When Dianna Boileau showed up in Toronto court in 1963, the clerk asked the question she had asked herself for years.

“Are you male or female?”

In the silence, the reporters jotted details: Pink fingernails, pink lipstick. Black tunic dress. Tiny pearl earrings. Double identity. Man. Woman.

In 1960s Toronto, gender identity just wasn’t something people talked about. The first major story about a trans person had made international headlines a decade earlier: Christine Jorgensen, a 26-year-old New Yorker, was called a “man turned girl,” offered Hollywood roles and dubiously honoured by a footwear company that created a shoe for “daring tomboys.”

Dianna faced a world that hadn’t come very far since then: “Wearing dress, man remanded in car death,” one headline read. “Woman driver, 32, found to be male.”

In 1962, Dianna and her best friend, Rosemary, were driving on Hwy. 401 near Leslie St. when her car crashed into the guardrail. Her friend died, and Dianna was charged with dangerous driving and criminal negligence causing death. Police took her to a female lock-up, then a male lock-up, and finally the Don Jail, where inmates whistled the “Wedding March.” Word leaked to the press.

The trial ended with an acquittal, and Dianna, who had been living in Toronto for a few years, said she planned to stay. “There are an awful lot of understanding people here,” she said, not telling the press about the kids who found out where she worked and came to gawk at lunch, forcing her to hide in the bathroom.

With the death of her friend and end of her anonymity, she drank heavily, lost her job as a legal secretary and lived on unemployment insurance and cheap wine. In her sober moments, her desire to erase her male characteristics grew.

By 1970, Dianna was back in the headlines, anonymously, as one of the first Canadians to have gender-confirming surgery — in those days called a sex change operation. Two years later, she shared her story publicly in one of Canada’s first trans memoirs, Behold, I Am a Woman. Then she disappeared. She married and gained a new last name that was never linked to the sensational car crash, or her status as a trans pioneer. It was a life she always wanted, in which she could be just another woman.

‘The loneliest people in all the world’

Dianna’s story begins when she was “born a boy” in Winnipeg in the 1930s and, as she would later write, adopted by a loving couple who named her Clifford. Her father was a forest ranger, and Dianna grew up with no electricity or running water. It was a lonely but active childhood — catching fish, nibbling on salt for the cows and collecting eggs.

Her father had bad eyesight, and the family moved around Manitoba and northern Ontario so he could find work. As a teenager, Dianna lived in Fort Frances, Ont., a paper mill town that for most high school students in the postwar years revolved around dances and school sports. Dianna hated sports. As she would later write in Behold, I Am a Woman, she went to the town doctor, looking for a medical excuse to skip that “torture.”

Dr. Harold Challis, tall, burly and British, moved to the land of white pines and paper mills with his family in 1950. Known as “Chally” by his friends, he brought the local doctors into a group practice, helped modernize the hospital and liked to joke with the nuns who ran it. He had blue eyes and dark, thinning hair, and was known as a “witty and urbane after-dinner speaker.”

Challis talked with Dianna and told her she was a transsexual (the medical terminology of the era — still embraced as an identity by some, but rejected by others as pathologizing). She became his patient as well as part-time receptionist, she wrote in her book, but the diagnosis stayed private.

Chris Lowe, a classmate who knew Dianna, remembers her presenting as a quiet boy with flawless skin, stylish rolled-up jean cuffs and beautiful fingernails.

“Our typing teacher, Miss Arthur, asked him to cut his fingernails because they were getting caught between the keys of the typewriter, says Lowe, 80. “Of course, us girls, we were envious of that.

“But you know, I think he led a really rough life. He didn’t really fit in anywhere.”

Dianna stole her mother’s Avon lipstick samples and practised in her room. She sent away for a wig and bought heels, dresses and lingerie to wear in her bedroom, she wrote in her book. She anticipated Halloween like a kid counting the sleeps until Christmas, and when Oct. 31 arrived, she was resplendent in a silk white gown, evening gloves and a beaded handbag.

Dianna yearned for a life in the city, where nobody knew her as Clifford. Her first trip to Winnipeg dressed in women’s clothing ended disastrously — police wanted to know why a young girl was hanging out in a hotel lobby by herself. When they found out she was 17, they called her parents.

“My very distraught parents arrived at police headquarters the next day to face life-shattering news concerning their son,” she wrote. “Never in their sheltered lives had they heard of a boy dressing as a woman. The sight of me in the complete attire of a woman made mother weep and father fume.”

