Profiles in Giving Fall ’25

By any measure, Winsor’s Class of 1987 has been remarkably generous. They have won the school’s yearly Giving Day competition, class members serve on Winsor boards and panels, and in November 2024 they established an endowed fund to support wellness initiatives at Winsor.

Notable as these accomplishments are, they spring from another powerful way class members have given over the last 38 years—to one another. For nearly four decades, the women of ’87 have stayed in close contact, lending their care and friendship and providing a sense of community and history for one another in both good times and bad. What was once a close-knit group of teens has evolved into a vibrant community of friends, peers, and advisors. They rely on one another for professional and personal insights, advice, and support. Classmate abigail crozier nestlehutt ’87 has found herself consistently inspired by the “collective intelligence” of her classmates and their dedication to one another.

In the fall of 2023, they lost classmate Diane Pfaelzer Levinson ’87. Her passing was the first time the class had mourned the loss of a classmate.

“Losing her brought the class together, but the class has come together so many times before and will continue to come together in difficult times. That’s what’s so special about this class,” shares Kimberly Heald Krawshuk ’87, P’20. “And so we [asked], how do we honor our class and do something in memory of Diane? She’s somewhat symbolic because we realize, sadly, we’re all going to pass away.”

“We asked our classmates how best to honor our class and our Winsor education, and how to do something in memory of Diane,” Kim and Cynthia Korb Wellington ’87, P’28 say. “We want to leave something to the school in appreciation for bringing us all together and giving us an extraordinary education.”

They resolved to start the Class of 1987 Endowed Fund to advance wellness initiatives at Winsor. The focus was inspired by Diane’s work as a mental health counselor and in recognition of the need to help students navigate their Winsor years and prepare for life after graduation. “We want to support something that in 50 to 100 years from now the school will still need,” Kim says. The fund will be endowed when it reaches $100,000, which Cindy and Kim aim to reach by the class’s 40th reunion, in two years.

The class is intentionally keeping the fund’s scope broad. “We discussed this and decided to leave it somewhat open to address what the school feels is its greatest need at any given time. Look at the pandemic: no one could have predicted it, nor what needs would emerge…. We want to make sure to give the school flexibility to address the pressing needs,” Cindy says.

Winsor has already made great strides in promoting wellness since Kim and Cindy were students, something they have experienced firsthand from both having daughters at Winsor. Kim, whose daughter Ashley Krawshuk ASHLEY ’20 recently graduated, says she has watched wellness become “this very elaborate, integrated program” that includes courses for students as well as counseling and nursing services.

Cindy, whose daughter Caroline Wellington ’28 is a current student, is excited about the Wellness Department growth at Winsor both for students and the wider community. “In addition to helping ensure that the existing programs continue, the Class of 1987 Endowed Fund could also be used to pay for educational opportunities for faculty and parents,” Cindy says.

While the pandemic underscored the importance of support and connection, for the members of the Class of 1987 it reignited something that’s been there all along. Cindy recalls how during those trying times class members would have a big get-together over Zoom every couple of months. “It was a wonderful way of supporting each other,” she says. These days, the group convenes a few times a year.

This habit of staying in touch started right after graduation, and their connection has only strengthened over time. From the paper photo calendar with everyone’s birthdays they took with them to college, to the Facebook group that provided a platform for connection decades later, their commitment to each other has been unwavering. Sometimes these conversations, emails and texts are about a classmate who needs help after surgery. Sometimes they are about career pivots and making new business connections. Sometimes they are about the merits of the Oxford comma.

Kim and Cindy say the class’s extraordinary connection has been the key to its fundraising success. In addition to the endowed fund, Winsor Giving Day is a big moment for the class each year. “That is a day when we just come together and start chatting over email and Facebook and get caught up on each other’s lives,” explains Kim. Launched in 2019, Winsor Giving Day is a 24-hour online event that galvanizes the Winsor community to make gifts of any size. The goal is to get the whole community involved. For the Class of 1987, the positive feelings classmates have about each other and the school translate into giving. Indeed the class is often at the top of the leaderboard on Giving Day, with participation numbers well over 60% and some years over 70%.

Now in their 50s, the women’s Winsor friendships mean more than ever. “No matter what situation anyone is in...we see our classmates as 17-year-olds and hopeful and full of life and potential. It’s just so invigorating that that’s how we see each other. We’re able to support each other, understand each other, and really believe in each other,” Cindy says. And that’s a tremendous gift indeed.