A Letter from Tom Gilder

A Letter From

Tom Gilder

This Summer marked the completion of my 35th year as Head of School and my 40th year at Windward. As I walk around campus and see the newly constructed Academic Hub, the future site of our Innovation & Arts Center, and the many happy faces of our students, faculty, and staff, I can only think how lucky I am to have a front row seat to so much forward progress these last four decades.

Though the School has grown exponentially since I began my career here in 1982, Windward’s core values continue to influence every aspect of our past, present, and future. Cultivating a sense of belonging, one in which every Windward community member feels seen, heard, and supported, continues to be an integral part of our School experience. We believe strongly that being one’s true self is the clearest path to sustained educational success, which is why we’ve made belonging the next essential pillar of our DEIB initiatives going forward. Whether it’s being greeted by one of our Divisional team members as soon as you step onto campus or sharing a personal anecdote with a familiar face on the Bridge, Windward will forever work to provide a place of acceptance and inclusion for all community members.

The 2021-22 school year signified a historic 50 year milestone for Windward. Half a century of advanced academics, specialized programs, student retreats, theater performances, music concerts, athletic games, and life long friendships, born from a place in which we feel seen and loved for exactly who we are. And our dedicated community of donors has been there to support us every step of the way.

More than ever, I am profoundly grateful for your commitment to our community. You’ve helped us navigate a global pandemic by supporting us in prioritizing the health, safety, and academic needs of our students—all while contributing to our Windward Fund and Innovation Campaign to ensure Windward maintains academic excellence as a premier educational institution. Your continued support and generosity has enabled us to uphold our educational promise of providing students a dynamic learning environment that encourages critical thinking and sparks curiosity and exploration. We recognize your meaningful contributions in our 2021-22 Donor Impact Report, beginning on page 43.

As we look ahead into Windward’s future, we are thrilled to envision the new footprint the campus will take on as we break ground on the Innovation & Arts Center and Milken Family Community Gathering Plaza next year. The Center will possess extraordinary flexibility to support a wide range of presentation formats that are on par with well-known professional venues and provide a space for discovery and creativity. The Milken Family Community Gathering Plaza, located between the two bridges, will allow Windward to create outdoor space for learning, collaboration, presentations, performances, and the opportunity to add additional greenspace to our campus.

I hope you enjoy reading about the exceptional achievements of our student body and the heartfelt generosity of our community in the pages ahead. I thank you again for joining me on this journey and witnessing such a transformative chapter in Windward’s history.

Tom Gilder

HEAD OF SCHOOL