Bulletin Spring ’26

Bulletin

Finding the Magic in Each Other

At the start of this year’s annual all-school convocation, “I got the magic in me” blared through the sound system of the David E. and Stacey L. Goel Theater as seniors made their grand entrance to “Magic” by B.o.B, featuring Rivers Cuomo. After introducing new faculty and staff, Head of School Meredith Legg P’32 nodded to the senior theme (more on that below), brandishing a flashing wand topped with a star and channelling Cinderella: “I can’t wait to go on this ‘bibbidi-bobbidi-boo’ journey with all of you.”

Ms. Legg then introduced President of the Winsor Corporation All ison Kaneb Pellegrino ’89, P’21, ’22, who reflected on her own Winsor journey and told students, “You stand on the threshold of a chapter of limitless possibilities.”
President of Collect Ha nnah Minn ’26 addressed the first-day jitters, quoting Winsor field hockey coach Euan Brown: “Nerves and excitement are essentially the same.”

After sharing specific advice for each class (encouraging Class VII to listen to family and friends who say “sleep is important,” for instance), Hannah told her fellow students, “Winsor is a place where you get out what you put in.” She urged them to “be a kind and generous friend to everyone around you.”

Senior Class President Liana Min ’26 spoke on the senior theme, Once Upon a Time, reminding students that the phrase often marks the start of a magical adventure. “We don’t need a fairy godmother to give us our magic; we have it in each other,” she said. For parting advice, she quoted Cinderella, challenging each person in the auditorium to “have courage and be kind, and always believe in a little bit of magic.”

“We advise everyone to keep an open and enthusiastic mind to new activities and experiences,” said Lower School Council Heads DadAni Peskin ’30 and Carys Musto ’30. Whether that new experience was trying a meal in the dining room—pierogis received a shout-out—or going out for a sport or play, they urged students to try new things.

Finally, Ms. Legg offered remarks, and told students the story of “a real-life hero,” Dr. Mona Hanna, framing in fairy-tale terms her fight to bring lead-free drinking water to her community. “Once upon a time there was an Iraqi American doctor who lived and worked in Flint, Michigan, just outside of Detroit,” she began.

Ms. Legg didn’t focus on the villain in the story, or the fairy tale ending. What struck her about Dr. Mona was her insistence on telling the whole story, “warts and all,” from personal setbacks and mistakes to feelings of embarrassment. Ms. Legg cautioned, “When we are surrounded by stories of perfection, we begin to think we should expect perfection from ourselves.”
Employing her voice and personal conviction, Dr. Mona saved lives and changed the future for a whole community of children. “She did something excellent. But my friends, she was not perfect,” said Ms. Legg, who went on to explain the difference between the two.

“Excellence is a practice. It is a mindset. It’s a philosophy. It is approaching school, sports, music, theater, and art with conviction, with the ability to make mistakes, and with the ability to learn, knowing that staying open to growth is how you will get better and better. It is how you will be excellent. Perfection is doing everything right all the time. Perfection is an impossible, unattainable standard. Perfection is a fiction.”

Ms. Legg asked that everyone commit themselves to excellence, and let go of perfection. “Let us all embrace our practice of excellence, lean into our mistakes and imperfections, and live this year happily ever after,” she said.

Convocation closed with everyone on their feet. Students Advocating School Spirit (SASS) had the gathered assembly stomping and clapping along to two classic school chants—“Red Hot” and “Hey All You Winsor Fans”—while Head of Performing Arts Felicia Brady-Lopez and Choral Director Andrew Marshall led everyone in singing “Jerusalem” by C. Hubert Parry. To officially start the school year, Lower School Council Heads Dani and Carys rang Miss Winsor’s bell. The gentle chime has opened and closed each school year since 1910. ●

Dr. Mona Hanna’s Challenge: Be Changemakers

Woman with dark hair, glasses and white lab coat

The Winsor comm unity gathered this fall for an inspiring virtual conversation with Dr. Mona Hanna, author of What the Eyes Don’t See: A Story of Crisis, Resistance, and Hope in an American City. Chosen as Winsor’s 2025 summer reading selection, Dr. Mona’s memoir chronicles her role in uncovering the Flint water crisis and her ongoing advocacy for children’s health, environmental justice, and the power of civic action.

