Dianna Boileau, the woman who changed the course of history: A profile

Merna Emara
Local Journalism Initiative Reporter

Pride month brings you a story of a woman that defied the conventions of her day. A story of resilience and perseverance. A story of Dianna Boileau as she unapologetically discovered herself.
Boileau was born in the mid 1930s in Winnipeg, Manitoba, as a “boy” before getting adopted and named Clifford. Boileau and her adoptive parents lived in Winnipeg to look for work before they all moved to Fort Frances, Ontario. Boileau’s mom was said to be a homemaker and her father worked as a forest ranger.

This all began when Boileau attended a co-educational school in Rainy River that was run by nuns. She said she was never intrigued by hockey, football or the violent wrestling games her male peers would enjoy doing. Instead, she would play with her female friends who were more gentle, and play with her dolls at home.

In an interview with Chatelaine magazine in 1971, Boileau said she slowly began to realize she was not just nonconformist, but also different. When she was about 17 years old and when her parents were away on a trip, she made the decision to dress as a woman and go on a trip to Winnipeg.

“I arrived in Winnipeg, in the forenoon of the following day,” Boileau said in her book. “I was dressed in women’s clothes, blonde wig, a light coat, cotton print dress, and high-heeled shoes. A taxi took me to a third-rate hotel near Portage and Main.”

However, after she spent her savings renewing her wardrobe with female clothing, cosmetics and wigs, the dream turned into a nightmare when her identity was discovered by a woman’s intuition. Women wearing wigs was not all that common and an invitation to suspicion.

Boileau was returned to her parents’ care after the police called them and delivered the shocking news that their 17-year-old “son” had been crossdressing in Winnipeg.

After years of fighting for a stable life, Boileau earned the independence that she had been yearning for when she moved to different cities as she navigated jobs as a stenographer, legal secretary and a model.

It was all going smoothly until her secret was uncovered on a national level. In 1962, while Boileau was working in Toronto as a legal secretary and stenographer, she and her friend, Rosemary Sheehan, got into a car accident on highway 401. Sheehan died at the hospital and Boileau was arrested and charged with reckless driving. Although Boileau was later acquitted, she attempted to commit suicide by ingesting pills.

Boileau lost her anonymity the minute she lost her friend. Headlines flooded newspapers and newscasts, not about Sheehan’s past, but Boileau’s present. Headlines included “Wearing dress, man remanded in car death,” “Woman driver, 32, found to be male,” “Dressed as Woman, Man Goes on Trial,” and “Dressed as Woman, Man Acquitted, Sobs.”

After the acquittal, Boileau’s life took a downward slump as the desire to erase her male characteristics grew bigger. Not long after that, Boileau anonymously made headlines again as the first transexual woman in Canada. Although she was not the first transexual in Canada, her story was the first to be made public, even under anonymous restrictions. In the same Chatelaine interview, Boileau said the previous surgeries were done in Casablanca and Mexico.

In 1970, Boileau was the first transexual patient to get approved for surgery that was financed by the Ontario Health Insurance Program. Three leading surgeons, including a gynecologist, a urologist and a plastic surgeon operated on Boileau at the Toronto General Hospital.

Two years after that, in 1972, Boileau publicly released her memoir titled, Behold, I am a Woman, where she described her life in detail, from the time she was adopted to her anonymous conference held at the Constellation Hotel in Toronto – the city where she had her surgery.

Although Boileau had her share of media attention, there is not a consensus on her exact age. It’s a number that continues to remain a mystery, besides the details of the life the camera lenses never got to see.

The book is no longer in print, but a PDF version is available for free download on the internet. After publishing her book, Boileau got married and took her husband’s last name. A name that is not known to the media and is not a Google search away from uncovering the flurry of events attached to Boileau from the appalling car crash to her journey transitioning to a woman. She fought to live the dream of being just a normal woman.

Boileau passed away in silence in 2014 after she chose to fade away from media. Her most popular sentence, however, will forever remain alive: “Behold, I am a woman.”