1. Sidney Reilly is alleged to have spied for at least four different great powers, and documentary evidence indicates that he was involved in espionage activities in 1890s London among Russian emigre circles, in Manchuria on the eve of the Russo-Japanese War, and in an abortive 1918 coup d'etat against Vladimir Lenin's Bolshevik government in Moscow.
Sidney Reilly is considered to be "the dominating figure in the mythology of modern British espionage".
Sidney Reilly himself told several versions of his background to confuse and mislead investigators.
Sidney Reilly's father was known locally as George rather than Gregory, hence Sigmund's patronymic Georgievich.
Sidney Reilly allegedly saved both the expedition and the life of Major Charles Fothergill when hostile natives attacked them.
Sidney Reilly continued to go by the name Rosenblum, living at the Albert Mansions, an apartment block in Rosetta Street, Waterloo, London, in early 1896.
Sidney Reilly created the Ozone Preparations Company and peddled patent medicines.
Sidney Reilly became a paid informant for the emigre intelligence network of William Melville, superintendent of Scotland Yard's Special Branch.
Akashi instructed Sidney Reilly to offer financial aid to Russian revolutionaries in exchange for information about the Russian Intelligence Services and, more importantly, to determine the strength of the Russian armed forces, particularly in the Far East.
Sidney Reilly reported his findings to the British Government, which paid him for the assignment.
Shortly before the Russo-Japanese War, Sidney Reilly appeared in Port Arthur, Manchuria, in the guise of a timber company owner.
Sidney Reilly achieved greater success in January 1904 when he and his Chinese engineer acquaintance, Ho Liang Shung, allegedly stole the Port Arthur harbour defence plans for the Japanese Navy.
Sidney Reilly quickly became an obvious target of suspicion by Russian authorities at Port Arthur.
Sidney Reilly discovered one of his business subordinates was an agent of Russian counter-espionage and chose to leave the region.
Sidney Reilly's meeting with Melville in Paris is most significant, for within a matter of weeks, Melville was to use Sidney Reilly's expertise in what would later become known as the D'Arcy Affair.
At the British Admiralty's request, Sidney Reilly located William D'Arcy at Cannes in the south of France and approached him in disguise.
The SIS agent quickly made detailed drawings of the German magneto, and when the aeroplane had been removed to a hangar, the agent and Sidney Reilly managed to restore the original magneto.
At the behest of British intelligence, Sidney Reilly was sent to obtain the plans for the weapons.
Sidney Reilly arrived in Essen, Germany, disguised as a Baltic shipyard worker by the name of Karl Hahn.
Sidney Reilly soon joined the plant fire brigade and persuaded the foreman of the importance of having plant schematics that indicated the locations of fire extinguishers and hydrants.
From Essen, Sidney Reilly took a train to a safe house in Dortmund.
Sidney Reilly resumed his friendship with Alexander Grammatikov, an Okhrana agent and a fellow club member.
Writers Richard Deacon and Edward Van Der Rhoer assert that Sidney Reilly actually was an Ochrana double agent at this point.
In earlier biographies by Winfried Ludecke, and Pepita Bobadilla, Sidney Reilly is described as living as a spy in Wilhelmine Germany from 1917 to 1918.
Historian Christopher Andrew notes that "Sidney Reilly spent most of the first two and a half years of the war in the United States".
However, when the United States entered the war in April 1917, Sidney Reilly's business became less profitable since his company was now prohibited from selling ammunition to the Germans and, after the Russian revolution occurred in November 1917, the Russians were no longer buying munitions.
Under Thwaites' direction, Sidney Reilly presumably worked alongside a dozen other British intelligence operatives attached to the British mission at 44 Whitehall Street in New York City.
On 19 October 1917, Sidney Reilly received a commission as a temporary second lieutenant on probation.
Sidney Reilly arrived on Russian soil via Murmansk prior to 5 April 1918, where he contacted the former Okhrana agent Alexander Grammatikov, who believed the Soviet government "was in the hands of the criminal classes and of lunatics released from the asylums".
Grammatikov arranged for Sidney Reilly to receive a private interview with either Sidney Reilly's longtime friend General Mikhail Bonch-Bruyevich or Vladimir Bonch-Bruyevich, secretary of the Council of People's Commissars.
The attempt to assassinate Vladimir Lenin and to depose the Bolshevik government is considered by biographers to be Sidney Reilly's most daring exploit.
Sidney Reilly began to agitate in diplomatic cables for an immediate full-scale Allied military intervention in Russia.
Concurrently, Lockhart ordered Sidney Reilly to pursue contacts within anti-Bolshevik circles to sow the seeds for an armed uprising in Moscow.
In contrast to his previous espionage operations, which had been independent of other agents, Sidney Reilly worked closely while in Petrograd with Cromie in joint efforts to recruit Berzin's Latvians and to equip anti-Bolshevik armed forces.