The event was hosted by Bezan Chair for Community and Inclusion and History Faculty Julian Braxton and the Winsor Parents’ Association, with a discussion moderated by Head of Upper School and Science Faculty Kimberly RamrAMos that featured Lower School History Faculty Ivana Brown and Winsor parent and pediatrician Liz Oh P’26, ’28 as panelists.
In her introduction, Head of School Meredith Legg P’32 reflected on how Dr. Mona’s work embodies Winsor’s core values. “Her story reminds us of what we hope to inspire in our students—the confidence and strength of character to know that one person, one woman, one voice, can make a difference,” she said.

Dr. Mona shared how her journey from a high school environmental activist to a pediatrician-turned-whistleblower has shaped her commitment to science, justice, and storytelling. “My ability to do the work that I did—and continue to do—was really created in high school,” she said. “Those experiences taught me the power of good policy, of teamwork, and of using your voice to make a difference.”

Dr. Mona emphasized that the Flint water crisis was not a story of one hero, but of a collective effort. “We accomplished what we did because people from all backgrounds came together,” she said. “I thought that maybe pediatricians had a monopoly on caring for children. I was proven so wrong. Because so do water engineers. And so do social workers, and so do lawyers, and so do teachers, and so do so many other people.”

Reflecting on her decision to go public with her research on lead exposure in Flint’s children, Dr. Mona described the sense of duty that kept her going. “Every data point was a child,” she said. “That’s what gave me the strength to keep fighting.” She also spoke candidly about the erosion of public trust in science and institutions, encouraging students and educators alike to engage with science through storytelling and empathy. “We can rebuild trust when we communicate clearly, tell human stories, and remember why we do this work—to make the world a better place.”

Dr. Mona also discussed her ongoing work in Flint, including the Rx Kids program, which provides direct cash support to new parents and infants to combat child poverty. “In a city once known for poisoning its kids,” she said, “we’re now reimagining what it means to care for one another.”

When asked what action she would want every Winsor student to take, Dr. Mona offered a simple but powerful challenge: “Just practice being a changemaker,” she said. “The change doesn’t have to be big—it can be a tiny thing. But take that first step.” ●

young girl of color hugging older man of color

Thankful for Grandparents and Grandfriends

On a Tuesday morning in late November, eager older learners streamed into the Wildcat Room ready to start their school day at Winsor’s annual Grandparents’ and Grandfriends’ Day. The special program brought more than 160 visitors to campus the day before Thanksgiving break.

In preparation for all the visitors, Winsor’s facilities team had set up dozens of extra chairs in classrooms all over campus. Faculty incorporated more than 100 golden-age learners into the day’s lessons. Grandparents and grandfriends settled in and participated in the hands-on learning and rigorous excitement of a Winsor education, joining courses such as Truth and Fiction, Middle Eastern Literature, Native American Literature, Information Sciences, Biology, Honors Geometry, and Precalculus.

In Class II Science, the lesson of the day was a chicken wing dissection, which garnered enthusiastic participation by grandparents and grandfriends who wore gloves and wielded instruments. The World Languages Department hosted a number of folks, with visitors to Mandarin Chinese 2, Class IV French, and Class IV Spanish. In Class IV Latin/Accelerated Foundations of Latin, World Languages Faculty and Winsor alum Caroline Burke ’07 incorporated Winsor’s urban campus location into her lesson plan, taking the class on a tour of classical architecture around Boston.

While some visitors attended classes, others heard from a student panel composed of seven Upper School students. The panelists shared some of their favorite Winsor traditions, teachers who go above and beyond, clubs that add to the Winsor experience, stories of sports teams and theater productions, and the best school lunches.

