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We featured the following story in the spring 2019 issue of Georgetown Days magazine just after Schuyler Bailer ’14 finished his national speaking tour (page 40).
Grateful for the Journey
The mission of Georgetown Day School reads like a description of lifer Schuyler Bailar’s experience at GDS and his advocacy work since graduating—and transitioning—in 2014. Schuyler, a Harvard graduate and the first openly transgender athlete to compete in any sport on an NCAA Division I men’s team, carries on the school’s work of honoring the integrity and worth of each individual within a diverse community.

In a recent interview following his 26-city speaking tour and the start of a new job in Seattle, Schuyler spoke about his gratitude for his GDS journey and his pride in who he is today.
Supportive Educational Atmosphere

Schuyler began at GDS in (recently retired) pre-K/Kindergarten teacher Joanna Phinney’s classroom. Though Schuyler was assigned female at birth, he spent most of his Lower/Middle School experience presenting and being (initially) read as male, with “short hair and canvas shorts.” When he disclosed he was "supposed to be a girl," peers, parents, and teachers then saw him as "tomboy."

“I think about how hard [P.E. teacher Peg Schultz] tried to get me to be involved in recess sports,” he recalled of Lower School. “I wanted to play football with the boys. People [at that time] knew I was supposed to be a girl, and nobody would pass me the ball or pick me for a team. Peg went up to them and said, ‘You will include people who are not the same gender as you. You have to include girls—you can't not include them, you can't not pass to them. You will include Schuyler in this game.’ That meant a lot to me.”

Schuyler’s journey through Lower and Middle School was populated with supportive teachers, like Joanna and Peg, who first helped him find comfort in authenticity—even in the boy-presenting girlhood he was experiencing at the time—and grow as an athlete and student. In so many of the examples he shared, it becomes evident that even small moments have lasting impact.

“I was aware that I was weird in how I presented my gender, in how I interacted [with peers], and in how I interacted with teachers,” Schuyler explained. “Yet, my interactions with teachers made me feel like that was okay. Everybody had a little stumble, usually the first week, because they'd call me male pronouns, and we'd have to tell them to call me female pronouns.” Schuyler chuckled and added, “I've had a lot of experience correcting people on pronouns in every single way possible.” 

Schuyler, who is Korean American, was competing in swim meets by age seven and by the end of Lower School was already competing in the Junior Olympics. By the end of 9th grade, Schuyler was one of the top 20 breast-stroke swimmers in the country. 

While still in Middle School, Schuyler felt connected to teachers, including [former math teacher] Carol Berenson, [former English teacher] Clay Roberson, and [former science and math teacher] Lida Salmani, for the ways they honored his authentic, if not untypical, presence. “Carol was my Algebra teacher, and I remember feeling so safe in her classroom. She was ready to be there for any of the weirdness, she didn't make me feel like I had to be somebody else, and she didn't call me the wrong pronouns. We had a lot of conversations about sports together, which resonated with me as an athlete. Clay was the first person to truly teach me how to write, and to show me that I love writing.* And Lida was such a cheerleader of my academics. That allowed me to really blossom academically.”

The meaningful relationships Schuyler developed with his many caring teachers at GDS served him well as a student, but also laid a foundation of confidence that continues to serve him well as an advocate today. He said, “I've said this often—many of my GDS teachers were better than my professors at Harvard. I had far deeper relationships with my teachers at GDS, which is important because those relationships are what drove me to feel confident when I couldn't feel connected to my peers.”

Concern for Others

So much changed for Schuyler in High School, where he experimented with hyper feminizing his gender expression, with dresses and long hair, and self-identified as lesbian. (Schuyler is a straight transgender man, who, as a woman-identifying High School Junior, knew he was attracted to women. Thus, gay was the descriptive term for his sexuality). Schuyler's struggles with body image and self-esteem led to disordered eating and self-harm. The only two constants during that time were Schuler’s strengths, as a student and as an athlete. Then, at the end of summer before junior year of High School, Schuyler broke his back in a cycling accident. 

“If you asked my parents how High School went, they’d tell you it was hell,” Schuyler said. “For them it was like I broke my back and suddenly I turned into a High School nightmare. A mental health nightmare. And that's how it felt to me, too. All of a sudden, my life was falling apart.”

With his identity as an athlete in peril that year, Schuyler clung to the only other piece of his identity that felt stable: academics. Yet, while the accolades continued coming, and even when he returned to the pool and began to make waves again nationally, the mental health crisis continued. Schuyler won all three DC 100-yard breaststroke championships, qualified as an All-American, and set a National Age-Group record with his 400-yard medley team at the 2013 National Championships. Schuyler was heavily recruited by top university athletic programs, including by the women’s swim team at Harvard. And he was miserable, a danger to himself.

