Celebrating the Class of 2025

“It is a pleasure to welcome you all here to the 131st commencement ceremony of The Winsor School,” said Head of School Sarah Pelmas. The entire student body of grades 5 through 12, faculty and staff, and family and friends of the graduating seniors gathered in a soaring white tent in the Winsor courtyard. The event drew nearly 1,000 people to campus.

Selected by the senior class, Sawyer Bowen-Flynn ’25 opened the program with a reading from C.S. Lewis’ The Lion, The Witch and the Wardrobe. “Yes, of course you’ll get back to Narnia again some day,” she read, an apropos choice for seniors on their last day at Winsor.

Led by Choral Director Andrew Marshall, Upper School choir Illumina sang “Blessing” by Katie Moran Bart before President of the Winsor Corporation Allison Kaneb Pellegrino ’89, P’21, ’22 took the stage and acknowledged Ms. Pelmas’s final commencement ceremony. Calling her nine years at Winsor “extraordinary,” she praised Ms. Pelmas as an administrator who “leads wisely and cares deeply” and who brought “warmth and humor” to the role. 

Citing the more than 4,000 Winsor alumnae scattered across the globe, Ms. Pellegrino emphasized the social and emotional network that spans continents and decades to which the seniors now belong. “We know it’s time for you to leave this place,” she said, “but Winsor is always here for you…supporting you wherever you go.” 

Ms. Pelmas, giving her last address as head of school, called the assembled seniors “thieves! tricksters!”—a reference to their Oceans 25 seniors theme—and shared, “I am glad and proud to be ‘graduating’ with you,” adding “I have always loved sneaking around with you guys, whether it was checking out the basement tunnels many years ago or being arrested [on senior prank day] for stealing the lamp.” 

Drawing on the Shakespearean tragedy Hamlet, Ms. Plemas offered advice to the graduates on themes of leadership and storytelling. After apologizing for the Hamlet spoilers, she shares that everyone dies—“not surprising for a Shakespearean tragedy”—except for Hamlet’s best friend, Horatio, who she identifies as the true hero of the play. “I imagine Shakespeare thought so, too,” she added.

As he is dying, Hamlet gives his blessing to Fortinbras of Norway as the next leader of Denmark and asks Horatio to tell his—that is, Hamlet’s—story. “These are the two things great leaders do,” explained Ms. Pelmas. “Name and support their successor, and ensure that their story is told by the right person.” Calling the job of a historian and storyteller “crucial,” she added, “it is how we know the truth, how we know who we have been as a people, and how we learn in order to do better the next time around. It’s not just true for the 15th century; it’s true for this very moment as well.”

She reminded students, “You are powerful, smart, thoughtful, funny people, who know very well how to speak your mind.” In fact, “It has been one of the great joys of my time at Winsor that you are so often willing and eager to come right into my office and speak your mind.” Calling it “a tremendous privilege” to “speak one’s mind, without fear of reprisal,” she emphasized voice as a core value of a Winsor education. “At Winsor, we have worked very hard to give you both the opportunity and the ability to speak your mind, as well as the tools and information you need to make up your mind in the first place.”

Ms. Pelmas’ ultimate message to students: “Be Horatio. The world is full of people who need a Horatio. Someone who will speak truth on behalf of others, who will talk directly to those in power and advocate, who will do so even if they would prefer not to—because it is the right thing to do and because we all benefit when we hear everyone’s story, not just the loudest voices or the most privileged.” 

After singing “Jerusalem” by C. Hubert Parry accompanied by Head of Performing Arts Felicia Brady-Lopez on piano under the direction of Mr. Marshall, Katina Handrinos ’25 spoke to fellow classmates about their years at Winsor and what lies ahead. “Just because we are leaving 103 Pilgrim Road doesn’t mean we lose what we created here. We make the meaning,” she explained. “Winsor may not be our house anymore, but it will always be one of our homes.” Becoming emotional on stage, she addressed her class’ next transitions. “You’ll pack your things up for this new adventure and plant your feet someplace else. The next house will be formidable in its newness, but only at first. Then you’ll make new friends, lay your head somewhere new, discover things to love intensely, be known in that somewhere else. It will blossom into a home, your home,” she said. 

