It is with deep gratitude that we recognize the following donors who have participated in this year’s Trinity-Pawling Fund to date. The success of the Trinity-Pawling Fund is made possible through the extraordinary generosity of leadership gifts, as well as strong participation throughout the School community.

Your investment enables Trinity-Pawling to provide outstanding students with an excellent educational experience marked by dedicated faculty, vigorous academics, need-based financial assistance, and exceptional opportunities in the arts, athletics, and many other extracurricular areas.

This Honor Roll of Giving list reflects donors who have made gifts or pledges to the Trinity-Pawling Fund in the 2016-2017 fiscal year (between July 1, 2016 and June 30, 2017). Click here to view the list of donors.




Trinity-Pawling Fund Honor Roll of Giving


Budding filmmaker, Hunter Olstein ’17 has been putting his passion and skills to the test through several academic opportunities at Trinity-Pawling. Last year, Olstein’s Winter Project (one of the components of the Practicum for Civic Leadership) focused on making a basketball tutorial video in Chinese. This year he is working on creating a video tour of the school narrated in Chinese.

The capstone component of the Practicum for Civic Leadership is the Senior Independent Project in which seniors are linked with an alumnus, parent, or friend of the School who has expertise in a similar interest. Olstein’s Independent Project was a 3-minute short film that he created. “My Project mentors Paul Rachman ’78, Gedney Webb ’86, and Roland Betts (producer of Gandhi and The Killing Fields) gave me a great amount of insight about working in the film industry,” Olstein remarks. “After having a few conversations with them I wrote out my script, planned the shoot, and filmed for about two days.” While meeting his academic requirements, Olstein had the opportunity to learn about filmmaking, and took this advantage to hone his craft.

Olstein also had a rare opportunity to become involved with the production of a feature film last March. The Netflix original film, “Coin Heist”, shot several scenes on Trinity-Pawling’s campus, and Olstein landed a position as a production assistant. “Working on set helped me a lot with networking,” Olstein says. “It was the first time I had to assert myself to contact, organize, and push for a role outside of school. I gained a lot of confidence in placing myself in a situation I was not used to.” Olstein adds, “For me it was one of the greatest experiences of my life. It was my first job, and I was getting a glimpse into the career I am hoping to follow.”

Watch Hunter’s Senior Independent Project, “The Cover Up” here.

Pursuing a passion for making films


Since graduating from Trinity-Pawling in 2007, Alex Dunn has been busy making waves in the business world. He started and sold his own company, Skyscope, and was recently featured in Worcester Business Journal’s “Top 40 Under 40”. He attributes much of his success to the tenacity he learned while at Trinity-Pawling. “When you start your own business you have to be tenacious,” Dunn says. “To do well at Trinity-Pawling you have to work hard and help others. Those two things are more than half of the puzzle for having a successful company.”

In 2012, he founded his first company. “Skyscope was founded on the belief that technology businesses deserve better video marketing. Our founding team had a lot of passion for tech and video and we thought we could help businesses create polished, edgy, and authentic video for marketing. We bootstrapped the company to a team of ten in a little less than two years.” Last year, Dunn and his co-founders were approached by a national public relations firm to buy Skyscope. “It turned out to be an ideal scenario as it was the perfect exit for our first successful venture,” Dunn says.

Dunn reflects on Skyscope’s success, saying “One of my favorite pieces of advice is that ‘you don’t have to be better, you just have to be different’. Skyscope was not the best video production house, but we had unique style, a defined production process, and a wacky team that customers liked to work with.” He continues, “One thing I learned at Trinity-Pawling was how to interact with and get along with a diverse set of people and cultures, something that has greatly helped in business relations.” What’s next for Dunn? Plans are in the works to relocate to New Orleans this month to begin his next venture.


“You don’t have to be better, you just have to be different.”


Leaders, teachers, coaches, and parents all seek opportunities to create positive and productive environments at home, at school, and everywhere in between. Positive and productive communities are built one relationship at a time. Leadership, vision, and common commitments are important, but our daily interactions and relationships continually build our culture.

One of the most important components of building these relationships says Headmaster Bill Taylor, “is the ability to collaborate with others across various different networks. This has been identified as a critical skill required to prepare young people for the opportunities they will have in the future.” Collaboration factors strongly into many new programs being initiated at Trinity-Pawling. Headmaster Taylor’s signature program, the Practicum for Civic Leadership, requires intensive collaboration among students and faculty.

Campus culture is made up of the interactions between community members, how our shared values are communicated and upheld, and the ease with which students and faculty take advantage of the opportunities available to them. “The Trinity-Pawling learning experience is grounded in the affirmation that this is a community of mutual engagement, and important school traditions reinforce this foundation,” says Taylor.

