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Roberta Cowell: The WWII fighter pilot who made trans history

Image: Deanos Photography /

Racing driver, fighter pilot, prisoner of war: Roberta Cowell played many roles during her long and remarkable life. But her greatest struggle of all was with her gender identity. In 1951, Roberta became the first trans woman in Britain to undergo gender reassignment surgery. Here’s her story.

Off to the races

Roberta was born in 1918. From a very early age, she took an interest in motor racing and engineering, and this was a passion she went on to pursue professionally. Her rebellious, headstrong nature became apparent during a childhood trip to Germany, where she was arrested for filming Nazis doing construction work with a cine camera. She tricked her captors into releasing her by making a big show of destroying some unused film stock, keeping the actual footage for herself.

Roberta studied engineering at University College London where she met her future wife Diana Carpenter, with whom she had two children. It was during her time as a student that Roberta started motor racing, winning the Land’s End Speed Trial and later competing in the 1939 Antwerp Grand Prix. Later on in life, she founded a motor racing team and competed in events all across Europe.

From pilot to prisoner

In 1940, she joined the Royal Army Service Corps as a second lieutenant and in 1942 became a pilot with the RAF. In 1944, she narrowly avoided death after the Spitfire’s oxygen system malfunctioned, leaving her unconscious and hurtling through German-occupied France. Regaining control just in time, she managed to return safely to her base. Just months later, her luck was tested again when German anti-aircraft fire hit her engine and she was forced to make a crash landing into enemy-occupied land. Although she survived the crash, she was arrested by German troops who, despite her attempts to escape, subjected her to interrogation for several weeks in solitary confinement before moving her to the POW camp Stalag Luft I.

After six months in captivity, the Red Army liberated the camp and Cowell eventually returned home.

Transitioning and trailblazing

Plagued by depression and trauma from the war, Roberta’s personal life began to break down. After separating from her wife in 1948, Roberta sought help from a psychiatrist who helped her to identify one of the causes of her internal conflict: the struggle with her gender identity. She later wrote in her autobiography that the therapist determined that her ‘unconscious mind was predominantly female’, and the revelations were so disorientating that she contemplated suicide.

However, Roberta chose to grapple with her situation and set herself on the right path. She began to take female hormones and forged a friendship with Michael Dillon, the first person in the world to undergo female-to-male gender reassignment. Supporting Roberta’s desire to transition, Dillon – who was training to become a doctor – agreed to secretly carry out an illegal orchiectomy, the surgical removal of her testicles. This enabled Roberta to be officially classified as intersex by a gynaecologist, allowing her to receive a new birth certificate stating her sex as female.

In 1951, Roberta underwent the first male-to-female sex reassignment surgery operation in Britain. It was performed by the pioneering plastic surgeon Harold Gillies. When commenting on his ground-breaking sexual reassignment surgical techniques, Gillies said: 'If it gives real happiness, that is the most that any surgeon or medicine can give.'

Fame and fortune

In March 1954, news of her transition hit the front page of Picture Post, a popular British magazine. Not only did Roberta receive £8,000 for her story (worth over £230,000 in today’s money), she claimed to have received ‘400 proposals… some of them marriage’. Shortly afterwards, she released her autobiography telling the story of how she transitioned into a woman ‘physically, psychologically, glandularly and legally’.

Now officially out and known by the general public, Roberta continued to pursue her passion of motor racing, gaining further publicity after winning the 1957 Shelsley Walsh Speed Hill Climb. However, despite dappled success, she was banned from racing in the Grand Prix and her racing car engineering company ceased trading.

Roberta’s fame dwindled as her financial difficulties persisted, interrupted by a brief return to the British media with her now-infamous 1972 interview with the Sunday Times. It was in this interview that she claimed to have been born with female XX chromosomes.

Remembering Roberta

Roberta’s questionable focus on chromosomal makeup and her critique of the trans community will be undeniably problematic to many observers today. But she was also undeniably a product of her time.

Both celebrated and marginalised, she withdrew from the spotlight and moved into sheltered accommodation in her latter years. When she died in 2011, aged 93, only six people attended her funeral.

Incredible as it sounds, the general public only learnt of her death two years later, when an article was finally printed in The Independent newspaper. Roberta Cowell is now remembered as one of the truly pioneering and pivotal figures in British LGBTQ+ history.