The American ruling class, such as it is, has long imitated the British ruling class. Old-time WASPs were notorious Anglophiles, and their fascination extended to espionage. At the beginning of World War II, the British intelligence service helped persuade President Franklin D. Roosevelt to set up a wartime spy agency, the Office of Strategic Services. The OSS, sometimes known as "Oh So Social" because its officers included so many society types, served as "the willing handmaiden of the British," writes Jennet Conant in her lively new history, "The Irregulars: Roald Dahl and the British Spy Ring in Wartime Washington." If the British spies in Washington—who included dashing authors Ian Fleming and Dahl—did not quite drag America into World War II (it took Pearl Harbor and Hitler's declaration of war on the United States to achieve that), they effectively wooed and spied upon the press and political establishment.
Britain badly needed to work its collective charm on America's opinion makers. Winston Churchill knew that U.S. intervention was essential to defeating Nazi Germany, but many Americans wanted no part of the war. So Churchill sent spies to discredit the isolationists and stir sympathy for joining the fight. The clandestine operation, known as the Rumor Factory, pulled some outrageous stunts, but the biggest coup came in March 1941. Roosevelt went on the radio to announce, "I have in my possession a secret map made in Germany by Hitler's government … of South America and part of Central America as Hitler proposes to reorganize it." FDR warned: "That map, my friends, makes clear the Nazi design not only against South America but the United States as well." The map was a British forgery.
The British spies were a romantic bunch who included the playwright Noel Coward and Fleming, the British naval intelligence officer who later created the James Bond novels. They referred to themselves as the Baker Street Irregulars, after the Sherlock Holmes stories, and the most irregular may have been Dahl, an RAF pilot and assistant air attaché in the British Embassy, who went on to write very clever, macabre short stories and hugely popular children's books ("Charlie and the Chocolate Factory"). Ideally, spies blend into a crowd, but Dahl was a 6-foot-6 Viking, handsome and outspoken to the point of rudeness. Conant writes, "With his reckless sense of humor and general air of insubordination, Dahl may have been mentioned to someone on high as having the makings of an ideal informant, if for no other reason than no one so badly behaved would ever be suspected of working for British intelligence."
Dahl initially wanted to stay in the United States to pursue his literary career, but he found he could play a role for British intelligence by putting on his RAF uniform and going to Washington parties. "All Dahl had to do was keep up a cheerful front and eavesdrop his way through the yawning Sunday breakfasts, hunt breakfasts, luncheons, teas, tea dances, innumerable drinks parties, banquets, and not infrequent balls," writes Conant. Dahl was a gambler— he lost $900 (his first literary paycheck) playing poker with Harry Truman—and swordsman extraordinaire. "Girls just fell at Roald's feet," according to Antoinette Marsh, daughter of a Texas newspaper publisher. "I think he slept with everybody on the East and West Coasts who had more than $50,000 a year."
One was Clare Boothe Luce, congresswoman, playwright and wife of Time Inc. publishing czar Henry Luce. Dahl was assigned to gather pillow talk from Mrs. Luce, who was regarded as anti-British. It was hard duty. "I am all f–––ed out," Dahl complained to the ambassador, Lord Halifax, after a three-night stand. "You know it's a great assignment but I just can't go on." Halifax reminded him of a scene from a movie about Henry VIII, in which Henry goes into the bedroom with Anne of Cleves: "The things I've done for England." According to Conant, Halifax told Dahl, "Well, that's what you've got to do."
Dahl's most important conquest was Eleanor Roosevelt, whom he won not with sex but with his literary imagination. The First Lady had read a Dahl story to her grandchildren and asked him to dinner at the White House. Dahl was duly charming and soon found himself invited to Hyde Park for the Fourth of July, 1943. FDR, though, was not fooled. Dahl found the president mixing martinis. Glancing up, Roosevelt announced, "I've just had a very interesting cable from Winston." Conant writes: "It was Roosevelt's way of letting Dahl know that he was aware that he was reporting back to British intelligence."
Conant might have followed up on Fleming, a close friend of Dahl's. In 1960, Fleming was invited to a Washington dinner party attended by the presidential candidate John F. Kennedy (a big fan of the Bond novels) and a high official at the CIA. Fleming held forth on all the ways that U.S. intelligence could undermine Fidel Castro. The next morning, the hostess of the party received a call from Allen Dulles, director of the CIA, looking for Fleming. It may be a coincidence, but shortly thereafter the CIA began working on a plot to make Castro's beard fall out. Sounds like the sort of story only Roald Dahl would dream up.