Transgender Pioneers: Roberta Cowell, Michael Dillon and Harold Gillies

A collage of Sir Harold Gillies, Michael Dillon and Roberta Cowell.
From L-R: Sir Harold Gillies, Michael Dillon and Roberta Cowell. Image credits: National Portrait Gallery, Courtesy of St Anne’s College (Oxford) and Digital Transgender Archive.

By Amy Kitchingman

It’s no secret that Thackray Museum’s collection is full of strange and curious objects. The Gillies Fine Hook, a slightly threatening-looking curved metal rod, is one of them. Still in use today, it is a surgical tool designed to holds flaps of skin in place. On first glance, I didn’t think much of it.

However, on further research, a fascinating corner of history revealed itself. I discovered that the tool’s inventor, Harold Gillies, was a prominent surgeon who, through a series of innovative operations, allowed two iconoclasts, Roberta Cowell and Michael Dillon, to make the first medical gender transitions in UK history. This single unassuming tool revealed to me an exceptional trio, whose stories represent a key moment in transgender healthcare. 

The Gilles Fine Hook
Gillies Fine Hook (609.005)

For Harold Gillies, inventing his Fine Hook tool was one of many contributions to modern medicine. Gillies is often regarded as an originator of plastic surgery, thanks to his innovations in facial and genital reconstruction for soldiers during WWI. Many photos circulate of soldiers who, for instance, have regrown a nose lost in a bomb blast, thanks to a skin graft procedure devised by Gillies. He remains famous for the thousands of operations he led, which allowed soldiers to heal from devastating injuries and avoid social stigma.

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. 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’ve been because he was a gay woman. He fell ‘madly into calf-love’ with a female fellow at his college, only to be rejected shortly after. However, Dillon continued to utilise his considerable intelligence to uncover his true identity. He began to live as a man and undertook training as a doctor at Trinity College Dublin.

Michael Dillon. Image credits: Private Collection of Liz Hodgkinson.

Elsewhere, a former Spitfire pilot and race-car driver, Roberta Cowell, was reading Dillon’s groundbreaking book, Self, a scientific-philosophical work which sympathetically considered homosexuality and gender identity. Cowell’s elegant blonde looks belied a swashbuckling personality. Born in Croydon, her father was a successful doctor who worked as a private physician to King George VI. She studied Engineering at University College London before becoming a Spitfire pilot in WWII, even spending a grim period at Stalag Luft I, a German POW camp, when she crashed a plane near the Rhine River. She was known as a sharp and witty thrill seeker. Cowell wrote to Dillon asking for help in finding doctors to facilitate her transition, after entering an unhappy marriage and realising she could not live any longer as Robert Cowell. 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.

Cowell’s bond with Dillon played a key role in her transition. He wrote to Gillies on her behalf, and arranged the details of her surgeries. Cowell even persuaded him to perform one procedure, while he was still completing his studies at Trinity College. Known as inguinal orchiectomy, this surgery allowed Cowell to present as intersex to her gynaecologist and have her birth certificate changed to list her sex as female. It also persuaded Gillies to complete Cowell’s transition. Before this operation, in which the testicles were removed, Gillies was hesitant to perform a surgery which legally amounted to the castration of a healthy male, a criminal offence at the time. Dillon’s procedure enabled Gillies to operate at less personal and professional risk. In 1951, he completed work on Britain’s first surgically created vagina for Cowell.

Roberta Cowell. Image credits: Digital Transgender Archive

However, the connection between Dillon and Cowell was much deeper than the sharing of medical resources. The details of their relationship are ambiguous but there was clearly a deep affection between them. There are many gushing letters from Dillon to Cowell which are full of declarations of love and even hints at sexual intimacy. Dillon wanted to marry Cowell, going so far as to buy her an engagement ring and begin to set up their martial home. None of Roberta’s letters to him survive. Cowell expressed in her writings that they never had any romantic connection, stating that it was ‘absolutely ridiculous’ to say that they had similar personalities, as Dillon often remarked. Her correspondence with Dillon peters out in the 1950s. Cowell maintained a close relationship with Eliza Morrell instead, her girlfriend at the time of her first meetings with Dillon, whom he nicknamed Tertium Quid or ‘Third Thing’. Presumably, Dillon saw Eliza as an annoyance obstructing him from his soul mate. Whatever Cowell’s true feelings were, Dillon was certainly deeply infatuated with her, and used his medical knowledge to lovingly realise her wish to transition.

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 and variously remarking that she was intersex and that her body began to transition ‘naturally’. She worked as a motorcar engineer and clothing designer but 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. Nonetheless, he and Dillon pooled their expertise to innovate operations which remain lifesaving for many. As gender affirming care continues to ignite debate in 2024, 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 archive. She is completing an MA in Art Gallery and Museum Studies at the University of Leeds.