T-P legend. Then I realized, today was right smack in the middle of Memorial Day weekend — I then realized why! Kidding of course — but seriously, gentlemen, you are moments away from having a new title — alumni. However, before it’s official you will have to endure this one last lecture. I hope it leaves you with the hope that someday you too can be standing up here, regardless of whether you believe it or not today.

I arrived at Trinity-Pawling as a 14-year-old Jewish kid from New York City and from a divorced home. I had been diagnosed with a learning disability as a kid and struggled with academics. It was the fall of 1984 — I was scared and felt like a fish out of water. Perhaps many of you felt the same when you first arrived.

During the next four years, I learned a sense of responsibility, independence, and gained confidence in myself. I had wonderful teachers and coaches whose words still echo in my head today. Including Mr. and Mrs. Kneeland, who made me feel like one of their own.

But by sitting here today, you’ve already accomplished something that I actually did not. To be quite honest, I didn’t get the privilege of graduating with my class in 1988. (In fact, I better make sure no one from my disciplinary committee hearing is in the audience today — they might kick me out again.) But seriously, it would be one of a series of failures that I made as a young man that changed my life, even though I didn’t realize it at the time.

Clearly, you have not made the same mistakes that resulted in my early exit from this school during senior year, but rest assured, you will make your own in life. Some big, some small. And I know they will provide some of your greatest lessons. Most of the time, even more so than your successes.

One quick story before I get started. When I first made varsity football, we were playing a game against Hotchkiss, and I wanted the ball so badly. I remember Coach Hutchinson saying, “Give Drath the ball — I know we’ll get some yards from him.” In the huddle, they called my number. I got the ball and ran through the line of scrimmage — 1 yard, 2 yards, 3 yards, 6 yards, 7 yards. As I’m turning to try to get 1 more yard, a defensive player makes a perfect tackle, his helmet down, and hits the ball out of my arm. It’s a fumble. It’s a turnover. The whistle blew and I was quickly out of the game. (I don’t think Mo Vaughn, who also played tailback, has this story.)

I remember being on the sideline so angry at myself and wanting desperately to get back into the game. I didn’t get my chance that day. And that day, that play, that experience still haunts me. To this day, I still want to get the ball back. What I would do to get back into that game!?

You might be sitting here thinking, “What a sad story.” But I don’t see it that way today. I love that memory. Because it reminds me that I’m still hungry. That I still want the ball. It drives me. I could’ve walked away with just a bad taste in my mouth, but instead, I walked away hungrier than ever to achieve that extra yard.

Sometimes it’s too soon after a failure to realize its value. It took me some years to learn that this was something positive. However, if you look for it, there is always a positive in your failures.

When I couldn’t graduate with my class, I was angry and resentful. I didn’t realize then that the cause and costs for those errors were my own doing. But now, I realize that my failures helped line the path that brought me here today.

I would love to say that my troubles ended right after Trinity-Pawling and I turned my life around. Unfortunately, that’s not my story either. I went to the University of Arizona, where I made another error in judgment and ended up back home the second semester of my freshmen year — with an outlook as bleak as ever.

Just so you know, both at Trinity-Pawling and Arizona, my failures were related to drugs and alcohol. Little did I know how dark it can be before the dawn.

With all my friends away in college and only a construction job as a prospect, I became determined to get the ball back. I made some changes in my life. I started going to meetings to help with my drug and alcohol problem, and I found a new faith in something greater than myself. A faith that to this day has never let me down. I am not sure exactly where it came from, but it was my inner understanding that knew the right thing to do. The good and hard things that are right. We all have it — it was always there, but I was ready to listen to it. I hope you will, too.

I knew I needed to get back to school. The prospects of a career without a degree did not seem promising. I applied for some classes at NYU and started to really excel. While I wasn’t matriculated, I took it more seriously than any studying I had ever done. While working as a bus boy and going to school, I happened to meet someone who would become an angel in my life named Peter Johnson — bless his memory. Peter was an example of God working in my life. He mentioned that Columbia University had a program for students who had promise but had lost their way. He said I would need to get straight A’s at NYU and take a test, and even then, it was no sure bet.

