Class of 2026 Celebrates Graduation

Surrounded by family, friends and faculty, the 133 members of the Class of 2026 gathered on Graduation Terrace on Saturday, May 30, for Commencement — a morning of reflection and new beginnings.

Middle school Latin and upper school history and religion teacher Ben Thorn opened the ceremony with the invocation, offering words of encouragement before concluding on a lighthearted note. Quoting what he called “the classical American musical poets, the Grateful Dead,” Thorn shared: “Fare thee well now, let your life proceed by its own design; nothing to tell now, let the words be yours, I’m done with mine.”

Joining him on the dais were Edgar M. Masters H ’98, lifetime trustee and great-nephew of school founder Eliza Bailey Masters; Beth Nolan ’69, chair of the Board of Trustees; and trustees Jonathan Resnick P’26 and Bernard Yancovich P’25, ’26, ’33.

Head of School Laura Danforth welcomed the audience on this “beautiful, blustery day,” reminding the attendees that “we are here not just celebrating our amazing seniors but to gather the full and enduring circle of the Masters community — teachers, mentors, families and friends. Each of you graduating today has a team that has been rooting with its might for you.”

Class of 2026 Co-President Jamie Milward followed, and reflected on the uncertainty of the future. He acknowledged that while he wished he could offer guidance to his classmates, he has yet to experience college or live on his own. The advice he could offer was a simple directive from his dentist: “It’s very important that you always remember to floss.”

On a more serious note, Milward encouraged his class to “wake up every day a new person, and by surrounding yourself with kindness, create more over the span of weeks, months and years. Each of you has so much to offer, so be your true, kind self. And of course, it wouldn’t be a Masters speech if I didn’t tell you to ‘Do it with thy might.’”

In her address to the senior class, commencement speaker Cheryl Mills, founder and CEO of the BlackIvy Group, spoke about her childhood in a military family, her distinguished career as chief of staff to Secretary Hillary Clinton and counselor to the U.S. Department of State. She shared personal stories, including a memorable moment with the late Nelson Mandela, that highlighted the importance of resilience, service and kindness. 

“If I leave you with nothing else, please remember that while people’s actions are observable, knowing someone’s intentions requires grace,” she said. “The belief that there may be more that you don’t know. Choosing compassion over judgement is the very essence of grace.”

After the senior members of Dobbs 16 sang the School’s alma mater and the class received their diplomas, the class participated in the traditional rose toss. Head of Upper School Peter Newcomb spoke fondly about the senior speeches that inspired him during the past year.

Before the graduates recessed down the aisle of applauding faculty members, Class Dean Darren Wood recited an original poem about special moments with the seniors. The Glee Club sang the “Old Irish Blessing,” wishing the seniors farewell as they move into the wider world.

Newcomb shared his gratitude for the Class of 2026: “Graduates, thank you for the wisdom you have shared with us. We are proud of who you have been, we are excited for who you are becoming, and we cannot wait to see the beautiful, imperfect, surprising lives you create.”