Schuyler said, “I started winning things, I started getting into college, I continued getting good grades, and nothing meant anything to me. They were checkboxes that I felt like I had to check or I would lose my identity, too. I had no other way of making sense of my identity, so I was ‘really good swimmer’ and ‘really good student.’ It’s important not to conflate productivity with any sort of feeling of togetherness in oneself. Grades, drivers license, getting into school, medals, winning things, whatever. If you're not feeding yourself, your soul, and who you are, those things are going to mean nothing. I wasn't feeding myself well. I wasn't safe most of the time. There were so many issues that were absolutely and obviously detracting from my ability to perform.”

Strength of Character

“Most people saw me as this uber-confident, can-get-things-done person” Schuyler said. “Suddenly in High School, I was not confident and wasn't getting things done. Up until that point, I had led the way for most of my life and [was able to say], ‘This is what I need. This is what I want.’ That’s why I think those [High School] years were so much more difficult. I stopped leading the way. I stopped being able to tell my parents what I needed, and instead, I was just a pile of anger and misery. And I think that terrified them, too. I know it really scared my brother.”  

Schuyler went to a lot of different therapists but nothing was working. He confided in [former HS math teacher] KC Lawler. “I felt safe with her. She was kind of quirky, and I liked that. I felt like I could really share with her.”

Schuyler took a gap year after graduating and entered residential treatment. During that time, it became clear that his issues were with gender identity. He came out as transgender. Schuyler’s choice that followed not only catapulted him into the national spotlight, but also echoed the strength of character that GDS seeks to foster. Schuyler chose “to transition and be authentic to himself,” rather than continue on the women’s team as a possible NCAA champion, “accepting the consequences and challenges it would entail.”

Schuyler’s story reached millions online and via broadcast media, including 60 Minutes, The Washington Post, and The Ellen Show—an appearance which has been viewed nearly 350 million times. The Harvard women’s team coach coordinated an offer from the coach of the men’s team to compete as a man. After declining at first, Schuyler went on to compete all four years on the winningest Harvard men’s swim team in 50 years. In 2019, he was awarded the seventh Harvard Athletic Director’s Award, an honor not given annually but only when an athlete has made extraordinary contributions to athletics through education.

As his personal journey as a transgender man and his advocacy work on a national stage began, Schuyler relied upon the communication skills and confidence developed at GDS. “People ask me all the time how I learned to be a public speaker,” said Schuyler, whose on-stage presence is marked by candor, wisdom, and humor. “I credit GDS with a lot of that ability. In academics, I was asked regularly to present what I was learning, whether that was traveling biographies in 5th grade, our books that we wrote in 1st grade, or the Greek play in 4th grade. There was always something we had to do that was presentation focused, and I always got excited about those. I think [those opportunities] aligned with my confidence and taught me how to present myself on a stage or present a message.”

Laying the Foundation

“My favorite part of the work that I do is interacting with young people,” Schuyler said. “Specifically, I love chatting with kindergarten through 8th grade students. Kids are much better at just being who they are first. They are in tune with their emotions, and they're ready to engage with me. As you get older, you learn to inhibit your emotions. You become a bit robotic in how you talk about topics about which you are worried you might be wrong.” 

According to Schuyler, conversations about gender, specifically trans-related topics, are challenging ones that leave many adults too worried about being wrong to articulate the pertinent questions, but a Middle School-aged child will ask it flat out, learn, and move forward. Schuyler said, “As we grow up, we learn who to be, as opposed to just learning how to express who we are.” For most of his journey, Schuyler found that in trying to “learn who to be,” he moved further and further away from his authentic self. And yet, while every identity journey—and specifically a transgender one—will be different, Schuyler deeply treasures all those parts of his story. 

“I am very thankful for my journey and for everything that I went through,” Schuyler said. “I wouldn't have told you that at the time, absolutely, but I love who I am today. Who I am today is absolutely a compilation of who I ever was and all the things I went through. I don't want those to disappear because they are absolutely parts of who I am. I tell my mom all the time that the womanhood that I experienced is an important part of who I am. She’s absolutely the one who raised a lot of that womanhood in me, and I believe that I am the man that I am today largely as a result of the womanhood that my mom taught me.” 

This fall, Schuyler gave the keynote address at the National Association of Independent Schools’s Student Diversity Leadership Conference (SDLC), attended by nearly 1,800 High School students, including six (the maximum permitted by SDLC) from GDS. It was his first trip to the conference. In High School, he’d been severely depressed, trapped in an eating disorder, and terrified of being outed. Sharing his truth onstage in front of all the students, Schuyler grinned broadly, felt the sting of joyful tears, and thought, “This is proof that it does get better.”

“I'll be back on [the MacArthur] campus on April 17 [for the All-Alumni Reunion Weekend],” Schuyler promised. “GDS is absolutely a home of mine. I had a lot of allies at GDS so I'm kind of getting teary talking about it. I'm very thankful for the school and for the time that I spent there. I'm sure the new school is going to be great, but I feel like that is where my childhood was. I'm definitely going to cry that weekend.”


*Schuyler’s short story “Catch Pull Drive” was selected for inclusion in an anthology of young adult literature published in 2018 by the We Need Diverse Books organization.

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