Transgender men and women have lived openly for decades in America. Most of them transitioned before it was remotely acceptable to the wider culture—and so made possible the social transformation in gender identity that we are seeing today. The three women and two men on these pages lived much of their lives as one sex and then, along with thousands of others, have lived long, accomplished (and dangerous) lives as another. They are a comment on the abiding nature of the human impulse to change sexual identity (at a moment when it's almost regarded as a fad) and also emblematic of those who did so when it was so much harder.

Jamison Green, 66

Delphine Diallo for Esquire

Speaker and consultant in San Francisco; President, World Professional Association for Transgender Health; Author of Becoming a Visible Man. Transitioned in 1988.

"I have a couple of theories about the fascination with male-to-female people, and the first one is: We are such a paternalistic and male-focused culture that a man willing to cut off his dick is sort of fascinating to people. But then if a woman wants to become a man—well, that's expected. Why wouldn't a woman want to be a man? I really do think it's just that stupidly basic. For a long time, the official statistic was that one in thirty thousand men would be a male-to-female transsexual and one in a hundred thousand women would become a female-to-male transsexual, though I don't think that's true. What happens is a lot of female-to-male people historically didn't get the genital reconstruction, so they wouldn't get counted. The technology wasn't there yet, and it was very expensive. It wasn't until I was in my mid-thirties that I even saw someone who went through [female-to-male reassignment surgery]. I finally realized that it was possible, and what pushed me over the line [to begin the transition] was having kids. It was the eighties, when the world saw me as a masculine woman, and my partner and I were part of the lesbian baby boom. We were just thrilled to have this little baby girl that my partner gave birth to, and we had gone to the sperm bank to get a donor that resembled me as much as possible. We had this wonderful little baby girl who started to call me Daddy. Then when we decided we wanted a second child, I thought: How am I going to deal with a son? How can I get him to see who I am? That was what pushed me over the line, and I started the medical transition in the fall of 1988. Nobody noticed me anymore. I was just a guy walking down the street, and the energy that I had always had to use thinking about how other people were responding to me, all of it got redirected in ways that were much more productive."

Christina Kahrl, 47

Delphine Diallo for Esquire

Writer and editor for ESPN.com in Chicago; Cofounder of the Baseball Prospectus. Transitioned in 2002.

"A benefit and a hazard of being trans is you can end up talking about being trans all the time, which can become kind of self-alienating. I'm visibly trans, I am out as trans, there was no way I was ever gonna hide being trans, but I'm not talking about being trans unless people wanna talk about it. For me, I preferred to focus on the things that I had in common with others. I always joke that sports is the ultimate social lubricant: It's the harmless subject; it's the thing that almost everybody has some facility with. Which, if you're at the ballpark, we're all talking about the ballgame. When I go into a Major League Baseball locker room, I'm just another schlub with a mic. And then that ends up being something of a transgressive act, because people realize: 'I met a trans person, and they're kind of like me.' This is an awesome moment in history, but it's also kind of a very transient moment. Making sure that trans people get all the same benefits of citizenship in this country, that's something that we will be working for lifetime after lifetime. Trans people, we don't get a blow-up-the-Death-Star moment. We're not going to get everything we need all at once. It's going to be a long haul."

Renée Richards, 81

Delphine Diallo for Esquire

Ophthalmologist in New York; Former tennis player And coach; Plaintiff In Landmark Richards V. Usta court ruling, which allowed her to compete professionally as a woman in the U. S. Open; Author of the memoir Spy Night & Other Memories. Transitioned in 1975.

"In my day, of course, everything was done secretly and quietly, and if somebody went through the transformation, they did it privately. It was called 'woodworking': You merged into the woodwork after your transformation and you tried to lead a new life without people knowing what your previous life had been. And that's what I tried to do. I changed my name, I moved three thousand miles away, I started my new life. I was taken care of by my friends and by my employer, who took me on as an assistant ophthalmologist. I tried to merge into the woodwork, and my undoing came when I played in a tennis tournament in California.

