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Roberta Cowell

Kathryn S Gardiner  | Published on 3/12/2021

Forgotten Foremothers

Profiles of lesser-known heroines in the fight for women’s rights





Roberta Cowell, Paris c1950, Wikipedia Public Domain
In March 1954, Roberta Cowell appeared on the cover of the British magazine Picture Post and received £8,000 (the equivalent of £220,000 in 2019) to tell her story. Namely, her life story as a transwoman and the first person in the UK to undergo gender reassignment surgery.

Roberta was born on April 8, 1918 in Croydon, London as Robert Marshall Cowell. Her parents, Sir Ernest Marshall Cowell and Dorothy Elizabeth Miller, were prominent and well-to-do members of London society. Sir Ernest served as a surgeon in the first World War and would do so again in the second. 

From childhood, Roberta had a love of cars. While attending Croydon’s public boys’ school, she was an active member of the Motor Club. At age 16, in 1934, she left school to join the Royal Air Force. This service was initially short-lived, however, as Roberta suffered air-sickness and was discharged.

Cars proved to be Roberta’s life-long love. While attending University College London, she began competitively motor-racing. She gained experience by donning coveralls and sneaking into the pit where the mechanics worked. By age 18, she owned three cars. Never one to be daunted, she also obtained her pilot’s license, air-sickness be damned.






In late 1940, Roberta joined the Royal Army Service Corps as a commissioned officer at the rank of second lieutenant. Six months later, she married fellow UCL student, Diana Carpenter, an engineering major and fellow motor-racing enthusiast. Together, the couple had two daughters: Anne, born July 1942, and Diana, born August 1944. 

Battle, danger, and near-escapes from death also marked these years in Roberta’s life as she served in the second World War. She flew aerial reconnaissance with the No. 4 Squadron RAF, piloting a camera-equipped plane called a Spitfire. During one incident, the plane’s oxygen system malfunctioned at 31,000 feet. Roberta lost consciousness and the plane flew, unpiloted, for upwards of an hour in German air space. Fortunately, she awoke and was able to steer the plane to an RAF landing spit. 

That same year, 1944, during another mission, German anti-aircraft guns shot out her wing and she was forced into a controlled crash landing. She had just enough time to radio RAF that she was unharmed. Then, she was taken prisoner by the German forces. 

Roberta remained a prisoner for five months, despite two escape attempts. She passed the time by teaching auto-engineering to the other prisoners. As the war neared its end, the camp’s food resources diminished and starvation began to claim lives. Roberta lost 50 pounds during her imprisonment.

In April 1945, as Russian forces neared, the German soldiers tried to evacuate the camp. The prisoners refused, forcing the Germans to flee without them. When the Soviets reached the camp on April 30, it was unguarded. The prisoners of war were returned to their home countries, flown on United States aircraft.

Like many veterans, Roberta’s life after the war was a confused and depressing time with symptoms recognizable as post-traumatic stress. While watching the 1947 Burgess Meredith film Mine Own Executioner, in which a pilot is shot down in a Spitfire, she experienced a traumatic flashback. After the war, she described feeling “restlessness and unhappiness.” In 1948, she separated from her wife. She would never see her daughters again.

Roberta spent the next several years in treatment with psychoanalysts, coming to the conclusion that her “unconscious mind was predominantly female. ... 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.”

She began taking hormones in 1950 and became close friends with Michael Dillon, a British physician and the first transman in the UK to have phalloplasty surgery. Meeting Michael was life changing. It was “so shattering that the scene will be crystal-clear in my memory for the rest of my life,” she wrote. He had written a volume called Self: A Study in Endocrinology and Ethics wherein he advocated that individuals should be able to alter their bodies and gender as they desired.

At Roberta’s request, Michael performed an inguinal orchiectomy (a removal of the testicles), a procedure which was then illegal under the UK’s mayhem laws. With this procedure completed, Roberta was able to see a gynecologist and receive documentation declaring her intersex. This official documentation opened the doors for Roberta to get a new birth certificate listing her sex as female. In 1951, she underwent gender reassignment surgery. 

How this all first became known is unclear, but Roberta leaned into the public’s rather salacious fascination with transwomen. Contemporary media heavily conflated gender identity with sexual orientation, therefore conflating transwomen with homosexual men. Homosexuality would be illegal in Britain until 1967 and the general perception of homosexual men was as flamboyant, “feminized men.”

Roberta, therefore, threw everyone for a loop. She was a pilot, a racecar driver, a veteran, and had children. Prior to her transition, she’d been “a man’s man,” further challenging society’s narrow definitions of “male” and “female.” Roberta published her autobiography not long after the Picture Post story. 

She continued racing, even winning the 1957 Shelsey Walsh Speed Hill Climb, a historic event in Worcestershire, but she largely disappeared from the public eye soon after. In the 1970s, she experienced financial difficulties that lead her to consider publishing a second book. She spoke with a journalist from the Sunday Times in March of 1972, defending her transition as an intersex person but largely condemning it for any other trans people. “The people who have followed me have often been those with male chromosomes, XY,” she said. “So they've been normal people who've turned themselves into freaks by means of the operation.” Her second book was never written and her life in the years following this interview were highly private, so we cannot know if this judgmental, limited view ever evolved with the scientific understanding of gender. 

In the 1980’s Roberta lived in Richmond, London, and had a small circle of close friends. Jane Ormerod’s home garden bordered Roberta’s and the neighbors visited frequently. Jane said of Roberta, “She was an extremely private person, though she could be garrulous after a glass of wine. She loved to talk about her racing, and flying, and her dream was that she would fly again. Betty would always say she was not a eunuch, she was unique.”

Roberta also befriended the owner of the local garage. They’d often talk about cars and her time in racing. “She was a strong lady: very proud and independent,” he said.

In 1990, Roberta moved to Hampton, where she lived for the rest of her life. Her neighbors there described her as reclusive and private. This private nature endured to the end of her days. She died on Oct. 11, 2011. Her funeral was only attended by six people, including Jane Ormerod, by Roberta’s request. Her death wasn’t publicly known until 2013. 

That’s when her daughters learned she’d died. "It's a relief to know something at last," youngest daughter Diana said in an interview with the Independent at age 69. Over the years, she had reached out to Roberta but had not received any response. Despite that hurt, she also described feeling proud of the person who had been her father. "He stood up for himself. He did what he felt was right. And what can you do? I think his actual words were, 'It's easier to change a body than a mind.'"

"She was an extraordinary woman," Diana said. " I would have loved to have been with her before she died, and said, ‘we are your family, and whatever happens there is a bond that nothing can change.’”