The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
The Spy Who Led an Army to its Doom With Fake Newspapers and Letters

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters

Khalid Elhassan - December 5, 2021

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
A colorized photo of master spy Sidney Reilly. Klimbim

13. A Master Spy With Flexible Loyalties

Early in World War I, Sidney Reilly was sent to the then neutral United States – an important source of weapons and munitions for Britain and her Entente allies. There, he got involved in the lucrative arms business. Although he had been a British spy for over a decade by then, and Britain was now at war with Germany, Reilly did not let notions of loyalty get in the way of profits. In 1914 – 1915, for example, he arranged weapons purchase deals for the army of Britain’s Entente ally, Russia, as well for the Entente’s enemy, the Imperial German Army.

While in the US, Reilly might also have conducted some false flag “German sabotage” operations on behalf of the British, to arouse the American government and public against Germany. Reilly’s profits as an equal opportunity arms dealer took a hit in 1917. When the US joined the war on the Entente’s side that year, he was no longer able to sell weapons to Germany, now America’s enemy. Later that year, the Russian Revolution erupted, and the Russians ceased their weapons purchases.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Photo from a fake 1918 German passport used by Sidney Reilly, with the alias George Bergmann. Wikimedia

12. A Star Secret Agent’s Return to Espionage

With his business as an arms dealer in decline, Sidney Reilly returned to Europe and his British spy masters. They sent him behind German lines on various missions to carry out espionage in occupied Belgium or Germany. He used a variety of disguises and forged identity papers. He sometimes presented himself as a peasant, and at other times as a wounded German soldier or officer on sick leave from the front. In April 1918, Britain’s MI6 sent Reilly to Russia, whose new Bolshevik government had signed a peace treaty that took the country out of the Entente and out of the war against Germany.

The British hoped to overthrow the Bolsheviks, and replace them with a new and more sympathetic government that might rejoin the war on Britain’s side. To that end, Reilly got involved in a variety of plots intended to destabilize the Reds. That spring and summer, he tried his hand at a variety of failed schemes. They included an abortive plot to bribe Kremlin guards and get them to launch a coup, and a plan to assassinate Vladimir Lenin that wounded but did not kill the Bolshevik leader.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Master spy Sidney Reilly. Muy Historia

11. The End of a Master Spy

After the failed attempt to assassinate Lenin, Sidney Reilly was forced to flee the USSR, and he made it out of the country just a step ahead of the Soviet secret police, the Cheka. The Reds tried him in absentia and sentenced him to death. Reilly’s endeavors to topple the Bolsheviks had not met with success, but Britain’s MI6 appreciated the effort and awarded him a Military Medal. However, the failure gnawed at Reilly, whose time in Red Russia had turned him into an implacable anti-Bolshevik, and he begged for an opportunity to have another go at the Soviets. His bosses declined, so the master spy decided to wage his own anti-Bolshevik campaign.

Unfortunately for Reilly, he had found his match in the Reds, whose deviousness was equal to his own. Soviet intelligence created an anti-Bolshevik organization known as the Trust, which was actually run by their own secret police, the Cheka. Trust members met Reilly, and lured him to Russia, under the pretext of a secret summit meeting with its anti-Bolshevik leaders. When he crossed the border in 1925, Reilly was arrested and taken to Moscow’s dreaded Lubyanka Prison for interrogation and torture. He was eventually executed on November 5th, 1925.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Dusko Popov. 011 Info

10. The Extraordinary Life of a Triple Spy

There are not that many people who have lived a life as extraordinary or as impactful as Dusan “Dusko” Popov (1912 – 1981), a Serbian WWII spy and triple agent who was decorated by both the Germans and the British. A mostly unsung and largely unrecognized hero, Popov played an oversized role in the success of the Allied invasion of Normandy. And he did it in style. Popov helped beat the Nazis while he traveled around the world and led a playboy life, as he partied in top-notch nightclubs and casinos with a bevy of beauties and famous actresses.

