Dianna Boileau, Dr. Harold Challis and Transgender Rights

On March 31, 2023, Trans Day of Visibility, this plaque was unveiled by the Ontario Heritage Trust and Borderland Pride at the Fort Frances Museum and Cultural Centre and then permanently installed in front of La Verendrye Hospital in Fort Frances.

The bilingual plaque reads as follows:


    In 1970, Dianna Boileau (c. 1930s-2014) became the first Canadian to receive gender-affirming surgery. The catalyst for Dianna’s transition was Dr. Harold Challis, a British physician at La Verendrye Hospital in Dianna’s hometown of Fort Frances, with a rare and progressive understanding of gender for the time. Dr. Challis saw Dianna frequently in her youth and learned of her struggles among her peers. His counsel helped Dianna and her family with her transition to begin living openly as a woman. In 1970, Dianna received gender-affirming surgery through the new Gender Identity Clinic at the Clarke Institute of Psychiatry in Toronto. In 1972, she told her life story in a ground-breaking autobiography, recounting her relationships and medical journey, but also incidents of harassment, discrimination and abuse. The international media blitz that followed traced the challenges of being trans in her time and provided a public face for transition when few existed. Dianna married in the 1980s and disappeared from the public eye. The fight for provincial funding for medical transition waged until 2008. It helped unify and focus the trans movement in Ontario for decades to come. By going public with her story, Dianna helped bring awareness to transgender rights and medical transition.


    En 1970, Dianna Boileau (v. les années 1930-2014) est devenue la première Canadienne à subir une chirurgie d'affirmation de genre. Le catalyseur de la transition de Dianna est le Dr Harold Challis, un médecin britannique de l'hôpital La Verendrye de Fort Frances, la ville natale de Dianna, qui a une compréhension rare et progressiste du genre pour l'époque. Le Dr Challis a vu Dianna fréquemment dans sa jeunesse et a appris les difficultés qu'elle rencontrait parmi ses pairs. Ses conseils ont aidé Dianna et sa famille dans sa transition pour commencer à vivre ouvertement en tant que femme. En 1970, Dianna a subi une chirurgie d'affirmation de genre à la nouvelle clinique d'identité de genre du Clarke Institute of Psychiatry de Toronto. En 1972, elle a raconté sa vie dans une autobiographie révolutionnaire, relatant ses relations et son parcours médical, mais également les incidents de harcèlement, de discrimination et de mauvais traitements. La tempête médiatique internationale qui a suivi a permis de retracer les difficultés rencontrées par les personnes transgenres à son époque et de donner un visage public à la transition alors qu'il en existait peu. Dianna s'est mariée dans les années 1980 et a disparu de la scène publique. La lutte pour le financement provincial de la transition médicale s'est poursuivie jusqu'en 2008. Elle a contribué à unifier et à orienter le mouvement trans en Ontario pour les décennies à venir. En racontant publiquement son histoire, Dianna a contribué à faire connaître les droits des personnes transgenres et la transition médicale.

Historical background


In 1970, Dianna Boileau (c. 1930s-2014) was the first Canadian to receive gender-affirming surgery. She went on to tell her life story in a ground-breaking autobiography, released in 1972. The catalyst for Boileau’s transition was Dr. Harold Challis (d. 1970), a British physician at La Verendrye Hospital in Boileau’s hometown of Fort Frances, who saw Boileau frequently as a young adult and learned of her struggles at school and among her peers. Dr. Challis had a rare and progressive understanding of gender for the time. He counselled Boileau and her family in the 1950s; his support encouraged Boileau to begin living openly as a woman.

Boileau’s life story unfolded in parallel to the history of transgender rights, struggle and recognition in Ontario and Canada, as well as the evolution of public acceptance, legal protection, social services and medical care for trans individuals. Boileau’s autobiography (Behold, I Am a Woman, as told to Felicity Cochrane) and the international media blitz that followed, provided many Canadians with their first glimpse of what we now know as gender-affirming medical intervention. For trans people especially of her generation, Boileau provided a public face for transition at a time when few trans people were publicly recognized.

Boileau’s story also recounts the challenges of being trans in her time. Her autobiography includes incidents of harassment, discrimination and abuse, including a high-profile criminal proceeding in which, while ultimately acquitted, she was outed in the national media and briefly incarcerated in a men’s institution. Many of these challenges and systemic barriers continue to impact trans people in Canada today. Trans people continue to be among the most vulnerable groups in society.

Who are trans people?

