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The Dark Truth Behind the Roberta Cowell Story

by Liz Hodgkinson and Andrew Bamji
18 February 2025 11:22 AM

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.

Tags: DisinformationFact checkRoberta CowellTransgenderismWoke Gobbledegook

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13 Comments
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RW
RW
3 months ago

As gender-for-humans hadn’t even been invented at that time, nobody could have been definitely-something-gender by then. This is an assessment in retrospect based on current political gender theories. As to “nature’s mistakes”, nature is not a person and cannot act and hence, cannot make mistakes. People who have troubles accepting and dealing with reality are by definition mentally ill (or deranged) and actually, people who phantasize about self-harming, including self-mutilation, are usually considered mentally ill, too (and often dealt with quite harshly when from less privileged backgrounds)

This means at the base of this, we have mental illness, combined with criminal activity and some guy whose attitude always was if it was possible, it should be tried or rather, in my rewording, If I claim I can do it, even despite it’s fraught with peril, and some people are willing to pay for it, I should be allowed to do it!

Fast forward from someone trying to build a career on ‘groundbreaking’ useless and oftentimes, harmful surgery to today’s NHS which tries to establish a human right of people to have such procedures performed at the expense of the taxpayers while dentists repairing broken teeth are for well-to-do people only and the stuff of legends for most others.

*kotz*

(imperative of the German verb for to puke).

4
0
wryobserver
wryobserver
3 months ago
Reply to  RW

To be clear, Gillies was not trying to build a career as he had already built it. Known as the father of modern plastic surgery, knighted for his First World War work, he was 64 when he began Dillon’s surgery and 69 when he operated on Cowell. I have studied him and his work for nearly 40 years, and would argue that his willingness to embark on this sort of work was borne out of compassion. But equally he had a mischievous streak that could get him into trouble and he sailed close to the line on other occasions. That said, just because you can do something doesn’t necessarily mean that you should.

6
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RW
RW
3 months ago
Reply to  wryobserver

Well, he was guy who had specialized in something which had basically no practical applications outside of war times, who was itching to try something he hadn’t tried before which would make him world famous if it could only be established as ‘standard’ medical procedure and who was willing to collude in breaking the law to do so if an at least remotely plausible option of denial was available to him once he had found someone who was willing to be the guinea pig of this medical experiment. Plus, he exploited an already mentally disturbed former voluntary guinea pig of another medical experiment in order to accomplish all that who – according to the article – ended up with the fever dream life which had been promised to her completely ruined to line someone else’s pockets.

I hope I’ll never be the subject of that kind of compassion.

Last edited 3 months ago by RW
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wryobserver
wryobserver
3 months ago
Reply to  RW

Once again, just to be clear, this was not done to make Gillies famous, because he already was. In Dillon’s case she had already gone through hormone treatment and mastectomy before reaching Gillies, and looked like a man, so all Gillies did was a cosmetic procedure to complete the illusion. And he had done it before in males with undeveloped organs. One may argue about whether it was right or wrong, as one still can.

0
0
RW
RW
3 months ago
Reply to  wryobserver

We don’t know anything about Gillies ‘inner motivation’, however, I certainly wouldn’t ever have heard of him without these two surgical procedures which did kickstart a whole industry. Maybe, the guy was just posssessed by the devil or he enjoyed mutilating and abusing people. But this doesn’t really matter because every reported detail of this story stinks badly.

1
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Mogwai
Mogwai
3 months ago

Well this is quite the contrast from that previous article about this person, isn’t it? I had quite a bit of sympathy for this ‘Roberta’ then. However, now that many more details have been revealed we get a much clearer picture. What a callous and self-absorbed person must he have been to father two children and then reject them, having nothing to do with them their entire lives, even denying they were his. It’s a shame the authors didn’t mention the wife in all this, because how traumatic it must’ve been for her to have to deal with all this back in those days. It’s like double the stigma. Not the typical way in which a woman finds herself becoming a single mother, is it? Mind, plenty of women dealing with similar circumstances now, when the man legs it and abandons them for whatever reason, forcing them to be raised fatherless.
This Robert was evidently mentally not quite right ( putting it mildly ), societal pressures and social conformity being very different to what they are nowadays, and the selfish git shouldn’t have had kids in the first place if he was just going to wash his hands of them and leave his wife in the lurch. What an inconsiderate, cold-hearted sod.

13
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Tintin
Tintin
3 months ago
Reply to  Mogwai

there is a very interesting documentary about Trans Wives on YouTube. Tells the story from the wife/pqrtner’s (and their children too) side.

0
0
godknowsimgood
godknowsimgood
3 months ago

Men cannot become pregnant.
Men cannot give birth.
Trans men can become pregnant.
Trans men can give birth.
Therefore trans men are not men.
As trans men are not men, then trans women are not women.

Yet trans zealots claim that trans women are women, that trans men are men, that men can therefore become pregnant, that men can give birth. If that’s not nuts, I’m a Chinaman.

10
0
Art Simtotic
Art Simtotic
3 months ago

Gruesome yet fascinating account, thank you. No arguing with two offspring (although biologically only substantiated by facial resemblance?), unless conceived outwith the marital bed.

Having only experienced necessary minor surgery a handful of times, volunteering for major mutilation seems utterly repugnant. Same goes for all those body piercings that nowadays abound. Yuck! Ditto, indulging in the wrong sex hormones.

Self-absorbed and callous to reject two young children. Also yuck.

Last edited 3 months ago by Art Simtotic
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Zack Stiling
Zack Stiling
3 months ago

I am profoundly grateful to Liz Hodgkinson and Andrew Bamji for the research they’ve undertaken into this subject and for setting the record straight. This puts things in a very different perspective and I can only apologise to readers for sending you down the wrong path. It is much to the credit of the DS, as well as to Hodgkinson and Bamji, that the full picture is now out in the open.

As an aside, when Cowell drove in the 1957 Shelsley Walsh Hill-Climb, he was awarded the title of Fastest Lady Driver and credited with setting a ladies’ course record of 40.41s. (F.T.D. at that meeting was 35.84s.). I wonder if that was the first ever incident of a man claiming a victory in ladies’ sport?

10
0
Curio
Curio
3 months ago

Some history is needed to bring about some calmness on the issue and not throw the baby out with the bathwater. Over several millennia, plenty of examples of men and women not happy with their sex. Nearer here and now, in the sixties and seventies it was not uncommon for men to undergo surgery in order to move to the other side. No one blinked an eyelid. Until the woke commissars took over, the likes of our current ONE (Our National Embarrassment) Prime Minister. Degenerate politicians and judges passed laws enabling male freaks to terrorise women in women’s private spaces. Backlash followed which discriminates against a few genuine transgenders. I felt obliged to say that because one my bosses, who helped me a great deal, was one of those ex-men and later surgically a woman (and a very kind person too).

3
0
godknowsimgood
godknowsimgood
3 months ago
Reply to  Curio

While I agree with you generally, and we can have sympathy for people like your former boss who had surgery to make him seem like a woman, surgery cannot make a man into a woman, just the appearance of a woman, and probably not a very good appearance of a woman.

3
0
ACW
ACW
3 months ago

Roberta Cowell AKA Miss interpreted?

2
0

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