‍IN THE heady days of cheque book journalism, one man became a household name when he pocketed a cheque for £20,000 (worth £200,000 today) for his story. Or rather her story.

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‍For in 1951 he became Britain’s first sex change patient and the heartache he had suffered all his life was finally revealed.

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‍ Robert Cowell, 32, had been a married father of two, a celebrated racing driver competing at the Belgian Grand Prix and a Spitfire pilot during the Second World War, ending up starving and eating cats raw to survive as a PoW in the notorious German camp Stalag Luft I.

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‍But Cowell was always desperately unhappy – he knew from a child he wanted to become a woman — and the nation was shocked when he officially became Roberta Cowell.

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‍ Newspaper readers were even more shocked when they discovered that the trainee surgeon who took off his penis was Michael Dillon, the world’s first transgender man, formerly a girl. And the headlines revealed they were in love.

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‍ This was a time of secrets in Britain, a time when homosexuality was banned and sex changes for transgenders were illegally precarious. But Dillon was so smitten with Cowell that he agreed to risk his medical license to illegally castrate the man he loved.

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‍ He knew how Cowell felt being trapped in the wrong body. He too had been unhappy in the wrong body from childhood. They were two people crossing a divide together.

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‍ But the Sunday Pictorial splashed on the scandal on March 14, 1954, saying: “Robert Cowell who has sold his change of sex story to a newspaper is not a woman in the full sense.

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‍ “Medical experts consulted by us do not accept that this could be. His birth certificate is changed to Roberta Elizabeth Cowell, and he wears women’s clothes, but experts say he is still not a complete female.”

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‍ The story began in 1948, when Cowell was separated from his wife and two daughters and seeking help from the depression that hung over him.

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‍ It was then that he read Dillon’s book, Self: A Study in Ethics and Endocrinology, where he argued that people should be able to choose their gender.

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‍ At this time, Cowell was taking large doses of hormones but still living as a man so he arranged to meet Dillon and struck up a friendship, which became a deep bond between them. Cowell wanted more and persuaded the love-struck Dillon to remove his testicles. Cowell then hired Harley Street gynaecologist Sir Harold Gillies who had created a penis for Dillon. 

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‍The eminent surgeon had already reconstructed penises for soldiers who had endured injuries in the war.

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‍Now, although it was it was technically illegal, the physician also created Britain’s first surgically produced vagina for Cowell. He felt that he could argue he was bringing his professional abilities to a procedure already begun.

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‍ The work that was carried out led to Cowell being able to obtain a document stating he was intersex, which allowed him to have a new birth certificate issued recording the sex changed to female. And so, she became Roberta Elizabeth Cowell on her birth certificate. He was now a She.

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‍ Cowell made headlines after selling the story of her transition to Picture Post, in 1954 and was much photographed. She muddied most of the medical details, saying she was intersex to begin with and that her body began to transition ‘naturally’. The magazine was deluged with letters from hundreds of men wanting to be women.

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‍ But the story was to have a tragic end. Roberta, known to be a thrill seeker, struck up an affair with another woman and went off to live with her and over 30 cats. Some said it was to make up for killing them and eating them as a PoW.

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‍ Dillon was heartbroken and left Britain for India in the late 1950s to become a Buddhist monk. He died aged just 47 in 1962.

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‍ There are many gushing letters from Dillon to Cowell which are full of declarations of love and hints of sexual intimacy. Mysteriously, none of Roberta’s letters to him survive.

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‍ Roberta borrowed money to buy a De Havilland Mosquito, in which she planned to cross the Atlantic. Sadly, the project stalled and she was declared bankrupt and withdrew from public life.

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‍ On October 11, 2011, Roberta, aged 92, died alone. She was found lying on the bedroom floor of her sheltered-housing accommodation in West London. The flat was so cluttered that the wardens struggled to remove her body.

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‍ Only six people attended the cremation. Even her own children did not know she had died, until contacted by The Independent on Sunday

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‍THE SUNRISE MIKE NEVER FORGOT

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‍I remember our old Express pal Mike Dean driving down Ludgate Hill in his slightly battered, grey TR7 and chugging to a halt outside the NCP car park a stone’s throw from the Old Bailey in the late 1970s. We hacks had a Press Concession for the car park fees if we clocked in after 3.30pm. It was arranged by the Express management in the days when they had a bit of a heart and cared about the well-being of their staff. That fell apart when HR got a hold on the Black Lubyanka some years later, of course.

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‍ We all stood chatting by our cars parked on the downward ramp, waiting for the arrival of 3.30pm and people like tough Jock Billy Montgomery would sweep by and park his red Ford Granada 3-ltre with the number plate WAR, which we all found incredibly funny given his reputation at the bar. We never told him of course.

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‍ Mike, as I recall, was going through a rough patch with his wife in St Albans at the time, and was very depressed, and yet melancholic. One afternoon as we stood alone waiting for the car park barrier to rise, he told me of the most beautiful moment of his life when he had a sense of real spiritual being.

