The Unknown Story of the Real James Bond in Manhattan

Ian Fleming (1908-1964), author of the Bond novels

Who was the real James Bond?  Was it someone Bond author Ian Fleming met during WWII?  Or perhaps a better version of Fleming, the chain-smoking, oversexed and underachieving spy turned author who suffered severe depression because his visions for himself never matched reality.  While the answer is surely some of each, one double agent whom Fleming shadowed one night during the war was a strong inspiration.  In rare documentary footage viewed by Hidden New York, Fleming said his first book Casino Royale was based on his experiences at the Casino Estoril and the spies he met there.
 

Dusko Popov (1912-1981), double agent during WWII

During World War II, neutral Portugal became a weigh station for espionage activity.  Enter Dusko Popov (1912-1981), a Nazi spy turned by the Allies to work for the British.  In August of 1941, the day before Popov was due to depart for Manhattan on what the Nazi’s believed to be an intelligence gathering mission, Popov was shadowed at the Casino Estoril by none other than Ian Fleming.  The British were keeping tabs on Popov to see where his loyalty really lied, but Popov instantly picked up on the fact he was being shadowed by the clumsy Fleming.  According to his autobiography Spy/Counterspy, An incident broke out at the Baccarat table.  Popov became irritated by an arrogant player who placed enormous bets knowing others could not match him.  Popov trumped him with a $50,000 bet to the dismay of all around, including Fleming who was watching from a distance.  According to Popov, Fleming turned the “green of bile” before flashing a sly smile to Popov when the player backed down.  This incident was memorialized in Fleming’s first book Casino Royale (1953).    

Casino Royale (1953), the first Bond novel

The next day Popov headed for Manhattan.  His assignment was to gather all information he could about the American outpost of Pearl Harbor and report it back to the Nazis.  Arriving in New York, Popov dropped his bags off at the Waldorf-Astoria Hotel before heading to a meeting with the FBI warning them of the impending attack and providing them a questionnaire on Pearl Harbor supplied by his Nazi handlers.  The FBI, however, brushed off Popov as an untrustworthy playboy who they felt was still secretly working for the Nazis.  Popov claims in his book to have had a confrontational meeting with FBI director J. Edgar Hoover prior to the attack on Pearl Harbor.  While Popov’s claims are shocking and have been denied by the FBI, there are many indications they are true.  Powerful people in British intelligence have backed Popov’s claims, including Sir John Masterman, the chair of Britain’s Double Agent Committee who recruited Popov.  Popov was even awarded the prestigious Order of the British (OBE) award for his service.  And the FBI has every reason to dispute Popov’s claims to avoid the blame for not heeding his warning on Pearl Harbor.

Brushed aside by the FBI and unable to return to Europe because the Nazi’s believed he was on a fact-finding mission for them, Popov was effectively marooned in Manhattan for nearly a year.  In the Big Apple, Popov did what he did best – enjoy life and live a playboy lifestyle.  True to the Bond form, Popov dressed in expensive clothes, rented a lavish apartment with a wrap-around terrace at 61^st and Park, went gambling, smoked and drank heavily, took beach trips to Miami and ski trips to Part City, Utah, and, of course, loved women.  His nights passed in a “blur of sex and alcohol.”

Daniel Craig (1968-), current Bond actor

He had numerous female companions, including most significantly Hollywood actress Simone Simon, whom he escorted to the finest restaurants and nightclubs in New York City.  “[Simone and I] became regular fixtures in the fashionable restaurants,” Popov writes, “an item of inventory in [Manhattan nightclubs] El Moracco and the Stork Club.”  But Popov, codenamed “Tricycle” by the British, was also serious about his work and put his life on the line many times for the Allies.  Had his Nazi handlers known he was working for the Allies, Popov would have faced most certain death.

In 1972, John Masterman, former chair of the British XX Committee that ran Popov published a history of the cloak and dagger committee that included a copy of the entire Pearl Harbor questionnaire that agent “Tricycle” had passed to the FBI with a stern conclusion that it represented a “somber but unregarded warning of the subsequent attack upon Pearl Harbor.”  Popov wrote his memoirs Spy/Counterspy just two years after the Masterman book, believing Masterman had opened the door to discussing his clandestine operations and discussing his meeting with Hoover and warning about Pearl Harbor.  Clarence Kelly, Hoover’s successor as FBI director, denied that Popov and Hoover had ever met and insisted that the FBI never had information that Japan would attack Pearl Harbor.  Popov set off on a book endorsement tour in which he was hailed as the real James Bond and glamourized by the media for his attractive wife over thirty years his junior.  When he died on August 10, 1981, forty years to the day when the then 29-year old spy left for New York City to warn the FBI about Pearl Harbor, his widow said “He lived how he wanted to live.”  Negatively viewed by many as a mere playboy, Popov once responded, “When you love life, good wine, good company, and can still do good serious work, it is not being a playboy it is living life to the full.”