He pulled that off because he was blessed with an abundance of natural charm and smoothness, good looks that set hearts aflutter, plus an agreeable presence that just drew people to him. That combination of charisma, coolness, wit and looks did not go unnoticed by a mid-level British intelligence officer named Ian Fleming, who went on after the war to create fiction’s greatest spy, James Bond. Indeed, it is almost a certainty that Fleming, who became acquainted with Popov during the war, modeled much of Agent 007 upon the smooth Serb.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Dusko Popov on the slopes. 007 Museum

9. One of Fortune’s Favorites, With an Ear for Languages

Dusko Popov was one of fortune’s favorites, and such favor began with his birth in 1912 into a wealthy Serbian family that had been affluent for centuries. His grandfather had been a rich banker and businessman who owned factories, mines, and retail establishments, and his father made the family richer still when he added real estate to its investment portfolio. Popov, an avid outdoorsman and athlete since childhood, thus grew up in the lap of luxury, attended by servants in the family’s numerous villas or while he sailed the seas in one of the family’s numerous yachts.

The future spy was set on the playboy path from an early age by an indulgent father, who built his kids a huge seaside villa and gave them generous allowances that allowed them to host lavish parties there. Although indulgent, Popov’s father did not simply spoil his kids rotten. He made sure that they got as great a top-notch education as his considerable wealth could afford. Thus, by the time Popov was a teenager he was fluent in French, German, and Italian, in addition to his native Serbian. Such linguistic skills came in handy down the road.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Dusko Popov’s time in Germany made him hate the Nazis. Encyclopedia Britannica

8. The Nazis Awakened This Dilettante Playboy’s Interest in Politics

After Popov studied in England – where he got expelled from a prestigious prep school – and France, he returned home to study law at the University of Belgrade. When he was twenty-two, not long after the Nazis came to power, he headed to Germany to pursue a law doctorate at the University of Freiburg. There, he befriended a rich German student named Johann “Johnny” Jebsen, who had anti-Nazi views. Until then, Popov had simply been a dilettante playboy with no interest in politics. His time in Germany caused him to loathe the Nazis and develop strong political opinions against them.

The young Serb was not discrete about his views, however, and that proved to be a problem in the totalitarian Third Reich. In 1937 he was arrested by the Gestapo, who suspected that he might be a communist, and was tossed into prison. His friend Johnny Jebsen came to his aid and alerted Popov’s father, who in turn got the Yugoslav government involved. After high-level contacts between Yugoslavia’s prime minister and Herman Goering, then head of the Gestapo, Popov was released from jail, and expelled from Germany.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Johnny Jebsen, left. Algunas Cositas Buenas

7. The Emergence of a Triple Spy

Dusko Popov’s experience in Germany did not improve his opinion of the Nazis, and when WWII broke out, he was primed and eager to pay them back if the opportunity presented itself. It presented itself when his friend Jebsen, whose family’s business needed favors from Popov’s, informed him in 1940 that he had joined Germany’s military spy agency, the Abwehr. Popov passed that information to a contact in the British embassy named Clement Hope, along with the observation that Jebsen was not that fond of the Nazis. Jebsen sought to recruit Popov as an Abwehr spy, and when he passed that on the British, they recruited him as an MI6 agent and urged him to play along with the Germans and join the Abwehr.

Popov was given the codename Ivan by his German handlers, while the British codenamed him Tricycle because he was in charge of three double agents. Popov eventually turned Jebsen, and recruited his German recruiter into British intelligence as a double agent. Popov also fed information to his native Yugoslavia’s intelligence, which made him a triple agent. He moved to London, and his family’s business activities gave him cover to travel back and forth to neutral Portugal. There, Popov met his Abwehr contacts and fed them information provided to him by the British service that ranged from harmless truths to half-truths, to outright lies.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Dusko Popov in Yugoslav Army uniform. Total Croatia News

6. A Triple Agent in the United States

The Abwehr was quite pleased with their spy Dusko Popov. Although some of his German handlers grew suspicious, their suspicions did not make their way up the chain of command. Among other things, an assignment to German military intelligence in Portugal was a cushy gig compared to less attractive ones, such as an assignment to the Eastern Front. Also, many in the Abwehr, from its chief Wilhelm Canaris on down to lower officials such as Johnny Jebsen, disliked the Nazis and did what they could to undermine them.

