The Dark Truth Behind the Roberta Cowell Story

Zack Stiling has written a lovely positive piece about Roberta Cowell but he is quite wrong when he says that ‘she’ was “intersex”. It is true that this is the story he put out about himself, and he maintained until the very end that he was a genuine female and most definitely not one of those dreadful transsexuals who deliberately mutilate themselves to become freaks.

Stiling writes about various articles asserting Roberta was the first male to female gender reassignment patient in England: “All the above-mentioned articles fall over themselves to accuse Cowell of being Britain’s first transgender woman, which is nothing better than an outright lie.” The articles appear to have been variously republished but refer back to the Science Museum’s ‘Seeing things Queerly’ exhibition, in which Roberta Cowell’s life is related to his past career as a wartime Spitfire pilot.

There was no lie. Roberta Cowell, known as Betty, definitely was transgender; there is no doubt about it. As Robert, and a perfectly normal man, biologically speaking, he married and fathered two children. He had, though, always been a cross-dresser and kept two separate wardrobes.

In 1948, he came across a book called Self by Michael Dillon – ‘him’-self an early sex-change from female to male – and wrote asking if anything could be done to transform him into a woman. They met, and Michael, immediately intrigued by this charismatic character, introduced him to Sir Harold Gillies, the leading plastic surgeon of the day, and also Dr Alison Macbeth, an early endocrinologist, who had prescribed cross-sex hormones to Dillon. Gillies had carried out Michael Dillon’s many operations and was sympathetic to “nature’s mistakes” as he called them; he referred to people with gender confusion as being “in the wrong sex pen”.

His plastic surgery expertise derived from work at the Queen’s Hospital, Sidcup, in the First World War, when he devised the tube pedicle for moving tissue from one part of the body to another, and between the wars used the technique to restore the penis after traumatic injuries or correct underdevelopment. Laura Dillon, who would become Michael, was the first woman in the world to undergo what was to become known as gender reassignment surgery. At the time, if the exact details had been known generally, Gillies might have suffered the opprobrium of his peers, but his attitude was always that if it was possible, it should be tried. Dillon’s surgery was fraught with complications; we know this because the case file from Rooksdown Hospital, Basingstoke, survives. It contains operation notes, photographs, diagrams and correspondence; one of the last exchanges indicating that a hysterectomy might be necessary to avoid awkward medical events in the future.

Gillies was, however, in a quandary with Cowell. He at first refused to begin transformative surgery on Robert as to ‘unman’ somebody by removing the testes without an established clinical reason was an offence punishable by being struck off the Medical Register and a prison sentence.

What do to? Robert pleaded with Dillon, then a fifth year medical student at Trinity College Dublin, to castrate him as then, he could go back to Gillies and say that he had never been a ‘proper’ man. Dillon at first wondered whether Robert’s father, Major-General Sir Ernest Cowell, and one of the leading surgeons of the day, might agree to perform the orchidectomy “as to some extent he is responsible for what you are”, but that was never even a vague possibility. The letters between Cowell and Dillon confirming this survive. Harold Gillies was adamant that to perform the orchidectomy himself was more than his life and work were worth.

Robert put on all his persuasive charm and eventually Dillon, with no surgical experience, reluctantly agreed, after getting Robert to sign a document saying that the operation might “per fortunam” be fatal, and exonerating herself from any responsibility if so. The agreement may have been made because by this time Dillon was infatuated with Cowell and perhaps saw compliance as a way to Cowell’s heart – though this was not to be.

The operation was performed on Alison Macbeth’s kitchen table, and was successful. Gillies could then agree to undertake the many operations that would convert Robert into Roberta. It would appear that he asked no questions. Cowell returned to Gillies to indicate that the obstacle had been surmounted, whereupon Gillies completed the transformation.

Gillies described both cases in his textbook The Principles and Art of Plastic Surgery, published in 1957. Dillon’s is headed ‘Female with Male Outlook’. The details were blurred, and Dillon was described as “an active and successful businessman” which she was not; she was a ship’s doctor. We can be sure that the description is of Dillon, however, as the photographs are those in the original case file. We know that Gillies only performed one operation the other way, and that was on Cowell. In the book the case heading is ‘Male with Female Outlook’, and once again the details have been subtly altered to avoid any risk of prosecution. Gillies was familiar with phalloplasty but not with vaginoplasty and so, as he writes: “On the night before, the bust of Virchow and the Waterford glass in the consulting-room had been moved out of the way to clear a place for three anatomists and three plastic surgeons to rehearse the steps of the operation on a dissected torso.” This was in 1951; a ‘corrected’ birth certificate was arranged (as it had been with Dillon) and Roberta immediately started thinking about how he (now ‘she’) could make vast sums of money from his transformation. He had to be careful, though, as he could get Gillies into serious trouble if he told the truth.

