This year Bill Taylor begins his third year as Headmaster of Trinity-Pawling. The transformation that he set in motion upon his arrival in 2015 is seen—and felt—throughout the campus.

Under Taylor’s leadership, the Dann academic building underwent a progressive facelift over the summer. New learning spaces have been specifically designed to allow for maximum creativity and collaboration. The Allen Reading Room is now the epicenter of our Center for Learning Achievement, which includes reading & writing labs, a resource that all students will have the opportunity to utilize. The former “fishbowl” now houses a Mac lab and is being developed with technology intended for students to imagine, explore, experiment, and create.

Trinity-Pawling opens the new 20,000 sq.ft. Smith Field House this fall, and will be the first prep school in the country to incorporate PlaySight technology in their athletic facilities. Playsight is the ultimate technology to make coaching and practicing more efficient at Trinity-Pawling—the addition of this advanced sports video and analytics software will create a connected community of athletes, coaches, and fans. The School strives to be on the leading edge of student performance and athletic development, and our partnership with PlaySight is further proof of that commitment.

Experiential learning is thriving— students and faculty alike are excited to immerse themselves in collaborative and independent projects. The Practicum for Civic Leadership, Trinity-Pawling’s own product-based program, has evolved to be more student-centric. The timing now allows for more concentrated focus, building meaningful mentor relationships, and product development.

The new academic year brings new commitments—to curiosity, conscientiousness, community, communication, and character—which Bill Taylor has pledged, on behalf of the School, to our students and to each other. These focus points are what gives Trinity-Pawling’s culture a distinct depth. They allow students and faculty to be life-long learners, to develop individual self-awareness, and creativity in a community that is supportive and caring. These commitments encourage healthy risk-taking and stepping out of ones comfort zone in order to develop self-reliance. This ethos allows our entire community to communicate openly and build meaningful relationships. And, our attention to detail enables us to recognize and celebrate the gifts and talents in our students and in each other.

As was written in Trinity-Pawling’s founding ideals: “Personal effort and God-given endowment, when properly combined, made personality and only the acquisition of personality could set in motion the beginnings of leadership.”



Josh Frost ’04 first arrived at Trinity-Pawling as an 8th grader in 1999, and went on to graduate in 2004 as a prefect. Josh continued his studies at Hamilton College, where he earned a B.A. in Hispanic Studies followed by a year abroad in Madrid. He then returned to Trinity-Pawling to work as a Spanish teacher from 2010 to 2013.

During summer vacations, Josh and his wife Ashley opened a farm business, where they ran a vegetable market garden and CSA, and also produced maple syrup and eggs. While successfully running the farm in Bedford, NY for seven seasons, they also had two daughters, Madison and Mackenzie.

Josh and his family have returned to Trinity-Pawling this year where he will resume his position as a Spanish teacher. In addition, Josh will be developing a farming program centered on teaching the concept of sustainability through active participation in activities such as campus based food production, composting, recycling, and renewable energy. The Frost family lives in the Barstow dormitory with their two dogs, Niko and Dakoda.



Jacques Zelnik ’11 began working as a Law Clerk at Cantor Fitzgerald this past May. He is in his final year of law school at New York Law, focusing on corporate transactional work. Between his rigorous schoolwork and demanding clerk responsibilities, Zelnik emphasized the importance of organization and time management—both skills he mastered during his years at Trinity-Pawling.

“The Effort System stuck with me,” Zelnik started. “I see it coming through in my work for law school and Cantor—both where I have to give 110% of my life. T-P kept me organized and taught me how to manage my time and maintain a disciplined schedule.” There are days when Zelnik is the first one to arrive at the Cantor offices and the last one to leave. That, he said, comes from his Trinity-Pawling education.

As an employee of Cantor Fitzgerald, Zelnik had the opportunity to attend the financial firm’s annual 9/11 Charity Day last week. He explained that the company was headquartered on floors 101 to 105 of the One World Trade Center when the tower was struck on September 11, 2001. Cantor lost two-thirds of their workforce—658 employees—to the terror attacks that day.

On September 11 of this year, as in past years, Cantor held its annual 9/11 Charity Day, which raises money for the memorial, funded by Cantor. Celebrities, including Robert DeNiro and Michael J. Fox, as well as famous political figures such as Bill Clinton, filled the trading floor. “The profits from the trades made throughout the day are donated to the memorial fund,” Zelnik shared. “Last year, Cantor raised about $15 million. It’s incredible.” Zelnik takes great pride in being a member of Cantor’s team this year as they continue to honor those who were lost and the families affected on that tragic day. He values the opportunity to be a part of such a community-conscious and compassionate organization. Zelnik is hopeful to stay with Cantor Fitzgerald following his graduation from law school next May.


