The Playboy Spy

The list of men who have been named as “the real James Bond” is long. Most of them insist there is no way they were the inspiration for 007. One of them outright scoffed at the idea. As far as he himself was concerned, Dusan “Dusko” Popov was much cooler than James Bond. A better spy. A better bon vivant. A better playboy. Popov famously claimed, during a 1974 television interview on the Mike Douglas Show in support of Popov’s memoirs (Spy Counterspy), that James Bond “wouldn’t last 48 hours.” If there was any spy to emerge from World War II who could boast of being “More James Bond than James Bond” and back it up, it was this brash, wild Serbian who was known during the war as Agent Tricycle.

Popov was born in 1912, in Titel, a region of what was then the Austro-Hungarian Empire and later became Serbia. His was a wealthy, well-respected family and he received the very best education Europe could give him. He was an athlete, a wild child, and a polyglot, taking to new languages very easily — including German. In 1936, he left home to pursue a PhD in law at the University of Freiburg in southern Germany. It was there that Popov met Johann “Johnny” Jebsen, a Dane whose parents — deceased by 1936 — had become German citizens. And it was in Germany, Hamburg to be exact, that Jebsen had been born, though he never identified with his German citizenship, joking that it was nothing more than a “flag of convenience” when conducting business for the shipping empire he’d inherited.

Despite being a German-born Dane, his heart was with England, a country he’d fallen in love with during a visit in his youth.  Like Popov, Jebsen was the scion of a wealthy family. The two became fast friends, cutting a wild path through university life. They were not particularly good students during this period. As Popov wrote, ““We both had some intellectual pretensions, but [we were] addicted to sports cars and sporting girls and had enough money to keep them both running.” The two playboys were also developing an increasingly belligerent view of the ascendant Nazi party. Popov was so vocal in his opposition that he was called in for interrogation and might have ended up in a concentration camp ha not Jebsen contacted Popov’s father, who then pulled some strings and arranged for Dusan to go free so long as he left Germany. Under these circumstances, the two friends parted ways. Popov went to Yugoslavia, where he established his own import-export business. Jebsen announced that he would be traveling to England, where he intended to continue his academic pursuits at Oxford. Jebsen, however, never made it to England, and Popov did not see his friend for the next three years. By then, Europe was at war once again.

By 1940, Popov had abandoned his attempt at becoming an import-export magnate and had opened his own law firm. One day, he received a letter from Jebsen, insisting, “Need to meet you urgently.” The two rakehells reunited shortly thereafter in Belgrade, at the Hotel Royal,  and immediately set about satiating their monstrous appetites for indulgence, hitting every notable nightspot and picking up a chorus girls to accompany them along the way. A couple days later, after they’d recovered somewhat from their reunion, Jebsen confided a secret to his old friend: he had joined the Abwehr — German military intelligence. Mostly, it had been to avoid being drafted into the infantry, but Popov could not believe his friend, who had been so opposed to the Nazis in college, had become part of the machine. What’s more, Jebsen, who occupied the role of “talent scout” for the organization, wanted to recruit Popov, to turn him into a Nazi spy operating in England. Dusko could not believe what he was hearing from his old friend, until Jebsen whispered one more thing to him: the best way to destroy a team is from within.

Popov agreed to meet with a representative from the Abwehr. The Germans for their part were happy to have a man like Popov, someone who spoke many languages, who had a lot of money and a lifestyle that had made him a familiar face across Europe and the United Kingdom. Abwehr head General Ernst Munzinger himself met with Popov and plied him with food, drink, and praise. Popov agreed. the next day, he was officially working for The Abwehr. His first act as a German spy, completed without the knowledge of his new masters, was to visit the British embassy, explain the opportunity that had been handed to him, and offer his services to England as a double agent.

His career as Agent Tricycle is full of the incalculable risks, unbelievable nerve, incredible indulgence, and improbable luck that seems like the stuff of spy thrillers. And in at least one case, it was exactly that. Popov was in Portugal at the time, 1941, gambling at the Casino Estoril just outside of Lisbon and connected to the Palacio Hotel, “the whispering hotel,” as it was called due to its popularity with displaced European royalty and spies from both the Axis and Allied powers. Portugal’s status as a neutral country (though German leaning) and one of the only open transit countries from Europe to the United Kingdom, and as its capital city, Lisbon was one of Europe’s most infamous nests of spies. Irritated by a particularly pompous opponent at the baccarat table one night — baccarat being Popov’s specialty — the daring Popov placed a bet for $38,000 (most of it British money earmarked for other purposes), forcing his opponent away from the table. In fact, Popov was known for his tendency to gamble against — and clean out — Nazi sympathizers and officers. But that night in particular at Casino Estoril, his shadow (England wasn’t entirely certain that the caddish Popov could be trusted) was a young Naval Intelligence officer by the name of Ian Fleming.