On an inclusive campus, all students, and faculty should feel that they belong, respect others’ right to belong, and have an equal opportunity to thrive and contribute. “Our community gathers regularly in chapel to learn the value of community and what is required of each of us to affirm and support an inclusive community,” Taylor continues. The positive value of diversity in creating a stimulating and vibrant community is well understood and respected at Trinity-Pawling.

Relationships take time – a precious commodity in the busy life of a school community. With little down-time, every interaction matters. One of the long-standing traditions at Trinity-Pawling is the family-style meal – an important affirmation of an inclusive community. “Over a meal, students from different age groups, different dorms, and different backgrounds gather together at table to share fellowship, “ Taylor reflects.

“The students’ advocacy of ‘The Brotherhood’ is also a powerful testament to the notion that this community, in its ideal, supports one another in its whole. Sometimes the reality of communal interactions fall short of the ideal, but the students’ advocacy for ‘their Brotherhood’ focuses attention on the support and care that the students have for one another,” says Taylor.

As an educational institution, Trinity-Pawling is committed to creating an environment where students and faculty members can successfully pursue their academic pursuits. “I believe that learning and growth are communal experiences and that community is enriched by diversity, including the differences of perspective,” says Taylor.

Excellence in learning is achieved when we take advantage of the diversity of opinions and experiences. As the leaders of the community, faculty members have an especially important role to play in creating an inclusive culture. “As the leader of Trinity-Pawling School, I aspire to build a common vision that will enrich the school today and in the future. As such, I seek to be collaborative in my leadership style, and invite input from others through mutuality, dialogue, and respect. This does not mean that there will always be unanimity in opinions. It does mean, however, that I welcome discourse as an opportunity to build common purpose and mutual understanding.” Taylor concludes.

The positive value of diversity


During the summer between junior and senior year and throughout the fall term, each senior at Trinity-Pawling works on an Independent Project. Students are linked with an alumnus or friend of the school in a mentorship capacity, whereby they are given the opportunity to learn about a passion or topic of interest in greater depth. The Independent Project consists of an oral presentation as well as a final presentation to the entire school using an alternative medium such as a chapel talk, newspaper article, video, etc.

Through his Senior Independent Project, Ryan Winn ’17 was able to immerse himself in his passion for videography. Like many of the Trinity-Pawling seniors who spent the fall completing their Independent Projects, Winn had the opportunity to be matched with a mentor who has expertise in his area of interest. Connie Rafferty, who provided inspiration and guidance throughout Winn’s project, is Trinity-Pawling’s Digital Media producer and teaches digital storytelling in the School’s Broadcast Journalism course. Project mentors have been a valuable component of the Senior Independent Projects.

Watch Ryan Winn discuss and work on his Independent Project here.

Original music by Imagine Dragons/On Top of the World.

Ryan Winn’s Lip Dub for Trinity-Pawling School


When Andy Cuello ’08 arrived at Trinity-Pawling in 2005, he immediately embraced the community and found himself involved in many activities. He wrote for the Phoenix, was a lead “prayer guy”, and pitched on the varsity baseball team. “Trinity-Pawling gives boys the chance to broaden their horizons and try new things while meeting all different types of people,” Cuello remarks. “Every single one of your classmates at Trinity-Pawling is a unique and crucial cog in the grand mosaic of your high school experience. That, to me, is the brotherhood of Trinity-Pawling.”

For Cuello, the brotherhood has an even deeper meaning as he was able to share his experience with his younger brother Sam ’10. “It was a blessing to have Sam at the School with me. I was able to watch him grow as my brother, a student, and an athlete for the two years we spent together,” Cuello recalls. “I have fond memories of long bus rides with him, travelling to faraway games in Connecticut and Massachusetts. He and I, still to this day, talk about the spring training trip we took to Disney World.”

After graduating, Cuello enrolled in the Carroll School of Management at Boston College, where he finished with a dual degree in Finance and Marketing. He says, “I loved my time at BC, largely because of the Jesuit message upon which the University was built: ‘Men and women for other’ resonated with me, and reinforced many of the principles that were forged at Trinity-Pawling.” Living by these virtues has implored Cuello to give back to his alma mater. “I am compelled to give to Trinity-Pawling because I would not be the person I am today without it, and donating to the Trinity-Pawling Fund is the least that I can do in order to repay the faculty and administration for helping me grow.”

Grateful for the brotherhood


Regan (Schubel) LaFontaine was recently appointed Trinity-Pawling’s Director of Advancement after serving as Interim Director of Advancement since June 2016. LaFontaine came to Trinity-Pawling in August 2012 and worked closely with her predecessor to help raise nearly $40 million for the School and to increase alumni giving participation from 9% to 28% and parent giving participation from 39% to 56%.