Lo and behold, one year after leaving the University of Arizona, I was enrolled and on the campus of Columbia University. If that wasn’t God intervening in my life, I don’t know what it was. It would change my trajectory and help me believe that with hard work, faith, and determination, anything was possible.

At Columbia, I threw myself into campus life. I joined a fraternity and one day on my way to lacrosse tryouts, I made a wrong turn and stumbled into the campus radio station, WKCR-FM. When I opened the door and saw the equipment, and another student behind the glass reporting the news, I was in awe. I wanted to get into that game. Three weeks later, I got my Class 3 FCC license and was broadcasting the news myself. I had no idea that would set my future career in motion.

Soon after, I applied and was offered an internship at ABC News. It was the beginning of the Persian Gulf War, and I was hooked. Getting coffee, running scripts, filing tapes — it didn’t matter what they asked. All I wanted to do was be there and learn everything I could. I wanted the ball.

I graduated from Columbia with a solid GPA and after a couple of smaller jobs, applied to CNN. I moved to Atlanta, Georgia without knowing anyone and found a home and a team at CNN. Again, I started at the bottom. I was making $17,000 dollars per year as a video journalist. (It sounds important, but really, they compensated in the title what they didn’t give us in dollars.)

I was at the bottom of the barrel. As a VJ, we would sometimes work overnights, we learned how to use the cameras, stage management, and teleprompters — it was like school all over again. I was hungry and was promoted after taking tests called newsmaker tests. What I loved most about CNN was that it was a true meritocracy. They didn’t care where you were from or what you had previously studied. They rewarded those who worked hard and proved themselves. Those who wanted the ball.

Another lucky turn — a friend of mine told me there was a new network starting in New York. I moved back to the city and helped launch the Fox News channel. It was my dream job. Back then, our mantra was, “We report, you decide,” and we believed that and that was how we covered the news. Of course, now, the mantra of Fox News is “We report, you decide, we get sued, we settle out of court, you don’t care…” Every day was a new assignment and a new lesson, and I didn’t take for granted how lucky I was to be doing what I dreamed of.

One night, a friend of mine asked me if I wanted to go to a boxing match. Honestly, I wasn’t such a big boxing fan. In fact, I was very tempted to say no and stay at home. But I said yes. I went up to Yonkers Raceway in the Bronx and into a field house — a large metal structure that was normally used to auction off horses. But that night, it was filled with cigar smoke, wise guys, and the excitement of an ensuing battle. One by one, each of the fighters walked through the crowd and into the ring. It was so gladiatorial in nature. I had never seen such a sight and was immediately hooked. It wasn’t the boxing itself — it was the environment and the characters that I thought only existed in movies. I found the promoter who would become another angel in my life. I asked him how I could get involved, and he said he’d give me a job as a publicist. Little did I know at that time, that being a publicist meant driving a van, picking up fighters at airports, bringing them to motels, getting them towels in the locker rooms, helping them get their medical tests done, and once in a while, writing something for the press. I didn’t care. I wanted the ball. I did anything and everything they asked. I had to start at the bottom again, and I did it happily.

Not so happy were my parents, who couldn’t understand how a college grad had become, in essence, a glorified driver. However, to be fair, they were impressed with how quickly I could get them a towel. But I had faith that this was a direction that I needed to take. I listened to my inner voice when the outside noise seemed to make the case that this would lead nowhere. That this was crazy.

I became enamored by the fighters themselves and their stories. I wound up becoming an agent and representing over 40 fighters. I traveled to Poland, Germany, England, Budapest, and many other places, bringing fighters, known as the B-side in boxing, opponents. I always identified with the underdog — surprise, surprise! But I became disenchanted when I realized my fighters were props who never stood a chance to win.