In 1941, the Abwehr furnished Popov with a small fortune and sent him to the United States to gather intelligence on American defensive measures. The information sought included an extensive list of questions about the defenses of Pearl Harbor, in which Germany’s Japanese allies were keenly interested. The British worked with the Feds to handle Popov while in the US, but FBI Director J. Edgar Hoover and his G-men lacked the vision and finesse of their British counterparts. Rather than use Popov as a double agent to suss out German intentions and feed them false information, Hoover simply wanted to use him to catch German spies.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Dusko Popov, looking as dapper in real life as James Bond could ever wish to be. Pinterest

5. Dusko Popov’s Party in the USA

J. Edgar Hoover failed to pass on Dusko Popov’s Abwehr questions to American military authorities – particularly the ones that sought information about Pearl Harbor’s defenses. After the Japanese attack wrecked the US fleet there a few months later, Hoover’s oversight should have wrecked his career. However, he buried it so deep that it did not come out until after his death. In the meantime, the prissy FBI Director, whose private life was even more scandalous than the Serb spy, got moralistic about Popov’s promiscuous lifestyle, nightlife escapades, and playboy antics. Hoover even threatened to have Popov arrested under the Mann Act for traveling with a woman across state lines “for immoral purposes”.

The British assigned a naval intelligence officer named Ian Fleming to watch Popov’s every move in the US. The future author of James of Bond followed Popov around as he made the rounds of American night clubs and casinos, womanized, splurged the cash furnished him by the Abwehr, and made a killing on the roulette tables. The style and panache left an impression that found expression years later in Agent 007. Indeed, some famous scenes from Casino Royale were based on Fleming’s observations of Popov in American casinos.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Dusko Popov and a friend. Tricurioso

4. The Serb Spy and the D-Day Deceptions

Eventually, Dusko Popov’s relationship with the FBI grew toxic, and as J. Edgar Hoover stewed over the double agent’s antics, things threatened to get worse. So British intelligence recalled their spy to London, where he continued to feed the Abwehr false information. His biggest contribution to the eventual downfall of the Nazis came in the intricate Allied deception plans, collectively known as Operation Bodyguard. Their ultimate aim was to mislead the Germans about the planned invasion of France, scheduled for the summer of 1944.

Operation Bodyguard had three goals. First, conceal the actual date and time of the invasion. Second, convince the Germans after the Allies landed in Normandy that those landings were just diversions intended to juke the Germans out of the Pas de Calais, where the real Allied invasion would land soon thereafter. Third, convince the Germans after the Normandy landings to maintain a strong defense in the Pas de Calais for at least two weeks, rather than send its defenders to reinforce Normandy. Popov played a key role in a sub-plan of Bodyguard, known as Operation Fortitude, which revolved around a fictitious First US Army Group (FUSAG) in southeast England under the command of General George S. Patton.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Johann ‘Johnny’ Jebsen. MI5 Archives

3. A Spanner Thrown Into the Works

Dusko Popov passed on to the Abwehr made-up details about FUSAG’s units, strength, and organization. His German handlers swallowed his misinformation hook, line, and sinker. Their faith in Popov’s information was reinforced when they eavesdropped on fake radio traffic between fictitious FUSAG formations. To further reinforce the deception, German reconnaissance planes were allowed to fly over and photograph concentrations of FUSAG tanks and transports that were actually inflatable dummies. A spanner was thrown in the works, however, when the Germans arrested Popov’s friend Johnny Jebsen, the Abwehr agent who had “recruited” him to spy for the Nazis.

