Surgeon Harold Gillies helped shape the future of transgender healthcare by performing some of the first gender-affirming surgeries in the 1940s. Amy Kitchingham explores Gillies’ groundbreaking work and the remarkable lives of Roberta Cowell and Michael Dillon, whose stories represent pivotal moments in the history of transgender medicine.
Harold Gillies is often regarded as the father of plastic surgery, and his groundbreaking techniques in facial and genital reconstruction changed the lives of soldiers during the First World War. His combination of surgery and artistry established a foundation for medical advancements, including inventing the Gillies fine hook – a surgical tool that holds flaps of skin in place to allow for precision – which is still in use today.
Enter Michael Dillon. After undergoing a mastectomy in the early 1940s, Dillon was put in touch with Gillies. Together, they devised a series of surgeries that would allow him to medically transition.
Dillon was an introspective intellectual with a passionate streak. Assigned female at birth, born to a family of minor aristocracy, he studied at Oxford, where he was a successful rower. Here, Dillon thrived in his studies and concluded that his lifelong unease in his body might have been because he was a gay woman. He fell “madly into calf-love” with a female friend at his college, only to be rejected shortly after. He began to live as a man and trained as a doctor at Trinity College Dublin.
Elsewhere, a former Spitfire pilot and race-car driver, Roberta Cowell, was reading Dillon’s groundbreaking book, Self, a scientific-philosophical work which considered homosexuality and gender identity. Born in Croydon, her father was a successful doctor who worked as a private physician to King George VI. Cowell’s elegant blonde looks belied a swashbuckling personality. She was known as a sharp and witty thrill seeker. She studied engineering at University College London before becoming a Spitfire pilot in WWII, even spending a period at Stalag Luft I, a German POW camp, when she crashed a plane near the Rhine River.
Cowell wrote to Dillon asking for help in finding doctors to facilitate her transition, forming a close bond. During their first meeting, which Cowell said ‘will be crystal clear in my memory for the rest of my life’, Dillon immediately confided in her that he was also transgender. He wrote to Gillies on her behalf, and arranged the details of her surgeries. Cowell even persuaded him to perform a procedure, while he was still completing his studies at Trinity College. Known as inguinal orchiectomy, or the removal of the testicles, this surgery allowed Cowell to present as intersex to her gynaecologist and have her birth certificate changed to list her sex as female.
The surgery also persuaded Gillies to complete Cowell’s transition. Before this operation, Gillies was hesitant to perform a surgery which legally amounted to the castration of a healthy male. This was a criminal offence at the time. Dillon’s procedure enabled Gillies to operate at less personal and professional risk. In 1951, Gilles completed work on Britain’s first surgically created vagina for Cowell.
The connection between Dillon and Cowell was much deeper than a medical partnership. The details of their relationship are ambiguous, but there was clearly a deep affection between them. Dillon’s surviving letters to Cowell are filled with declarations of love and Dillon wanted to marry Cowell. He went as far as buying her an engagement ring and started setting up their marital home. Cowell expressed in her writings that they never had any romantic connection. Her correspondence with Dillon peters out in the 1950s. None of Roberta’s letters to Dillon survive.
Both went on to lead storied lives. Cowell made headlines after selling the story of her transition to a magazine, Picture Post, in 1954 and was much photographed thanks to her good looks. Notably, she muddied any medical details, neglecting to mention Gillies or Dillon. She variously described herself as intersex and that her body began to transition ‘naturally’. She worked as a motorcar engineer and clothing designer but sadly died in destitution in 1972, while working on the second volume of her memoirs.
After qualifying as a doctor, Dillon delved into a spiritual journey. He travelled to India, where he became a Buddhist monk, changed his name to Lobzang Jivaka and wrote his memoirs. He died abruptly aged 47 in 1962.
Gillies is in many ways a supporting character in this extraordinary story of two pioneering personalities. But without the revolutionary work of Harold Gillies, and one unassuming little hook, some of the first gender-affirming surgeries on record wouldn’t have been able to take place, paving the way for lifesaving operations for many.
As gender affirming care continues to ignite debate, Gillies’ reflections on his legacy feel especially valuable. On his work for Cowell and Dillon, he remarked: “If it gives real happiness, that is the most that any surgeon or medicine can give.”
Amy Kitchingman is one of a team of voluntary researchers who are uncovering hidden histories within the Thackray Museum stores and archives. She is completing an MA in Art Gallery and Museum Studies at the University of Leeds.