During this period, I spent a lot of time in boxing gyms. There, I met a guy named Luis Resto. Luis was a quiet, pleasant man with a dark past. I heard many whispers that he was banned from boxing for life, that he killed a man, that he went to jail, and that he could never enter a ring again. He was there, living in the basement of a dark, dank gym in the Bronx, training kids. My journalistic instincts perked up and I knew there was more to the story.

Back in 1983, 25 years prior, Luis Resto fought a fighter named Billy Collins, Jr. Billy was an Irish kid from Tennessee. Good looking, undefeated, and what the boxing world loved. Definitely the favorite that night. But what happened in the ring was a terrible tragedy. Luis would win by upset, and Billy’s face would look like he had elephantiasis, eyes swollen shut beyond recognition. Resto would go over to Billy Collins’ corner as a good sport might to shake hands with Billy and his father, Billy Collins, Sr. Billy’s father grabbed Luis’ gloves and immediately started yelling, “There’s no padding in these gloves! There’s no padding in these gloves!”

What ensued after that was a terrible tragedy. Billy Collins, Jr. would suffer permanent eye damage, and less than 8 months later, was dead. Some said suicide. Some said drunk driving. It was unclear.

So, when I found Luis Resto proclaiming his innocence 25 years later, I knew that I had to tell this story and I had to uncover the truth. I had no experience in documentary filmmaking, but I had faith deep inside that this was what my next chapter would bring. Again, many, including my parents, thought I was nuts.

A year later, I was able to get the rough cut of the film to a friend who was coaching a girls’ lacrosse team. One of the parents was an executive at HBO. He watched the film and Assault in the Ring premiered on HBO. We were even lucky enough to win the Emmy for Best Sports Documentary in 2010. Another God moment.

I’ve gone on to make many films since then and have learned many valuable lessons along the way. I made a film about Renee Richards, the transexual tennis player who was born Richard Raskind and played as a female at the US Open tennis tournament in 1977. Richard Raskind was a nationally-ranked tennis player at Yale who became a world-renowned eye surgeon, which might seem like a charmed life. But what I learned from Renee was that no matter what, you need to be true to yourself and your own identity at all costs — whatever those on the outside say.

I made a film about Pete Rose for ESPN, and I learned about a man enslaved in his own hubris, unwilling to admit fault and ask for forgiveness.

I made a film about Roberto Duran and Sugar Ray Leonard and their legendary fight commonly known as No Mas. I saw the difference between one who had moved on and one who was stuck in the past, refusing to be honest with himself.

I made a film about a man, Hector Macho Camacho, who was unwilling to face his own demons and wound up murdered, and his family’s search for closure.

I’ve made a lot of other films, but one of the most recent ones has perhaps the most poignant message no that I can leave with you today. The Dream Whisperer is about a 10-year quest by a now 86-year-old man, NY Knick legend Dick Barnett, to never give up on a dream. Dick’s selfless quest for his civil rights-era teammates to make sure they were remembered in the Basketball Hall of Fame showed me the importance of having a dream and never giving up. Always wanting the ball.

I pray and hope that all of you here today have a dream and a passion and a desire that keeps you up at night, waiting for the excitement of the morning. To have a meaning — a purpose, is the greatest gift a person can have for a career.

About 12 years ago, I wrote a letter to Arch Smith apologizing for my behavior back in 1988 and asking if I could do service and help in any way with the School to try and make things right. I returned to campus over a dozen times talking to you boys about filmmaking, sharing rough cuts, and talking about your dreams. Arch Smith surprised me one time and handed me my diploma — 25 years later. If that’s not God, then what is it?

T-P, again, taught me. I learned that it’s always better to give than to receive. What can you offer, not what can you take? That you will be measured by what you give rather than what you acquire.