Doctors who worked with trans people in the 1950s were very rare. For the next couple of decades, this was still a “crazy idea” for most people, says Aaron Devor, the chair in transgender studies and founder of the Transgender Archives at the University of Victoria.

“Most professionals thought that they needed to be convinced out of these odd notions,” he says, adding that physicians who worked with trans people “were thought to be a bit odd by their colleagues as well … It was very hard to get anybody to help you.”

Dr. Challis was an exception. He told Dianna’s parents to be supportive.

“He would fit in, in today’s world,” says Challis’s daughter, Deborah.

Surgery was being performed in other countries, and one day would be offered in Canada, Challis assured her family. Dianna’s parents were bewildered, but understanding. They moved to Thunder Bay to start over: father, mother, daughter.

Without the Internet, there was no easy way to reach others, and trans people in rural communities were especially isolated. “The loneliest people in all the world,” the Toronto Daily Star wrote, in a 1967 article about the “rare group of men and women” in North America known as transsexuals.

In 1971, Rupert Raj, a young trans man, tried to place an ad in the Ottawa Journal seeking “transsexuals and transvestites” to form a support group.

“They refused (the ad),” he says. “They found those words problematic; somehow they thought they were sexual recruitment because they didn’t understand the difference between gender identity and sexual orientation.”

He submitted an article to a gay newsletter, and eventually met trans people through organizations for gay people.

“The isolation and the stigma is hard to imagine in today’s world,” says Devor. “But this is a time when, in most jurisdictions, it was still illegal to even be gay.”

‘This is Mr. Boileau saying goodbye’

Dianna always dreamed of independence, and she found it in Calgary and Edmonton, working as a model and stenographer.

She was outed to a friend following her arrest when she and a group of pals drank too much and snapped off a car antenna in a parking lot one night. She was sent for psychiatric evaluation as part of the arrest. Not long after, Dianna left Edmonton for Toronto, where she found work as a legal secretary and stenographer.

Things were going smoothly, until a humid June morning in 1962 when Dianna, with her friend Rosemary Sheehan sitting beside her, crashed into the guardrail of the 401, spinning down an embankment. Sheehan died in hospital, and Dianna was charged and outed to the entire city in a sensational trial. Although she was acquitted, the notoriety was crushing. She tried to kill herself with pills.

In the aftermath of the trial, Dianna met two other trans people in Toronto and researched gender-confirming surgery, not yet available in Canada. She heard of doctors in Casablanca and Mexico, but the costs were “astronomical.” Dianna took some comfort in the fact that Canada was catching up to the U.S.

In 1966, Dr. Harry Benjamin, a German-American physician, published The Transsexual Phenomenon, the first book that sympathetically argued trans people should receive treatment. It spawned a major change in attitudes and treatment models, and gender clinics were beginning to open in other countries. Dianna spoke to a local surgeon, consulted U.S. doctors and began taking hormone pills.

During the summer of 1969, Dianna and a friend travelled to New York for castration surgery. Their recovery was excruciating; neither could walk and they had to keep the maids away from their motel room, where “it looked more like a case of an illegal, unsuccessful abortion than a castration,” she wrote. When they returned, Canadian customs asked: had they brought anything back? Dianna whispered to her friend: “No, but let’s tell him we left our balls floating in the Hudson River.”

Not long after that procedure, Dianna consulted a team of doctors at Toronto General Hospital, seeking out further surgery to remove her male sexual organs and create female genitalia. They told her it was possible, but only if endorsed by Toronto’s newly opened gender identity clinic at the Clarke Institute. OHIP would then pay for it.

She submitted to medical exams and interviews. During a two-week stay at the Clarke in spring 1970, she met doctors and fled a “distasteful test” to measure her sexual response to pictures of naked and clothed men, women and children. Toward the end of the process, the clinic’s director, Betty Steiner, tried to dissuade her, emphasizing there would be no turning back.

Steiner was known for being conservative: in 1982, she told the Star that of 600 individuals who came to the gender clinic, only 75 were approved for surgeries. “We have to weed out the emotionally unstable and intellectually subnormal, and spot the ones who are serious, because there is no going back after,” she said.

Back in 1970, Dianna had made up her mind, and chose her words carefully.

“Dr. Steiner, this is Mr. Boileau saying goodbye.”

Dianna tells her story

The morning rain had cleared into a warm spring day and Felicity Cochrane was reading the Globe and Mail in her Don Mills home on April 23, 1970. The front page had a story about the first Earth Day, but Cochrane was more interested in a smaller item: “Identity concealed: Sex change surgery is first for Canada.”