MacGregor Robinson 1964-2017

MacGregor Robinson, 53, died on September 4, Labor Day, at “Mungo Park,” his beloved home in Norfolk, after being diagnosed with cancer of the liver in mid-August. Born February 5, 1964, in nearby Winsted, MacGregor was predeceased by his parents, Hugh Robinson and Isabel “Tibby” (MacGregor) Browne Robinson and his sister, Isabel Browne Driscoll. His survivors include brothers Belmore Browne and James Robinson, sister-in-law Melissa Robinson, niece Ann Robinson and nephews Lars Robinson and Ian Robinson, and legions of loving friends and grateful former students.

First and foremost, MacGregor was, in his own words, “a boarding school guy,” starting as a student at Brooks School in North Andover, Mass. After graduation from Princeton University in 1986 and a stint as a reporter for the Lakeville (Conn.) Journal, MacGregor embarked on a 30-year odyssey throughout the independent school world: as an English teacher, administrator, student advisor and housemaster at Berkshire School in Sheffield, MA, (1989-93, 1996-99), and then as an admissions professional and student advisor at The Gunnery in Washington Green, CT (1993-95), Trinity-Pawling School in Pawling, NY (1999-2015), and King’s Academy in Madaba, Jordan (2015-17). During the 1990’s he also had the honor of working for King Hussein I and Queen Noor of Jordan while tutoring Prince Hashim and working with Prince Hamzah and the Princess’ Raiah and Iman.

In August, MacGregor returned to Trinity-Pawling as its Director of External Relations. Throughout his career, MacGregor, who also held a Master of Art in Teaching from Brown University, traveled far and wide. He was invited into the lives of countless families. He deliberately focused on international admissions, making connections and befriending students and parents the world over. His calling led him to assess and embrace differing cultures while honing the professional art of mentoring with students of varied backgrounds and disparate aspirations. He relished young men and women for who they were and helped them to weave themselves into the fabric of their school community and move on to the global common.

Every summer, MacGregor would return to his native Norfolk and head right for the shores of Doolittle Lake. He was a past president and member of the Board of Managers of the Doolittle Club. Well-read, voraciously curious, and possessed with a biting wit, MacGregor was a man of many passions, ranging from California painters to Tchaikovsky, yellow labs to London, cribbage to Christmas, Volvos to leg of lamb. He was intensely devoted to his niece and nephews, whose journeys through life he eagerly followed. MacGregor and his family wish to express eternal gratitude to his lifelong friends for a great journey, and to the people and professionals at Smilow Cancer Hospital at Yale New Haven and Foothills Visiting Nurse Association for their radical compassion.

A memorial service will be held at All Saints’ Chapel, Trinity-Pawling School on Saturday November 11, 2017 at 11:00 AM. A private burial will be held in June of 2018 in the family plot in the Doolittle Woods.

Donations in MacGregor’s memory may be made to the MacGregor Robinson Endowed Chair for Mentoring at Trinity-Pawling School, in care of Regan LaFontaine, Director of Advancement, Trinity-Pawling School, 700 Route 22, Pawling, NY 12564. See also:



Originally from Budapest, Hungary, Gyuri Dragomir ’13 came to Trinity-Pawling to pursue a two-fold dream: to play hockey and receive an excellent education. Now a college graduate and ambitious entrepreneur, Dragomir looks back on his years at the School grateful for so much more – particularly its lessons in perseverance and, perhaps most importantly, problem-solving.

Dragomir is the CEO and Co-Founder of Deals en Route, LLC, a coupon distribution app built to serve the college town market. The idea for the app came to Dragomir and his co-founder, Ato Bentsi-Enchill, during their sophomore year at Hobart and William Smith College, when they recognized the major gaps in the coupon industry. “You don’t have to have the next best thing to be successful. The key, I think, is identifying a problem and finding a solution. We found several problems in the coupon industry and strategized a smart solution,” Dragomir shared. During his junior year at HWS, Dragomir submitted the app concept to the Idea Lab at Hobart and their idea began evolving into a reality.

Deals en Route has one mission: to become the most convenient, personalized, and user-friendly app in the coupon market. Using geo-fencing, Deals en Route creates specific hot spots at storefronts, based on the users’ likes, dislikes, and preferred price points. Thus, users receive targeted, personalized coupons on-the-spot.