Trans or transgender is an umbrella term referring to people with diverse gender identities and expressions that differ from stereotypical gender norms. It includes, but is not limited to, people who identify as transgender, trans woman (male-to-female), trans man (female-to-male), transsexual, cross-dresser, gender non-conforming, gender variant or gender queer.1 The 2021 Canadian census found that 0.33 per cent of the population over 15 (around 1 in 300 people) identified as transgender or non-binary.2

Trans people come from all walks of life and are represented in every social class, occupation, race, culture, religion, region and sexual orientation. While federal and provincial human rights laws now offer protection on the basis of sexual orientation, gender identity and gender expression, trans people remain one of the most disadvantaged groups in Canadian society. According to the Ontario Human Rights Commission, “Trans people face these forms of social marginalization because of deeply rooted myths and fears in society about people who do not conform to social ‘norms’ about what it means to be female or male. The impact is significant on their daily lives, health and well-being.”3

Studies have reported that trans people continue to experience barriers and discrimination in health care and employment,4 escaping poverty5 and accessing justice.6 Some trans people experience social isolation, avoiding public spaces for fear of harassment.7 Over three-quarters of trans people have had suicidal thoughts and 43 per cent have attempted suicide.8 Canadian courts and tribunals have recognized prejudice, discrimination, harassment and violence targeting trans people as “substantial and disturbing.”9

What does it mean to transition?

The term “gender identity” typically refers to a person’s internal, individual experience of gender, whereas the term “gender expression” generally refers to how people publicly present their gender, such as through behaviour and outward appearance. “Transitioning” refers to the period during which a person begins to live publicly according to their gender identity.

Transitioning looks different for every person, and a person’s reason for choosing to transition is both personal and unique. Social transitioning involves changing one’s appearance, clothing, name or pronouns. Legal transitioning involves changing names or gender markers on identity documents. Medical transitioning can include hormone replacement therapy or gender-affirming surgery.10

Gender-affirming health care is vitally important for those who want and need it, though not all trans, non-binary or gender-diverse people choose to transition medically or surgically.11

The history of medical transition in Ontario

In medical terms, gender-affirming care today can best be defined as the psychological, social and medical health care designed to affirm an individual’s gender identity.12 It is a patient-led approach to care that is about supporting people as they seek medical, social and legal affirmation.13

But this was not always the dominant paradigm. In fact, it was not until 2013 that the stigmatizing concept of “gender identity disorder” was removed from the Diagnostic and Statistical Manual of Mental Disorders, in favour of more inclusive and supportive approaches to care.14 In making this change, it was noted that gender non-conformity is not in itself a mental disorder.

Indeed, early approaches to medical care for trans people were characterized by such stigma and obstacles. One of the earliest gender identity programs in Ontario was at Toronto’s Clarke Institute of Psychiatry (now the Centre for Addiction and Mental Health, or CAMH), which opened the doors of its Gender Identity Clinic in 1968-69.

It was not until 1978, however, that the Ministry of Health provided funding to the Clarke Institute clinic. In 1980, the Ministry added sex reassignment surgery (or SRS) to the schedule of benefits, making it an insured benefit under the provincial Health Insurance Act. The Clarke Institute clinic alone was authorized by the Ontario Health Insurance Plan (OHIP) to determine whether an Ontario resident was suitable for SRS procedures. That recommendation was a precondition for OHIP to decide whether to approve the reimbursement of the patient’s SRS procedures, though the clinic’s recommendation did not mean automatic eligibility for reimbursement.15

Notably, during this period, what constituted SRS procedures was never defined in regulation, but by convention it was limited to only the reconstruction of genitalia in the female-to-male and male-to-female transitions, bilateral mastectomy and the attendant contouring for the female-to-male transition. OHIP funded the attendant surgical and hospital services only. Surgical procedures to reconstruct the genitalia were not done in Ontario.

Even with this available resource, trans people in Ontario seeking to medically transition through gender-affirming surgery had to overcome a number of other barriers. One of the requirements for support from the clinic was that the individual seeking surgical treatment had to live “in their gender” for at least two years, including changing names and designations (a process that was challenging until recent years).16 The Gender Identity Clinic’s process also subjected patients to several physical and psychological tests that individuals found uncomfortable, offensive and inappropriate.17 Boileau describes some of these in her autobiography.

On August 26, 1998, the Ontario government de-listed public coverage for SRS from the schedule of benefits that the government would pay for insured physicians’ services. Cabinet added a grandparent clause, however, which provided that SRS and any supporting services would be insured for a person who had completed the CAMH clinic by October 1, 1998.