(Although the media called this a “first,” a 1967 story in the Star mentions a surgery in Toronto, and trans historians note there were other people who had surgery around the same time.)

The English-born Cochrane had been an actress, a journalist, and a front-page story in 1965 as Toronto’s only female Tory candidate in the federal election, blond hair whipped into a beehive on page 1 of the Star. By 1970, the 41-year-old mother of three was managing a local Dixieland band. She knew little about trans people, but sensed a good story. Cochrane was discussing the surgery with a friend — she can’t remember where — when a stranger approached. She apologized for listening in, but she happened to know Dianna and wondered if Cochrane wanted to meet her.

A few days later, Cochrane walked into Toronto General, hoping to write a story for Chatelaine, and posed as Dianna’s best friend, breezing past security guards.

“She had doctors that had never done this before,” Cochrane, now 86, remembers from her winter home in California. “She did not just have one operation; she had several afterwards, because everything wasn’t perfect.”

Once Cochrane began the interviews, she realized Dianna’s life would be best suited to a book. The women agreed to split profits on Behold, I Am a Woman.

Dianna was frank with details she was comfortable sharing, but not with her age, as Cochrane would learn years later. In publicity for the book in 1970, she is said to be in her late 20s, but media reports from her 1963 trial say she was then 32. (Her real age is never clear, but as she was a teenager in Fort Frances in the early 1950s, she was likely born in the mid-1930s.)

“By no means has my life been a series of tragedies,” the book’s preface says. “I’ve really never taken anyone very seriously, least of all myself. My life has been a combination of laughter, fear, and sadness.”

When the women sent their pitch to publishers, they learned Canada wasn’t ready for chapters that began with sentences like “One does not usually associate castration with roast beef, but I do.”

“It was too hot to handle,” Cochrane says. “They wouldn’t touch it with a barge pole.”

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But Cochrane found a New York publisher. She and Dianna went on a publicity tour in September 1970, where coverage was equal parts sensationalism and advocacy. Dianna dedicated the book, published in 1972, to her parents, to Betty Steiner and to the doctors and nurses at Toronto General.

Chris Lowe, Dianna’s former classmate, saw her on the news and recognized her voice.

“She was really quite pretty,” Lowe says. “We kind of thought, hmm, she’s better looking than we are.”

As part of the media blitz, Dianna was interviewed for a CBC program on women’s issues.

“Even from infancy, I think that there’s a forcible genderization placed upon us,” she says in the 11-minute clip. “Basically I’ve always been a woman.”

She is poised, using words the world would take decades to learn.

But this was 1972. The interview didn’t air.

Out of the spotlight

Dianna enjoyed the spotlight but grew tired of it.

“She had to put up with so much discrimination,” Cochrane says. “She’d meet somebody, and they’d find out about it, and they would drop her like a hotcake.”

Aaron Devor of the University of Victoria says some trans people accept a degree of publicity because they remember how lonely they were, but “most people reach a point where they go, OK, I’ve done my bit for the cause and now I want to have my life.”

After 1972, Dianna made no further public appearances. Journalists called Cochrane occasionally, but she was sworn to secrecy and never gave interviews. Dianna was grateful. She was done talking about it.

A few years ago, Chris Lowe went online, hoping to find Dianna and invite her to their 60th high school reunion.

“She probably didn’t have any happy memories of going to high school,” she says. “I just hope when she had the transformation that life was easier for her.”

In the 1980s, Dianna married and settled into life in an Ontario city, taking her husband’s last name. The Star is using the name Dianna Boileau, the name she used in her dealings with the media.

Dianna eventually went grey, but still wore a red wig. She kept up with fashions and loved a good pantsuit. She was happily married, Cochrane says, and then widowed. She grew old.

Every few months, the friends would catch up. Dianna always spoke in a whispery voice that reminded Cochrane of Jackie O. She was usually cheery — only on one occasion was Dianna “down in the dumps,” wondering if she had done the right thing by transitioning.

The friends eventually lost touch and calls from journalists stopped as Dianna faded from public memory. When Cochrane called her to see if she might speak to the Star for this story, there was only a clipped message that the number was out of service.

The next day, Cochrane called the reporter back, her voice breaking with news of what she discovered online: Dianna had died in 2014. She wanted to send condolences but didn’t, unsure of whether people in Dianna’s life knew about the book they had written together, about Dianna’s history as a trans pioneer. Dianna cherished her anonymity, her life as just another woman.

