Joe O’Donnell’s Legacy at Winsor

Dear members of Winsor community,

On Sunday, January 7, the Winsor community lost a dear friend, a man whose love for this school was abiding and whose commitment to sustaining its excellence inspired those around him and changed the school forever. Joe O’Donnell entered the Winsor community as a parent, joined the Board of Trustees shortly after, and remained an integral part of Winsor from that point forward. He was a major force in every fundraising campaign at Winsor during his time, an advisor to three heads of school, and a friend to every trustee he served with. His loss is devastating, and his legacy is remarkable.

Arriving at the steps of Winsor as a prospective parent, he immediately embraced Winsor’s commitment to empowering young women and to helping them pursue their aspirations and contribute to the world. His own experience growing up in Everett, attending Malden Catholic, Exeter, and then Harvard, showed him the power of an excellent education and the essential role that philanthropy plays in ensuring that all students, regardless of circumstance, can access that education. Together with his wife Kathy, and his daughters Kate ’05 and Casey ’07, he brought that wisdom and passion to everything he did at Winsor.

To say he was instrumental in the evolution of the school is to vastly understate the obvious—his name graces the largest building on campus and the endowed chair that I hold. But his impact extends far beyond his philanthropic support of the school. Former Head of School Carolyn McClintock Peter recalls the start of their friendship, which began during regular 5:00 p.m. calls he’d make to her office. What began as simple conversations about the day-to-day evolved into deeper discussions about their shared vision for Winsor. She recalls, “Joe was never pushy or aggressive; he led from the back. He shared his ideas and advocated in a diplomatic, respectful way.” 

Former President of the Board of Trustees Nancy Gardiner P’04, ’09 remembers, “Serving on the Winsor board with Joe was truly a privilege. We worked hard, but…he made it fun. He encouraged us to dream and his vision helped us embark upon the Winsor Promise Campaign, the biggest in the school’s history up to that point. [That campaign] transformed the campus physically and provided needed ballast to the endowment at the same time. The building that bears the O’Donnell and Lubin names is the physical representation of everything that was great about Joe: dreams, generosity, and partnership. For Joe, it was about the girls, as much or more than the campus; they were one and the same. The entire design experience became an educational process. The spirit around the campaign was palpable, all due to Joe’s galvanizing energy.” 

Former Head of School Rachel Friis Stettler remembers Joe as a tremendous ambassador with an incredible capacity to get people involved, and how Winsor benefitted immeasurably from his advocacy. As Ms. Stettler puts it, “People who had never heard of Winsor heard about it through Joe.” In fact, when she first met the Boston’s then-mayor, Thomas Menino, and said she was from Winsor, he shook her hand and exclaimed, “Joe O’Donnell’s school!” She laughs as she talks about this memory: “It was classic Joe.” 

Board of Trustees President Allison Kaneb Pellegrino ’89, P’21, ’22 characterizes Joe’s inimitable impact on Winsor, saying, “Joe O’Donnell has been the single most impactful volunteer, trustee, and one of the most influential people in Winsor’s history. I am privileged to have known him, and in a lovely way he took me under his wing and taught me not about fundraising, but about how you treat people. If you love a place like he loved Winsor and you are willing to share it with people, the support for the institution comes naturally and authentically. If you’re patient and real—and you better make it fun—then the rest will follow.” But he was never in the spotlight during campaigns; he was always a co-chair, always having critical conversations behind the scenes, and allowing the school and its leaders to shine. This was especially true for the Winsor Promise campaign and for the soon-to-be announced Winsor Leads campaign. Any accomplishments were celebrated as a co-chair group; all credit was shared. After all, it was always Winsor that was first and foremost. 

Ms. Gardiner remembers evidence of that commitment and authenticity during his time at Winsor. “Joe was there for so much…. He showed up and demonstrated that he cared, whether at Under the Lights, the Annual Meeting, or ‘off campus’ asking the Winsor Small Chorus to sing at the Joey Fund Event. He took an interest in the students, the faculty, the present and the future. Winsor is lucky to have so many friends and Joe was one, in a class by himself.” He delighted in hearing anecdotes about the teachers and students, in meeting alumnae and hearing about their experiences, and in telling stories about the years his daughters attended. He was proud of the school, and loved it, every single day.

And Joe was a constant connector. When Ms. Stettler began her tenure as head of school, she found her New York roots made her a little bit suspect in Joe’s eyes. He told her later that he had learned she was from New York and didn’t care about baseball, and thought, “That’s not acceptable. A head of school in Boston who’s not a Red Sox fan? No way.” He made sure she became one. Likewise, Ms. Stettler remembers how he connected so many people to Winsor, saying “The most important thing to him was that a place like Winsor be accessible to qualified folks, whether or not they could afford it financially.” That commitment to accessibility fueled his efforts to help ensure that Winsor was on exceptionally sound financial footing, a legacy that continues today.

