Lieutenant Sidney George Reilly, MC (c. March 24, 1873/1874 – November 5, 1925), famously known as the Ace of Spies, was a Jewish Russian-born adventurer and secret agent employed by Scotland Yard, the British Secret Service Bureau and later the Secret Intelligence Service (SIS). He is alleged to have spied for at least four nations. His notoriety during the 1920s was created in part by his friend, British diplomat and journalist Sir Robert Bruce Lockhart, who sensationalised their thwarted operation to overthrow the Bolshevik government in 1918.
After Reilly's death, the London Evening Standard published in May, 1931, a Master Spy serial glorifying his exploits. Later, Ian Fleming would use Reilly as a model for James Bond. Today, many historians consider Reilly to be the first 20th century super-spy. Much of what is thought to be known about him could be false, as Reilly was a master of deception, and most of his life is shrouded in legend.
According to Lockhart, the German Kaiser was expanding the war machine of Imperial Germany in 1909, and British intelligence had scant knowledge regarding the types of weapons being forged inside Germany's war plants. At the behest of British intelligence, Reilly was sent to obtain weapons plans (Lockhart 1967).
Reilly arrived in Essen, Germany, in 1909 disguised as a Baltic shipyard worker by the name of Karl Hahn. Having prepared his cover identity by learning welding at a Sheffield engineering firm, Reilly obtained a low-level position as a welder at the Essen plant. Soon he joined the plant fire brigade and persuaded its foreman that a set of plant schematics were needed to indicate the position of fire extinguishers and hydrants. These schematics were soon lodged in the foreman's office for members of the fire brigade to consult, and Reilly set about using them to locate the weapon plans (Lockhart 1967).In the early morning hours, Reilly used lock-picks to break into the office where the weapon plans were kept but was discovered by the foreman. Reilly strangled the foreman and completed the theft. From Essen, Reilly took a train to Dortmund to a safe house, and tearing the plans into four pieces, mailed each separately. If one was lost, the other three would still reveal the gist of the plans (Lockhart 1967).
Cook casts doubt on this incident but concedes that German factory records show a Karl Hahn was indeed employed by the Essen plant during this time and a plant fire brigade was in formal operation (Cook 2004).
The endeavour to depose the Bolshevik Government and assassinate Vladimir Ilyich Lenin is considered by biographers to be Reilly's most daring scheme. The Lockhart Plot, or more accurately the Reilly Plot, has sparked debate over the years: Did the Allies launch a clandestine operation to overthrow the Bolsheviks? If so, did the Cheka uncover the plot at the eleventh hour or had they unmasked the conspirators from the outset? Some historians have suggested that the Cheka orchestrated the conspiracy from beginning to end and possibly that Reilly was a Bolshevik agent provocateur (Cook 2004).
In May 1918, Robert Bruce Lockhart, an agent of the British Secret Intelligence Service, and Reilly repeatedly met with Boris Savinkov, the head of the counter-revolutionary Union for the Defence of the Fatherland and Freedom (UDFF). Savinkov had been Deputy War Minister in the Provisional Government of Alexander Fyodorovich Kerensky, and a key opponent of the Bolsheviks. A former Social Revolutionary Party member, Savinkov had formed the UDFF consisting of several thousand Russian fighters. Lockhart and Reilly then contacted anti-Bolshevik collectives linked to Savinkov and supported these factions with SIS funds. They also liaised with the intelligence operatives of the French and U.S. consuls in Moscow (Cook 2004).
In June, disillusioned members of the Latvian Riflemen began appearing in anti-Bolshevik circles in Petrograd and were eventually directed to Captain Cromie, a British naval attaché, and Mr. Constantine, a Turkish merchant who was actually Reilly. As Latvians were deemed the Praetorian Guard of the Bolsheviks and entrusted with the security of the Kremlin, Reilly believed their participation in the pending coup to be vital and arranged their meeting with Lockhart at the British mission in Moscow. At this stage, Reilly planned a coup against the Bolshevik government and drew up a list of Soviet military leaders ready to assume responsibilities on the fall of the Bolshevik government. While the coup was prepared, an Allied force landed on August 4, 1918, at Arkhangelsk, Russia, beginning a famous military expedition dubbed Operation Archangel. Its objective was to prevent the German Empire from obtaining Allied military supplies stored in the region. In retaliation for this incursion, the Bolsheviks raided the British diplomatic mission on August 5, disrupting a meeting Reilly had arranged between the anti-Bolshevik Latvians, UDFF officials, and Lockhart (Cook 2004).