Thank you, Phil Smith, for making sure I paid for my mistakes. Arch Smith, for granting me forgiveness. And Bill Taylor, for giving me the opportunity to speak to you today and continuing to lead this great institution and its core values forward.

Have faith in God and never quit on yourself. If you don’t think you have a connection with God, go deep within yourself and ask for the next right step, and the answers will come. Be persistent and determined and never quit on yourself. May God bless you, and to all of you new alumni, I pray that you always have the desire to get back into the game and always want the ball!

Go Big Blue — Roll Pride!

by Eric Drath ’88

Watch Eric’s full Commencement Address here.

Trinity-Pawling School Class of 2023 Valedictorian Alex Anderson speaking to the Class of 2023


Address to the Class of 2023:

Mr. Olstein, Mr. Taylor, Mr. Drath, Board Members, Faculty and Staff, Parents, and the Class of 2023, thank you all for making the past six years of my life possible.

I would also like to thank my grandparents, mother, father, sisters, and a special thank you to Ms. Moore for helping me in the writing of this. Those closest to me must realize someone is missing from that list of thank yous. This person is my brother, Austin, who is the reason why I am even here today on this campus. Without my brother Austin, none of this would have ever been possible. He was always the “smart kid” and when he got into our local middle school, the school – to put it simply – was not challenging enough. So with my parents wanting the best for him, they went searching for private schools in the area, finding Trinity-Pawling, which was close enough to be bussed daily. As time went by, it was clear this was the right fit for him, and three years later it was my turn. My parents asked me if I would like to go to Trinity-Pawling, I’d be lying if I said there wasn’t hesitation, especially considering the all-boy atmosphere, but I came to the conclusion that I too wanted to go. My desire to attend Trinity-Pawling came from each night my brother would come home and share all he had done that day.

Coming into a new school was certainly not an easy adjustment, however, I was fortunate enough to come in with a friend Ethan Nevid. With the new school came a new way of doing things, one of which was sit-down dinners. Many of you have never experienced the wonderful sit-down dinners — disclaimer: they were awful. Nevertheless in my first week as a 7th grader, my brother needed to stay late for a club and I had to eat dinner at school. This might not seem like all that big of a deal for most, but as I walked into the dining hall and looked up and down, up and down the seating list, my name was nowhere to be seen. I stood there in the lobby of the dining hall waiting for my brother to ask what I should do. He finally showed up and said go ask any teacher to sit with them. The little 7th-grade me couldn’t muster up the courage to talk to any teacher, not a single one, so I ran out of the dining hall and called my father saying, “I’m going to need dinner tonight.” He was confused, but picked me up pizza. My next experience with the dining hall was the following night; however, this time would be different — I prepared a plan, which was asking my brother to find a seat for me. Mr. Kellogg welcomed me with open arms and told me I could sit there anytime. It was at this moment that I knew I belonged.

Having had this experience so early in my Trinity-Pawling career gave me the opportunity to do for others what my brother did for me. So when my fellow 7th-grade classmates, Kojo, for example, came to me asking what they should do when they didn’t see their name on the list at dinner, I was able to answer with all the confidence in the world as if I was an expert. I never would have thought that something so simple as asking a teacher for a place to sit would open up my mind to all Trinity-Pawling has to offer. Asking teachers for help in classes I was struggling with, going out of my comfort zone and joining clubs, and playing sports I never had before all became easy. The most important realization was that I was cared about here, that everyone had my back and wanted me to succeed. I did not take this lightly, so I invested more and more time on campus joining more clubs, as I wanted to give the community what it gave me.