Grandparents and grandfriends partook in a delicious luncheon prepared by Chef Heather and the dining services team while Class IV Rock On wowed the crowd with James Brown’s “I Got You (I Feel Good).” At lunch, Head of School Meredith Legg P’32 shared remarks reflecting on her first fall at Winsor. She spoke about her unexpected path from engineering to girls’ education, and her deep belief in the transformative power of girls’ schools, noting, “This is a place where girls can shed their self-consciousness.” She went on to talk about the excellence of Winsor’s faculty, who “scaffold and develop deep analytical thinking, creativity, and problem solving,” and the bright future the school looks toward as we write the next chapter of our history.

“Winsor is indeed a very special place, and we’re grateful that our precious granddaughter is part of the community,” said Wendy Guiles-Trombetta GP’32, grandparent of a current student. “The hospitality and kindness we experienced was so gracious and lovely, and lunch was delicious.”

As the afternoon drew to a close, grandparents and grandfriends departed with fuller notebooks, new memories, and a deeper glimpse into the joy, rigor, and community that define a Winsor education. For students, the day offered a treasured chance to welcome loved ones into their daily world. It was a celebration of the learning that happens here, but also of those who loved and supported our students long before they walked through our doors. ●

History Faculty Erin Cantos Awarded the Pennypacker Prize

The Pennypacker Prize is awarded each year to a teacher who is in at least their third year of full-time teaching at Winsor. Created in 2002, the award is “given annually in the name of Henriette Pennypacker Binswanger ’52, with respect and admiration for the educational excellence of the Winsor School and the memory of an extraordinary experience.” As is tradition, the recipient is kept secret until the final moments of the presentation at the annual event, with clues woven into the speech and speculation rippling through the audience—including, of course, the eventual winner.

This year’s Pennypacker Prize was awarded to History Faculty Erin Cantos, and as Head of School Meredith Legg P’32 began her speech, many in the room quickly recognized the teacher being described. “This year’s recipient,” Ms. Legg hinted, “is someone whose intellect is matched by her warmth, whose rigor is matched by her joy, and whose enthusiasm for her subject could make even the most reluctant student lean in.”

From the moment Ms. Cantos arrived on campus, colleagues sensed something special. Ms. Legg recalled an early conversation that left Institutional Researcher and Science Faculty Denise Labieniec thinking, “Now I completely understand why everyone is so excited about her coming to Winsor!” Ms. Cantos, Ms. Legg noted, is the rare educator who combines deep expertise with what she called “joyful geekery”—the ability to transform a casual exchange into an intellectually rich and energizing experience.

A gifted historian and devoted teacher, Ms. Cantos is known for her creative, student-centered instruction and her unwavering belief in her students. English Department Head Courtney JackACKson, who worked closely with Ms. Cantos on the Indian Global Studies course, described her as “a fabulous, open-minded collaborator,” noting that Ms. Cantos brings her “warm, supportive, inquisitive, energetic persona” to her work with students. Ms. Jackson added, “She has high expectations for them, and she is not afraid to give them direct feedback, but they also know that she cares about them and believes in them.”

Ms. Cantos’s classrooms are animated by curiosity, humor, and intellectual rigor. Her use of memes, Ms. Legg shared, has become “almost legendary,” sparking laughter while making history feel immediate and alive. Beyond the classroom, Ms. Cantos is a devoted advisor to The Banner, where she works closely with students to help them cultivate their voices as journalists and citizens of the world.

Ms. Legg also highlighted Ms. Cantos’s close partnership with English Faculty and Banner Co-Advisor SamasAMAntha SiMPson. She shared Ms. Simpson’s recollection of knowing almost instantly that Ms. Cantos was “a shoo-in,” explaining, “A person can’t be that enthusiastic and joyful about history and education and not get the job.” Reflecting on their shared work, Ms. Simpson added, “I am grateful for every minute that I’ve worked with [Ms. Cantos],” describing her as “my friend, my sweatshirt twin, my sister.”

