Trinity-Pawling School Headmaster Bill Taylor


In his I Have a Dream speech, The Rev. Dr. Martin Luther King, Jr. began his unforgettable address with an indictment against America for its history of racial injustice and segregation that had spanned the 100 years between the Emancipation Proclamation and the year in which he gave this address at the Lincoln Memorial in Washington, D.C.

“In a sense we’ve come to our nation’s capital to cash a check. When the architects of our republic wrote the magnificent words of The Constitution and The Declaration of Independence, they were signing a promissory note to which every American was to fall heir. This note was a promise that all men, yes, Black men as well as white men, would be guaranteed the unalienable rights of life, liberty, and the pursuit of happiness. It is obvious today that America has defaulted on this promissory note insofar as her citizens of color are concerned. Instead of honoring this sacred obligation, America has given the Negro people a bad check; a check which has come back marked “insufficient funds.” But we refuse to believe that the bank of justice is bankrupt. We refuse to believe that there are insufficient funds in the great vaults of opportunity of this nation. So we have come to cash this check — a check that will give us upon demand the riches of freedom and the security of justice.”

King’s words, his challenge to America to live up to the objectives of its ideals, reflect a progressive call to action that has historically kept this nation moving forward towards its promise of being “a more perfect union” for all. This type of challenge is a distinctive aspect of the American Experience that has kept this nation advancing forward in generative ways since before its actual founding as a nation.

When thinking about the importance of Black History Month, its tremendous value lies in the fact that this month affords all of us the opportunity to reflect on and, for many to learn about, the critical contributions of Black Americans to the life of this nation. Through this process, we also are challenged to reflect on and bear witness to the fact that these voices and contributions were too often omitted from the larger narrative of American history. During the month of February, and indeed through the other eleven months, we stand to benefit from this type of reflection, learning, and witnessing if we are truly going to live out the true meaning of our ideals so that freedom may ring and our nation may forge a more perfect union.

by William W. Taylor

Trinity-Pawling Faculty Jim McDougal with Scott Draughon '06


As a history teacher, cross country coach, father, and mentor, Jim McDougal has guided an entire generation of students through Trinity-Pawling. Arriving in the fall of 1994, McDougal has explored a passion for civil rights and racial justice during his tenure; many students see his Race in Sports course as a landmark history elective. With dry humor and empathy, McDougal’s rich knowledge of American History has helped shape the Trinity-Pawling experience for countless students as they grow from learning boys to intellectually prepared young men.

McDougal explained how the idea for his Race in Sports class originated: “When Headmaster Taylor began teaching the American Experience course, I had just begun to show some 30 for 30 documentaries around Martin Luther King, Jr. Day. Some African American students came up to me afterward and wanted to talk more about ‘The U.’ We started to meet on Thursday evenings for an hour, stopping to discuss the racial images in the film. The students said, ‘Mr. McDougal, you need to make a class out of this.’ So, I began to use sports videos to have in-depth discussions about race, using sports as a way to get in.”

McDougal strives to keep these conversations going both in and out of his classroom. “The real question is, how do we contemplate the history of our country and what this means? Do we want to read the ‘I Have a Dream’ speech or do we take the challenge to really examine economic and social inequities?” he pondered. “To what extent we choose to think is up to the individual,” he said.

Since the nineties, McDougal has been supporting minority student groups on campus. “Most of what I do is try to help kids figure out Trinity-Pawling. With students from the city, this means how to live in Pawling — how to deal with higher expectations. How do you manage the complexity of code-switching? I’m just helping these students prepare for the world,” he said.

Recently, McDougal and students in his Race in Sports class welcomed Scott Draughon ’06 to campus for a discussion on social justice. Draughon is a police officer with the NYPD and spoke with the boys about his decision to join law enforcement, how he and his fellow officers make a difference, and the many challenges he faces as a police officer. Draughon emphasized the importance of communication and respect and challenged the students to get out of their comfort zones and embrace every opportunity to learn from people who have different interests and backgrounds.

Thank you, Officer Draughon, for sharing your experiences and insights with us, and for your bravery and service in the NYPD — and thank you, Jim, for your commitment to creating a supportive and engaging environment where boys can develop into confident young men.

by Cyrus Rothwell-Ferraris

Miles Mufuka Martin ’16


As a collegiate track athlete and entrepreneur, Miles Mufuka Martin ’16 knows one thing for certain: relay teams are faster than individuals. Martin was a standout member of the Pride’s track and field team during his time at Trinity-Pawling, and continued his running career in college at Sewanee: The University of the South. It was his extensive experience running the 4×100-meter relay that sparked the idea for Relai, his start-up supply chain logistics company that is set to launch later this year.