It would take until June 3, 2008 – following a decade of persistent advocacy from the trans community – for the province to reinstate coverage for gender-affirming surgery.18 It would take even further activism from the trans community to update the 1998 guidelines, which continued to require that patients be approved by several specialists and boards before becoming eligible for surgery.19

Today, for those seeking gender-affirming care covered by OHIP, a diagnosis of gender dysphoria is required before medical interventions like surgery can take place.20 Not all forms of gender-affirming care are covered by OHIP, and many people are still required to pay out of pocket.

Who was Dianna Boileau?

Dianna Boileau was born in the 1930s in Winnipeg, Manitoba. Orphaned at a young age, she was adopted and raised by loving parents (who she appears to give pseudonyms to in her book, presumably for privacy reasons) who gave her the name Clifford Cayer. Boileau took the name Dianna Adams for a period of time, and eventually became Dianna Boileau.

Boileau grew up in the 1940s and 1950s in Rainy River and Fort Frances, which are small communities in Northwestern Ontario. Boileau attended school at Fort Frances High School and later worked in the offices of a local physician and a lawyer.

In 1970, Boileau went on to become the first Canadian to receive gender-affirming surgery. She later documented her life experience and transition in a ground-breaking autobiography titled Behold, I Am A Woman, as told to Felicity Cochrane. It was published by Pyramid Books in 1972. While now out of print, second-hand and digital copies can be found online.21

Boileau’s autobiography recounts her discovery at an early age that, despite being born with male anatomy, she identified as a woman. During her adolescence, Boileau developed her identity in secret until a fateful trip to Winnipeg. Travelling alone by train, Boileau changed into women’s attire before arriving in the city – the first time that she would appear as a woman in public. She was eventually outed to a hotel manager, who summoned the police. The police kept her overnight and took her to a hospital for examination. They, in turn, called her parents to pick her up, telling them that she needed medical help.

Back in Fort Frances, Boileau gained the support of Dr. Harold Challis, a prominent local physician. While trans medical research and sexology date back to the late 1800s, they did not form part of most practices in the 1950s and 1960s. Dr. Challis, a general surgeon, was ahead of his time in understanding issues of gender identity and gender expression. He counselled Boileau and her family on her transition, and it is through his support that Boileau was able to assume her female identity publicly. She went on to work part-time at Dr. Challis’s office as a receptionist, and later in the office of Charles Russell Fitch, QC, a local lawyer and former judge.22 An account of Dr. Challis’s role in Boileau’s story is chronicled in a 2016 article in the Toronto Star by Katie Daubs.23

Boileau’s family eventually relocated to Port Arthur (which became Thunder Bay in January 1970) in order to allow Boileau to have a fresh start living as a woman. In adulthood, Boileau moved to Alberta, where she lived in Calgary and Edmonton, working as a model and stenographer. At one time, she entered the Miss Calgary Stampede pageant, but was unable to complete the application due to the requirement to supply a birth certificate.

After encountering risks of exposure as a biological male, Boileau and her friend Rosemary Sheehan moved to Toronto. Boileau continued to work there as a legal stenographer.

Boileau’s story took a tragic turn in 1962 when she was involved in a car accident on Highway 401 that claimed Sheehan’s life. Boileau was charged with criminal negligence causing death in operation of a motor vehicle and with dangerous driving. Bail was set at $1,000. Boileau was represented in her criminal proceeding by lawyer Anthony Bazos, who offered a reward for information about the other driver involved in the accident. Boileau was eventually acquitted after the prosecution was unable to corroborate the evidence of its only witness.

Despite Boileau’s legal victory, the publicity that the case received was devastating, leading to her alcoholism and attempted suicide. Boileau’s arrest and examination at the Belmont Street police station had outed her as a biological male, triggering sensational media coverage and nationwide newspaper headlines that repeatedly misgendered and ridiculed her. The national headlines included, “Woman Driver, 32, Found to Be Male” and “Dressed as Woman, Man Acquitted, Sobs.”24 The local newspaper in Rainy River printed a derisive piece about her trial, seemingly without realizing her local roots.25

In the aftermath of her criminal trial, Boileau made connections with other trans-identifying people in Toronto and began to research what we now know as gender-affirming surgery. At the time, it was not yet available in Canada. Boileau arranged to undergo a procedure in New York. Her recovery is recounted in her autobiography.

On returning to Toronto, Boileau consulted a team of doctors at Toronto General Hospital to seek a further surgery to remove her male sexual organs and create female genitalia. The operation was determined to be feasible but would only be funded by OHIP if Boileau’s physical transition earned the support of the Clarke Institute, then headed by Dr. Betty Steiner (1920-94). Boileau went through a series of medical exams and interviews before receiving the surgery in 1970.