The last six years have led me to the conclusion that giving back what I have received from this community is simply not possible, as it has prepared me for the future and left me with relationships that will last a lifetime. The last thing I wish to do is leave all of you with a small piece of advice. Going back to my brother for a brief moment, as the most recent thing he has taught me is relevant to each and every one of us. Many of you never met him since he graduated in 2020 and was unfortunately not able to have a formal graduation like we are lucky enough to have today. Nevertheless, as I said before, he was always the smart one until his freshman year of college. He took it for granted and thought things would be easy — the reality was that things weren’t easy. Austin came out of his first semester with a GPA so low, for his sake, I won’t say. But the point of me sharing this terrible moment for him is not to embarrass him. Rather, I want each and every one of you to learn from his mistakes. Enjoy however much time you have until your next chapter begins, but when that chapter starts give it your all, and hold nothing back. Because when that chapter ends, you’ll be wishing it had been longer. Thank you — Roll Pride!

by Alex Anderson ’23

Watch Alex’s full Address to the Class of 2023 here.

Curry Bradley ’98 speaking to the Class of ’23 at Trinity-Pawling School


“Tonight, I do not stand before you with some profound message or the secrets to life,” began Curry Bradley ’98, Trinity-Pawling’s alumni speaker at the recent Senior-Parent Dinner for the Class of 2023. “I am here as a man who once stood in your shoes, with little cookie crumbs of knowledge that might help you as you begin your journey.”

Before arriving on campus to address the Class of 2023 and their parents that evening, Bradley realized that — besides a brief visit five months ago — the last time he was at Trinity-Pawling was the day he graduated in May 1998. “It’s an incredible feeling to be back, to see the many improvements and transformations, and to witness the investment that people have put into the School that we love so much,” he shared. “It’s an honor and a privilege to speak to the Class of 2023. To be able to share a little bit of my background and pass on the crumbs of knowledge that have helped me along the way.”

Throughout his address to the graduating class, Bradley focused on four important concepts: passion and purpose, success and failure, empathy, and gratitude. He reminded the class to prepare themselves for adversity and the highs and lows of life that will inevitably come. Perhaps most importantly, he encouraged the graduates to say ‘thank you’ — to their parents, teachers, and all who have played a role in their successes thus far.

“Tomorrow’s Commencement is an enormous step in all your lives. Your parents, the faculty, and staff here at T-P have helped prepare you for the next step in your journey. Take a moment between now and graduation to thank them,” he shared with a smile. “My parents dropped me off here 28 years ago, and I had little idea of the tremendous sacrifices they were making as an investment in my future. I had little appreciation for the work and dedication that the team here at T-P puts into each and every one of our lives. So, take time to thank them today.”

Looking back on his time at Trinity-Pawling, Bradley is grateful for the lessons he gained in effort and self-confidence. “The many skills I learned here at the School became the foundation of the person I am today. They helped me succeed in college, during my enlistment in the Army, in building an industry-leading business, and most importantly as a father, husband, and member of the community,” he concluded. “Never lose faith in yourself — T-P taught me that and I’ll be forever grateful.”

In closing his speech, Bradley left the Class of 2023 with a relevant quote from former First Lady Eleanor Roosevelt: “‘The future belongs to those who believe in the beauty of their dreams.’ Enjoy tomorrow, celebrate your accomplishments, and go do great things. Congratulations, Class of 2023!”

by Emma Quigley

Trinity-Pawling School Stepping Up Ceremony 2023


Trinity-Pawling’s beloved Stepping Up Ceremony was held in All Saints’ Chapel last Friday afternoon, May 26, 2023. The Stepping Up tradition traces its roots all the way back to the 1930s. In this service, held just before Commencement, each class steps up to the next level. Underclass academic honors are awarded, leadership roles for the following year are announced, and the service concludes with naming the next group of Prefects who will lead the School forward. We’d like to congratulate all students on a fantastic school year!

At the Stepping Up Ceremony, the 2023-2024 Prefects were announced in style! Congratulations to these rising seniors who were voted Prefects for the 2023-2024 school year. We look forward to their leadership on campus!

  • Brayden Lahey, Head Prefect
  • Ethan Fehrenbaker, Junior Prefect
  • Trey Boula
  • Asa Caramico
  • Harry Clark
  • Aidan Grahn
  • Maddox Rivera
  • Sean Wyman

We also extend congratulations to all of the students who won awards and honors at the 2023 Stepping Up Ceremony. To view the full list of Stepping Up 2023 awards, please visit our website.

