“Teachers and scholars of the oldest school in continuous existence in North America, good morning and welcome back,” began Head of School Sam Schaffer in Rousmaniere Hall on Wednesday, August 26. “What a great place to be, here in this splendid Hall, surrounded by our friends and classmates, teachers, coaches, and advisors, in this sanctum sanctorum, gathered with one another as we begin our ancient Latin school’s 382nd year.”

Together, along with new and returning faculty and staff, were 303 boys—all ready to kick off the year together. Dr. Schaffer went on to recognize the boys in Classes I and VI, those oldest and youngest in the school, as they stood to applause and recognition from the community. He also honored members of the faculty and staff celebrating significant anniversaries at the school, and welcomed new members of the faculty and staff, joining us this year. Among robust renditions of America the Beautiful, Commemoration Hymn, and The Founder’s Song, Class I President James Skeffington read excerpts from a sermon delivered by General Joseph Warren, RL Class of 1755, at Boston’s Old South Meeting House on March 6, 1775. 

Dr. Schaffer continued by offering gratitude for the work of various individuals over the summer, who carefully maintained and prepared the school for the arrival of a new academic year. He then moved on to his opening address, celebrating the generalist.

“I will note that sometimes the term ‘generalist’ gets a bad rap,” he said. “Some people associate it with shallowness or dabbling… But that’s not what we mean here. We also don’t mean someone who does everything. Being a generalist isn’t about counting. There isn’t a number of things that you do that makes you a generalist—not three or five or eight or ten. It’s not about the numbers, or checking off a box, or filling up a resume. It’s about trying more than one thing. It’s about engaging meaningfully. It’s about having depth as well as breadth.  

“Ultimately, being a generalist at Roxbury Latin is about the approach. It’s about a willingness to try something new, to take a risk. It’s about curiosity. It’s about cultivating habits of mind and body and spirit. A generalist at Roxbury Latin doesn’t necessarily do everything. He learns from everything. He seeks to make connections. He draws on multiple experiences. He appreciates multiple perspectives. He embraces the approach of a generalist.

“So that’s what a generalist is, but what about the value of being a generalist? Why do we think it is so important? Why is it so central to Roxbury Latin? There are many reasons, and we believe them as much as we believe in honesty in all dealings, as we believe that the kind of person you are matters most, as we believe in the life of the mind.

Dr. Schaffer went on to underscore the value of being a generalist—that it teaches you empathy, makes you a better learner, and can help you find a passion or talent that you didn’t know about. 

“We believe that being a generalist makes you a better person,” he continued. “You learn to take risks. You learn to interact with new people. You learn how to stretch yourself. You learn how to be uncomfortable. You learn humility. You learn to fail and to succeed. Sometimes it is great to be the best player on a team. And it is equally great to be the worst player on that team. You can be a leader in either situation. All of this will make you a better adult, too. A better parent, or spouse, or employee, or leader. In all of those situations, you will have to display the skills and inclinations of a learner. You will have to see experiences from a different lens. You will have to grapple with failure and novelty. You will have to take risks. You will have to understand different perspectives. And if you have experience as a generalist, you will be better at it.”

After the final remarks, students, faculty, and staff then gathered in the main courtyard, around the Senior Grass, relishing the sunshine and cooling air of late-August, to welcome new members to the community and wish one another a wonderful school year.

Watch the morning’s Opening of School Hall, and hear Dr. Schaffer’s complete remarks.

View a gallery of photos from Opening Day.

On July 22, Head of School Sam Schaffer announced that Alessandro Ferzoco, Class of 2014, will serve as Roxbury Latin’s next Director of Development. Throughout a search process resulting in several excellent finalists, it became clear to all members of the search committee that Alessandro was the right individual to lead Roxbury Latin’s philanthropic and constituent engagement efforts, now and into the future.

