The Taylor Hollander Campaign for The Pearl Fund

For 26 years, Taylor Hollander has been a pillar of Orchard House Middle School as a beloved teacher, mentor, and guide. His creativity and passion for history have shaped generations of students. Since the earliest days of the school, Mr. Hollander’s dynamic teaching style has inspired students to see the world through a broader lens and understand how cultures have come together over time. He encourages them to think critically about their place in history, all the while making learning engaging, entertaining, and fun.

“Mr. Hollander allowed us to be creative and independent in our learning. My favorite lessons involved my class writing and performing full skits, costumes included,” says Elizabeth Munyan ’06.  Like he did for so many others, Mr. Hollander helped foster Elizabeth’s love of history, and she continued on to be a history major in college.

Kelsey (Butler) Fatsi ’04, also remembers Mr. Hollander giving her class creative freedom, with memorable lessons that included songwriting and rapping. One song in particular—"Becky's Hitman Agency"—lives on 20 years later. Even Kelsey’s children know the words!

Orchard House alumnae also remember Mr. Hollander for his trademark Canadian accent, his creative and engaging teaching style, and his love of a good practical joke. Beyond the memorable lessons, many recall the steady support he offered during the often turbulent middle school years. “He was the one who I felt really prepared me for high school and beyond. He has the ability to see each girl’s strengths and potential and help them recognize that within themselves,” shares Phoebe Samet ’11. Abby Zinsser ’12 echoes that sentiment, remembering how Mr. Hollander was always there when her classmates needed support: “His calm presence was definitely needed sometimes in the sea of chaos that is middle school girls!” For Caleigh (Reid) Barnett ’05, Mr. Hollander was one of her class’s favorite teachers. “He kept us grounded while allowing us to be ourselves. We were a very opinionated and outspoken group, and he was a safe space for us to feel free to explore those parts of ourselves.”

Other former students credit Mr. Hollander with inspiring them to become educators themselves, especially in the field of history, carrying forward his legacy of curiosity, compassion, and critical thinking. “I think the lessons he taught us and the questions he made us grapple with formed the foundation of my love for the humanities,” says Rosie Reavey-Gilbert ’17.

This year, in honor of Mr. Hollander’s 26th and final year at Orchard House, we’re celebrating his incredible legacy with a campaign to support The Pearl Fund, our Tuition Assistance Endowment. Mr. Hollander elected for the Orchard House community to honor his legacy by raising funds for tuition assistance because he deeply believes in the transformative power of an Orchard House education and its ability to open doors. In celebration of Mr. Hollander’s incredible contributions to the school and in recognition of his lasting impact, we are proud to launch the Taylor Hollander Campaign for The Pearl Fund.

Formerly known as the Richard L. and Eugenia Williams Endowed Scholarship Fund—in honor of the parents of the founding Head of School, Nancy Davies—the endowment is now renewed as The Pearl Fund, honoring the resiliency, strength, and brilliance of Orchard House girls and women. Like the gems for which it is named, The Pearl Fund reflects the diversity, luminosity, and enduring legacy of our students that will be carried forward.

By providing need-based tuition assistance, The Pearl Fund opens doors for students from a wide range of backgrounds to grow, thrive, and lead at OHMS. With continued community support, this endowment will serve as a lasting resource, empowering generations of Orchard House students for the next 26 years and beyond to experience the nurturing, creative, and engaging learning environment that Mr. Hollander helped shape.

The Pearl Fund is essential to sustaining a vibrant, dynamic school community. Your gift ensures that our student body reflects the richness of our community while advancing our mission to educate and inspire middle school girls to become confident, curious, and capable young people.