On August 17, Reilly conducted meetings between Latvian regimental leaders and liaised with Captain George Hill, another British agent operating in Russia. They agreed the coup would occur the first week of September during a meeting of the Council of People's Commissars and the Moscow Soviet at the Bolshoi Theatre. However, on the eve of the coup, unexpected events thwarted the operation (Cook 2004).
On August 30, a military cadet shot and killed Moisei Uritsky, head of the Petrograd Cheka. On this same day, Fanya Kaplan, a member of the Socialist Revolutionary Party, shot and wounded Lenin as he left a meeting at the Michelson factory in Moscow. These events were used by the Cheka to implicate any malcontents in a grand conspiracy that warranted a full-scale campaign: the "Red Terror." Thousands of political opponents were seized and executed. Using lists supplied by undercover agents, the Cheka arrested those involved in Reilly's pending coup. They raided the British Embassy in Petrograd and killed Cromie, Reilly's accomplice, who put up an armed resistance. Lockhart was arrested, but later released in exchange for Litvinov, a diplomat who had been arrested in London in a reprisal. Elizaveta Otten, Reilly's chief courier, was arrested as well as his other mistress Olga Starzheskaya. Another courier, Maria Fride, with papers she carried for Reilly, was arrested at Otten's flat (Cook 2004).
On September 3, the aborted coup was sensationalized by the Russian press. Reilly was identified as a leader, and a dragnet ensued. The Cheka raided his assumed refuge, but Reilly avoided capture and met with Captain Hill. Hill proposed that Reilly escape Russia via Ukraine using their network of British agents for safe houses and assistance. Reilly instead chose a shorter, more dangerous route north to Finland. With the Cheka closing in, Reilly, carrying a Baltic German passport, posed as a legation secretary and departed Moscow in a railway car reserved for the German Embassy. In Kronstadt, Reilly sailed by ship to Helsinki and reached Stockholm. He arrived in London on November 8 (Cook 2004).
The day before Reilly and Hill met with Sir Mansfield Smith-Cumming ("C") in London for their debriefing, the Russian Izvestia newspaper reported that both Reilly and Lockhart had been sentenced to death in absentia by a Revolutionary Tribunal for their roles in the attempted coup of the Bolshevik government. Their sentence was to be carried out immediately should either of them be apprehended on Soviet soil. This sentence would later be served on Reilly when he was caught by the OGPU in 1925. Yet, within the week of their debriefing, the British Secret Intelligence Service and the Foreign Office again sent Reilly and Hill to Russia under the cover of British trade delegates. Their assignment was to uncover information about the Black Sea coast needed for the Paris Peace Conference of 1919 (Cook 2004).
In Ian Fleming, The Man Behind James Bond by Andrew Lycett, Sidney Reilly is listed as an inspiration for James Bond. Reilly's friend, former diplomat and journalist Sir Robert Bruce Lockhart, was a close acquaintance of Ian Fleming for many years and recounted to Fleming many of Reilly's espionage adventures. Lockhart had worked with Reilly in Russia in 1918, where they became embroiled in an SIS-backed plot to overthrow Lenin's Bolshevik government. Within five years of his disappearance in Soviet Russia in 1925, the press had turned Reilly into a household name, lauding him as a master spy and recounting his many espionage adventures. Fleming had therefore long been aware of Reilly's mythical reputation and had listened to Lockhart's recollections. Like Fleming's fictional creation, Reilly was multi-lingual, fascinated by the Far East, fond of fine living, and a compulsive gambler. He also exercised a Bond-like mastery of women, his many love affairs standing comparison with the amorous adventures of 007 (Cook 2004).
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