For the past three years, Alessandro has served as RL’s Director of the Annual Fund, leading the school’s annual giving strategy and overseeing fundraising efforts supporting those goals. Under Alessandro’s leadership this past fiscal year, RL’s Annual Fund surpassed $5 million for the first time in the school’s history. He has led this remarkable fundraising effort while also maintaining more than 50% alumni participation, 99% parent participation, 100% faculty participation, and coordinating and supporting 40+ parent volunteers and 200+ alumni fundraising agents.

In addition to successfully leading RL’s Annual Fund, he has directed three successive Giving Day campaigns (raising nearly $1.2 million in 2026), secured major gifts, stewarded capital contributions, and been increasingly involved in leadership-level cultivation, stewardship, and solicitation efforts involving some of the school’s most loyal supporters. He has proven successful in mobilizing volunteers, cultivating relationships, and articulating a compelling vision for philanthropy that is grounded in Roxbury Latin’s history, mission, educational philosophy, and strategic priorities.

Unsurprising to anyone who knows him, Alessandro’s connection to Roxbury Latin’s fundraising efforts began long before his professional return to the school. As a student, he was the recipient of an endowed scholarship fund. As a Class I boy, he was selected as the student speaker for the annual Kick-Off Dinner, and as an undergraduate at Harvard he began serving as a Class Agent, spearheading his class’s reunion and Annual Fund efforts.

“These experiences showed me, firsthand, the ways that intentional stewardship can create truly consequential support between institutions, donors, and students,” says Alessandro.The greatest strength Alessandro brings to this role, however, is his ability to build and sustain trusted relationships across the RL community. He also possesses a deep institutional understanding of the school itself: its traditions, its culture, its language, and the people who have shaped it across generations.

In his own words: “I have had the privilege of learning from and working alongside many of the figures who have defined Roxbury Latin over the last fifty years. Those relationships have given me an appreciation not only for the school’s legacy, but also for the responsibility of stewarding its future. I am grateful to have benefitted from the mentorship and example of the previous leaders of Roxbury Latin’s Development Office: Tom Guden, Tobey O’Brien, and Phil Thornton. Our work is always a team effort. Successful institutional leadership depends upon trust, collegiality, and a shared commitment to the school’s mission: to instill in students a desire to live intentional lives of purpose, through a commitment to ethical formation and rigorous academic training. This role is an opportunity not only to sustain and strengthen Roxbury Latin’s culture of giving, but also to help shape the school’s strategic direction during an important moment in its history. Roxbury Latin has endured for nearly four centuries because generations of alumni, parents, faculty, trustees, and friends understood that excellent institutions do not sustain themselves. They survive only when people choose to sacrifice for them, steward them carefully, and hand them forward stronger than they inherited them. I am so grateful to be taking on this important role for a school that I love.”

As Director of Development, Alessandro will build upon Roxbury Latin’s many strengths to galvanize others in support of its mission, ensure its immediate success, and secure its position for future generations.

Thank you for helping us achieve an extraordinary year in fundraising for Roxbury Latin. Through your contributions to the Annual Fund and through your capital gifts, you allow us to realize Roxbury Latin’s distinctive mission: to democratically assemble the most capable, bright, aspiring group of boys, regardless of their families’ means; and to bring together and support the most talented, dedicated faculty to know and love those boys. We are so grateful for your support.

Your steadfast commitment to RL has allowed us to achieve a major milestone in annual fundraising, and to—once again—set an Annual Fund record, raising more than $5,100,000 for this school. This marks the first time that Roxbury Latin’s Annual Fund has surpassed $5 million—an astonishing feat. While RL boys and faculty are the living markers of your gifts, the statistics below show the impact and extent of your generosity in annual and capital giving, and provide yet another way that Roxbury Latin is distinctive. Rest assured that we pass along this commitment to our current students, who know that “from those to whom much has been given, much will be expected.” For your generosity and what it makes possible, thank you.

