Sidney Reilly, the Infamous Spy Who Inspired James Bond

Many of the great spy novelists had firsthand experience in espionage. John le Carré (author of The Spy Who Came in from The Cold) and Graham Greene (author of Our Man in Havana) both worked in intelligence before becoming writers. But by far the most famous example is that of Ian Fleming. Born in 1908, Fleming was the Eton College-educated son of a parliamentarian. After a stint as a journalist, Fleming joined the British Naval Intelligence Division in 1939 and stayed on throughout World War II, eventually rising to the rank of personal assistant to the Director of Naval Intelligence.

After the war, Fleming retired to Jamaica and wrote novels. His books were smash hits, thanks in part to their iconic hero: a British secret agent, code-named 007.

James Bond was the consummate cold warrior, sparkling with charm and radiating intellect in spite of his role as a blunt instrument for Her Majesty’s secret service. Over the course of 12 novels, Bond crisscrossed Europe and the Caribbean, kneecapping the Soviets, tangling with flamboyant criminals, and breaking the hearts of dozens of mysterious women (known as “Bond girls” in the fandom.) In 1961, President John F. Kennedy listed one of the Fleming books as among his favorite reads of the year.

After Bond caught on, there was fevered speculation as to who Fleming had used as the model for his hero. Fleming himself said Bond was a chimera composed of spies and soldiers he encountered during the war. A saucier theory had Fleming basing Bond on his own exploits.

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Although Fleming had a wild streak that led him to drink, gamble, and travel internationally with a cyanide cartridge concealed in a fountain pen, he spent most of WWII benched behind a desk. Still, the overlap between Fleming’s biography and the plots of his novels led many to believe that there was truth in the Bond stories.

Writing for The Journal of Modern History, historian Edward W. Bennet describes an era in which “the line between the stories of real spies, such as Sidney Reilly, and fictitious ones...was by no means hard and fast, and sometimes fiction gave a better idea of what espionage was like than the purportedly true stories.”

Sidney Reilly, the strongest candidate for directly inspiring James Bond, was more a contemporary of Fleming’s father. He was born in the late 1800s and was active in the World War I and interwar periods.

Like Bond, Reilly was known for his charm, ruthlessness, and turbulent relationships with women. He may have had as many as 11 identities, with passports to match. Reilly spoke seven languages including Russian, English, French, German and Polish. His motto was “trust no one,” and his code name was “17F.” 17F doesn’t have quite the same ring as 007, but Reilly was also known by his fitting nickname "the Ace of Spies.”

Reilly was born far from MI6 and Eton College, in Odessa, Ukraine. Ukraine might seem like an unlikely place to spawn the inspiration for one of Britain’s most iconic characters, but Reilly’s non-Britishness was typical for a spy. According to Stansfield Turner, former director of the Central Intelligence Agency, a lot of frontline intelligence work is carried out by people who are not-citizens of a given agency’s sponsor country.

“The James Bond type thing where he’s always climbing into a castle or jumping out of airplanes, to the extent it’s done at all, is usually done by someone else,” said Turner in an interview with The Christian Science Monitor.

Reilly was born with the given name Sigmund Rosenblum. He studied chemistry before traveling abroad, supposedly to go adventuring in Brazil. There, he may have crossed paths with British Army officers. Reilly was working as a dishwasher when, as the story goes, a local tribe attacked, and his quick thinking saved the officers. This earned him passage to England. Reilly soon became an asset for British intelligence, funneling the Crown information on the Germans.

sidney reilly — The Krupp armaments factory in Essen, Germany, c. 1915.
Photo Credit: Wikipedia

Many of Reilly’s greatest hits read like mid-tier Bond adventures. For example, in the runup to World War I, Reilly took a gig as a welder at Krupp Armament Works, a company playing a key role in arming Germany. While working the night shift as a welder, Reilly broke into the secret files and sent copies of sensitive documents regarding weapons development to the British. Reilly also spent part of the war in Russia spying on German shipbuilding. In a move that’s almost more Bond than Bond, he gained access to key documents on German naval development strategies by sleeping with the wife of Russia’s Minister of Marine.

Throughout his career, Reilly impersonated a Russian arms dealer in Holland during the Boer Wars and worked stateside in New York City to counter German efforts at sabotaging American factories. Thanks to his skills with disguises and tricks, he even supposedly once made it into a meeting with the German Kaiser. (Which is more of an Indiana Jones move, but close enough, we’ll take it.)

Reilly executed what is believed to be his best work of espionage on the banks of the French Riviera. Britain was thinking about changing the fuel in its ships from coal to oil, and Iranian oil fields had the potential to make the transition possible. Unfortunately, William d’Arcy, an Australian businessman, had already been granted permission by Iran’s shah to develop the oil fields. D’Arcy was in talks with France to partner on the project, and the British were in danger of being iced out. However, after gaining access to the oil mogul while disguised as a priest, Reilly convinced d’Arcy to partner with the British Petroleum company instead of the French.

After making a name for himself working for the British to counter the Germans, Reilly turned his attention toward the ascendant Bolsheviks, who had taken control of Russia in the wake of the bloody 1917 revolutions.

Reilly’s plan to take on the Bolsheviks was to flip Vladmir Lenin and Leon Trotsky’s Latvian mercenary bodyguards. The scheme rested on the theory that the Latvians’ loyalty to the Bolsheviks was paper thin, and that they could be bought off for the right price. Reilly worked on this plan with a team of legendary spies, including Robert Bruce Lockart and Xenophon Kalamatiano. According to Lockhart, Reilly wanted to publicly arrest the Bolshevik leaders and march them through the streets in a state of undress. Reilly hoped that this humiliation would destroy their reputations.