Just a few days later, on the evening of Tuesday, May 30, the Trinity-Pawling community gathered in All Saints’ Chapel to celebrate Middle School Stepping Up, a ceremony in which the Middle School students celebrate the past year and step up into their new roles at the School. We extend heartfelt congratulations to all of our 7th and 8th graders for a terrific year!

For the full list of awards presented at Middle School Stepping Up 2023, please visit our website.

Thank you to all students, faculty, and staff for another fantastic year at Trinity-Pawling!

Trinity-Pawling School's Class of ’24 during leadership activities


Once classes and exams are in the rearview mirror and summer vacation is within reach, the junior class at Trinity-Pawling comes together one last time — shifting their collective focus to the school year ahead and the important role that they will play as seniors on campus.

Trinity-Pawling has a rich history of leadership programs for rising seniors, ones that distinguish strong student-leaders at the School and foster meaningful relationships among the class. Formerly known as the Ropes Course, the Rising Senior Leadership Program features a slate of leadership-building activities held over the course of three days on campus. From boat building and engaging group discussions to completing a small ropes course and planning activities for the next school year, members of the Class of 2024 work together to set goals, build character, develop new skills, and perhaps most importantly, make lasting memories.

We recently caught up with Director of College Counseling Slade Mead — the fearless co-leader behind the Rising Senior Leadership Program this year — to learn more about this important part of the Trinity-Pawling experience.

How does the Rising Senior Leadership Program add value to students’ experiences at Trinity-Pawling?

“Three ways. First, it gets the rising seniors to focus on the fact that they are now the leaders of the School and therefore set the tone for the 2023-2024 school year. Second, the program gets everyone out of their usual groups and is a great opportunity for the new seniors to get to know one another better. Third, we have some really fun activities. This week allows the students to go back home for the summer feeling good about school and feeling a true sense of pride. Leaving right after exams can be a bit of a downer, but leaving after huge, class-wide activities allows them to leave on an emotional high!”

What are the primary skills and lessons that students take away from the program?

“There are so many great skills the boys come away with, but the two that I feel are of special quality are inclusion and spit-balling. During the leadership program, every rising senior has an opportunity to be heard. If someone has a good idea for next year, he throws it out on the table. The prefects are the elected leaders, but all members of the Class of 2024 can be true leaders. Spit-balling is related…perhaps someone throws out an idea, which sparks a variation off of that idea, and so on. Before you know it, a new plan or activity is hatched.”

What is your favorite aspect of the program?

“Everyone gets to know one another in a really fun environment. Exams are over…and it is time for the group to play. Here on campus, we are situated on nearly 300 acres of amazing beauty and facilities. Let’s use them and have some fun!”

In your opinion, what makes a great student-leader?

“Someone who does the right thing when no one is watching. I know it’s a cliché, but it is true. Every now and then, someone actually is watching. The younger students emulate the seniors. If EVERY senior puts in the effort to set a positive tone, next year can and will be amazing!”

by Emma Quigley

Stepping Up ceremony at Trinity-Pawling School


Stepping Up is one of Trinity-Pawling School’s most cherished traditions. Held in All Saints’ Chapel the day before graduation, this ceremony brings the school community together to honor the boys: those who have stepped up in the classroom and community, juniors who will be stepping up to positions of leadership in the coming year, and the graduating seniors who are stepping up to join our alumni.

When you give to Trinity-Pawling:

  • The opportunities you create will inspire boys to step up and embrace excellence in their lives.
  • Dedicated mentors will step up and instill character in our next generation of men.
  • Students will pursue their curiosity and step up to be the problem solvers of tomorrow.
  • Young men will follow your philanthropic example and step up as influential, productive leaders for their communities.