Ms. Pellegrino shares how Joe reinvented fundraising at Winsor. “Historically, [Winsor] had viewed fundraising as unseemly. He forced us to change the way we were thinking, understanding that if we didn’t, we wouldn’t exist anymore. Joe challenged us to be respectful and grateful, but unapologetic. He made us bolder than we would have been otherwise.” If the goal of a Winsor education is for graduates to speak their minds and pursue their passions with kindness and generosity of spirit, then Joe truly embodied the mission. He delighted in mentoring the next generation of philanthropists, another gift he has given Winsor that will last forever.

Perhaps most importantly, Joe was a dear friend to many. He had a singular ability to make whomever he was talking to feel like the most important person in the room. Ms. Stettler notes that “there are probably 500 people who think of Joe as a good friend.” And Ms. Peter remembers how “Joe never seemed to be in a hurry, but still got so much done. It always felt like he had time for whoever he was talking to. You never felt like he was in a rush to get anywhere else.” Ms. Pellegrino agrees, explaining, “Joe genuinely listened, processed what you said, and responded thoughtfully. He made sure you knew you were heard.” Many of us can recall times that he called us at 8:00 p.m., when his evening was just getting started, to have a leisurely conversation that ultimately ended in a sage piece of advice or an offer to help with something. He never ended a conversation with me without reminding me that he was always there for whatever I might need, and that he was proud of the school. 

Ms. Stettler notes that “On the surface, Joe may be known for his philanthropy, whether to Winsor, the Joey Fund, the Cystic Fibrosis Foundation, or Harvard. But anyone who really knows him knows it was the force of his personality, his commitment of time and his leadership that made the most impact in the world. There are generous people, but Joe was a unique human being.” Joe had a talent for making people feel truly special because, to him, they were. It could sometimes take him many minutes to get into the boardroom because there were so many people to greet and so much to check in about, whether it was a business question, a social engagement, or a shared delight in the latest Red Sox victory.

This morning, the entire school gathered for our weekly assembly in the Goel Theater at the heart of the Lubin-O’Donnell Center to see the Class I play. This annual tradition puts all our youngest students on stage, singing and dancing as the rest of the school cheers and laughs and applauds. It is one of many moments at Winsor that seem emblematic of Joe’s legacy here: the joy and delight the oldest generation of students takes in the accomplishments of the youngest among us; the true excellence of the work here at Winsor; and the acknowledgment of our remarkable fortune, being together in this beautiful space, honoring one another. After the play, I took a moment to honor Joe, to make sure every student knows that he believed in them, and that he spent much of his life ensuring that this remarkable school would always be here for them. When I said to them that “he is the O in the LOC,” the entire theater took in a breath, recognizing the magnitude of the gifts he gave us. 

Joe’s legacy at Winsor is extraordinary, and those of us lucky enough to be here every day get to see his name and be so very grateful for his dedication, generosity, and love. More significantly, however, he has changed this school for those who are not yet part of the Winsor community, whose lives will be richer because of his profound commitment to the school. I know you join me in keeping Kathy, Kate, and Casey in your hearts, as they mourn this tremendous loss and celebrate a man who had no equal.

Warmly,
Head of School
Sarah Pelmas
O’Donnell Family Chair

Tributes

Nancy Skinner
1/12/2024 @ 12:41 PM
These moving tributes recall so many warm memories of working with Joe on The Promise Campaign. He was a champion, a force for good and for the girls, and wise counselor and friend to so many. What a gift. I will always be grateful.

Kristin Bennett
1/12/2024 @ 6:44 AM
What a beautiful empowering tribute I am so sorry to learn of Joe’s passing, a true legacy to Boston, Winsor and nearly everyone who had the honor to cross his path. I met Joe and Kathy at the Winsor Foundation evening when I gave a talk. He made it a point to find me after, despite the many people in his path to talk to him, and make me feel extra special. He gave me some beautiful advice I have kept close ever since – including always giving back. Thank you Winsor for another gift of allowing us all this honor of crossing Joe O’Donnell’s path. Sincerest of condolences to the family, our Winsor Community, Boston and the world’s blue skies. Kristin

Benjamin Flaim
1/11/2024 @ 6:52 PM
My very first introduction to Winsor as a newly admitted parent of a ’30 was at Joe’s house on the Cape. I went there not knowing a soul and left a couple of hours later having made multiple friends in the Winsor community. Joe and his family were so incredibly kind and welcoming to someone they had never met. What sad news. But what an incredible legacy he left—not just to the people who knew him best, but as an example of the kind of person we should all be.