"I am mystified to this day by the celebrity part of [being transgender]—with Chaz Bono and now Caitlyn Jenner, and people going on television announcing that this week I'm Christopher and next week I will be Christine. These were things beyond my imagination when I was trying to become accepted as a woman and I was found out and became a public figure. I never wanted to be considered somebody who was a trans-something. I've had a wonderful life, and I can't complain, and I happily spent forty years as a man and then happily forty years as a woman. But would I wish I would never have been born a transsexual or transgender? Yes. I don't wish being a transgender individual on anybody. The transgender community gets battered on both ends. They get battered by society from people who are hostile to them, and they need the protection of the law against violence and assault, and they get battered on the end of their own families, a lot of whom don't accept them and don't understand them. The work that needs to be done is primarily societal and legal, but from my standpoint as a scientist, as a physician, I would love to know whether there is some prenatal or hormonal or genetic preconditions that set it up for someone to announce when they're only two years old that they are a girl rather than a boy. If you could prevent the condition from ever getting started, that would be desirable. I don't like the world of yellows and browns and grays. I like the world of blue and pink. I think that the spice of life is the fact that there are men and women. And I think that if there could be no transgenders in the next one hundred years, I would go for it."

Kylar Broadus, 52

Delphine Diallo for Esquire

Attorney and college professor in Washington, D. C.; Cofounder and executive director, The Trans People of Color Coalition. Transitioned in 1994.

"I grew up in what we called the buckle of the Bible Belt, and I prayed every day after school, asking God to fix me. I never understood why people related to me in a female sense—I've always been a man, I've never thought different in my head. Until the Internet took off, [transgender] people felt they were alone, in their own little silo, and really most people thought they were mentally ill, because that's what transgenderism was considered: a mental illness. My folks—meaning brown and black folks—have traditionally transitioned much earlier in life, and we face the stigmatism of having transitioned early as well as our race and ethnicity. Those barriers are hard to overcome in this society. Even though I was older doing the transition, it was awkward for me in corporate America. The mid '90s, [gender identity] just wasn't anything to be talked about, and I was a go-getter, I wanted to be top in the corporation, and I couldn't be that being in the position I was in. Being me was a problem, and when I lost my job and went job hunting, as soon as they found out who I was, nobody was trying to give me a job. I never thought I would live beyond the age of thirty-two or thirty-three. Because being trans, living a trans life, is very difficult, and my life has been in danger several times. Although we now see more trans feminine people being killed, if you're identified as any kind of trans, anywhere, and people don't like you, you're going to be killed. We've made tons of strides, but let's not be fooled—we've only broken some of the barriers."

Marci Bowers, 57

Delphine Diallo for Esquire

Gynecologial surgeon in Burlingame, California; Pioneering sexual-reassignment surgeon. Transitioned in 1996.

"I took out extra life insurance when I started doing these surgeries because I had three young kids. We had a bomb threat [where I practiced] in Colorado, and I had this fear that people on the extremes might see us as some sort of threat to society. All the people coming up today, and probably even Caitlyn: She'll probably be a wonderful spokesperson, and she is bringing visibility to the community, but all due respect, if she had done this twelve years ago, I'd have even more respect for her. It was so difficult back then. She and many of the others who come out today, they do so much more easily—they stand on the shoulders of all of us who went earlier. The standard of care in the 1970s, it was like a witness-relocation program. People were forced to divorce, they had to avow themselves to be exclusively heterosexual, and in general people were required to leave their area. In fact, when I went for my second opinion [prior to sexual-reassignment surgery], the doctor was kind of shocked: 'You're gonna leave, aren't you? You need to start over.' This was a psychiatrist who was very well known, and I was just floored. I said, 'No. In fact, I'm gonna stay with my family [a wife and three children].' In my first few years of practice [in Colorado in the early 2000s], I used to have women [patients] who just disappeared and erased everything. People used to burn their own photos, and now I rarely see that—there's family and intimacy support that just wasn't there not very long ago. It's exciting to see all sorts of people proudly standing out, but people often forget history. It wasn't very long ago that Berlin, Germany, was the most liberal place on earth as far as LGBT issues—it's where the modern transgender movement, the world's first transgender surgery, all that happened in pre–World War II Berlin. And when Adolf Hitler came to power, the LGBT community was singled out even before the Jewish community, hence the Pink Triangle. That's my fear: If you fly too high, there can be backlash. I don't think it's gonna happen, though. I'm an optimist."

Richard Dorment Richard Dorment is the editor-in-chief of Men’s Health.

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