Please step up today by making a gift to the Trinity-Pawling Fund, and help instill the School’s values of Excellence, Character, Community, and Curiosity in the leaders of tomorrow.

Give now at:

GIVE BY JUNE 30, 2023!

Trinity-Pawling call for class notes


Alumni, as you reflect on this past year, we hope you will share an update with Trinity-Pawling!

Did you get married, enter retirement, welcome a new baby into the family, switch careers, or win a prestigious award? Did you declare a major, graduate from college with a new degree, or land an internship? Do you have any exciting plans? Let us know!

The deadline for the next Trinity-Pawling Magazine is June 28, 2023 — submit your class notes today.

Questions? Reach Out! Email or contact MJ Davenport at 845-855-4883. We look forward to hearing from you!

Michael Kovner ’58, Jean Doyen de Montaillou and LIZ ALLEN


The Trinity-Pawling community recently gathered for our Spring 2023 Greenwich Reception at the Indian Harbor Yacht Club, graciously hosted by Jean Doyen de Montaillou and Michael Kovner ’58. The venue was beautifully adorned with blue and yellow flowers in honor Trinity-Pawling and provided stunning views of the harbor. Guests enjoyed the views of passing yachts and swooping seabirds.

We were thrilled to have alumni spanning from 1958 to 2022, as well as current parents, all there with us to connect and celebrate the School for which we all share a love. A delectable spread of charcuterie and tasty hors d’oeuvres, including mini lobster rolls, sliders, and coconut-encrusted shrimp, was served — satisfying everyone’s palates.

Ever the consummate host, Mr. Kovner expressed his gratitude to the guests with a short speech. Head of School Bill Taylor provided an update on the state of the School, keeping everyone informed and engaged.
As the evening progressed, guests were treated to a breathtaking sunset over the harbor. During this time, an evening colors ceremony took place, which involved a single stroke of the ship’s bell, followed by a cannon signaling sunset and the lowering of the American flag.

Overall, the Greenwich Reception was a memorable event, combining beautiful scenery, delicious food, and meaningful speeches — and creating a wonderful atmosphere for Trinity-Pawling School alumni, parents, and friends. View the reception photos here.

by Tom Javery

Upcoming Events


Trinity-Pawling School has an exciting lineup of upcoming events that promise to captivate and inspire. Whether you’re an alumnus, parent, or member of the wider community, mark your calendars and get ready to experience the events that Trinity-Pawling has to offer. Stay tuned for more details!

September 22-23, 2023
Homecoming and Reunion Weekend
Trinity-Pawling School
Register here today!

October 28, 2023
Admissions Open House
9:00 AM
Trinity-Pawling School

December 4, 2023
Boston Holiday Reception
6:00-8:00 PM
Harvard Club of Boston
374 Commonwealth Avenue, Boston, MA
Hosted by Peggy and Phil Haughey ’53

December 10, 2023
Candlelight Service for Parents & Community
5:00 PM
Service held in All Saints’ Chapel followed by Reception at Gamage House
Hosted by Head of School Bill Taylor and Jennifer Taylor

December 11, 2023
New York City Holiday Reception
6:30-8:30 PM
Union Club of New York City
101 East 69th Street, New York, NY
Hosted by Jean Doyen de Montaillou and Michael Kovner ’58

March 19, 2024
Palm Beach Florida Reception and Golf Outing
5:30-7:30 PM
Reception: Palm Beach, FL
10:45 AM
Golf Outing: Old Palm Golf Club
Hosted by Dick Bauer ’70

April 11, 2024
New York City Spring Reception
6:30-8:30 PM
New York, NY
Hosted by Polly and Mike Brandmeyer P’25

Visit our website for a complete list of the year’s events, and keep an eye out for additional event information in your mailbox and email inbox. If you haven’t done so already, please ensure we have your current contact information on file.

Questions? Please contact Jenna Jonke in the Office of Advancement at or call 845-855-4886.