SIDNEY REILLY
Spied for: Britain
Thought to be Ian Fleming's main inspiration for the character of James Bond, Sidney Reilly is often referred to as the original "gentleman spy," though given that he was once married to three women at the same time, that's a rather loose definition of the term. It's a little difficult to separate the facts of Reilly's life from the legend and self-aggrandizement, but we know that he was born Shlomo Rosenblum, in Ukraine, in 1873. He began working for the War Office Intelligence Division in China during the Russo-Japanese War and later worked for the British in Russia during the Bolshevik Revolution.
His tactics were often over the top and crude -- he once showed up at the Kremlin without authorization, pretending to be a British diplomat and demanding to meet with Vladimir Lenin. He also participated in several failed plots to capture or kill the Soviet leader and depose the Bolsheviks.
In the 1920s, he allegedly participated in a plot by high-ranking MI5 officers to discredit and oust the newly elected Labour government. He disappeared on an undercover mission in Russia in 1925. It's believed that he was making contact with a shadowy anti-Bolshevik group called the Trust, which was in fact a sting operation set up by the OGPU, the forerunner of the KGB, and is thought to have been tortured and executed. Reilly remains the most famous figure in British spy-lore, despite persistent rumors that he was a double agent.
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