Popov’s intelligence work played for similarly higher and higher stakes. When he came into possession of a German checklist, Popov realized it was the beginning of a plan for the Japanese to bomb the American Naval base at Pearl Harbor, Hawaii. He was sent to the United States by his German handlers, who knew him under the code name Ivan. While in the United States, Popov continued to live the high life, even striking up a scandalous affair with French actress and Cat People star Simone Simon. He also tried to communicate a warning about Pearl Harbor to the United States, but FBI head J. Edgar Hoover despised Popov, who he regarded as a degenerate, a foreigner, and a sex maniac. Hoover not only dismissed Popov’s information about Pearl Harbor; he orchestrated the deportation of Popov from the United States, using the Mann Act as his excuse (the Mann Act made it illegal to transport a woman across state lines for lascivious purposes; Popov had taken one of his many “Popov Girls” from New York to Florida).

Years later J. Edgar Hoover would administer the same dour judgement on another famous playboy British agent: James Bond. During the filming of Goldfinger, released in 1964, the FBI — still under the thumb of Director Hoover — grew concerned that the film might mention the FBI, and in doing so associate the Bureau with the stories of Ian Fleming, which, an internal FBI memo noted, “are generally filled with beautiful women presenting themselves to [Bond] in scanty attire” and “generally center around sex and bizarre situations, and certainly are not the type with which we would want to be associated.” J. Edgar concurred — literally; at the bottom of another FBI memo that asserted “in the event the Bureau is contacted for permission to portray an FBI agent in the movie, it should be flatly denied,” J. Edgar wrote, “I concur.”  Lucky for James Bond, the CIA were more than willing to help him out, eating Kentucky Fried Chicken and gunning down Goldfinger’s terrorists in the gold vault at Fort Knox in Kentucky.

Dusko Popov’s friend, Johann Jebsen — who had been conspiring with his college chum all along — played a similarly dangerous game, one for which he eventually paid the ultimate price. On April 29, 1944, Jebsen ran afoul of German suspicions and abducted from Lisbon and driven overnight to France. Losing Jebsen was perhaps an even greater blow than it would have been to lose Popov. Jebsen not only knew about Agent Tricycle, but he also had important information about another of England’s most famous double agents, Joan Pujol Garcia, codename Agent Garbo. Garcia was the lynchpin of Operation Fortitude — the Allied effort to fool the Germans into thinking the D-Day invasion would land in Calais. Despite constant interrogation and torture, Jebsen did not crack. In July of 1944, Jebsen was transferred to a concentration camp. In February 1945, agents of the Gestapo arrived to take Jebsen away. He was never seen or heard from again. It is suspected that, ironically, Jebsen was disappeared after his duplicitous nature was discovered in order to protect the man the Abwehr considered among their most valuable spies: Dusko Popov, who the Germans feared Jebsen my expose as a German agent to the British.

After the war, when Popov discovered the fate of his friend and accomplice in fooling the Germans, he sought revenge against the man he held responsible for Jebsen’s death. After tracking the man down, the former commander of the Sachsenhausen concentration camp where Jebsen had been imprisoned, Popov beat the former Nazi senseless but could not bring himself to kill someone he regarded as so pathetic. “How can you put a bullet in a bag of shit?” he wondered in his autobiography.

That night at the Casino Estoril made an indelible impression on Commander Fleming. So impressed was Fleming by Dusko’s brash and cool demeanor that he decided to copy the double agent’s style, seeking to bankrupt Nazis at the gambling table on his own. Fleming, however, proved rather a less able gambler than Popov. He lost spectacularly, and his boss, Admiral John Henry Godfrey, had to cover Fleming’s debts. However, the idea stuck with Fleming and he had considerably more luck with it in fiction, when Dusan Popov became James Bond and the Casino Estoril became the Casino Royale.

“The scent and smoke and sweat of a casino are nauseating at three in the morning. Then the soul erosion produced by high gambling, a compost of greed and fear and nervous tension, becomes unbearable and the senses awake and revolt from it.” — Casino Royale