“Why do we have to wait so long for online, non-food orders? How can we get our items delivered faster? These were the driving questions behind our idea for Relai,” Martin began. “When starting our research, my co-founders and I jumped down a supply chain rabbit hole and learned so much about the shipping and distribution industry.” Martin and the Relai team discovered that there are no digital outlets for consumers to buy products that are already in a nearby store. Even a brick-and-mortar store that takes online orders reserves warehouse space elsewhere for their online products. “There are a tremendous number of products already accessible in local stores — we want to tap into those resources. Relai allows a consumer to support a local business, reduce waste, and still receive their order in a timely manner,” Martin explained.

Here’s how Relai works: the company aims to deliver packages in less than an hour from stores located no more than seven miles away from the consumer who places the order. It does this by utilizing “sprinters” to relay packages directly from storefronts to homes by bicycle, scooter, or on foot. The delivery can also be broken up into segments, in which the first sprinter hands off the package to another sprinter at a strategically-located exchange zone. Then the second sprinter completes the delivery.

Relai is set to launch in Richmond, Virginia, later this year. After concluding a successful round of beta testing this past January, Martin and his co-founders are excited to be nearing the finish line. Now, the team is primarily focused on fundraising to complete the build and ensure a successful launch.

As Martin looks back on his years at Trinity-Pawling, the entrepreneur most appreciates the supportive environment and can-do spirit of the campus community. “There are so many resources at Trinity-Pawling for a student to do and try anything,” he reflected. “I am grateful for my parents teaching me early on how to advocate for myself, so I knew how to maximize all of the opportunities available to me on campus. I’m also thankful for my teachers and mentors who supported me during my time at the School, and helped to build my self-confidence.”

Martin’s best piece of advice for current Trinity-Pawling students? “Communicate fearlessly! Don’t be afraid to ask for what you want and need. Be sure to master your email etiquette and you’ll find that everyone, even the CEO, is accessible.”

And speaking of accessible: “My co-founders and I would welcome the chance to share the value of Relai with anyone who wants to learn more. Reach out to us on our website or social media channels, or if you’re in Richmond, stop by! We’d love to hear from you.”

The Trinity-Pawling community wishes Miles and the Relai team continued success!

by Emma Christiantelli



“To whom much is given, much will be expected.” (Luke 12:48)

This powerful verse is inscribed above the fireplace in Scully Dining Hall and carries significant meaning for Trinity-Pawling students and alumni alike. Last December, it was Nick Caruso ’24 who personified this verse and reminded the School community why it is so important to give back.

At the conclusion of Wintersession 2021, a cake auction was held on campus to raise money for brain cancer research. “I immediately thought of my Trinity-Pawling brother, Matt Dooley, who was battling brain cancer at the time and sadly passed away at the beginning of this year,” Caruso shared. “I knew there were also lots of kids having to spend Christmas in the hospital instead of in the comfort of their own homes.” Inspired to give back and make a difference for those affected by brain cancer, Caruso was the highest bidder at the cake auction and made a generous donation to the cause. His act of compassion and generosity stemmed from a place of gratitude.

“I am extremely blessed to have the privilege to attend Trinity-Pawling. A lot of people don’t have the opportunity to attend a private institution and I believe it’s important to acknowledge this and give back to the community in any way we can,” he shared. “God has been very good to me and I’m very thankful for my many blessings.”

Caruso enjoys the subject of history and plays baseball, snowboards, and is a skilled mountain biker for the Pride. He is also a guitarist in the Trinity-Pawling Jazz Band and serves as an acolyte in All Saints’ Chapel.

We extend a heartfelt thank you to Nick for his kindness, commitment, and for continuing to set a positive example of giving back in the Trinity-Pawling community and beyond.

by Emma Christiantelli

Trinity-Pawling alumni Peter Geagan '88 and Joe Webber '18


It’s no secret that the Trinity-Pawling brotherhood reaches far and wide. The bonds formed between alumni, faculty, families, and friends are strong, and the shared experiences are cherished. Peter Geagan ’88 and Joe Webber ’18 — both former Head Prefects at the School — are no exception.