Following her surgery, Boileau was once again thrust into the public eye.26 Felicity Cochrane, who co-wrote Boileau’s autobiography, published the text of an interview with Boileau in a 1971 issue of Chatelaine27 and, in 1972, Boileau was interviewed for television by Margo Lang of the CBC. The CBC deemed Boileau’s interview too controversial and it never aired (although the clip is now publicly available in online archival footage).28 Boileau was also interviewed for CTV’s W5, national newspapers and other media.29 A 1972 article in the Fort Frances Times about Boileau’s book failed to recognize that the autobiography was about her time in their own community.30

After 1972, Boileau made no further public appearances. She married in the 1980s, adopting her spouse’s name31 and, according to the Toronto Star, eventually settled in another Ontario city. Felicity Cochrane advised the Toronto Star that Boileau died in 2014. While Boileau was able to live as a woman until her death, it is unknown whether the people closest to her in her final decades knew of her transition, her book or her time in the public eye.

Boileau’s historical significance

Dianna Boileau was the first Canadian to receive gender-affirming surgery. That medical treatment enabled her to transition as she wished and to live as a woman. In doing so, she overcame challenges, systemic barriers, prejudice and struggles that LGBTQ2+ and especially trans people continue to face today.

What is perhaps most notable about Boileau’s story is that it took shape against the unlikely backdrop of rural Northwestern Ontario at a time when few would have had any understanding of trans people beyond stigmatization. At the time when Boileau realized that her biological sex did not match her gender, she likely had no model to emulate, no access to positive representations of LGBTQ2+ people, and no ability to “blend in” in her small community. Many trans people of her generation, especially outside of larger population centres, would not have known any other trans person until the 1990s. In fact, most would not have been familiar with a vocabulary to describe their identity or experience,32 even if they felt safe and supported enough to do so.

The only reason that we know of Boileau’s story today is that, against all odds, she survived this ordeal and decided to tell others about it. The catalyst for her journey began in her youth, with the support of a progressive local physician. Interviewed by the Toronto Star about Boileau’s story, Aaron Devor, the Chair of Transgender Studies and the founder of the Transgender Archives at the University of Victoria, said that doctors who worked with trans people in the 1950s were exceedingly rare, and for the next several decades, this was still a foreign concept for most people, with most professionals having the view that trans people ought to be “convinced out of these odd notions.”33 Boileau’s chance encounter with Dr. Challis in a remote northern community likely provided her and her family with the necessary support and confidence for the journey that followed.

While Boileau’s gender-affirming surgery was personally fulfilling, the public profile that she generated in the years that followed also provided courage to others in transition and created awareness of trans identities for the first time in many parts of Canada. Until the publication of her story and the international media that followed, gender-affirming medical interventions, like surgery, would have been relatively unheard of.

The ArQuives – Canada’s LGBTQ2+ archives – notes that most LGBTQ2+ historians and community activists agree that the fight for gender-affirming surgery as a medically covered procedure helped to unify and focus the trans movement in Ontario.34 That movement ultimately led to other achievements, such as the passage in 2012 of Toby’s Law (also known as Bill 33), which added gender identity and gender expression as prohibited grounds of discrimination under Ontario’s Human Rights Code.35

Boileau was among the earliest pioneers in Canada to navigate this challenging policy and medical landscape and to seek out medical support for her identity. Her courage and conviction, in the face of public controversy and tepid institutional support, was instrumental in her personal and medical transition. The public profile and openness of her story would have built awareness of the gender-affirming care in her time. Read in contemporary context, her story also reflects the vital role of supportive and understanding members of the medical community, such as Dr. Challis, in the survival and self-actualization of trans and gender-diverse people.

© Ontario Heritage Trust, 2022-2023

The Ontario Heritage Trust gratefully acknowledges the research of Douglas W. Judson in preparing this paper. The Trust also thanks Borderland Pride, the ArQuives, Canada’s LGBTQ2+ archives, the Fort Frances Museum and Professor Aaron Devor, Chair of Transgender Studies at the University of Victoria, for their research and assistance in reviewing drafts of this paper.

1 Ontario Human Rights Commission, “Policy on Preventing Discrimination Because of Gender Identity and Gender Expression” (January 31, 2014), at p. 3, available here. Dianna uses the term “transsexual” in her book, though many people now find that term pathologizing.

2 V.S. Wells, “Transgender”, The Canadian Encyclopedia (September 16, 2022), available here; “Sex at birth and gender – 2021 Census promotional material”, Statistics Canada (April 27, 2022), available here.

3 Ontario Human Rights Commission, “Policy on Preventing Discrimination Because of Gender Identity and Gender Expression” (January 31, 2014), at p. 5, available here.

