Sidney Reilly, World War I Spy and Scoundrel

Author Ian Fleming, when asked about the escapades of his fictional spy James Bond, reportedly replied, “He’s no Sidney Reilly.” Who was Sidney Reilly and why did Fleming’s remark indicate that the smooth, suave licensed-to-kill ladykiller was inferior to him? Perhaps because what Agent 007 accomplished with the gadgets provided by the ingenuity of Q and a shaken, not stirred martini, World War I spy Sidney Reilly was able to do by relying on his cunning, his wits, his appeal with the ladies, and a complete lack of a moral compass.

Sidney Reilly.

Reilly was born on March 24, 1874 in Ukraine, the son of an affluent Jewish contractor father and a pianist mother. His birth name was Sigmund Georgievich Rosenblum but the details of his origins, his life, and even his death are submerged in so much mystery that no one can be sure of what is true and what is fabrication.

But in 1909, the British Secret Intelligence Service, which would later become MI6, sent him to Essen, Germany. Their purpose was to get a behind-the-scenes perspective on how Germany, which was known to have militaristic intentions, was expanding its arsenal. Reilly, in the guise of a Baltic shipyard worker named Karl Khan, was able to get a job working in one of the Krupp armaments plants. The plant had a vigilant security system and during the day, guards kept watch over the workers to make sure that the rule against taking photographs inside the plant was maintained. But the ever-wily Reilly decided that if he joined the fire brigade, which worked during the night shift, he could get the information that he needed. Of course, the plant was still under guard, but that was no obstacle for Reilly; he strangled a security guard, stole the plans, and made his way back to Great Britain. His British supervisors were aware that Reilly was not ruled by patriotism. Secret Intelligence Service Captain Mansfield Smith-Cumming assessed Reilly candidly, acknowledging that the spy was “a man of indomitable courage, a genius as an agent, but a sinister man who I could never bring myself wholly to trust.”

His next assignment was to discern the strength of the German Navy; the British were the acknowledged masters of the seas, but there was no reason to assume that imperial Germany was going to accept that verdict. Reilly’s geography savvy was independent of the map; by traveling to Russia and pretending to be an armaments distributor, he began the sponsorship of races for Russian aviators. That made it possible for him to fly over the Baltic Sea to photograph German vessels. But Reilly, being somewhat of a ladies’ man, also preferred to enhance his spying with a little bit of philandering and the British weren’t fussy about how he obtained his information. Seducing Nadine Massino, the wife of the assistant to a Russian Minister,  demonstrated that for Reilly, pillow talk was a most effective means of personal data mining.  When he found out that the Russians were looking to rebuild their Navy, he persuaded the German company that won the contract to name him as their St. Petersburg agent. The German builders sent copies of their designs, based on what they’d created for their own ships, to Reilly and his make-believe company. Reilly photographed the designs and sent them on to the British, who were making their own preparations for the inevitable war that loomed.

After World War I broke out in 1914, Reilly, who conveniently spoke German, used his linguistic adroitness to join the German Army on the Western Front Great Britain was the recipient of his detailed information on German troops, sent by carrier pigeons.

Reilly had few core values, but he was motivated by a driving loathing of the Bolsheviks. For the Allies, Russia’s volatile status was a concern, particularly after the Romanov government under Czar Nicholas II was overthrown by the Bolsheviks. For Reilly, this was personal. What better way to overthrow the Bolsheviks, Reilly reasoned than to assassinate Vladimir Lenin? Working with Sir Robert Bruce Lockhart, head of Great Britain’s Moscow mission, the two devised a plot involving Lenin and Trotsky at the Bolshoi Theatre. But when their plot was uncovered, the two men, who managed to flee Russia in the nick of time, were convicted in absentia and sentenced to death.

Vladimir Lenin.

The Russians had long memories and Reilly had an exaggerated notion of his own ability to elude capture. Still determined to overthrow the Bolsheviks, Reilly asked to be sent back to Russia but his request was declined. It didn’t matter. Reilly formed an alliance with opponents of the Bolsheviks but when he crossed from Finland into Russia on February 27, 1925, he was arrested and interrogated at Lubyanka Prison. The sentence was death, but Reilly, ever the negotiator, offered his services to the Bolsheviks. His offer to provide intelligence information from American and British sources was declined and it’s believed that Reilly, ace of spies, was executed by firing squad on November 25, 1925.