In closing, Ms. Legg captured the spirit of the evening by noting that Ms. Cantos “embodies all that the Pennypacker Prize is meant to recognize.” Through her scholarship, teaching, collaboration, and care, Ms. Cantos makes Winsor wiser, warmer, and more joyful each day. ●

Milestone Honorees

5 Yearsof Service
Chuck Applin
SueBanerji-Cook
Nicole Barbuto
Julie Callanan
Khanard Channer
Raquel Hitt
EeveeThompson
Ariel Tu
Emily Valenza
Ezer Vierba

10 Yearsof Service
Caroline Burke
AmyLieberman
PeterMedrano
Danica Mead
Jessica Pribble
Connie Wong

15 Yearsof Service
Ann-Marie Holland
Dana Martin

20 Yearsof Service
Caitlin Miles

25 Yearsof Service
KarenGeromini
Tiffany Marshall

teacher and student sitting on bench and talking

Caitlin Miles—20 Years at Winsor

Over the course of her 20 years at Winsor, Mathematics Faculty Caitlin Miles has proven herself to be one of those rare educators whose influence is both deeply felt and quietly sustained. A longtime member of the Winsor Mathematics Department, she has taught generations of Lower School students; served as a coach, class coordinator, and advisor; and consistently stepped in—often without fanfare—whenever the community needed her.

Former student Ariell e Mitropoulos ’15 remembers Ms. Miles—then “Ms. Blois”—as one of the first people she met in her Winsor journey, sharing, “How lucky was I that she was my introduction into this incredible and sacred space.” Arielle describes her as “kind, warm, and absolutely, utterly patient,” recalling how Ms. Miles “always made me feel like I deserved to be at Winsor, and that I was just as intelligent as any of my classmates.” Even when understanding didn’t come easily, Arielle remembers, “that was okay too, because she would help me get there.” At a time when “being a young girl can be so vulnerable,” she says, “she made every space feel safe.”

That care extended beyond the classroom. As a homeroom teacher, Ms. Miles navigated what Arielle describes as “the craziness of 30 to 60 seventh-grade girls” with humor, professionalism, and warmth. “Even at 12, you can tell when a teacher genuinely cares about who you are—and that was Ms. Blois,” Arielle writes. “No matter how many years pass, every student she teaches gets the same wonderful teacher, who made us all feel like we belonged.”

Colleagues speak to that same steadiness. Head of Upper School Kimberly RamrAMos recalls coaching mid soccer alongside Ms. Miles and learning from her “balanced, easygoing approach alongside her willingness to give the feedback that needed to happen in the moment.” On bus rides home from practice, Ms. Ramos remembers Ms. Miles as “an expert at multitasking,” checking in with students, helping with homework, and offering “important and perceptive observations about how we could best set our athletes up to succeed as a team together.”

In the classroom, Ms. Miles’s dedication is equally clear. Mathematics Faculty Em ily Moran shares that Ms. Miles is “always coming up with interesting and captivating lessons,” while also being “one of the most generous and empathetic people I know.” Mathematics Faculty Mary Butcher describes her as “steadfast, unshakeable, and the funniest person in any room she is in,” adding that she “fully embodies the quote, ‘Knowledge speaks, but wisdom listens.’”

Retired Mathematics Faculty Lisa Reynolds, who describes Ms. Miles as “a positive force in her students’ lives [due to] her honesty, integrity, and de-escalating nature,” traces Ms. Miles’s Winsor story back to a moment of urgency in 2006, recalling her “unassuming confidence” in stepping into a complicated situation. Just weeks into the fall semester, the Mathematics Department was suddenly and unexpectedly in need of a talented, qualified teacher who could seamlessly step in on short notice. A former student of Ms. Reynolds, Ms. Miles was an easy choice, but the stakes were high. Ms. Reynolds remembers making clear to Ms. Miles that if she failed, her failure would reflect poorly on both of them. Ms. Miles’s response at the time, Ms. Reynolds notes with a smile, was simply, “OK, great…so, no pressure.”