After graduating from Trinity-Pawling, Peter attended Bowdoin College, where he met Mike Webber P’17,’18, Joe’s father. Peter and Mike remained close after college and their families stayed connected through various class reunions and family gatherings over the years. When Peter and his family moved to Park City, Utah, Mike and his sons, Joe and Larry ’17, would occasionally travel out west to visit and ski the local areas. More recently, Peter and his family moved to Hailey, Idaho.

Joe is currently a senior at the University of Vermont studying Community and International Development and serving as a leader in the school’s Backcountry Skiing and Avalanche Awareness Program (BSAAP). This winter, Joe and eight of his teammates drove cross-country to Hailey, Idaho for a 10-day backcountry ski trip. In true Trinity-Pawling fashion, Peter welcomed the group graciously and looked forward to joining them on the slopes.

Peter led the group through Sun Valley, exploring the well and lesser-traveled peaks and hotspots, navigating the tough terrain, and even discovering natural hot springs along the way. It was on this ski trip that Peter and Joe also discovered that they had both served as Head Prefects at Trinity-Pawling, exactly 30 years apart. At that point, a new and stronger bond began, as two former members of the prefect lineage.

“Going to Hailey, ID with Pete and his family is an experience I am deeply grateful for,” concluded Joe. “Despite being on the other side of the country, I felt close to home as Pete and I shared our most cherished memories from our time at Trinity-Pawling — remembering and appreciating the things we took away. Good character, hard work, and a commitment to lifelong learning. Roll Pride! The legacy lives on!”

by Emma Christiantelli

Trinity-Pawling School Varsity Hockey


Through snow and ice, the boys have played hard this winter season, competing with both team and individual success across the NEPSAC and the challenging Founder’s League.

WRESTLING: PG Devon Diaco ’22 won the Brunswick Tournament and is currently 15-2 overall and ranked Number 1 in New England at 126 lbs. He placed second in the Western New England Tournament. Kyle Lee ’22 is 15-3 overall and is ranked third overall in New England, and took second in Western New England at 170 lbs. Robbie Accomando ’22 is 10-2 on the year and is currently ranked second overall in New England at 160 lbs. Congratulations to PG Joey Patierno ’22 for winning the heavyweight division in the Western New England Tournament this past weekend! Patierno is currently 11-2 and ranked 5th in New England. Other wrestlers doing well this year are Michael Pelliterri ’22, who since dropping to 152 lbs is 15-6 and took 3rd at Brunswick Tournament and at Western New England’s. Axel Caramico ’26 went 5-1 in the month of January, and Joey Tumolo ’24 also had a great month, going 9-7 and placing third at the Western New England Tournament. The wrestlers will compete at the New England tournament this weekend and the top six finishers will qualify for the national tournament.

VARSITY BASKETBALL: The Pride has improved to 8-4 in Class A competition, with big wins at Choate School and against the visiting Berkshire Bears. The team is fighting for a playoff spot with games remaining against Salisbury, Suffield, and Kent School. Captains Deandre Williams ’23 and Nzube Mekkam ’22 lead the Pride in scoring, while PGs Suhayb Choaibi, Austin Williams, and Sean Conroy provide strong minutes for the Pride each game. Starting center Mikkel Cintron ’22 has been an excellent all-around contributor, bolstered by strong minutes from big men Amadin Colete-Ighele ’23 and Vincent Chaudhri ’25.

VARSITY HOCKEY: The Pride varsity hockey team has had a season of both ups and downs. A combination of new players to prep hockey and some young talent has allowed for a fun and exciting season. Experience upfront from co-captains Ryan Walker ’22 and Tyler Fogu ’22 has held steady all season. Other contributors including Gavin Bloder ’22 and PG Tobias Iantorno have helped round out the top six forward group. A talented group of juniors and sophomores have followed suit and contributed to the Pride scoring, including Jackson Graber ’23, Lucas Buchanan ’23, Owen Robitaille ’23, Caleb Owens ’23, and Hunter Dickey ’24. The back end saw an entirely new defensive core this season that the Pride will look to return for 2022-2023. PG Michael Santonelli provided steady experience and leadership at the blue line position. A solid group of juniors: Anthony Kahl ’23, Nikita Bykov ’23, Raphael Denis ’23, Ryan Drust ’23, Ethan Flintoff ’23, and Michael Fremgen ’23 will be leaders going into next year. Senior Dario Cantini ’22, juniors Garrett Simpson ’23 and Ethan Fenhrenbaker ’23, and freshman Gavin Geraghty ’25 all saw time in the crease for the Pride this season. The team has had big wins against Kent and Frederick Gunn School this winter, and the Pride’s record stands at 6-12-1.