4 Jake Pyne et al., “Improving the Health of Trans Communities: Findings from the Trans PULSE Project”, Presentation to the Trans Health Advocacy Summit (August 24, 2012), available here.

5 G. Bauer et al., “Who are Trans People in Ontario?”, Trans PULSE e-Bulletin (20 July 20, 2010), available here.

6 J. James, et al., Legal Problems Facing Trans People in Ontario, TRANSforming JUSTICE: Trans Legal Needs Assessment Ontario Summary Report One (September 6, 2018), available here.

7 A. Scheim, G. Bauer & J. Pyne, “Avoidance of Public Spaces by Trans Ontarians: The Impact of Transphobia on Daily Life”, Trans PULSE e-Bulletin (January 16, 2014), available here.

8 Supra, note 4.

9 Brodeur v. Ontario (Health and Long-Term Care), 2013 HRTO 1229 at para. 41, available here; see also XY v. Ontario (Government and Consumer Services), 2012 HRTO 726 at para. 15, available here.

10 Some resources use the term “gender-confirming” instead.

11 Supra, note 2.

12 “The ‘life-saving’ science behind gender-affirming care for youth”, Medical News Today (n.d.), available here.

13 Timothy M. Smith, “What to know about gender-affirming care for younger patients”, American Medical Association (December 21, 2021), available here.

14 “Gender Dysphoria”, American Psychiatric Association (2013), available here.

15 A detailed history is set out in Hogan v. Ontario (Health and Long-Term Care), 2006 HRTO 32, available here.

16 “History of CGS in Ontario”, The ArQuives: Canada’ LGBTQ2+ Archives (n.d.), available here.

17 Ibid.

18 Rob Ferguson, “OHIP to cover sex changes”, Toronto Star (May 16, 2008), available here.

19 Supra note 15; Laura Fraser, “Ontario boosts access for trans people seeking gender confirmation surgery”, CBC (March 6, 2016), available here.

20 “Gender confirming surgery”, Government of Ontario (n.d.), available here. Gender dysphoria is the feeling of discomfort or distress that might occur in people whose gender identity differs from their sex assigned at birth or sex-related physical characteristics. According to the Mayo Clinic, transgender and gender-diverse people might experience gender dysphoria at some point in their lives; however, some transgender and gender-diverse people feel at ease with their bodies, with or without medical intervention: see

21 D. Boileau and F. Cochrane, Behold, I Am A Woman, Pyramid Books (1972), available here.

22 In the Matter of the Judge’s Act, R.S.O., c. 138, and In the Matter of an Investigation into Certain Charges Against His Honour Justice Charles Russell Fitch, District Judge of the District of Rainy River, Under a Royal Commission Issued to the Honourable Mr. Justice Hodgins, dated the 24th day of April 1915; John Cousineau, “C.R. Fitch, Q.C.”, Fort Frances Times (March 13, 1998, reprinted on February 11, 2021).

23 Katie Daubs, “The woman who was trans before her time”, Toronto Star (March 27, 2016), available here.

24 "Woman Driver, 32, Found to Be Male", Globe and Mail (June 16, 1962); "Man Dressed as Woman; Lawyer, Magistrate in Conflict", Globe and Mail (July 21, 1962); "Dressed as Woman, Man Acquitted, Sobs", Globe and Mail (September 7, 1962); "Dressed as Woman, Man Goes on Trial", Globe and Mail (February 8, 1963); "All-Male Jury Acquits Driver in June Death", Globe and Mail (February 12, 1963).

25 “She’s a He”, Rainy River Record (August 2, 1962).

26 Kathleen Rex, “Canada’s first sex-swapper asks for understanding”, Globe and Mail (September 16, 1970).

27 Felicity Cochrane, “The Canadian Man who became a Woman”, Chatelaine (November 1971).

28 Margo Lang, “Dianna: Canada’s first sex change patient”, CBC (May 19, 1972), available here.

29 Daniele Hamamdjian, “Dramatic increase in children and youth seeking gender treatments has some experts alarmed”, CTV News (October 23, 2021), available here.

30 “Dianna writes of sex change”, Fort Frances Times (April 12, 1972).

31 Supra, note 3: as noted in this 2016 Toronto Star article, “Boileau” is the surname Dianna used in her dealings with the media. Her married surname (the surname of her spouse) is unknown.

32 The term “transsexual” is used by Dianna in her book and other interviews.

33 Supra, note 23.

34 Supra, note 16.

35 Toby’s Act (Right to be Free from Discrimination and Harassment Because of Gender Identity or Gender Expression), 2012, S.O. 2012, c. 7, available here.