For some of these big-name personalities, spying taught them the skills that made them famous; for others, being famous made them the perfect spies.
Roald Dahl
Long before he wrote Charlie and the Chocolate Factory and James and the Giant Peach, Roald Dahl was a fighter pilot for the British Royal Air Force during World War II. But after sustaining several injuries in a horrific crash in 1940—including a fractured skull and temporary blindness—Dahl was rendered unable to fly. In 1942, he was transferred to a desk job at the British Embassy in Washington, D.C. Dahl quickly charmed his way into high society and became so popular among D.C. ladies that British intelligence came up with a whole new role for him: seducing powerful women and using them to promote Britain’s interests in America.
It wasn’t all fun and games, though. Clare Booth Luce, a prominent U.S. Representative and isolationist who was married to Time magazine founder Henry Luce, was so frisky in the bedroom that Dahl begged to be let off the assignment. In the end, however, his work with the ladies paid off. Dahl managed to not only rally support for Britain at a time when many prominent Americans didn’t want the country to enter the war, but he also managed to pass valuable stolen documents to the British government. Dahl’s stint in D.C. also helped him realize his talent for writing; it was a skill he discovered while penning propaganda for American newspapers.
Ian Fleming
By trade, author Ian Fleming was a journalist with a sharp memory and a keen eye for detail. In fact, he created James Bond, his famed international man of mystery, by plundering his own experiences as a spy.
During World War II, Fleming put his writing talents to use as part of British Naval Intelligence. Although he looked the part of Bond—tall, blue-eyed, and dapper—Fleming worked a desk job. He managed communications between the British Admiralty and the branch of intelligence tasked with sabotage behind enemy lines. Fleming was good at what he did. Not surprisingly, he proved particularly adept at conceiving outlandish spy schemes familiar to Bond fans.
Fleming’s work eventually extended to the United States. He was responsible for helping to create an American organization focused on international intelligence gathering. In 1941, he drew up a detailed chart for the chief of the OSS, showing how the new organization should be run. For his efforts, he was awarded an engraved .38 Colt Police Positive revolver.
Despite being a desk jockey, Fleming did get to witness one active operation—a break-in at the Japanese Consul General’s office at Rockefeller Center. As Fleming watched, British operatives sneaked into the office, cracked a safe, and made copies of the Japanese codebooks. Fleming later used the incident for Bond’s assignment in his first 007 book, Casino Royale.
Lucky Luciano
As head of the Genovese crime family, Charles “Lucky” Luciano did more for organized crime than any other mobster of his generation. Luciano smoothed out the Mafia’s rough edges and turned families of thugs into well-oiled, organized-crime machines. Not only that, but Lucky also embodied the gangster image—palling around with Frank Sinatra and giving girls $100 bills just for smiling. With a track record like that, it’s no wonder he ended up working for U.S. intelligence.
The story goes like this: In 1936, Luciano was convicted on 62 counts of “compulsory prostitution” and sentenced to 30 to 50 years in prison. But while he was incarcerated, the government discovered that it needed his help. In 1942, a French ocean liner, the Normandie, was being converted into a troop transport ship when it suddenly caught fire and sank. American officials suspected sabotage. But the dockworkers, who were under the Mafia’s thumb, refused to spill any information. The government needed an in, and Luciano was the key.
In many ways, Luciano felt an intense loyalty to America; after all, it’s where he’d earned his fortune. So, he used his influence to urge the dockworkers to cooperate with authorities. In exchange, the mobster enjoyed unsupervised visits from friends and associates for the rest of his time in prison. It was a sweet deal for the U.S. government, too; in a matter of weeks, eight German spies were caught and arrested for the destruction of the Normandie.
Luciano continued to help American forces for the remainder of World War II, using his contacts on the docks to feed information to the Office of Naval Intelligence. Later, as the Allies were planning their invasion of Italy, Luciano, who also had strong ties to the Sicilian mob, offered invaluable information on where to counterattack.
As a reward for his help, Luciano was released in 1946 after serving only 10 years in prison. However, the terms of his release required that he be deported to his birthplace of Italy and never allowed back into the United States. Luciano died in exile in 1962. Before he passed away, he told two biographers that he’d had his own men set fire to the Normandie as part of a creative plot to pressure the government to release him. But as The New York Times noted, Luciano was “known to exaggerate his own cleverness.”
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