So he concocted the lie that his transformation had begun by nature, and that Gillies had simply completed the process. He gave as the reason that, as a fighter pilot and champion racing driver, he had gone all out to be as masculine as he could, and this halted the feminisation. In fact, much of the feminisation was brought about thanks to massive doses of female hormone prescribed by Alison Macbeth and not by nature. Once again, these hormones were prescribed in deadly secret. Gillies completed the process with breast implants – it is believed this was the first time this procedure was ever carried out – and much facial surgery. Roberta told Liz Hodgkinson that Gillies “was making it up as he went along”.

His 1954 book was a sensation. But why did he perpetuate a lie?

We believe it was mainly to protect Gillies, who would have lost his entire profession if the truth had come out; and it might have done. Subsequent early sex changes such as those of April Ashley and Jan Morris had to go to Casablanca for their operations as they were illegal in this country. Men sometimes requested castration to enable them to avoid military service and this, we believe, was one reason for castration being illegal on adult males. We doubt whether Robert Cowell would have been accepted as a fighter pilot if, on examination, he had been found to be an incomplete male.

In an interview, Betty’s father said that he had performed a tonsillectomy on his son when aged 12 or 13, and that he was a perfectly normal male then.

The reason Betty’s second book was never published was because Liz stumbled on the truth while doing research and he could not take it. Liz felt she had to wait until Roberta died to publish From A Girl to a Man, which tells the whole combined story of Dillon and Roberta.

Liz first met Roberta in 1970 when living in Richmond. She saw him in the local post office, told him she was a young journalist and asked whether he might agree to an interview, upon which he uttered the immortal words, “If you pushed me down into the gutter and said, while you’re down there, what do you think of short skirts, I would still agree to an interview.” This was priceless and typical of Betty.

After that Liz and Betty became great friends and he asked Liz to write his second book. They got a deal and advance from a major publishing house, but when Betty gave Liz Michael Dillon’s letters to read, which told the whole story, and Liz confronted him with them, he went ballistic and said he had some very nasty lawyers poised ready to sue her if any of the medical stuff from the letters was published. He could not exactly deny them, as Dillon was a very straightforward honest person and the facts were there, but he would not agree under any circumstances to Dillon’s letters being published. This meant that, really, there was no book and the deal was cancelled.

At some level Liz thinks he wanted her to know the truth but could not admit it, even to himself. When she first met Betty, her son Tom, then aged two, piped up from his pushchair: “Mummy, is that a man or a lady?” Out of the mouths of babes…

When, many years later, Liz met Betty’s daughter Diana, she was struck by the likeness. It was so obvious that Diana was Roberta’s daughter. Diana told Liz that when her father’s story came out, she and her sister Anne had to be kept hidden as the likenesses were so strong. When confronted about the children after his story was published, Roberta hinted that they were not his, and so confusion continued to reign.

As it was, he played no part in their upbringing and refused to see or acknowledge them, right to the end of his life. Diana said that she and her sister tried many times to make contact, but there was never any response.

Roberta made a reasonable killing for selling his story to the newspapers, but later decided he might make more by spilling the beans on Michael Dillon, who in her career on board ship had managed to stay below the radar. He tipped off the Daily Express and a gaggle of journalists confronted her as she stepped off her ship in the United States. Realising she was out in the open and there was no return, she fled to Ladakh in Northern India and became a Buddhist monk, dying in poverty. Loyal to the last, she never ever told anybody about the illegal operation she had carried out to enable Robert to be transformed into Roberta. The extensive private letters are the only source of this information.

From a Girl to a Man tells the definitive story. A Channel 4 programme, The Sex-Change Spitfire Ace, led to our own collaboration on this remarkable story of the beginnings of gender reassignment surgery in Britain.

Liz Hodgkinson is an author and journalist. Her latest book, My Covid Diary, is now available.

Andrew Bamji is a retired consultant rheumatologist. He has also documented the origins of 20th Century plastic surgery in his book Faces from the Front: Harold Gillies, The Queen’s Hospital, Sidcup and the Origins of Modern Plastic Surgery (Helion Press, 2017) and is the Gillies Archivist at the British Association of Plastic, Reconstructive and Aesthetic Surgeons.