Before arriving at Trinity-Pawling, LaFontaine served as a Senior Development Officer at Amherst College where she was a member of their campaign team that raised $502 million.  Prior to that, LaFontaine was a major gifts officer and assistant director of the annual fund at Wesleyan University and was part of their initial campaign planning which resulted in $482 million in gifts for the University.  She also worked in international travel planning for Road Scholar and drove the Oscar Mayer Wienermobile as a Hotdogger for a year.

LaFontaine graduated from Wesleyan University with a BA in government and certificate in international relations and earned her MALS (Master of Arts in Liberal Studies) from Wesleyan.  She is a graduate of Choate Rosemary Hall.  She and her husband, Nick LaFontaine, live on Trinity-Pawling’s campus.  Nick is a math teacher at Trinity-Pawling, is the School’s head football coach, and oversees the juniors’ Global Collaborative Challenge.

Please join us in congratulating Regan on her excellent work that has led to this opportunity!



At Trinity-Pawling we are transforming the curriculum and giving our students the experiences they need to become:

  • Global citizens – ready to thrive in a complex, ever-changing world.
  • Men of honor – eager to serve our world in ways both large and small

When you support the Trinity-Pawling Fund you help to provide the enduring gift of a Trinity-Pawling education. Make your gift today.

You can direct your gift to the area of Trinity-Pawling that matters most to you. Find your giving options online at or inside the gift envelope included in this magazine.

Thank you for your support.

Provide the enduring gift of a Trinity-Pawling education


“I feel incredibly lucky. Mr. Dann plucked me from an orphanage in Millbrook, New York in 1951 and brought me to Trinity-Pawling. Next thing I knew, I was walking up the front steps of Cluett into a place where everyone wore coats and ties. I was in total awe.”

Since Scott had arrived mid-year, he spent that first year living in the third floor of the headmaster’s house. Prior to the orphanage, Scott had been living in New York City with his grandmother. “I suspect my grandmother must have known Mr. Dann from New York. Quite honestly, I never had the foggiest idea how I came to land at T-P, but Mr. Dann became my legal guardian and the School saved my life.”

Scott made Trinity-Pawling his home for those three years and lived on campus during the summers. “I drove the tractors, cut the grass, did maintenance work inside and out for those summers. I actually loved it.”

Matt Dann was still running both his school in Pawling as well as Trinity School in Manhattan, and Bob Scott served as one of the students who regularly drove the headmaster between the two schools. “Mr. Dann spent the bulk of his time at T-P but still had obligations in New York. We would leave Pawling early in the morning, I would drive him into the city, and we would return home that evening. I suppose I must have missed classes sometimes but I got to know Trinity School quite well.”

Scott reflects on his years in Pawling. “Mr. Tirrell, Mr. Dunbar, Mr. Riddleberger, Mr. Emerson, Mr. Weber, Mr. Darling – these men provided me with a first class education. They also taught me how to comport myself, to keep my mouth under control, to dress properly.”

After graduating in 1954, Scott spent two years at Trinity College and played for two seasons on the Bantams’ back-to-back undefeated football teams. He graduated from the University of Richmond in 1959 and entered the Marine Corps. “I was a pretty good shot so they made me a rifle trainer. I am fortunate that I never had to fire a shot in anger nor see Vietnam.”

Scott spent his career in pharmaceutical sales based in North Carolina and Virginia. He now resides in the Shenandoah Valley where he lives with Tomlin, his wife of 16 years, who worked in financial aid at Mary Baldwin College. Scott’s three children and six grandkids live in the Richmond area. “At eight-oh, I maintain that keeping active is the only way to go. Life’s too short to sit around and do nothing.”

Though Scott wishes he could return to campus more frequently, he has remained a steadfast monthly supporter of the Trinity-Pawling Fund. “I did make it back for my 60th reunion in 2014 and had a marvelous time. A prefect toured me and I couldn’t get over how the School has evolved! I picked up a T-P hat and sweater and they’re now part of my wardrobe. I’m eternally grateful for Trinity-Pawling.”

Advice for current students? “Appreciate what you have.” And for fellow alumni? “Never forget those who labored to make you a better person.”

“The School truly was my home.”


Trinity-Pawling moves into February following a very cold January filled with team wins and individual achievements.

Last Wednesday the varsity wrestling team faced off against Choate in a matchup of the two top teams in the Founders League.  The Blue and Gold got off to an early lead with pins from sophomores Brett Ginac and Jake Conlan.  The Wild Boars fought back with a couple wins at the upper weight classes, but Captain Jeff Thompson ’17 then secured a win over the Choate captain in the most anticipated match of the afternoon. Thompson remains undefeated on the season with a record of 20-0.  Juniors Matt Trainor and Conrad Adams concluded the victory for the Pride with two pins in the lower weight classes to bring home the Founders Championship for the boys.