Dragomir and Deals en Route took first place in the 2016 Finger Lakes Regional Business Plan Competition. In August, Deals en Route was submitted to the App Store and ready to beta test with 140 stores in Upstate New York. College towns are their main market—for now.

“I think there is great value in connecting college students with their surrounding areas,” Dragomir said. “Deals en Route makes those connections. It gives users a personalized and positive experience while supporting local businesses. It’s a win-win.”

Dragomir greatly values his experiences at Trinity-Pawling, particularly those that pushed him out of his comfort zone, and continues to use the skills in the way he runs his business. “T-P taught me to take risks. As a first year, I remember not knowing what to expect. I was so scared. But my teachers and coaches pushed me and taught me not to settle—for anything. Everything I learned there has helped me tremendously.”

Interested in getting involved with Deals en Route? Dragomir and Bentsi-Enchill welcome any fresh expertise! Feel free to reach out: Deals en Route is available in the iTunes and Android app stores.



The weeds had been overtaking the greenhouse behind Gamage House, a growing family of mice had been nestling in for the winter among rolls of plastic sheeting used to protect young seedlings, and the homegrown kale had been missed from the Trinity-Pawling dinners. No more! Josh Frost ’04 (previously a faculty member from 2010-2013) has returned to the Trinity-Pawling faculty after a 4 year hiatus, during which time he was managing an organic vegetable farm in Bedford, New York.  Teaching upper levels of Spanish, Frost has also been tasked with reinvigorating the farming program he began in partnership with Maria Reade in 2011.  Reade subsequently moved her base of operations to Vermont, where she splits her time between writing for several publications and running an organic farm.

With the help of twelve of the Pride’s finest—Nico Bonasera,  Hayden Carillo,  Georgie Chen, Tim Colmey, Alex Connors-Mallory, John Critz, Xander DiSanto, Blake Erdmann, Doug McHale, Aiden Pincombe, Kevin Sausville, and Peter Zhang— Frost, and fellow faculty member Anne Pearson, has cleared six outdoor beds in the field north of Gamage House and the interior of the adjacent greenhouse.  An impossibly hardy specimen of kale with a stem diameter of four inches was discovered, marveled over, and then added to the compost pile. Potting trays have been cleaned and seeded with quick-growing varieties of kale, spinach, bok choy, lettuce, and kohlrabi, and are being tended in the Dann Building greenhouse nursery.

The group took their first field trip to assess the open spaces of campus, and to determine which areas might be suitable for cultivation. Josh is working to line up Wednesday field trips to local composting facilities, dairy and crop farms, farm-to-table style restaurants, and renewable energy plants, such as Trinity-Pawling’s solar field. The goal of the program is to teach the students about the concept of sustainability through exposure to and participation in local agriculture, composting, and renewable energy. Membership on the farming team is open to students in place of a sport during the Fall and Spring Terms.



Head Prefect Joe Webber ’18 has an impressive vision for the upcoming school year: to build a more forward-thinking, inclusive, and globally aware Trinity-Pawling community. And that’s just the beginning!

In planning for the 2017-18 school year, Webber, with his fellow prefects and Headmaster Taylor, chose several areas of school life to focus on, including balance, positivity, and connectivity, to name a few. Of all these priorities, for Webber, balance is the key.

“Our focus this year will be balancing positive change and progress with Trinity-Pawling’s traditions, which make this school so unique and authentic,” Webber shared.

When working to make positive changes on campus, it is important to Webber that he and his fellow upperclassmen lead by example. “We want to inspire the underclassmen to challenge themselves and use their voices to make T-P a better place. Instilling a culture that promotes problem-solving, acceptance, and understanding is monumental.”

On the academic front, Webber is eagerly anticipating a year full of project-based learning, as it provides an avenue to engage with material he and his classmates are truly passionate about. For Webber, the balance between textbook information and real-world experience is exciting.

In all other aspects of Trinity-Pawling life, Webber is simply looking forward to making a difference. “I have spent nearly my whole life here and I have one year left to make something of it. That is crazy! My excitement comes from a desire to make T-P a better community and a truly special place to go to school.”

Although very proud to be Head Prefect, Webber emphasized that he couldn’t do anything without the help of his fellow prefects and classmates, and the support of the faculty and staff. “This is a team effort,” Webber started. “We are all in this together. I am one of many. Everyone has a unique contribution to this place, and I am one piece to the puzzle. Let’s have a great year!”

In addition to his Head Prefect duties, Webber can also be found on the varsity soccer and lacrosse fields, squash courts, and Gardiner stage. With a busy year ahead of him, he is looking forward to making his vision a reality.