Within the Canadian trans community, where the writing of history is still in its infancy, Dianna is not well known. Her book is out of print, rare copies selling for about $80 online.

Dianna came of age in a world with no words to explain how she felt.

“When you talk to people from that generation, it’s very common for them to say that until somewhere in the 1990s, they never knew another trans person,” Aaron Devor says. “It took an incredible amount of courage and fortitude and perseverance to make it through the obstacles that existed.”

Into that world, Dianna sent 208 pages of her life, by turns tragic, ribald and triumphant, ending the story on a Monday morning in 1970, three months after her surgery.

“As I walked down the hospital steps toward the waiting taxi, my suitcase in hand — I experienced a sort of rhapsody, an ecstasy before the cadence,” she wrote. “Behold, I am a woman.”

Trans history: A lifetime of change

1950s: New Yorker Christine Jorgensen has a series of surgeries in Denmark in 1952, and becomes the first trans person to receive widespread media coverage. “I’m happy to have become a woman and I think many more people who are unhappy as I was before should follow my example,” she says, for the first time giving many trans people the sense they are not alone.

Stories mentioning the word “transsexual” in the Toronto Star in the 1950s: 0

1960s: The gender clinic opens at Johns Hopkins University in Baltimore in 1966 and leads to the first mention of the word “transsexual” in the Star. The Clarke Institute in Toronto opens its gender clinic in 1968-69. Trans and gender non-conforming people are among those resisting arrest in a raid on the Stonewall Inn in New York in 1969, igniting the modern LGBT rights movement.

Stories mentioning “transsexual” in the Star, 1960-69: 19

1970s: Dianna Boileau has gender-confirming surgery in 1970 and publishes her memoir in 1972, leading to a Canadian media blitz. In 1975, tennis star Renée Richards has gender-confirming surgery and in 1977 she wins the right to compete in women’s professional tennis, leading to a flurry of international coverage. Trans people start to organize their own advocacy groups.

Stories mentioning “transsexual” in the Star, 1970-79: 83

1980s: Talk shows “discover” trans people, although many are sensational and exploitative. Aaron Devor of the University of Victoria says the “brave souls” who appeared on these shows gave comfort to others. Rupert Raj went on the Sally Jessy Raphael show in 1986. “The producers said this and this will happen, and we got on camera and something different happened,” he recalls. “It wasn’t the end of the world, but it was still a little too sensationalizing, too simplifying, which talk shows tend to be.”

Stories mentioning “transsexual” in the Star, 1980-89: 143

1990s: Trans people are early Internet adopters. Gwendolyn Smith, a trans woman working in desktop publishing, creates the Transgender Community Forum on AOL around 1993. After the murder of trans woman Rita Hester in Massachusetts in 1998, Smith speaks with others on the forum about similar murders and creates the website Remembering Our Dead to track them. Out of that website comes the first Transgender Day of Remembrance in San Francisco in 1999.

Stories mentioning “transsexual” in the Star, 1990-99: 237

First appearance of “transgender” in the Star: 1993

Total mentions of “transgender” in 1990s: 55

2000s: The aughts see small steps toward a paradigm shift in Canada, with more attention paid to the trans population as a defined group, says Rupert Raj. The Sherbourne Health Centre, with a focus on LGBT health, opens in 2002. The centre develops a reputation beyond Toronto, with doctors across Ontario seeking advice on serving LGBT clients. To formalize that relationship, in 2008, the centre creates Rainbow Health Ontario, a program to improve health-care access for LGBT communities. Gender-confirming surgery, delisted from OHIP in 1998, is relisted in 2008.

Stories mentioning “transsexual” in the Star, 2000-09: 338

Stories mentioning “transgender”: 429

2010s: More mainstream media representation for gender-diverse people, including Caitlyn Jenner, Jazz Jennings and the TV show Transparent. In 2012, the Ontario Human Rights Code is amended to include gender identity and gender expression. The following year, the Diagnostic and Statistical Manual of Mental Disorders (DSM) replaces the term “gender identity disorder” with “gender dysphoria,” in a bid to remove stigma, noting that gender non-conformity is not in itself a mental disorder. The critical element of gender dysphoria is the presence of “clinically significant distress” associated with the condition. Debate continues as to whether the condition should be removed from the DSM and no longer seen as a psychiatric diagnosis. But for OHIP coverage, the diagnosis is needed before medical interventions such as surgery can take place.

Stories mentioning “transsexual” in the Star, 2010-16: 125

Stories mentioning “transgender” as of Feb. 29: 608