Twenty years on, Ms. Miles remains exactly that presence—calm, capable, generous, and deeply committed to her students and colleagues. It is difficult to imagine Winsor without her, and easy to understand why so many are grateful she has been here for so long. ●

In Winsor’s Parents’ Association, Everybody Has a Role to Play

“Like ma ny paPArents, I felt both excited and a bit daunted when our daughter joined Winsor,” says Parents’ Association (PA) Co-Chair Fawn Andersen P’29. “There is always that natural worry about whether your child will find her footing—academically, socially, and emotionally—and whether she will truly feel at home in a new school community.”

Seeking to build her own connection with Winsor, Fawn decided to attend a Parents’ Association meeting. “I was immediately welcomed and encouraged to get involved,” she says.

Every parent or guardian of a Winsor student is a member of the PA, which supports the school by coordinating volunteer activities, organizing social gatherings, and assisting at various Winsor events. The PA, and its all-volunteer leadership team, aims to connect parents to each other and to Winsor. This happens through a wide variety of events and initiatives: volunteering at campus events and service days, building community around Winsor’s student activities and performances, supporting the Winsor Fund in its fundraising efforts, and supporting other Winsor programs and departments.

“Being a part of the Parents’ Association is one of the best ways for parents to connect with their student’s experience and support the school,” says Head of School Meredith Legg P’32, a Winsor parent herself. “Parent volunteers play an essential role in shaping the Winsor experience, bringing energy, leadership, and heart to our community.”

The PA leadership team has expanded in the past few years, with new opportunities to get involved including Athletics and Performing Arts Liaisons; Community Connections, which facilitates off-campus events for parents and guardians; and co-hosting the spring semester’s newly revived International Night. The list is constantly expanding. It includes the chance to be a part of iconic Winsor moments—decorating campus for UTL or serving treats on Pi Day, hosting the Lower School Community Service Day, and coordinating faculty and staff appreciation events.

“Even before the school year started, we were warmly welcomed by a volunteer host family,” recalls Evelyn Chen P’33. “Two PA community events—cookie decorating and ikebana—introduced us to many parents from other grades.” Evelyn has since volunteered at several campus events, including helping to decorate the courtyard red for Under the Lights and dispensing whipped cream at Pi Day. “The parent volunteer efforts helped ease our transition as a new family and made us feel welcomed into the community right away,” she says. “So it was natural to want to roll up our sleeves and be part of it.”

The PA leadership team includes a variety of roles, some with large virtual components, such as coordinators for appreciation events and the Lower School Community Service Day. Several roles are almost entirely virtual, such as class reps and Community Connections liaisons. But other roles include more of an in-person, on-campus component for parents and guardians who want to build relationships face to face.

“Being on campus and supporting the PA has given us a firsthand view of how intentionally the school nurtures not just academic excellence, but also character, leadership, and community,” say Prem Swaroop P’31 and Pashanthi SylaLAda P’31, parents of a Class III student. The couple have served in multiple roles in the PA—Prem is the former Host Family Coordinator, now Performing Arts Liaison; Pashanthi was Community Connections Co-Chair and now serves as a class representative. “Volunteering at Winsor has become a deeply meaningful part of our family’s connection to the school.” They recall favorite memories, such as “seeing the girls smile when we served them Chef Heather’s pie, serving breakfast to faculty and staff, connecting with parents over a hike at the Blue Hills, welcoming families at UTL, and Class III family potlucks.”

“We simply love being part of and bringing the community closer together,” they say. “Giving our time feels like an investment in something larger than ourselves: a community that lifts girls up and equips them to lead with purpose.”

Fawn agrees. “Volunteering has allowed me to feel part of my daughter’s Winsor experience in a meaningful way, rather than simply observing from the sidelines, and it has been incredibly rewarding.” ●