Roberta Cowell, Trans Trailblazer, Pilot and Auto Racer


Roberta Cowell is the first transwoman known to undergo sex reassignment surgery in Britain. But after a splash in the 1950s, she withdrew from public life and died in obscurity.

Roberta Cowell in Paris in 1954. She achieved fame — and received several marriage proposals — when her story was told in newspapers and in Picture Post magazine.
Credit … Maurice Ambler/Picture Post and Hulton Archive, via Getty Images

At the height of Roberta Cowell’s celebrity status, in 1954, her face adorned the cover of Britain’s popular Picture Post magazine. When her story appeared in a newspaper, “I received 400 proposals. Some of them of marriage,” she said in an interview for The Sunday Times in 1972. “I could have had titles, money, the lot.”

She achieved this fame when she became the first person in the UK known to have her gender reassigned from male to female. Her transition — and all of the yearnings and hopes that came with it — involved hormone treatments and surgeries despite what some regarded in strait-laced 1950s Britain as flouting contemporary laws.

“Since 18 May 1951, I have been Roberta Cowell, female,” she pronounced in her autobiography. “I have become a woman physically, psychologically, glandularly and legally.”

Yet by the time Cowell died in 2011 at age 93, her voyage across the lines of gender and social norms had faded into obscurity.

People were perhaps more familiar with Christine Jorgensen, a former US Army clerk who transitioned in Denmark just months after Cowell. When Jorgensen died of cancer in 1989 at age 62, the event was recorded in an obituary in The New York Times.

Cowell’s death, by contrast, went all but unremarked upon, even in Britain. Her body was found on 11 October 2011, in her small apartment in south west London by the building superintendent. A handful of friends attended her funeral, but, apparently at her request, there was no fanfare for the woman who had helped pioneer gender reassignment at a time when it was virtually taboo.

Only in 2013 — two years after her death — was her passing reported, by The Independent on Sunday.

“So complete was her withdrawal from public life that even her own children did not know she had died,” the article said.

The disclosure of her death inspired a brief resurgence of media interest in her story, focusing partly on what was broadly depicted as the severing of all ties with her two daughters and on the circumstances of her transition.

Roberta Cowell on the cover of Picture Post magazine in March 1954. She wrote about her transition in “Roberta Cowell’s Story.”
Credit … Maurice Ambler/Picture Post and IPC Magazines, via Getty Images

After World War II, she developed an interest in the idea of a combination of hormone therapy and surgery to more closely align her body with her gender identity. This had been reinforced by a book called “Self: A Study in Ethics and Endocrinology” (1946) by Michael Dillon, a medical student whom she sought out in 1950.

Michael Dillon

Cowell wrote in her autobiography “Roberta Cowell’s Story,” that during their meeting, over lunch, Dillon revealed that he had himself changed his gender identity through doses of testosterone and gender-affirming surgery – he was the first transman to get a phalloplasty.

Together they agreed that he would help her transition by performing a procedure that was prohibited under so-called “mayhem” laws, forbidding the intentional “disfiguring” of men who would otherwise qualify to serve in the military. If discovered, Dillon would almost certainly have been prevented from completing his studies to become a physician. The operation – an inguinal orchiectomy was conducted in great secrecy, and its success enabled Cowell to seek medical affidavits from a Harley Street gynaecologist stating she was intersex.

This allowed her to have a new birth certificate issued, with her recorded sex changed to female.

Soon afterward, Cowell became a patient of Harold Gillies, a pioneer of plastic surgery who had performed gender-affirming surgery on Dillon, according to the book “The First Man-Made Man: The Story of Two Sex Changes, One Love Affair, and a Twentieth-Century Medical Revolution” (2006). She had a vaginoplasty on 15 May 1951 – an entirely novel procedure, which Gillies had only performed experimentally on a cadaver.

“If it gives real happiness,” Gillies wrote of his procedures, “that is the most that any surgeon or medicine can give.”

Roberta & Michael

By several accounts, Dillon fell deeply in love with Cowell, but she ultimately rejected his proposal of marriage.

Roberta Elizabeth Marshall Cowell was born on 8 April 1918, in Croydon, south of London, one of three children born to Dorothy Elizabeth Miller and a high-ranking military surgeon, Major-General Ernest Marshall Cowell, who had served as a physician in both world wars and, in 1944, was appointed honorary surgeon to King George VI.

In the social order of the time, it was guaranteed that Roberta Cowell would be educated at Whitgift School, a male single-sex public school. Towards the end of her school days, she visited Belgium, Germany, and Austria with a school friend. At the time, one of her hobbies was photography and film making, and she was briefly arrested in Germany for shooting a cine film of a group of Nazis drilling. She secured her release by agreeing to destroy the film, but was able to substitute unused film stock, and keep the original footage. She developed an abiding interest in cars and racing. “It was the be-all and nearly the end-all of my existence,” she said in her autobiography.

From an early age, she wrote, she felt conflicted about her gender, compensating for feminine “characteristics” with an “aggressively masculine manner” that persuaded gay men to take her “for one of themselves.”

