The college freshman, who was originally recruited to the women's swim team and now competes for the men's team, chronicles his physical and emotional transition on social media.
Bailar speaks openly about the changes he's been through over the past few years – and the struggles he currently faces competing for the men's team.
"I know I made the right decision. But I think sometimes… I'm like 'Oh, I really wish I could compete as a girl. Because I want to win that race.' It's fun to win, and it's something that I worked really hard for. And, you know, I work the same amount. But now I'm working the same amount for 16th place, you know?" Bailar told CBS's Lesley Stahl on 60 Minutes.
He adds, "And that's okay. It's the way it is. And it's also a lot of fun. It has other kinds of glory in it… It's a glory that, like, fills me inside."
Bailar, who received an athletic scholarship to compete on the Harvard women's swim team in high school, came out as transgender during a gap year he took before heading off to college.
During that time, the 19-year-old underwent a double mastectomy to remove his breasts – the first step in his journey.
"I never knew I'd be able to unlearn parts of my body and what they meant – unlearn my breasts, teach myself and my body a new meaning, a real me. But it was possible," Schuyler wrote on Instagram after his surgery.
A year ago today. My top surgery. Changed my life. They say growing up is about unlearning all the things you've been taught that are not you so you can become you -- and this was a part of that unlearning. A family friend sent these balloons (right) for me and I cried for the second time that day. (First time right after I woke up and realized that my chest was flat.) I'm so blessed and thankful. To everyone who needs hope: there is always hope. I never knew I'd be able to unlearn parts of my body and what they meant -- unlearn my breasts, teach myself and my body a new meaning, a real me. But it was possible. It is possible for you. #ThrowbackThursday Photocreds: dad @1ghoti2ghoti
Harvard women's swim coach, Stephanie Morawski, agreed to allow Bailar to join her team this fall, citing the NCAA rule that allows an athlete that was born female, but identifies as male, to compete on a women's team, according to CBS.
But Morawski says she struggled thinking about Bailar existing on campus as a man, while competing in the pool as a woman – essentially living with a dual identity.
"…He wanted to reinvent himself as Bailar as a male, but was being held back by the athletic piece of it," Morawski told Stahl.
a l c h e m y - a seemingly magical process of transformation (@soul_alchemist411) #TransformationTuesday Left: March 9, 2015. The day before surgery. I was giggling and grinning and being silly as we took documentation pictures. I didn't hate myself; I loved myself, and I was ready for a change. You can love yourself and still want to change. Right: March 29, 2016. I have changed, and I am still me. I feel more aligned, and I still love myself.
Morawski met with men's swim coach, Kevin Tyrrell, and the two agreed that their recruit should be swimming for the men's team.
"I mean, it made sense, right? If you're happy being a male – and that's what you want to identify as, then it makes sense…" Tyrrell told Stahl.
Bailar started his collegiate career at Harvard this fall, swimming for the men's team as planned. He takes an NCAA-approved amount of testosterone to lower his voice and broaden his shoulders.
At a recent meet against Columbia University, Bailar – who recognizes "it's not realistic" for him to win right now – met his goal to beat one person in every race he swims.
"I’m really happy about it," he told Stahl.
Bed head turned my hair into curls last night wild hair for a wild boy Getting nervous for the show coming out tonight but I'm so surrounded by love and support that it doesn't matter what the response is. Last night the guys on my team (and of course the women's team, too) kept telling me how excited they are to watch and how proud they are of me and stuff and it just made me so happy and thankful and loved and known. I am so proud of how far I've come and the work I've done to get here; but I also know how lucky I am to have the opportunities and people in my life that I do. Thank you, world
In one of the teenager's recent Instagram posts, he thanks his Harvard teammates for their unyielding support.
"Last night the guys on my team (and of course the women's team, too) kept telling me how excited they are to watch and how proud they are of me and stuff and it just made me so happy and thankful and loved and known. I am so proud of how far I've come and the work I've done to get here; but I also know how lucky I am to have the opportunities and people in my life that I do. Thank you, world," he wrote on Sunday.