Performing for the last time together, Senior Small Chorus sang “Somewhere Only We Know” by Richard Hughes, Tim Rice-Oxley, and Tom Chaplin, originally performed by Keane. In response, three boxes of tissues circulated among the rows of seated seniors and even the singers became verklempt.

“Looking back on my Winsor experience, my most cherished memories are the ones surrounded by all of you,” Senior Class President Elizabeth Fitzpatrick ’25 told fellow classmates. Introducing this year’s commencement speaker, she shared, “When our class had the pleasure of meeting with Ms. Shuster earlier this spring, we were quickly captivated by her wit, humor, and candor as she spoke with us about her experience at Winsor and how it prepared her for her adult life and working in a male-dominated field. She shared how attending Winsor helped her find her voice and confidence and offered us advice as to how we may do the same as we embark on this next chapter in our lives.”

Recently profiled in the fall 2024 issue of Winsor’s Bulletin magazine, Emmy Award–winning sports journalist Suzy Shuster ’90 is a nationally recognized broadcaster known for her work on ABC Sports, ESPN, and FOX Sports Net. She currently co-hosts and executive produces Women’s Sports Now, exclusively on Roku Channel, a groundbreaking weekly series dedicated to women’s sports and the celebration of female athletes as cultural leaders and change-makers. She also co-hosts What the Football with Suzy Shuster and Amy Trask during the NFL season and is the official guest host of The Rich Eisen Show. 

Thanking her mom for pushing her through the doors at Winsor 37 years ago, Suzy’s advice for the graduates was grounded in storytelling and lived experience.

Beginning with a physical exercise, she asked seniors to “Reach out your hand. Feel that bond.” With eyes shining, seniors held hands as Suzy encouraged them to “Be in the moment because you may never ever be in the same room again…forever more, this is your team. And it always will be. Remember this moment, remember how it feels to extend your hand.”

Ahead of commencement, the seniors met with Suzy to ask questions and learn about her journey. Suzy shared, “The number one question you all had of me was how did I find success in the sports world…how did I make it in the ultimate man’s world? I can stand here today and emphatically tell you that the answers lie here at Winsor.”

Calling Winsor’s expository writing program a “North Star” and “an absolute and total life saver,” Suzy underscored precise ways in which her Winsor education makes an appearance in her daily life. “Every single live shot on television I have ever delivered has come via thesis statement. I am able to speak for hours at a time unscripted because I prepare, I organize, I research, and I follow a thesis statement in my head.” And even though she believes writing at Winsor provides a “scaffolding for life,” the education goes even deeper. 

“I became confident in my voice here,” she said, “confident in my academic abilities, definitive in my convictions. I truly believed I deserved to be in the room where it happened.”

And when she was in the rooms where it was indeed happening, she made an impact. “Whether through precise and targeted questioning in an NBA Finals press conference or perseverance in the middle of a media scrum after a triple overtime college football game on ABC… I thrived on being doubted by the men who believed women shouldn’t be covering men’s sports. The more they doubted, the more I doubled down. The harder I worked. The stronger my voice became.”

She explained, “I was ready because I was a Winsor graduate and we use our voices. We use them loudly, with authority, we stand up for what we believe in. We believe in ourselves.”

Amid advice to stop apologizing and always have a firm handshake, Suzy reminded students that life is unscripted. “The road ahead will twist and turn. It’s how you deal with those moments of trepidation, those moments when the teleprompter goes black and you are live on the air. In those moments, hear me saying to you, ‘breathe, pause, you will be ok.’ Just look for the hand extending back to you. Know that it will be there.”

Stopping to give hugs to Ms. Pelmas, Class VIII Dean Jenny Albright, Head of Upper School Kimberly Ramos, and even Ms. Shuster, seniors accepted their diplomas on stage in front of cheering friends and family. “Assembled friends and family, on behalf of the faculty and staff, and the trustees of the Winsor School, I present the graduates of the Class of 2025,” Ms. Pelmas told the crowded tent.

Congratulations to the Class of 2025!