Schuyler Bailar became the 1st openly transgender NCAA Division 1 swimmer while at Harvard. Now, he’s written a book. 

“I wanted to provide real examples of what it looks like to support a trans person through their life.”

Schuyler Bailar holds a copy of his book, "Obie Is Man Enough." Courtesy of Schuyler Bailar

Schuyler Bailar made history when he was a student at Harvard University, becoming the first openly transgender NCAA Division 1 swimmer

Now, the outspoken advocate for transgender rights, body acceptance, and mental health, is adding “author” to his accomplishments. 

The Harvard graduate’s book for middle grade readers, “Obie Is Man Enough,” was published Sept. 7. A coming-of-age story, the book introduces readers to Obie, a trans middle school swimmer navigating life and his boyhood after his transition. 

Set in Watertown, Massachusetts, Bailar chronicles both the support the tween encounters on his journey and the bullying he experiences by his peers and adults. 


Bailar told he knew he didn’t want to create a perfect world for his protagonist. Rather he wanted to show in a realistic way the support trans kids can have from their communities, while representing the very real transphobia and bullying trans individuals experience in society.

“I know people who have experienced very similar things to Obie, having support and not having support,” he said. “But I really want non-trans readers to understand that this happens, and that it shouldn’t. And I think that comes through as you read, and you root for Obie. You’re like, ‘Yeah, that shouldn’t happen to Obie.’ And hopefully you can extrapolate — that shouldn’t happen to anybody.”

Below, Bailar shares more about his approach to writing the story, how he drew on his own experiences, and what he hopes readers will take away from his book. 

The conversation has been edited for clarity and length. Obviously there are similarities between you and Obie, between swimming, being set here in Greater Boston given your time at Harvard, being Korean American and having Catholic grandparents. But how much of Obie’s story and his experience reflect your own? 

Schuyler Bailar: Obie is fiction completely. The characters are made up … The way I’ve been characterizing Obie specifically is that he and the book are an ode to the boyhood I never had, that I wish that I could have had, in that Obie transitions much earlier, Obie is able to swim as himself from a younger age, he has friends who see him as him, he gets to navigate the world in his boyhood in a way that I didn’t get to do and that a lot of trans kids don’t get to do. But more and more are able to do that now that there are more resources, more availability, more awareness. 


I think there are similarities with the other characters as well … Pooch and Mikey are pieces of my teammates in college that I wished I’d had in grade school, but they’re not really specific people in my life. I would say that the most similar characters to real life are Obie’s grandparents. Obie’s Korean grandparents are probably almost exactly my grandparents — their history and their culture and the way they speak to me, all woven into a fake story from their real life … I set it in Boston or in Watertown because I wanted it to be something that I knew, but not my hometown. 

Why was it important to write the story in this way, given the similarities you were talking about, rather than writing your memoir or directly about your own experience? Why did you choose to focus on middle school/middle grade readers? Who did you think of yourself writing this for?

I didn’t write a memoir because I’m not ready to write a memoir. I have more life to live and more experiences to have before I want to write a memoir. I do want to write one, but I’m just not ready yet. So that’s the reason it’s not a memoir.

And then the other reason, why middle grade/why this story/why Obie/why all these similarities — the reason is right now, and for a while now, there’s a lot of attacks on trans kids. And we have resources, somewhat, not amazing resources, but there are resources out there for trans adults. There are ways for us to get access to hormones, to play in the rec leagues or sports leagues that we want — there are actually inclusive rules in a lot of elite level sports for trans folks. But right now, specifically in the past year, there’s been a record number of anti-transgender sports bills and anti-transgender health care bills all targeting children. We’ve had over 100 anti-transgender bills in sports and in health care, all targeting children. 


So I wanted this book to be a beacon of possibility both for trans kids and for adults who are working with kids, whether that be middle school teachers, educators, principals, to realize that trans kids are actually kids. They are not this demonized, crazy, mentally ill “other” that we can’t understand. Obie is a child who likes sandwiches, who argues with his brother, who grumbles about having to put shorts on instead of long pants, who likes to play with his friends, who’s a really good swimmer. He’s a whole human. And he’s transgender. 

I really wanted to humanize the trans experience, or a trans experience rather, because there’s no one trans experience. And hopefully the way the book is written you root for Obie. You want him to succeed. You hate when he experiences transphobia. You don’t like the people who are perpetuating the transphobia. At least that’s the goal, that you root for Obie even if you don’t know anything about trans people or maybe you don’t even like trans people. 

You describe some very distressing scenes of bullying and transphobia — both by adults and by kids — how did you approach writing and including those traumatic moments? You do include a warning at the start of the book — but why was it important for you to include those scenes and include them in the way you did, with the details and the words that are used?

