When he coached the boys’ cross-country team at a private boarding school in Rhode Island, Alex Myers would sometimes outpace the students to push them to run harder.
“Look,” he’d say, needling, “you’re getting beaten by a 30-year-old transsexual.”
Myers, now 35, has been living as a man for half his life, having come out as transgender before his senior year at Phillips Exeter Academy. Through adolescence, he was a tomboyish girl named Alice Myers.
Now a first-time novelist, Myers is using the historical tale of a distant ancestor, the Revolutionary War figure Deborah Sampson, as a literary parallel to his own determination to live as a man. Sampson, a native of Plympton 45 miles south of Boston, disguised herself as a man and served in the Continental Army during the war for independence.
Advertisement
“Revolutionary,” Myers’s debut novel, imagines Sampson’s struggle to keep her secret and her will to live as she chose. Frustrated by her indentured servitude and the social and professional limitations she faced as a woman at the time, the tall young woman cut her hair and dressed as a young man, binding her breasts with strips of cloth, and enlisted.
As a child, the writer traveled each Patriots Day with his family from their home in Paris, Maine, to visit his grandmother, a member of the Mayflower Society who took them to the annual reenactment of the Battles of Lexington and Concord.
“That was right at my level,” recalls Myers, speaking from his home in Washington, D.C., where he moved last year, “all those guys dressed in uniform, firing muskets.” His grandmother’s stories about their famous ancestor, the woman who fought as a man during the Revolutionary War, grew in significance for Myers as he matured.
As a little girl, when asked what she wanted to be when she grew up, Myers recalls that he usually answered, “I want to be a boy.
Advertisement
“I just didn’t know it was possible,” he says.
During the summer after his junior year at Exeter, Myers joined BAGLY, the Boston Alliance of Gay Lesbian Bisexual Transgender Youth. On a “no booze” cruise for teenagers, he met an aspiring singer named Ilona Tipp.

She introduced herself by apologizing in advance for her rudeness: “I’ve been trying to figure out if you’re a man or woman.”
“You know, so have I,” Myers replied.
Later that summer, he called school officials at Exeter to let them know that he would be returning that fall as a young man. “I asked them to call me ‘he,’ ” Myers says. “I went to class in a coat and tie. Some people, both teachers and students, were appalled and couldn’t deal. Some people didn’t recognize me, and the new students just thought I was a guy.”
Myers went on to become the first openly transgender student, he believes, at Harvard, where he helped draft changes to the University’s nondiscrimination clause in the mid-1990s
“You check a box on the housing forms, and he literally was outside that box,” recalled Kristin Scheible, a Bard College professor who was a resident tutor at Harvard’s Dudley House. As a tutor, Scheible specialized in sexual assault and harassment incidents, and she got to know Myers well.

“Alex was very much a vocal proponent about changing the language in official Harvard documents to be more inclusive,” said Scheible.
Advertisement
After Harvard, Myers began teaching at schools around New England; he married Tipp in 2002. They were first wed in a same-sex civil union that took place in Vermont. Myers later petitioned the state of Maine to officially change his birth certificate to read “male”; the couple had their civil union annulled and were remarried in 2010 as man and woman.
Unlike some who identify as transsexual (Myers uses that term and transgender interchangeably), he has not had any surgery and has no intention to do so. Myers says he takes testosterone, which has lowered his voice.
He’s happy to use his own experience to educate people on transgender issues. “I’m not a political activist,” he says, “but I love to do it. I think Deborah’s story is a great way to illustrate some of the more subtle components.”
“From the beginning, he was a solid, poised, mature teen,” says Grace Sterling Stowell, BAGLY’s longtime executive director. That Myers would write a book based on a transgender role model “doesn’t surprise me at all,” she says.
“It’s important to tell the history of transgender folks and folks on the transgender spectrum,” says Stowell. “It’s important for transgender people to see that, to know we’ve always been here.”

Even before he was old enough to fully understand his gender identity, Myers was used to explaining his differences. His father’s side of the family is Jewish; in small-town Maine, where there were few Jews, “that was kind of like being transgender, as you can imagine,” he says. “I used to teach the other kids what Hanukkah was.
Advertisement
“Being the only Jewish family in Paris probably started me being an evangelist for marginalized groups.”
Maine was a unique place to grow up, he says. “I like to say I was a feral child. I’d come home off the bus, and my mother would give me some Oreos and throw me out the back door, and say, ‘See you at dinner time.’ There were fields, apple orchards, woods. You could ride your bike anywhere. It was the 1950s.”
On one level, gender assignments were more fluid than elsewhere: “Women were inclined to wear flannel shirts and go cut wood like men. It was a great place to be a tomboy.” But Alice’s budding attraction to women and her feeling that she was more a boy than a girl — “lesbian didn’t feel quite right,” Myers says — made her acutely aware that her rural hometown harbored its share of homophobia.
In “Revolutionary,” when a fellow soldier tells the disguised Deborah she seems “contemplative, a bit more mild than the others,” Myers imagines her surprise: The words “weren’t insulting, exactly, but she had never before been called mild — quite the contrary, in fact. Perhaps she’d discovered the corollary of her transformation: a cantankerous woman equaled a mild man.”

Deborah Sampson ultimately married and had three children, after living as a man for a time after the war. (Myers spells his ancestor’s name Samson, as she did during her lifetime, he says; subsequent generations of the family have spelled it Sampson.) Her friend Paul Revere petitioned on her behalf for a military pension, as her male counterparts received. The town of Sharon, where Sampson died at age 66 in 1827, has several landmarks named for her.
Advertisement
Amateur historian Steve Connolly, who made a miniseries about Sampson for community television, said Myers’s book is “spot on” in its depiction of a underappreciated historical figure.
“She lived in very patriarchal times, and she fought against those old rules,” he said.
In 1797 Sampson published a memoir of her war experience called “The Female Review.” It’s highly unreliable, according to Myers.
“She lies like you wouldn’t believe,” he says, placing herself, for instance, at the Battle of Yorktown, a full year before she signed on.
“But it’s fascinating — that’s the story she wanted to tell . . . What Deborah wanted more than anything was to be self-governing. Her number one driving goal was not to be a man, but to be free, I think.”
James Sullivan can be reached at jamesgsullivan@gmail.com. Follow him on Twitter @sullivanjames.