The First Super-Spy Dies: Sidney Reilly Executed

Soviet secret police executed Sidney Reilly, the flamboyant British intelligence agent whose daring operations against the Bolsheviks earned him the title of the twentieth century's first "super-spy." His exploits later inspired Ian Fleming's James Bond character and established the archetype of the gentleman spy in popular culture. Born Sigmund Rosenblum in 1873 in Odessa, then part of the Russian Empire, Reilly reinvented himself multiple times before entering British intelligence. He assumed at least seven identities during his career, married multiple women simultaneously, and operated businesses as cover across Europe and Asia. His most audacious operation was the Lockhart Plot of 1918, an attempt to overthrow the Bolshevik government by bribing Latvian soldiers guarding the Kremlin. The plot failed when the Cheka infiltrated the conspiracy, and Reilly fled Russia with a death sentence on his head. Throughout the 1920s, he worked with anti-Bolshevik emigre organizations, running agents into the Soviet Union and financing resistance networks. This obsession proved fatal. In September 1925, the OGPU lured him back into Russia using a fake anti-Soviet organization called the Trust, which was actually a sophisticated Soviet counterintelligence operation designed to identify and neutralize foreign agents. Reilly crossed the Finnish border on September 25 and was immediately arrested. He was interrogated for weeks before being shot on November 5, 1925, in a Moscow forest. The Soviets did not confirm his death for years, allowing rumors of his survival to circulate. Ian Fleming, who worked in British naval intelligence, acknowledged drawing on Reilly's legend when creating James Bond.