Overlooked No More: Roberta Cowell, Trans Trailblazer, Pilot and Auto Racer

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

Roberta Elizabeth Marshall Cowell (no relation to the author of this article) was born on April 8, 1918, in Croydon, south of London, one of three children born to Dorothy Elizabeth Miller and a high-ranking military surgeon, Maj. Gen. 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 in tuition-based, single-sex schools. 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 R.A.F.”

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 racecar 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 R.A.F. 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.

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