Each summer, RL boys have the opportunity to participate in a variety of study abroad experiences and immersion trips that deepen their understanding of history, language, and culture. Over the years, students have traveled to locations across the globe, including France, Spain, Costa Rica, and Senegal. This summer, 17 Class II boysGreece, accompanied by Mrs. Morris-Kliment, Mr. Beam, and Mr. Phillips, while a group of twelve boys studying French traveled to Caen to begin their month-long immersion program, accompanied by Monsieur Diop and Madame Kostur.

The Greek students embarked on an immersive journey packed with cultural and historical highlights. Their itinerary began with a visit to Cape Sounion and a swim in the Saronic Gulf, followed by a sunset hike to the Temple of Poseidon. In Athens, they explored the Roman and Ancient Athenian Agora, the Acropolis, and the Acropolis Museum. The group strolled through Syntagma Square, climbed Mt. Lycabettus, and visited sites like the Temple of Olympian Zeus and the Panathenaic Stadium. Beyond Athens, the students traveled across Greece, stopping at the National Archaeological Museum, Eleusis, the Corinthian Canal, Ancient Corinth, Nemea, and the Venetian seaport of Nafplio. They toured the ancient ruins of Mycenae, swam at Karathona Beach, and experienced the ancient sites of Epidaurus and Olympia—home to one of the original four Panhellenic Games. The journey also included time in Delphi, where students explored the Athenian Treasury, the Temple of Apollo, and the ancient stadium, connecting deeply with the myth and history they had studied. Each day was filled with opportunities to sample Greek cuisine, hike through breathtaking landscapes, and reflect on the significance of the ancient world in modern times. These trips not only offer delicious food and historical wonder but also provide memories and lessons to last a lifetime.

Meanwhile, in France, students were settling in with their host families, adjusting to their new home away from home, and beginning their studies, gaining firsthand knowledge of the French language and culture. Though stationed in Caen for the first leg of the trip, the group took many excursions to nearby towns and villages, such as a memorable field trip to Fleury-sur-Orne—the hometown of one of their new French teachers, Jacqueline. Students explored local history on walking tours, visited one of the last pre-Normandy battle walls and beaches of Normandy, made overnight excursions to St. Malo and the iconic Mont-Saint-Michel, swam in the English Channel, and culminated these adventures with two days in Paris, where they cruised the River Seine and ate in the French Quarter. Throughout the trip, the boys continued to work on their understanding of the French language through various lessons and activities, including writing a script, recording, editing, and presenting a podcast titled Normen vs. Saxons.

These special experiences—the opportunity to practice language skills, discover regional architecture, and reflect on the resilience of local communities—deepen students’ appreciation for the language, history, and culture they study during the school year. Studying abroad at RL, as part of these immersive adventures, connects classroom learning with real-world experiences, shaping students’ global perspectives, and making them more informed and empathic citizens of the world.

Read the French students’ firsthand accounts and view photos from their adventures at the French immersion trip travel blog.

We simply cannot thank you enough for helping to make Roxbury Latin’s eighth annual Giving Day an extraordinary success. With your help, we raised more than $1,145,000 for the Annual Fund—including $150,000 in match money from generous trustees—from more than 1,200 donors, in 24 hours. Every dollar raised will go directly toward supporting our students and faculty, ensuring that Roxbury Latin boys are able to learn, grow, create, compete, build, perform, strive, give, collaborate, and discover. To ensure they grow into men of character—men who go on to lead and serve in their communities and in our world.

Your generous support made this year’s Giving Day our most successful yet. For your excitement, for your generosity—for your love of, and belief in, this school—we are deeply grateful. On this year’s Exelauno Day, thank you for marching forth with us. Roxburienses Sumus.

Giving Day Participation Leaderboard 

Top Current Parent Class
Class of 2029: 95% 

Top Three Alumni Classes
Class of 1991: 81%
Class of 2015: 64%
Class of 2014: 61%