Washington: Sydney Reilly, often hailed as one of Britain’s most formidable intelligence operatives, lived a life so dramatic that it later inspired author Ian Fleming to create the iconic fictional spy, James Bond. Reilly’s extraordinary espionage missions, daring escapes and complex personal life shaped the foundation of the world’s most famous secret agent.
A Cold-Blooded End in Moscow
On November 5, 1925, prisoner number 73 was removed from his cell in Moscow’s notorious Lubyanka prison. Escorted by OGPU officers, he was taken to the Sokolniki forest on the outskirts of the city. The walk he was ordered to take seemed routine — something he had been subjected to over previous days. But within moments, he was shot in the back by OGPU agent Abraham Abisalov, acting on Stalin’s direct orders.
The prisoner was Sydney Reilly, whose covert missions across continents had made him a marked man for the Soviets.
From Odessa to London: A Spy Is Born
Born in 1873 into a Jewish family in Odessa, Reilly migrated to London in the 1890s. Reinventing himself, he married an Irish woman and adopted her surname, masking his origins. This ability to transform his identity became one of his greatest assets as a spy.
Throughout his early career, Reilly presented himself alternately as a businessman and an undercover agent. His network spanned Europe, Russia, Japan and the United States, allowing him to operate with unusual freedom and influence.
A Master of Secrets Across Two Empires
Reilly’s espionage work often served multiple nations. He supplied Britain with intelligence on oil reserves in the Caucasus and leaked Russian military strategies to Japan during the Russo-Japanese War.
By 1914, he had successfully stolen German naval expansion plans from St. Petersburg — a feat that bolstered his reputation within British intelligence.
Daring Moves in Revolutionary Russia
Following the 1917 Bolshevik Revolution, Reilly expressed interest in joining the British Army. Despite warnings about his lack of loyalty, the chief of the British Secret Intelligence Service, Mansfield Cumming, approved his mission to Russia in 1918.
Reilly used charm, deception and relationships with influential women to access sensitive documents. In Moscow, he developed ties with actresses and informants — connections that opened doors inside the Kremlin.
In a bold gambit, he infiltrated high-level Soviet circles by posing as a researcher studying communist progress. His daring culminated in plans to overthrow Lenin’s government. Working with fellow agent George Hill, he plotted to seize top Bolshevik leaders during a state council meeting.
However, a series of violent incidents — including the assassination attempt on Lenin by Fanya Kaplan — derailed the operation. Russian security forces cracked down on foreign spies, forcing Reilly to escape through Finland. A Russian court later sentenced him to death in his absence.
The Final Mission and Execution
Reilly continued intelligence work in Europe until 1925, when he embarked on one last operation to gather information about Soviet military capabilities. Captured soon after, he endured intense interrogation. Decades later, former Soviet agent Boris Gudz confirmed that Reilly was executed in the forest outside Moscow.
The Man Who Became Bond
Reilly’s personality, lifestyle and spycraft profoundly influenced Ian Fleming as he crafted the character of James Bond. Many Bond-like traits — fluency in multiple languages, impeccable style, expertise with cars and weapons, and a cool emotional distance — were hallmarks of Reilly’s real-life persona.
His resourcefulness, charm and fearlessness made him a legend in intelligence circles, and his dramatic life continues to shape popular culture’s understanding of the modern spy.
Sydney Reilly may not have survived his final mission, but his legacy lives on through the enduring figure of 007.
