She was the quintessential recruit for the women’s swimming team at Harvard University: a nimble breaststroker with a fierce work ethic and sharp intellect. But when Schuyler Bailar jumps into the school’s Olympic-size pool this fall, he instead will be a member of the men’s team, the first openly transgender collegiate swimmer in U.S. history.

Emerging from a tortuous year of self-reckoning and a lifelong quest to feel comfortable in his own skin, Bailar, 19, will be navigating far more than the usual freshman challenges; he also will be a pioneer and role model as society openly grapples with shifting mores about traditional male/­female gender lines.

Bailar, a 5-foot-8, 170-pound athlete, struggled for years through depression, self-harm, suicidal thoughts, eating disorders and a broken back. As a girl, Bailar competed at a high level — setting a national relay record on a girls’ team with future Olympic champion Katie Ledecky — but she was confused and pained.

“I was a very lost kid who didn’t understand why I spent my entire childhood being a boy but not really, one who focused intently on studies and swimming to distract from anything that came up in my mind,” said Bailar, who grew up in Virginia and attended the private Georgetown Day School in the District. “I was caught between two worlds.”

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