Unfortunately for Reilly, a woman tried to kill Lenin just as he prepared to execute his plan. In the security crackdown that followed the assassination attempt, Reilly’s conspiracy was exposed. Reilly barely escaped with his life, but was determined to return and finally topple the regime.

For his next attempt, Reilly turned to a mysterious cabal known as "The Trust". Reilly believed that The Trust had cells operating throughout Europe and embedded in the Bolshevik government.

The Trust, also known as the Monarchist Organization of Central Russia, was in reality a creation of the Cheka, a security agency founded by Lenin. Its primary function was to diffuse any military or intelligence plot against the Bolsheviks by enticing would-be attackers into instead funding an insurgency within Russia…an insurgency that was actually a creature of Bolshevik intelligence. Then, with their enemies duped, The Trust had a free hand to spread disinformation disguised as intelligence. It was their proficiency in disinformation that allowed The Trust to lure Reilly back to Russia.

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Reilly was last seen crossing the Finnish border into what was then the Soviet Union, where some say that he was executed at the orders of Joseph Stalin himself.

Many hailed Reilly as a hero for his work as a spy. Others saw him in a less flattering light. One Soviet media figure thundered that Reilly was a terrorist. Documents from the American Federal Bureau of Investigation called Reilly a dangerous con artist.

It is difficult to discern who Reilly really was, in part because there are contradictory accounts of many aspects of his life. Much of his biography, heroic exploits included, is unconfirmed. Even his parentage is disputed. His father may have been a colonel in the Russian army, or he may have been a Jewish doctor. Some say finding out about his true parentage was what set Reilly off on his odyssey to Brazil.

One of Reilly’s biographers believes that the swashbuckling Brazil story is probably a fabrication, and that Reilly may have arrived in England flush with cash after violently robbing a cell of anarchists. Another says the British may have poached Reilly from the Imperial Russian Secret Police while he worked on a job in Paris.

In any case, once he did arrive in England Reilly set himself up as a businessman, using his knowledge of chemistry to cook up “miracle cures.” One of his customers was a 63-year-old man who came to him for help with a kidney disease. The man died soon after seeking Reilly’s assistance, leaving behind a 24-year-old wife whom Reilly married.

When the money from the miracle cures was no longer sufficient, Reilly turned to Scotland Yard. There he found steady work narcing on political radicals in Russian immigrant communities.

As a spy, Reilly was even suspected of being a double-dealer. While working in Manchuria, he may have sold intelligence to the Japanese on the side while officially working for the British.

Reilly was also behind the ethically questionable “Zinoviev Letter,” a scam that derailed attempts by Britain’s Labor government to normalize relations with the Soviet Union. The forged letter called for leftist uprisings in Britain, spearheaded by Labor supporters. Labor was clobbered in the next election cycle, and talks between the two governments fell apart.

None of this makes Reilly so different from Bond, who started out as a morally gray hero and has gotten grayer over the decades. A description Fleming once gave for Bond could have almost referred to Reilly: “Bond is not a hero, nor is he depicted as being very likeable or admirable,” said Fleming. “He’s not a bad man, but he is ruthless and self-indulgent.”

The most on-brand Bond move Reilly ever pulled was leaving his own death ambiguous. Daniel Craig’s incarnation of Bond has been presumed dead no fewer than three times: at the beginning of Skyfall, at the end of Spectre, and at the end of No Time To Die. (Fleming also gave Bond a false death in You Only Live Twice.) Reilly was almost certainly executed in a lonely Russian forest after being captured by the Soviet secret police. But people across the globe claimed to have seen him alive after he disappeared in 1925. Reilly’s own wife said as late as 1934 that she believed he was clinging to life somewhere in a Soviet prison.

But in the end, Reilly was more of a Fleming than a Bond. Both men were storytellers. Reilly’s characters were in his many identities, and in the patchwork of stories that make up his biography. Fleming’s characters lived on the page, but his ideas may have impacted 20th-century history as much as Reilly’s schemes did.

Throughout his life, Fleming crossed paths with J. Edgar Hoover, General William Donovan and Alan Dulles. General Donovan, who during WWII ran the Office of Strategic Services, once picked the Bond-creator’s brain on how a new spy agency should be constructed. Legend has it that the postwar spy agency of Fleming’s imagination eventually became the CIA. National Security expert Christopher Moran wrote in the Journal of Cold War Studies that Fleming “may have played a part in encouraging the CIA down the path of fantasy.”

When Fleming met Dulles, the first director of Central Intelligence, the two stayed up late swapping intelligence techniques and chatting about spy gadgets. Dulles supposedly returned to Langley determined to turn as many of Fleming’s ideas as possible into reality.

The Bond books helped to tailor a dashing, heroic public image for the agency that endures today. Paul O’Sullivan, former Director General of Australia’s Security Intelligence Organization, once wrote about how stories like Fleming’s shape how the public sees intelligence agencies.

“There is necessarily a limit on the amount of information available on what actually goes on in intelligence organizations,” O’Sullivan wrote. “Employees are sworn to secrecy, documents are classified, and decisions are made behind closed doors or out of the public eye. As a result, in the absence of other detailed information, many impressions that the general public have of the work of intelligence agencies are drawn from the genre of spy fiction.”

Fleming’s books make for fun romps, but they make little mention of the less savory activities spies have been known to engage in, including the deposing of democratically elected leaders, attempts to use psychedelics for mind control, and legally nebulous interrogations. As a result, it’s hard to say whether they truly give us a “better understanding of espionage” or simply provide us with entertaining fantasies in the absence of real information.

This criticism probably would not have bothered Fleming. In his mind, there was a clear division between fiction and reality.

“James Bond is just a piece of nonsense I dreamed up,” Fleming once said. “He’s not a Sidney Reilly, you know!”