The varsity wrestling team is 11-4 on the year and will be fighting for the Western New England Championship on February 11th.  Thompson along with sophomores Jake Conlan, Zack Conlan and Dave Bancroft will look to repeat as individual Western Champs from 2016.

Varsity basketball is 10-5 on the season and looking strong going into the final month of the season.  In the past few weeks, T-P dominated Avon 80-53 and took down Taft twice in as many weeks.

Last Saturday the Pride defeated Hotchkiss 55-54 in a game that came down to the last second.  T-P, down by six points in the fourth quarter fought back to take the lead in the final minutes and held off the Bearcats until the final buzzer.  Luis Cartagena ’17 led the way with 20 points as Nikkei Rutty ’18 dominated with 10 rebounds.  Co-Captain Kevin Salis ’17 added 11 points while Korey Lee ’18 came off the bench and chipped in with nine big second half points of his own.

JV basketball is 2-6 led by Will Rickert ’19 and Shane Montague ’18.  Thirds Basketball is 8-0 on the season led by sophomores Max Kesicki and Ryan McBeth.

The varsity squash team is 5-5 on the season with big wins over Kent (5-2) and Westminster (6-1).  According to the coaches, it has been over 10 years since T-P defeated Westminster in squash.  Oosie Imoro ’17 defeated Westminster’s #2 player with ease as he continues his dominance for the Blue and Gold.  On a side note, a few weeks ago, in a team loss to national powerhouse Avon Old Farms, Oosie had a memorable match against a top ranked Rhino that ended in a five-set loss, but resulted in Oosie being put on the map as one of the best high school squash players in New England.

Brothers, Ibrahim Bekhiet ’19 and Abdallah Bekhiet ’18 have been fantastic at the #1 and #3 spots respectively.  Ibrahim has held his own against some of the top players in the nation, while Abdallah has dominated against Founders League teams.

JV squash is 3-5 thus far led by Henry Chong ’17 and William Yau ’18.

Varsity hockey is 3-12 on the year with wins over Kent (6-3), Choate (4-1) and Lawrenceville (7-2).  Against Choate, Chris Connolly ’17 returned from injury to score two goals in his first game back on the ice for the Pride.  Brendan Lantieri ’17 and John Garvey ’19 each added another goal for the Blue and Gold to secure a victory over the Founders League foe.

Justin Lampert ’17 has been solid between the pipes for the Pride, while seniors Jordi Jefferson, Ray Zimmerman, and Zack Mazur have taken over as leaders of the young Pride team.

JV hockey is 3-6 led by Griffin Moore ’19 and Will DePalma ’18.  Thirds hockey is 3-5 led by goalie Sam Arquit ’19 and AJ O’Buck ’19.

Varsity skiing is led by Tommy Poulin ’19 and Jackson Wang ’17.  The team next competes at the BSL David Rockwell GS Championship at the Sundown Ski Area.

Roll Pride!

Roll Pride!


Homecoming and Reunion Weekend

October 6-7, 2017

Mark your calendars now to come back to Trinity-Pawling to celebrate 110 years of educational excellence and brotherhood!

Weekend highlights include:

  • Friday night cocktails at Gamage House
  • Alumni clambake and reunion celebration
  • Athletic Hall of Fame induction
  • Homecoming football game (wear your blue and gold!)
  • Oktoberfest party

And more!

Event details (schedule, hotel, etc.) will be posted on the website later this spring.


Reunion Classes 2017

2012- 5th reunion

2007- It’s your 10th reunion!

2002- 15th reunion

1997- 20th reunion

1992-It’s your 25th reunion!

1987- 30th reunion

1982- 35th reunion

1977- 40th reunion

1972- 45th reunion

1967- It’s your 50th reunion!

1926 to 1966- Honor Guard Reunion


Want to serve as a Reunion Chair or on a committee? Email

Questions? Contact Hannah Keller, Director of Alumni Relations, by email or phone 845-855-4829

Homecoming and Reunion Weekend 2017


Thank you to the 155 alumni, parents, and friends who joined us for our two winter receptions in Boston and New York City. The T-P community proved strong with alumni from class years 1940 to 2012 attending the events. We would like to thank Kathleen and Robert G. Ix ’83 for hosting Trinity-Pawling at the Boston College Club on December 7 and Michael Kovner ’58 and Jean Doyen de Montaillou for hosting us at a private club in New York City on December 14. Thank you for graciously rolling out the blue carpet for the Trinity-Pawling community!

If you would like to view photos from the events, please click here the Boston and New York City albums.

Thank you!