Sidney Reilly arranged a meeting between Lockhart and the Latvians at the British mission in Moscow while purportedly expending "over a million rubles" to bribe the Red Army troops guarding the Kremlin.
Sidney Reilly's knowledge covered many subjects, from politics to art, but it was superficial.
Sidney Reilly informed Dzerzhinsky's Cheka that Reilly approached him and that Allied agents attempted to recruit him into a possible coup.
Unperturbed by these raids, Sidney Reilly conducted meetings on 17 August 1918 between Latvian regimental leaders and liaised with Captain George Alexander Hill, a multilingual British agent operating in Russia on behalf of the Military Intelligence Directorate.
That night, Sidney Reilly had no difficulty in travelling through picket lines between Moscow and Petrograd due to his identification as a member of the Petrograd Cheka and his possession of Cheka travel permits.
At this point, Sidney Reilly was notified by fellow conspirator Alexander Grammatikov that "the [Socialist Revolutionary Party] fools have struck too early".
Sidney Reilly's corpse was bundled into a rusted iron barrel and set alight.
Sidney Reilly "was hunted through days and nights as he had never been hunted before," and "his photograph with a full description and a reward was placarded" throughout the area.
The Cheka raided his assumed refuge, but the elusive Sidney Reilly avoided capture and met Captain Hill while in hiding.
Hill proposed that Sidney Reilly escape from Russia via Ukraine to Baku using their network of British agents for safe houses and assistance.
Sidney Reilly instead chose a shorter, more dangerous route north through Petrograd and the Baltic Provinces to Finland to get their reports to London as early as possible.
In Kronstadt, Sidney Reilly sailed by ship to Helsinki and reached Stockholm with the aid of local Baltic smugglers.
Sidney Reilly identified four principal factors in the affairs of South Russia at this time: the Volunteer Army, the territorial or provincial governments in the Kuban, Don, and Crimea, the Petlyura movement in Ukraine, and the economic situation.
Sidney Reilly advocated Allied assistance to organise South Russia into a suitable place d'armes for a decisive advance against Petlurism and Bolshevism.
Apart from echoing a suggestion made by General Poole for a British or Anglo-French Commission to control merchant shipping engaged in trading activities in the Black Sea, Sidney Reilly did not offer any solutions to what he called a state of "general economic chaos" in South Russia.
Lack of funds was one reason offered by Sidney Reilly to explain the Whites' blatant inactivity in the propaganda field.
Sidney Reilly claimed that the Special Council had fully recognized the advantages of propaganda.
In 1918, Sidney Reilly began to work for MI1, an early designation for the British Secret Intelligence Service, under Sir Mansfield Smith-Cumming.
Sidney Reilly was allegedly trained by the organisation and sent to Moscow in March 1918 to assassinate Vladimir Ilyich Lenin or attempt to overthrow the Bolsheviks.
Sidney Reilly had to escape after the Cheka unraveled the so-called Lockhart Plot against the Bolshevik government.
Sidney Reilly was then discharged in 1921 because of his tendency to be a rogue operative.
Nevertheless, Cook concedes that Sidney Reilly previously had been a renowned operative for Scotland Yard's Special Branch and the Secret Service Bureau which were the early forerunners of the British intelligence community.
At the Soviet-Finnish border, Sidney Reilly was introduced to undercover OGPU agents who posed as senior Trust representatives from Moscow.
Sidney Reilly was brought across the border by Toivo Vaha, a former Finnish Red Guard fighter who now served the OGPU.
Whether Sidney Reilly was tortured while in OGPU custody is a matter of debate by historians; Cook contends that Sidney Reilly was not tortured other than psychologically, through mock executions designed to shake the resolve of prisoners.
The diary contained a detailed record of OGPU interrogation techniques, and Sidney Reilly was understandably confident that such unique documentation would, if he escaped, be of interest to the British SIS.
Gudz confirmed that the order to kill Sidney Reilly came directly from Stalin.
In 1895, Sidney Reilly encountered author Ethel Lilian Voynich, nee Boole.
Alternatively, Sidney Reilly modelled himself on the revolutionary hero of Voynich's novel, although historian Mark Mazower observed that "separating fact from fantasy in the case of Sidney Reilly is difficult".
Sidney Reilly was portrayed by many different actors of various nationalities, including: Vadim Medvedev in The Conspiracy of Ambassadors ; Vsevolod Yakut in Operation Trust ; Aleksandr Shirvindt in Crash ; Vladimir Tatosov in Trust, Sergei Yursky in Coasts in the Mist, and Harijs Liepins in Syndicate II.
Sidney Reilly was portrayed by actor Sam Neill, who was nominated for a Golden Globe Award for his performance.
In Ian Fleming, The Man Behind James Bond by Andrew Lycett, Sidney Reilly is listed as an inspiration for James Bond.
Sidney 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 Sidney Reilly's espionage adventures.