Physically, she was sensitive about being overweight, displaying what she called “feminoidal fat distribution.” In her teenage years, other pupils nicknamed her “Circumference” and “Bottom.” She left school at 16 to work briefly as an apprentice engineer until she joined the Royal Air Force in 1935. Her ambition was to become a fighter pilot, but she was found to suffer from acute airsickness and was deemed “permanently unfit for further flying duties with the RAF”.

From then until the start of World War II in 1939, she studied engineering at University College London and entered a series of automobile races including the Antwerp Grand Prix in Belgium. She enlisted in the Army in 1940.

In 1941 she married Diana Margaret Zelma Carpenter, a fellow engineer and race car driver whom she had met in college. They had two daughters, Anne and Diana. They separated in 1948 and divorced in 1952.

Despite her earlier dismissal from flying duties, Cowell was allowed to return to the RAF in 1942, flying combat and aerial reconnaissance missions in Spitfires and other aircraft. After the Allied D-Day landings in Normandy in June 1944, she flew out of a Belgian air base in a Hawker Typhoon airplane that was shot down by ground fire over Germany on a low-level attack east of the Rhine River. The flight, she said, had been scheduled as the “very last trip of my second tour of operations.” In fact it was her last flight of the war.

She crash-landed the stricken warplane and was taken prisoner.

Fearing that her captors would treat her harshly, she twice sought to escape and twice she failed. She was transferred to Stalag Luft I, a prison camp for Allied aircrews in north Germany near the Baltic Sea between Lübeck and Rostock.

In her autobiography, she described the surreal elements of wartime life, relating perilous adventures with ironic detachment. She spoke of blacking out at 40,000 feet when her oxygen supply malfunctioned but somehow reviving after her plane plummeted almost to the ground. And, on another occasion, she recounted making an emergency landing atop a cliff on the English coastline just as her plane ran out of fuel.

In the early days of her captivity, she said, an Allied air raid on Frankfurt forced her and her captors into a bomb shelter where angry German civilians realised that she was an enemy pilot. She persuaded them “in my halting German” that she was not a bomber pilot and told them the untruth that her mother and father had been killed in a German raid on London. “It seemed to do the trick and the angry growling died down,” she wrote in her autobiography. “I wonder what would have happened to a Luftwaffe pilot discovered in an air-raid shelter during the blitz.”

Conditions at Stalag Luft I worsened as the end of the war approached, with Soviet Red Army troops advancing across Germany toward Berlin. Food supplies were so meagre, she lost 49 pounds. In May 1945, as German forces surrendered, their captors abandoned the facility, leaving it unguarded until Soviet troops liberated it. Within days, Cowell and other British captives had been flown home aboard American Flying Fortress bombers.

The immediate post war years confronted Cowell with the practical problems of earning a living, variously building and racing cars and renovating houses to sell at a profit. But she also detected a mounting sense of “restlessness and unhappiness,” she wrote in her autobiography, and resolved to undergo Freudian psychoanalysis. “It became quite obvious that the feminine side of my nature, which all my life I had known of and severely repressed, was very much more fundamental and deep-rooted than I had supposed.”

Cowell participating in the women’s race car competition in Sussex, England, when she was 39. After the war, she earned a living by building and racing cars.
Credit … PA Images/Alamy Stock Photo

She began to live a double life, taking hormone treatments to enhance her femininity while still living as a man.

People, she wrote, would speculate openly on her gender. “I preferred to steer clear of children and elderly ladies; they were too observant or at least too outspoken in their remarks.”

Then came the turning point when she met Dillon. The encounter was “so shattering that the scene will be crystal-clear in my memory for the rest of my life,” she wrote.

After three years of therapy and surgery, Cowell seemed to find emotional contentment that was matched only intermittently by material security. Two business ventures, in experimental car engineering and women’s clothing, did not survive.

The publication of her story in Picture Post in 1954 and her autobiography earned her the equivalent of several hundred thousand pounds. In 1957 she won a noted hill climb auto race and bought a wartime Mosquito fighter-bomber in which she planned to break the speed record for a flight across the South Atlantic. But the attempt never came about. In 1958 she appeared in bankruptcy court where she said she had no assets and significant debts, owed mainly to her father.

Cowell’s name has been summoned as a trailblazer in the years since her death, her transition having preceded by decades the public discourse over gender identity and LGBT rights.

Perhaps because she was one of the first to transition medically, she didn’t recommend it easily to others, saying, “Many of those people will regret the operation later. There have been attempted suicides.”

Whether her views would have changed over time will never be known; in 1972 she said she was writing a second autobiography, but it was never published.







2 thoughts on “Roberta Cowell, Trans Trailblazer, Pilot and Auto Racer

  1. Tony Wow thank you so much for this amazing article. The story is pertinent to many Trans folk. Both trans men and women will be touched by this in fact whilst raising questions it will also answer many for those people that may be questioning kind regards Helen x


  2. Thank you Tony. I did know about Roberta Cowell’s story and her transition and also that of Michael Dillon, however I wasn’t aware that Roberta died in such tragic circumstances. She was indeed a trailblazer and her life illustrates how vulnerable so many trans people are and also how many of us need therapy and support even when we seem to be in a “good place”. I can understand why she adopted a low profile after all the publicity. Hopefully the launch of Indigo last week will help many trans, non binary and bisexual people accept who they are and also, if they want to then be a able to transition fully. Pauline xxx


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