Winsor Leads Fall ’25

Many families find themselves in a difficult position when considering the cost of an independent school education. For some, full tuition is not financially feasible, yet they may not qualify for the level of financial aid that would make such an educational opportunity possible. As a result, students from these families sometimes decide not to apply, leading to their underrepresentation in the student body and the community as a whole.

Jean Hynes and Mark Condon, who sent their four daughters—sarah ’16, caroline ’18, grace ’18, and eve ’21—to Winsor, are concerned about what is known as a barbelling effect taking hold at the school, in which students tend to come from either end of the economic spectrum. “You don’t want any gaps to this great education,” Jean says. “People from a diversity of backgrounds is partly what makes Winsor so special.”

With the goal of building up the barbell’s center, and providing life-changing opportunities for middle-income students, the family recently established the Hynes Condon Family Endowed Scholarship.

The gift is one of the largest in the school’s history: a $5 million commitment over the course of five years. Once fully implemented, it will provide support for eight students at any given time.

Recipients will be awarded the scholarship each year they attend Winsor, with the amount adjusted annually based on their family’s financial need. The first award will be made for the fall semester in 2026.

“Winsor Leads is expanding financial aid and wraparound support for our exceptional students. Jean and Mark’s investment is a demonstration of their belief in the school, and of their values as a family,” says Head of School Meredith Legg. “The Hynes-Condon Scholarship is creating opportunities for every qualified girl to see a pathway to Winsor. Our community will be stronger thanks to Jean and Mark’s visionary leadership.”

A Stepping Stone

Jean knows how a scholarship can change a life. Her parents moved to the United States from Ireland in the 1950s. Here, her father worked as a bricklayer and her mother raised six children.

The couple worked hard to send their children to Catholic schools. Jean earned a scholarship to attend Wellesley College, but her family continued to stretch to pay the remaining tuition.

“In some ways, my education and life path were sort of enabled by the generosity of the Wellesley College alumnae,” says Jean, who is now the CEO of investment management firm Wellington Management. “It’s so ingrained in me, the opportunities that I received that enabled me then to go on to start at Wellington and succeed. That is something Mark and I want to give back, so education has been our main focus of giving.”

Educational opportunities have also lifted up Mark’s family over a couple of generations. His grandparents had only a middle-school education, but worked hard to be able to send their own children—Mark’s parents—to state universities.
“My mother getting a college degree in the ’60s was a huge thing. A lot of my grandmother’s friends were like, ‘Why are you educating a woman? She’s just going to be a wife and a homemaker,’” Mark says. But his parents used their education to help prepare their own children to reach for the highest level of education, including Tufts University, Rhode Island School of Design, and Mark’s alma mater, Massachusetts Institute of Technology. Mark says he saw firsthand how middle-class kids who happened to be gifted in math or science were able to leverage their MIT education to imagine any future for themselves and their families.

Sarah Condon ’16 says her parents made sure she and her sisters understood how educational opportunities shaped their family’s history. “The means by which they have gotten to where they are, the support and scholarships that allowed them to get there, and the importance of education more broadly was repeatedly emphasized to us,” she says.

“Going to Winsor was when we first started to have those conversations at home,” Caroline Condon ’18 says. “We had discussions openly from a younger age, which opened our eyes to differences…. Continuing to have conversations about that, which we did at home and in the classroom at Winsor too, is just super important for everyone.”

Leading Ladies

Today, all four Condon sisters express appreciation for their Winsor educations. In particular, they are grateful for the sense of community, which has remained with them, and for the way that Winsor continually encouraged them to voice their ideas.
Sarah has seen this trend in her male-dominated field of private equity. “I found that there are a lot of other women who are pretty quiet. They might be extremely smart, but I think the ability to just be forward and confident in what I’m saying has really helped me and made me stand out,” she says, crediting Winsor for developing her ability to express herself in a clear, logical, and straightforward manner.

Eve Condon ’21 says she noticed in college that she spoke up more than other women did.

