Transgender Athlete Schuyler Bailar Addresses Student Assembly

Schuyler Bailar has a ready laugh, an easygoing manner, and the physical ease and grace of a former star college athlete. He also has a remarkable story to tell, which he shared at an all-school meeting earlier this week: Bailar was the first NCAA Division I swimmer to come out as transgender.
In an hour-long presentation, much of it in the form of a Q&A session, Bailar kept students riveted as he told his story and invited students to ask questions, however difficult or uncomfortable those questions might feel. Assigned female at birth, he was candid about the struggles and the triumphs that accompanied his journey to embracing his identity as a man. 
 
Bailar’s visit to Rivers was part of a year-long DEI focus on “Gender: Beyond the Binary.” Other events have included presentations for parents, students, and faculty by teacher, author, and transgender advocate Alex Myers; on April 13 (rescheduled from February 16), Drs. Jeremi Moss Carswell P’22, ’24 and John McKenna will visit campus for a parent/caregiver session on supporting transgender, non-binary, and gender-diverse youth.
 
Bailar shared a slideshow of family photos from his childhood and teen years. He was humorously self-deprecating about his youthful fashion choices—zip-off cargo shorts, glasses with transitional lenses, a Justin Bieber haircut—but became more serious when describing the pressures to conform that accompanied adolescence. “In high school, I decided I needed to fit in,” he said. He showed a few slides of his younger self wearing dresses and makeup and sporting long, silky hair—unmistakably female and, he said, unmistakably miserable.
 
Through it all, there was swimming, the sport he pursued with a passion. He was talented enough to attract recruiters from a number of Ivy League colleges; he ended up choosing Harvard. But after high school, he could no longer deny the conflicts he felt within, and before heading to college, he spent several months at a residential facility to work on his mental health. His presenting issue was an eating disorder, but before the gap year ended, he had figured out that he was transgender.
 
That’s how his personal journey became a public one. With the support of Harvard’s swimming coaches, Bailar made the difficult decision to compete on the men’s team, despite having been recruited for the women’s team. It was a groundbreaking move that turned his life in the direction of activism and advocacy for inclusion, body acceptance, and mental health.
 
At Monday’s presentation at Rivers, Bailar was disarmingly candid about his experiences. He had top surgery—a mastectomy—early on, and the scars were clearly visible when he wore a swimsuit. His teammates joked that he should pass it off as a shark-bite injury. “The funny thing was one, that they said it, and two, that it actually worked,” said Bailar.
 
During the Q&A session, a student asked if teammates had generally been accepting. Bailar reported that they were, for the most part—but not unanimously. He learned that one teammate whom he’d considered a friend made hurtful remarks behind his back. His response? “It sounds silly, but I taped a big piece of paper to the wall and wrote on it, over and over, ‘His words do not define me,’” said Bailar.
 
Bailar urged students to share any and all questions, and they responded in kind, asking about Lia Thomas, a transgender woman who currently swims at Penn, about advice for people who are coming out, about locker room culture, about the particular cultural challenges faced by Bailar, who is half Korean. He pulled a male student seated in the front row up on stage to demonstrate how readily boys know how and when to proffer a bro-hug handshake—something Bailar said he had to master when he transitioned. 
 
While on campus, Bailar also visited a ninth-grade English class, had lunch with the Middle School book club (whose members had read Bailar’s middle-grade novel, Obie is Man Enough, beforehand), and met with the Upper School LGBTQ+ affinity group. Students debriefed the presentation in their advisory groups, and teachers reported that they were deeply engaged and thoughtful, with one senior remarking that Bailar was “the best speaker we’ve ever had.”
 
Bailar’s journey has been unique, but it also has elements of the universal, with takeaways for all young people as they navigate the waters of growing up and understanding their truest selves. In words that seemed to resonate broadly, he told the students at the assembly: “Your identity doesn’t ever have to hold you back from pursuing your passion.”
Back
333 Winter Street Weston, MA 02493
P: 781.235.9300 F: 781.239.3614