VARSITY SQUASH: Shun Shiraishi ’23 has improved immensely and jumped two spots in the order. With an impressive win against Millbrook at the start of the season, he has pushed to improve all season. Francisco Bendezu ’22 has also improved immensely, with the highlight of pushing his Avon opponent to 5 games. This past weekend, the Pride won all their official matches against Williston at the New England Tournament at Dexter Southfield.

JV BASKETBALL: Utilizing a defense-first mentality and consistently strong effort, the Trinity-Pawling JV basketball team has a 7-3 record. Twice the Pride has used big second halves to earn important wins against Canterbury and Hotchkiss. The team relies on the scoring of Matt Yamin ’22, Jace Emerson ’25, and Gianni Fidanza ’25. Garrett Backus ’23 has been a steady presence and supplies leadership and defensive intensity, while freshman Ryan Bellamy has shown great improvement throughout the season.

JV HOCKEY: Seniors Joe Porto ’22 at center and Michael Blaymires ’22 on defense have led the JV hockey team to a 6-3-1 record this winter. They are backed by the excellent stopping power of PJ Angotti ’24 and Marcell Saviano ’24 in net, who have combined for a .921 save percentage!

Stay tuned for playoff news from our top winter athletes as the postseason nears.

by Cyrus Rothwell-Ferraris and Chris Gillman ’05

Trinity-Pawling School HomecomingReunionWeekend


We have been talking to many of you who are celebrating your 25th and 50th reunions, as well as many other alumni, and this is what we’ve heard:  You want an OCTOBER REUNION! You want the excitement of the Homecoming football game, the beautiful fall foliage, and to reconnect with your beloved teachers and coaches. We hear your excitement about the first TRIPLE REUNION ever held at Trinity-Pawling, and the possibility of connecting with your class and a multitude of other reunion classes. Therefore, to best accommodate the expected hearty enthusiasm for our first in-person reunion in three years, we have moved the date from June to October.

Mark your calendars for A Reunion To Remember!

September 30 – October 1, 2022

Celebrating 0s, 1s, 2s, 5s, 6s, and 7s

The Trinity-Pawling Homecoming and Reunion planning committee is currently making plans for this grand celebration. More information will be forthcoming and posted on the website and registration will open this Spring. Get ready to gather on the quad, renew acquaintances, make new friends, and have a ton of fun!

Here’s how you can help:

  • Share this message with your classmates!
  • Get involved — reunion is a perfect time to volunteer to help create a meaningful milestone celebration for your class. Whether you have lots of time to give or just a little, contact Associate Director of Alumni and Parent Relations John Newman to learn about the many ways you can help shape this special time.

Homecoming and Reunion Weekend is one of our most honored traditions and ways to celebrate our cherished alumni — it means a great deal to the entire Trinity-Pawling community. We look forward to the long-overdue reconnection!


All events are subject to change if forced by the response to COVID-19.

Trinity-Pawling campus with students


Our campus’s natural and architectural beauty provides a solid bedrock on which our boys build their futures. Every day the young men at Trinity-Pawling find inspiration in this gift you have given them, honoring the contributions of the past and leading the way to a better tomorrow.

This campus is custom-built for active learning, from state-of-the-art classrooms to tranquil outdoor learning spaces. Here boys can immerse themselves in missions of true meaning, living their learning daily.

Your support ensures that Trinity-Pawling will continue to be the next-generation school for boys. Make a gift today by calling 845-855-4830, online at, or via Venmo @TrinityPawlingSchool.

Upcoming Events at Trinity-Pawling School


This year marks the beginning of a new Strategic Vision for Trinity-Pawling. Throughout the coming months we will be gathering once again to reconnect and share Trinity-Pawling’s plans and goals for the future. We hope you’ll join us!


Tune in for an introduction to the new Trinity-Pawling Mission and Core Values, and a presentation of our 2021-2022 Strategic Vision — featuring Headmaster Bill Taylor and Board President Erik Olstein ’86, P’11,’14,’17.  We look forward to connecting with you on Zoom!


We look forward to gathering together once again!


Get ready to join old friends and new, as we celebrate Trinity-Pawling!

More details will be forthcoming in your mail and inboxes, so make sure we have your current information on file. Questions? Contact  John Newman, Associate Director of Alumni and Parent Relations, at or call 845-855-4831.


All events are subject to change if forced by the response to COVID-19.