He spoke seven languages. He had spied on behalf of at least four countries. In Moscow’s Lubyanka prison he was prisoner number 73. O Sidney Rileyalso known as the “Ace of Spies”, was perhaps the most legendary spy ever. After nearly thirty years of active duty, he was to drop dead under mysterious circumstances, in a forest in the northeast Moscow.
Riley was born as Sigmund Rosenblum around 1873 in Odessa, which then belonged to the Russian Empire. In the early years of his life he moved frequently, reportedly fleeing to England under mysterious circumstances and adopting the British identity of ‘Sydney Riley’. With his remarkable appeal to languages, Riley he masterfully embodied the role of a well-connected, multilingual British gentleman. Some accounts even claim that his early career was marked by a scandalous affair, in 1897, when he married the wealthy Margaret Thomas, shortly after her husband’s suspicious death, thus gaining access to considerable funds and his first British passport.
By the early 1900s, Riley was drawn into her dark world espionageoperating within the British Secret Intelligence Service (SIS), which was then headed by Captain Mansfield Smith-Cumming. Riley undertook risky missions throughout Europe and Asia, gaining recognition for his intelligence work during his Russo-Japanese War (1904-1905), where he allegedly gave Russian naval secrets to the Japanese. He is believed to have taken advantage of his position as an arms dealer, eventually helping the Japanese navy launch a successful attack on the Russian fleet at Port Arthur.
His life was full of gambling and investments with risky high amounts, which created financial problems for him.
Riley’s work as an intelligence agent continued into World War I, where he allegedly collected military intelligence in Germany. With his charm and cunning, he manipulated contacts and connections to serve British interests, but his life was not without gambling and investments with risky high amounts which created financial problems for him. His voracious pursuit of profit made him a complicated figure, sometimes questioned by his own superiors at SIS.
Reilly’s most daring mission came in 1918, when the SIS recruited him to overthrow the fledgling Bolshevik regime. Known as “Lockhart design”, the plan was to overthrow Lenin and install a government friendly to the White Army in Russia. Riley, along with fellow SIS agent Robert Bruce Lockhart, recruited the disillusioned Latvian Guard, who were initially willing to help eliminate key Bolshevik leaders. However, the operation fell apart when an assassination attempt on Lenin by Fanya Kaplan in September 1918 exposed the plot. Riley narrowly escaped, but the Bolsheviks sentenced him to death in absentiacharacterizing him as a wanted man.
Returning to London, he became an outspoken critic of Bolshevism, inciting various investors to support anti-Soviet movements.
In the years following the Lockhart conspiracy, Riley remained a high-profile enemy of the Soviet state. Returning to London, he became an outspoken critic of Bolshevism, inciting various investors to support anti-Soviet movements. During this period Riley was shuttling between Britain and the US, trying to gain financial support for building a post-Bolshevik Russian economy. However, his zeal eventually led him back into the Soviet trap. In 1925, Soviet counterintelligence agents as part of the “Enterprise Trust(Operation Trust) devised an elaborate plan to deceive anti-Bolshevik officials. Posing as members of an underground resistance network, they lured Riley to Finland and then to Soviet territory, where he was arrested at the border.
Once arrested, Reilly was taken to the notorious Lubyanka prison in Moscow, where he was subjected to harsh interrogation. Although he was reportedly undeterred, writing notes on cigarette papers to detail interrogation techniques, his hopes of rescue or release were dwindling. Riley’s execution reportedly took place on November 5, 1925 in a forest in the Sokolniki district of Moscow, although the exact details are unknown. Some have speculated that his death was designed to be a symbolic warning to other anti-Bolsheviks, showing the lengths to which the Soviet secret police would go to eliminate threats. The Soviet leaders, however, reported that it was a suicide.
Portrayals in literature and film have immortalized him as one of history’s most enigmatic spies,
Riley’s career and reputation profoundly influenced British espionage, leading to depictions in literature and film that immortalized him as one of history’s most enigmatic spies. His complex character – intelligent, ambitious and with a special talent for manipulation – inspired later fictional spies, most notably Ian Fleming’s James Bond. Elements of his life, such as his work with the SIS, his charm and his dangerous missions, were reflected in Bond’s fictional adventures.
Column editor: Myrto Katsigera, Vassilis Minakakis, Antigoni-Despina Poimenidou, Athanasios Syroplakis