You are cordially invited to the Dedication of Trinity-Pawling’s

Smith Field House in honor of former Headmasters

Phillips Smith P’79, Headmaster Emeritus

and Archibald A. Smith III


Friday, October 6, 2017

5:30 PM

Reception to follow at the Smith Field House Terrace

RSVP by phone: 845-855-4830 or email:


Special thanks to Marlynn and Bill ’57 Scully for their generosity.


Follow the Smith Field House progress progress here.



Forget reciting the right answers. Instead, learn how to ask thoughtful questions.

At Trinity-Pawling, students gain the skills and self-awareness to navigate a complex and ever-changing world. We believe that critical thinking is key, and we teach our students to think outside the box. We also teach something that can’t be measured—students will learn to respect themselves, their fellow brothers, their surroundings, and their future. Trinity-Pawling students graduate as the next generation’s problem solvers, game changers, and thought leaders.

Join us for our Open House on October 9, 2017.

For more information or to register, visit or call 845-855-4825.




Rekindle old friendships, make new ones, and CELEBRATE Trinity-Pawling!

Highlights of the weekend include:

Friday, October 6​, 2017

10:30 AM      Alumni Golf Game at Quaker Hill Country Club

5:30 PM         Smith Field House Dedication & Reception

7:00 PM        New England Clambake

Saturday, October 7​, 2017​

9:00 AM         Clay Shoot at Orvis Sandanona Shooting Grounds
11:00 AM        Alumni Memorial Service

12:00 PM        Athletic Hall of Fame Induction​ & Alumni Awards

4:00 PM         Homecoming Football Game vs​.​ Taft

Oktoberfest Celebration following the game


CONGRATULATIONS TO THE TRINITY-PAWLING ATHLETIC HALL OF FAME 2017 INDUCTEES—Wally Danforth ’82, Peter Kirchmaier ’41, and the 1967 Lacrosse Team. 

The Induction ceremony will take place Saturday, October 7th.

The Athletic Hall of Fame was established in 1998 to honor former teams, student-athletes, and coaches who have reflected honor upon Trinity-Pawling by virtue of outstanding performance and exemplary contributions to their alma mater, community, and profession, and in doing so, reflect the philosophy of a college preparatory education and the ideals of sportsmanship.

For a full schedule of events and to register, visit or contact Janet Hubbard at 845-855-4830.




MacGregor was a collector. He collected paintings, interesting art pieces from his worldly travels and gifts from his students. MacGregor also collected friends. Many Trinity-Pawling students (and a great number of parents) found refuge with MacGregor either in his Cluett 4 apartment which looked like a suite at Blenheim Palace, in his tidy admissions office with oil paintings adorning the wall or at his table at McKinney and Doyle. MacGregor always had time for the boys.

MacGregor loved to network. He arranged for two of his nephews to work at Trinity-Pawling (Rowan Driscoll and Ian Robinson) as well as orchestrated others to come to Pawling either as a student, teacher or trustee. He was a master at making personal connections. MacGregor always had time for the boys.

MacGregor often cancelled limo pick ups and would race down in his beloved Saab and then Volvo to Kennedy or Newark and meet a new international student outside customs making that frightened new student feel welcome, wanted and important. MacGregor would take in students from far away places over Winter and Spring holidays or long weekends giving them a local home away from home. MacGregor always had time for the boys.

Although MacGregor was of the older generation, he was that rare adult who embraced the modern world of social media. He loved reaching out to former students on Facebook catching up on news, planning to see them during his annual trip around the world or checking in if he felt one of his boys needed help. When MacGregor felt someone needed help, he rallied the troops and would send in the proverbial cavalry. He enjoyed helping people. MacGregor always had time for the boys.

MacGregor was the master of the pen. His college recommendation letters were legendary where college admissions counselors would hold his letters up as shining examples of how to write a letter. MacGregor used words like a painter uses colors. One regret he expressed during his last weeks is that he never wrote the books he had written in his mind. Those beautiful words sadly died with him and the world is a sadder place not to have read them.

MacGregor will be missed.

by Slade Mead

MacGregor always had time for the boys.


Trinity-Pawling is inspired in its approach to education.

Students are engaged in hands-on learning projects, evaluated not only for scores but effort, and encouraged to participate in all aspects of campus life, from athletics to the arts.

This progressive model is unique and its results—profound.

Trinity-Pawling is truly AHEAD OF THE CURVE—educating young men for life.

Your gift to the Trinity-Pawling Fund provides the engine—the necessary materials, environment, and resources—that drives this exceptional experience.

Thank you for your support.

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