They were difficult to write. I almost didn’t include them for one reason, and that’s because I didn’t want other trans kids to read them and have to re-experience the harm that they have experienced. But that’s actually why I kept it in as well. Because they experienced that harm, and I want people to know that it happens. 


The transphobia is included in there because it’s real, and this is something that a lot of trans kids have to experience, either to the same degree that Obie experiences it or worse. A lot of trans kids experience a lot of bullying both verbal and physical from everybody in their life. Their parents, their friends, school, teachers, doctors. And Obie actually is very lucky and very fortunate in many ways that he has supportive friends, that he has supportive family structure, that his doctors are supportive, and that he has access to gender affirming health care. He’s not in a state where he doesn’t get that. He has a lot of support, but there are also people who don’t support him and I wanted that actual dichotomy. I wanted to show that this is very real for a lot of people — and still, Obie is lucky. 

I want to ask you more about the supportive characters. In your author’s note, you say Obie is “one trans kid with a lot of support.” You include a lot of models for being an “upstander” versus a “bystander.” Can you talk about the importance of giving Obie those supports and what you hope readers — both kids and adults — can take away from those supportive characters, whether they’re part of the trans community or not? 

That’s drawn very directly from my life in many ways. I have parents who supported me, they didn’t throw me out. They understood as best they could and have supported my transition. I had coaches who did the same, and I had teachers who did the same. 

And from that example, I’ve seen it work in real life in that I’ve said, ‘Hey, these people support me — my teammates support me, my family supports me.’ And it encourages other people to do the same. It’s kind of like good peer pressure, if you will. It’s like, ‘Well, if the Harvard swim team can accept Schuyler, maybe it’s kind of normal to accept trans athletes. Maybe we can do that too, right?’ There’s absolutely a domino effect where people see people supporting me as a trans person, and they’re like, ‘Oh, OK. I can do that. I can do that too. That makes sense.’ …  I wanted to provide real examples of what it looks like to support a trans person through their life in a way also that doesn’t pull out their transness and say, ‘Oh, Obie I affirm your transness.’ Nobody does that. In the story, we have [Obie’s teammates] Mikey and Pooch who just let him live his life. And who are just supporting him when he goes on his first date and who just want him to be good in the pool. I just wanted that to be real examples — because they are. 

Schuyler Bailar graduated from Harvard in 2019. – Rose Lincoln/Harvard Staff Photographer

At the end, you include notes addressed to both cisgender and transgender readers. In some ways it felt to me like an acknowledgement and reminder for everyone that Obie’s story is just one story. Can you talk a little bit about the importance of emphasizing that message to every kind of reader?

Obie is a trans kid. And I am a trans person. I am a trans author. I am a trans athlete. And it’s really easy, especially when there is a limited amount of visibility already for us, to look at one person and say, ‘Oh, that’s the trans experience. That’s how it is for the trans people and all trans athletes.’


The reality is that no one person can ever accurately or comprehensively represent a group of people. I don’t know if I can even accurately represent myself to be honest with you. I’m a complex person. I can’t stand up in front of you and give you everything about myself. Obie is an attempt to give you a lot of pieces of myself, but it isn’t everything still. So I really want people to remember that when they read this story, it is one example of one trans kid by one trans person in an attempt to give you one story about a trans person. And yes you can extrapolate pieces of it. You can undersand what it means to be transgender, but also there’s lots of different ways people understand their own transness. 

So I really want it to be taken with openness and digested with that same kind of openness. That this is adding a perspective to my understanding of humanity. And mostly what I hope it adds is humanity to transness. I think we often get our humanity as trans people stripped from us, taken from us, challenged by other people in us. And I want Obie to be an example that trans people are human and we deserve that dignity of our own humanity. That I do think can be representative of all trans people. 

What would it have meant to you to read a book like this in middle school? What do you hope your book may provide to young trans readers? 

I want to believe that had I read a book like this as a kid it would have changed my life. And I think it would have. Honestly it would have. I can’t promise you anything because I can’t go back — I don’t know if it would have gotten through my thick head …  [But] I really think it would have changed my life because I think I would have read the book and been like, ‘Oh my God, that’s me.’ … I hope that for other people, trans kids, they see possibility. They don’t have to read it and see exactly themselves … I want them to see possibility of ‘Wow, even if I don’t fit in, even if I don’t see myself, Obie didn’t see himself, Obie didn’t have people around him, so maybe I can actually do my thing, too.’ 

Hope encourages connection — connection to self and connection to others. And for the non-trans readers, I hope it really reminds them that everybody deserves to be fought for — that even trans kids deserve love and acceptance. Especially trans kids right now deserve love and acceptance. I hope it reminds educators, parents, teachers, anybody who interfaces with kids that they should fight for trans kids just like they’d fight for any other kid — in fact maybe even more because trans kids are under attack right now.