Roald Dahl, Beloved Children’s Book Author and… Sex Spy?!

You may know Roald Dahl as the brilliant children’s book author of Matilda, Charlie and the Chocolate Factory, James and the Giant Peach, The BFG, and The Witches. But did you know he was also a WW2 sex spy?

Roald Dahl (1916-1990) was born in Cardiff, Wales to Norwegian immigrant parents. When he was only three years old, he lost his father and sister within months of each other. Shipped off to British boarding schools, he endured corporal punishment that would go on to inspire his many books, empathetic to children’s fights against cruel authority figures. As a young adult, he joined Shell Oil instead of college, and was posted in modern-day Tanzania. During WW1, he joined the Royal Air Force, training as a fighter pilot. Eventually, he was declared unfit for duty after a near-fatal crash in Libya left him with temporary blindness, chronic headaches, and other serious head injuries. It is this setback where our interesting story begins.

After his accident, British intelligence shipped him off to Washington D.C. during World War II. He was originally recruited by Canadian spymaster Sir William Stephenson (code name: Intrepid) in 1942, attached to MI6’s covert branch, which would eventually merge with Special Operations Executive (SOE). His plan was to weaken American isolationist thinking by influencing American journalists and politicians. While he was operating undercover as a RAF liaison officer at the British Embassy in Washington, D.C., his duties included gathering technical intelligence on American aircraft, briefing Allied commanders in Washington, assisting SOE planners with sabotage operations against German targets, and using his position to access high-level American political circles. You can actually view his official service records at the UK National Archives. Dahl was considered very handsome for the time. Although he didn’t have a trust fund, nor did he work in finance, he was 6’6” and had blue-grey eyes. He was also allegedly promiscuous, using his looks, wit, and charm to infiltrate elite circles in Washington, D.C. He became friends with Eleanor Roosevelt and had ties to Vice President Henry Wallace. Rumors have it that he would seduce women, particularly American socialites, to extract intelligence. Some of these women included Clare Boothe Luce who was married to Congressman Henry Luce, and Millicent Rogers.

Clare Boothe Luce was a famous playwright, best known for her hit play The Women in 1936, starring an all-female cast. It ran for 657 performances, opening at the Ethel Barrymore Theatre on Broadway. Her first husband was George Tuttle Brokaw, the millionaire heir to the Brokaw Brothers clothing empire, before divorcing due to his alcoholism. Her second husband was, also millionaire, Henry Luce, magazine publisher and founder of Time, Life, and Sports Illustrated. Although he was wildly successful, he was a newsman through and through, lacking his wife’s skills as a social butterfly. Supposedly they were “open”, with her list of lovers including Ambassador Joseph P. Kennedy, CIA Director Allen Dulles, and Randolph Churchill. Dahl was instructed to seduce Clare, who was thirteen years older than him, to see if he could persuade her to the British position, and then influence her husband and friends to the cause. One CIA publication on the subject suggested Dahl was “at best only peripherally involved in the romantic world of espionage.” However, he did submit a request begging to be extracted from the position as Clare’s lover as he found it to be too physically demanding… the married women were “too frisky” for him.

Millicent Rogers, socialite, fashionista, and Standard Oil heiress, was another lover. Before her entanglement with Dahl, she was engaged to a young steel company executive, had a relationship with Prince Aimone Duke of Aosta and heir to the Italian throne, a relationship with a married Russian aristocrat Prince Serge Obolensky, eloped and got divorced to penniless Austrian Count Ludwig von Salm-Hoogstraeten, married and divorced Argentinian aristocrat Arturo Peralta-Ramos, and lastly married and divorced an American stockbroker. All of this happened before the age of 39. You could say she was busy! During WW2, she bought and restored the historic estate Claremont Manor, transforming it into a working farm and rehabilitation center for Navy pilots, where she of course had relationships with the Secretary of the Navy and Commander Ian Fleming. Yes, the author who wrote the James Bond series. I guess you could say she had a type? So when Dahl, Fleming’s close friend and colleague, came around, a writer, a pilot, and a spy… Their affair was brief but passionate, spending time together at her 300-year-old estate in Montego Bay, Jamaica called Wharf House. (Fleming also had a home in Jamaica too.) Her friends Noel Coward and Cecil Beaton were also frequent guests. While the details of how their affair fizzled out are lost to the sands of time, Dahl made quite the impact as she made a 18-20k gold statuette titled Death of an Airman in honor of their relationship. Her son kept the statuette on his bedside after her death, and now you can see it exhibited at the Millicent Rogers Museum.

It is interesting to consider of if any of Dahl’s real life dalliances were used as inspiration for Fleming’s world famous womanizing spy. Considering how they were such close friends and colleagues, it seems likely; especially since Dahl wrote the screenplay for Fleming’s Chitty Chitty Bang Bang in 1968. Both would go on to become some of the most successful writers of their generation, creating characters that are beloved by millions and continue to inspire cinematic adaptations to this day. I guess you could say, all is fair in love and war and writing.