“They didn’t have that high school environment that teaches girls to have your voice be heard, even if you’re not 100 percent sure that you’re right,” she says, adding that she’s had professors ask her if she went to an all-girls school.

Though voicing an opinion in a large college class can be intimidating to many people, Grace Condon ’18 says she “never felt that sense of nervousness, or worried that the answer was going to be wrong or that my thought process was going to be wrong.” Winsor, she says, gave her plenty of opportunities from a young age to be wrong without feeling shame. “You look back and think, ‘Wow! That was such a unique environment.’”

Jean and Mark appreciate the way their girls were taught to advocate for their ideas as part of a holistic education that cultivated their academic, creative, and social minds. “I think all of our girls came out of Winsor with a confidence to speak their minds and know that they have the problem-solving and learning skills to be an equal voice,” Jean says. “And an institution like Winsor, which trains young women to have these skills, is still 100 percent necessary in a world where women are still in the minority of leadership positions,” she adds.

Class Connectors

Jean and Mark say a principal reason they established the scholarship is that they’d like to see tomorrow’s leaders come from across the economic spectrum. “The school is so special and unique in terms of educating young women to be future leaders,” Jean says, adding that the family’s hope is that access is open to all girls who are academically qualified to attend Winsor, that “it’s not limited to people of a certain means. We feel so strongly about that.”

The Hynes-Condons feel strongly that Winsor classrooms should reflect the full range of socioeconomic diversity in Boston. Scholarships not only provide direct support to recipients, but also strengthen the entire learning community by ensuring that students bring a wide variety of experiences into the classroom.

“People have such different perspectives on things based on their life experiences. Being able to hear and understand those is important,” Grace says.

Moreover, students from a wide range of economic backgrounds often help connect different perspectives and strengthen the community. “Every student brings something unique, and together they create an environment where belonging is possible for all,” Mark says, adding that socioeconomic diversity is not a single experience but a spectrum. “That range gives everyone the chance to broaden their understanding of the world and the people around them.”

Audra McFarland, Winsor’s director of Admission and Financial Aid, says she’s noticed that it’s often kids from the center of the socio-economic spectrum who are sensitive to the extremes of the barbell and who drive school discussions about socioeconomic differences. “To be able to widen the funnel and potentially then be able to increase the number of those students, we think it will help to just bring this conversation more prominently into the culture of Winsor to make sure that we’re creating that sense of belonging for all students.” Winsor’s commitment to maintaining its community of students from diverse backgrounds, experiences, and viewpoints is central to the mission of the school’s need-based financial aid program, which supports access to Winsor’s program regardless of a family’s financial circumstance.

Leaning In

The endowed scholarship is the largest gift the Hynes-Condon family has given to Winsor, but not the first. Jean and Mark have donated other funds over the years and have also given their time. Current members of the Winsor Corporation, they have both served on the board of trustees, and Jean co-chaired the last capital campaign, the Winsor Promise, which concluded in 2016 after raising more than $82 million for the school. Mark’s contributions as a leader in the Parents’ Association reflect the breadth of his Winsor journey, from leadership as a class parent and Class VIII Gift Committee co-chair to his time as a Parents’ Association co-chair.

Sarah, too, has started to give back. Now living in New York City, she co-hosted a young alumnae gathering there earlier this year, and is serving on the Winsor Leads Campaign Alumnae Committee to support the school’s current comprehensive campaign. She’s inspired to give her time because of the strong sense of community and friendship she felt at Winsor, and still feels today.

“The world of Winsor, and the relationships that are built, still continues to move forward. So I get excited to be able to help continue that along,” she says.

Her hope for scholarship recipients is that they experience the same sense of community and the same avenues for intellectual and personal enrichment that she did. Her advice for them would be to lean into these opportunities.
“You get more out of Winsor the more you participate in the community, the more that you challenge yourself, even when classes are hard and you’re doing a lot of things,” she says. Eve agrees: “Some advice I would give [all students] is to take advantage of all Winsor has to offer, whether it’s the sports teams, the art, all of those things. It’s not just about going to class. It’s about immersing yourself in the community.”