Winsor’s Annual Associates Dinner: Reflecting on the Impact of Belonging

Tuesday, November 8, 2022—More than 130 guests came to campus on a balmy and clear November evening for the annual Winsor Associates Dinner. The celebration honored those who, through generous leadership-level financial support, sustain the Winsor Fund and bring the fullness of the Winsor experience to the daily lives of both students and faculty. 

Allison Kaneb Pellegrino ’89, P’21, ’22, president of the board of trustees, welcomed everyone in Carolyn McClintock Peter Hall, and spoke about the collective impact of the Winsor Associates on the student and faculty experience here at the school. Looking forward, Ms. Pellegrino shared the purpose behind the activation of the quiet phase of an “ambitious and historic campaign” for Winsor, securing the future of our school and ensuring that the best and brightest applicants can access Winsor and all of its offerings, regardless of financial barriers. 

During the dinner, masterfully prepared by Winsor’s Culinary Director Heather Pierce and her team, Head of School Sarah Pelmas spoke to attendees about what it means to “belong in a place,” echoing the resounding school theme of the year: Belonging.

Ms. Pelmas continued to share her own observations on the different ways Belonging manifests in ways large and small at Winsor. It’s students of Mandarin becoming fast friends over their five to eight years of studying together, or cast members of the fall play becoming so well acquainted with one another that they can “finish each other’s sentences.” In these moments, shared affinity and belonging are what make this place home for many. 

In referencing the history of the school, Ms. Pelmas spoke about our connection to the past that threads through Winsor today. From the beginning, “there was an expectation from those teaching at Miss Winsor’s school, and from those attending it, that the graduates would make a difference.” She also acknowledged that while Winsor is still a school for intellectual powerhouses, who will go on to make an impact on the world, the community now is much more diverse and therefore more likely to disagree or see things from different perspectives. Ms. Pelmas raised the question: How do we reconcile our theme of Belonging with the diversity at our school? She stated that “we need to see our diversity of viewpoints, and our differences, as essential ingredients in what it means to belong.”

The centerpiece of the dinner included an extraordinary panel of alumnae representing different backgrounds, class years, and career paths, who were invited back to campus to speak about their own Winsor experience. The panel included Pamela Smith Henrikson ’58, Marisa Greenwald Kenney ’02, Anshi Moreno Jimenez ’15, and student moderator Anissa Patel ’23. Through their stories, they illustrated the transformative power of a Winsor education and the impact of this special school on their lives.  

In one moving moment, the panelists were asked to speak about a Winsor faculty or staff member's impact on their life who challenged, inspired or supported them. Director of Community and Inclusion Julian Braxton’s name was mentioned several times as someone who provided a safe space for students. One panelist noted his support when she “faced hardships…or academic setbacks” and another recalled Mr. Braxton was there for her when facing difficult conversations about race “following the death of George Floyd.” Mr. Braxton was also helpful when Anshi Moreno Jimenez ’15 applied for her position with Mayor Wu’s election campaign. 

Pamela Smith Henrikson ’58 fondly recalled memories of a “very young and beautiful English teacher,” Ms. Virginia Wing, Winsor’s fifth head of school from 1963 through 1988, “who could do anything.”

In closing, panelists shared wise words to their younger selves: “Stay close to your friends” and “Your choices don’t have to be terminal. You can be versatile. Life has many chapters, so try things out versus looking at life as a finite set of choices.”

We thank the Winsor Associates for their generous support and ambassadorship for this special school, and we are grateful to our panelists who enriched this very special evening with their insights.