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November 5, 1925, a man named Sidney Reilly was executed by the secret police of the Soviet Union. But it was not an execution like any other. Reilly was the greatest spy of his time. He had behind him an activity of over two decades, tens, maybe even hundreds of completed missions (for several beneficiaries!), and personal history so tangled that historians have not been able to decipher it until today.

Who is this Mystery Man?

Information about his origins has never been confirmed, but some biographers claim that Sidney Reilly was born in Rosenblum, March 1874, in Odessa, a city in the Russian Empire, into the family of a Jewish doctor. He studied chemistry in Vienna from 1890–1893 before moving to South America, Brazil, where he worked.

In Brazil, he came in contact with a group of British explorers, whom he got out of a mess in the Amazon jungle. They invited the young man to go with them back to the UK, where he came into contact with the secret service community because of his talents and the fact that he spoke several languages.

The man became Sidney George Reilly in 1899 when he obtained British citizenship following his marriage to a young widow, heiress, to a significant fortune (it seems that Reilly was also involved in the death of the young woman’s first husband).

Spying on his own kind

His first missions were to his native Russia in 1899, where he was sent by British services to gather information on oil deposits in the Caucasus. Upon returning to the country with valuable information, Reilly received a permanent position in the British Navy’s intelligence services. He also spied during the Boer War, then in the Middle East (also on the fields, of great interest to the British), and in 1904, he spied for the English and Japanese during the Russo-Japanese War.

During the Russian Civil War, Reilly served as the eyes and ears of British intelligence while attached to General Anton Denikin’s White Russian Army. (Source: Wikimedia Commons)

In 1909, Reilly was sent to Germany to obtain information on the military development of the Reich, tasked with collecting data on German arms factories. Reilly was also extremely active during the First World War, when he successfully performed dozens of missions, infiltrating behind enemy lines.

The inspiration for James Bond

Reilly was described by his relatives as having a great flair, a self-control that saved him in many situations, extraordinary courage, and a special inventiveness. He was also a master of disguise and a very good actor, which allowed him to enter many circles over the years. He also had great confidence in himself and his powers, accepting even the most dangerous missions.

Different actors playing the role of James Bond (Source: James Bond Movies)

However, his loyalty was not to the country but only to himself and his bank account, which is why his superiors never fully trusted him. After all, a spy who is more interested in money is an easy target to seduce. Reilly was no exception, as he apparently spied for countries in different countries.

Reilly also had an extraordinary passion for luxury and women. It was said of him that the number of his mistresses was at least equal to that of his passports.

Towards the end of the war, Reilly was sent back to Russia, tasked with finding a way to overthrow the Bolshevik regime. In this regard, he plotted to assassinate Lenin. He managed to get in touch with two bodyguards of the Bolshevik leader, whom he bribed, but he did not manage to carry out his plan.

When Fanny Kaplan shot Lenin and Russian secret police began investigations, they also discovered the two men bribed by Reilly. He was therefore exposed and convicted, but in his absence, the spy managed to flee the country in time. However, he insisted on returning to Russia to continue his mission and was finally captured in February 1925.

Sidney Reiley’s corpse in 1925 (Source: Wikimedia Commons)

Arrested and imprisoned in Lubianka, Reilly allegedly tried, according to Soviet reports, to save his life by offering to divulge British and American secrets. The tactic did not work, and Reilly was executed — by direct order of Stalin — on November 5, 1925.

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