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‍ He had travelled to India, just him and a rucksack with his pyjamas and a toothbrush, wanting to get away from this mad world. He had been told about the love story of the Taj Mahal and one night he camped on the banks of the India’s Yamuna River in Agra, Uttar Pradesh, and woke early to experience the sun coming up over the wonderful, white marble mausoleum that the Mughal Emperor, Shah Jahan, built to house the tomb of his favourite wife, Mumtaz Mahal in the 17th century.

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‍ “It took my breath away Tel,” he said, “I was filled with awe. I literally tingled. It was a spiritual moment I had never had before, and probably never will again. I can see it and feel it now. An unexplainable feeling of deep love and perfection. I can’t properly explain. If you ever go there,  go at dawn. It’s like God has drawn you a picture.”

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‍ More than 20,000 artisans and stone masons took 22 years to build this masterpiece of white marble and precious inlays in memory of Mumtaz. She bore the emperor 14 children and was at his right hand on every matter of state. She was his friend, lover and adviser in all things. He was heartbroken when she died at 39, giving birth to her 14th child, a girl in 1632.

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‍ I have never forgotten that moment with Mike on Ludgate Hill, just him and I and his memories. I hope he has found that peace again whatever he is doing up there with the Gods.

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‍OLD NEWS IN BRIEF

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‍A funny thing happened …

‍IN HER book on dying called ‘The Funny Thing About Death’, comedian Jo Caulfield talks about losing her sister Annie to the ‘ratbag disease’ of cancer. Annie wrote her own obituary before she died, saying: “If you don’t know how to die, don’t worry; nature will tell you what to do on the spot, finely and adequately.” Scottish Sun, July 2923.

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‍Crackers! A time of no peace or goodwill

‍WAR broke out Christmas Day in 1859 then the 24th Regiment of Foot and the Tower Hamlets Militia had their Christmas dinner at Aldershot Barracks.

‍The Tower Hamlets Militia dined first on beef and pudding, washed down with a pint of beer each. The next sitting was the 24th Regiment who had a more upmarket meal of goose and punch.

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‍ When they met to wish each other a Happy Christmas, the Tower Hamlets lads boasted of their superior dinner. Words were exchanged in drink, there was a push, then a shove, then coal lumps were thrown with the punches; chairs came down on heads, windows were smashed and a gun appeared.

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‍One soldier was shot dead and it was the last of the camp Christmas dinners for a while, reported the Reading Mercury.

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‍Corset saves wife in a tight spot

‍In 1900, a tailor lost his temper with his manager over his poor pay. When the manager’s wife arrived at the shop in Faversham, Kent, with his sandwiches, the tailor produced a gun and, in the struggle, shot the wife in the chest. She survived when the bullet was deflected from her heart by her new steel-ribbed corset, The Sunderland Daily Echo and Shipping Gazette reported. The story led to hundreds of women turning up at the shop to buy the underwear.

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‍DID TOP JOURNALIST DIE ON BRINK OF EXPOSING TRUTH OF JFK SHOOTING?

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‍JOURNALIST Dorothy Kilgallen was a popular panellist in America’s TV version of What’s My Line in the 1960s but she was a tough and gutsy reporter too. Is that why she may have been murdered?

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‍ Dorothy was found dead in her Manhattan townhouse from an overdose of alcohol and barbiturates in November 1965, just days after claiming she was close to uncovering a major conspiracy into the killing of President John F Kennedy.

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‍ She was writing a book that would “blow the JFK case wide open”, she said. But no copies of the manuscript, her research notes or files on the shooting were found in her apartment.

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‍ And her death went against the grain. Friends said Dorothy drank too much, and was disappointed in her husband and three children, but she was not desperately unhappy and drowning in a haze of booze and pills.

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‍ Her knowledge came from an exclusive, private interview she had with killer Jack Ruby during his 1964 trial for the murder of JFK assassin Lee Harvey Oswald. He shot JFK who was travelling with his wife Jackie in an open top car in Dallas in November 1963.

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‍ Dorothy, former crime reporter and columnist for the New York Evening Journal, had received an advance from a publisher for her book in which she claimed Oswald did not act alone. Once hailed as ‘the most powerful female voice in America’, she always carried her manuscript with her and kept it under lock and key when she could.

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‍ “If the wrong people knew what I know about the JFK shooting, it would cost me my life,” she said, explaining why she had purchased a gun for the first time.

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‍ Her death was treated by some as just another highly-strung female checking out of Hotel Earth, but friends said she believed the JFK assassination touched the soul of America and she wasn’t going to stop investigating those in power.

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‍ After she died it was revealed that two additional barbiturates had been found in Kilgallen’s system in addition to Seconal, for which she had a prescription.

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‍ It was also discovered that there was powder residue in the glass by her bed, suggesting that someone had broken up the capsules. She had also been found dead in a bed she never slept in, in sleeping clothes she didn’t wear, next to a book that she’d told people she’d finished reading.

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‍ Dorothy believed that the Mob had had something to do with Kennedy’s death and claimed that a New Orleans mobster had orchestrated the president’s assassination.

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‍ But now her research will never be known.

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‍TERRY MANNERS

‍29 June 2026

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