Jebsen was kidnapped in Lisbon and smuggled back into Germany. There, he was tortured, then sent to a concentration camp where he disappeared and is presumed to have been killed near war’s end. Jebsen knew that his friend Popov was a double agent – indeed, Popov had turned him and made Jebsen a double agent for the British. The Germans did not know that, however, and had snatched Jebsen because they thought he was about to defect, not that he had already turned. They did not suspect Popov, and ironically, had arrested Jebsen because they feared that he would inform the British about the Serb, whom they viewed as one of their star spies.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
One of Operation Fortitude’s inflatable tanks. Mashable

2. A Double Agent’s Key Contribution to the Allies’ Success in Normandy

When British intelligence learned that Johnny Jebsen had been arrested by the Germans, they feared that he would reveal that Dusko Popov had actually worked for the Allies all along. They thought it was all over for their Agent Tricycle, and suspended his activities and those of his network. Despite torture, however, Jebsen did not let slip that Popov, Agent Ivan to the Germans, was a British spy. When British intelligence realized that the Abwehr still trusted Popov, they put him back to work to continue the deception. He and Operation Fortitude paid off for the Allies in a big way.

After D-Day, the Germans were convinced that the Normandy invasion was not the main event, but only the first in a series of landings. So instead of rushing all available reinforcements to contest the Allies in Normandy, they kept powerful formations in the Pas de Calais, to defend it from the “main invasion” by the fictitious FUSAG. Popov’s British handlers had hoped to convince the Germans to keep the Pas de Calais formations in place for two weeks after D-Day. Things worked out better than their wildest hopes: instead of two weeks, the Nazis kept their units there for seven weeks. By the time the Pas de Calais defenders were finally released, it was too late for the Germans.

The Spy Who Led an Army to its Doom With Fake Newspapers and Letters
Dusko Popov in later years. Amazon

1. A Spy Rides Off Into the Sunset

The Allies took advantage of the breather afforded them by the success of the Operation Bodyguard and Operation Fortitude deceptions to build a powerful beachhead in Normandy. From there, they eventually broke out to liberate France and Western Europe. After Paris was freed from the Nazi yoke, Dusko Popov was sent to the French capital to help establish a British intelligence network. When Yugoslavia turned communist after the war, there was no future for the playboy Popov back in his home country, so he decided to stay put in the West.

Popov was awarded the Order of the British Empire for his wartime exploits – a nice accompaniment to the medals given him by the Germans during the conflict – and eventually became a British citizen. He prospered as a businessman and had no intention to reveal his wartime activities. In 1972, however, John Masterman published The Double Cross System in the War of 1939 to 1945, a deep dive into British wartime intelligence. That convinced Popov to write up his own account, and in 1974 his autobiography, titled Spy Counter-Spy, was published. A playboy to the end, he died in 1981, after years of heavy smoking and drinking, and many, many, women.


Where Did We Find This Stuff? Some Sources and Further Reading

Cook, Andrew – On His Majesty’s Service: The True Story of Sidney Reilly, Ace of Spies (2002)

Encyclopedia Britannica – Benjamin Tallmadge: American Continental Army Officer

Encyclopedia Britannica – George Sidney Reilly

Encyclopedia Britannica – Karl Schulmeister

History Collection – These Well-Known People Were Also Spies or Intelligence Agents

Lockhart, Robert Bruce – Ace of Spies (1967)

Loftis, Larry – Into the Lion’s Den: The True Story of Dusko Popov, World War II Spy, Patriot, and the Real-Life Inspiration For James Bond (2016)

Macintyre, Ben – Double Cross: The True Story of the D-Day Spies (2012)

Madeira, Victor – Britannia and the Bear: The Anglo-Russian Intelligence Wars, 1917-1929 (2014)

Maude, Frederic Natusch – The Ulm Campaign, 1805 (1912)

Misencik, Paul R. – The Original American Spies: Seven Covert Agents of the Revolutionary War (2013)

New England Historical Society – A Spy For a Spy: John Andre Hanged

New York Times, December 15th, 1985 – Remembering a Master Spy at Home

Popov, Dusko – Spy Counter-Spy (1974)

History Collection – 8 True-Life Spy Stories Beyond Any Imagination

Rose, Alexander – Washington’s Spies: The Story of America’s first Spy Ring (2007)

Rowan, Richard Wilmer – The Story of Secret Service

Russell, Miller – Codename Tricycle: The True Story of the Second World War’s Most Extraordinary Double Agent (2014)

Study dot Com – The Role of New York in the American Revolution