Springside Chestnut Hill Academy’s Upper School students participated in their last “Moment of Understanding” of this school year recently. These Moments of Understanding are an impactful part of SCH’s “Diversity, Equity, and Inclusion” curriculum. They aim to provide windows into the experiences of others, as well as mirrors for some members of our community. They equip students with information, as well as the time and space to participate in conversations and digest these topics that directly affect them no matter how they identify. 

In a year with little allowance for an outside speaker to come into the classroom, Schuyler Bailar joined Upper School advisories via Zoom to recount his story about coming to understand his gender identity and subsequently becoming the first openly transgender athlete to compete in any sport on an NCAA Division 1 men’s team.

Schuyler’s choice – to be true to himself – has been historic. His story has been internationally recognized through thousands of media outlets from The Washington Post and 60 Minutes, and The Ellen Show. MTV cited his story in their list of “2015’s Best Moments for the Trans Community”. In 2019, Schuyler was awarded the prestigious Harvard Athletics Director’s Award – granted only to 7 others at Harvard – for outstanding contributions to Athletics through education. 

Bailar captivated his remote audience with his words and energy.

“Your identity never has to hold you back,” he said, clarifying that this holds true no matter which identities we hold.

Bailar spoke in-depth about what it was like to face depression and body dysmorphia, and how he coped with being the first trans person on the Harvard swim team. He reinforced, “Other people’s hatred, words, and feelings do not define me. [In those difficult moments] I created the necessary space between myself and my truth in order to move forward.”

Devoted to educating people about what it means to be trans, Bailar welcomed questions and opened it up for all SCHers to approach the Zoom camera and ask in real-time.  

After his talk and Q & A, students were invited to reflect with each other about Bailar’s journey, and the school’s Student Facilitators encouraged their peers to unpack the heavy feelings, definitions, categories, and moment(s) that may directly affect them in this pivotal time. In these guided discussions, students engaged in conversation that transcended education about the LGBTQ+ spectrum and pushed students to consider other instances of how we all struggle to be true to ourselves.

Bailar’s website offers various resources for those interested in learning more: https://pinkmantaray.com/

Karen Tracy is Director of Communications at Chestnut Hill Academy