Sidney Reilly Lieutenant Sidney George Reilly , MC ( c . 24 March 1873 – 5 November 1925 ) , famously known as the Ace of Spies , was a Jewish Russia n - 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 publicized their thwarted operation to overthrow the Bolshevik regime in 1918 . After Reilly ' s death , the " London Evening Standard " published in May 1931 a " Master Spy " serial imparting 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 . Origins and youth . The origins , identities , and activities of Sidney George Reilly have befuddled researchers and intelligence agencies for more than a century ; hence , much of his purported life and many of his notorious exploits should be cautiously examined . Reilly himself told several versions of his origins to confuse and mislead investigators . Reilly claimed to be the son of ( a ) an Irish merchant seaman , ( b ) an Irish clergyman , and ( c ) an aristocratic landowner and habitué of the Imperial court of Tsar Alexander III of Russia . Some sources say Reilly was born Georgi Rosenblum in Odessa , then a Black Sea port of the Russian Empire ( now Ukraine ) , on 24 March 1873 or 1874 ; however , other theories of Reilly ' s birthplace and origins exist . In " Ace of Spies : The True Story of Sidney Reilly " ( pg . 28 ) , author Andrew Cook states that Reilly was born on 24 March 1873 , in the Jewish Kherson gubernia of Tsarist Russia , as Salomon ( Shlomo ) Rosenblum , and later that " Sidney Reilly " was the illegitimate son of Polina ( or " Perla " ) , his acknowledged mother , and Dr . Mikhail Abramovich Rosenblum , the trusted first cousin of Reilly ' s putative father , Grigory ( Hersh ) Rosenblum . There is speculation that he was the son of a merchant marine captain and the above - mentioned mother . Early life . According to Rosenblum , in 1892 , the Imperial Russian Secret Police arrested him for being a messenger for the Friends of Enlightenment revolutionary group . When he was released , Grigory ( Rosenblum ' s assumed father ) told his son that his mother was dead , and that his true , biological father was her Jewish doctor , Mikhail A . Rosenblum . Renaming himself Sigmund Rosenblum , he faked his death in Odessa Harbour and stowed away aboard a British ship bound for South America . In Brazil , young Sigmund adopted the name Pedro and worked odd jobs : dock worker , road mender , plantation labourer , and in 1895 , cook for a British intelligence expedition . Rosenblum allegedly saved both the expedition and the life of Major Charles Fothergill when hostile natives attacked them . Rosenblum seized a British officer ' s pistol and , with expert , single - hand marksmanship , killed the attacking natives . Appropriately for a fantastic story , Major Fothergill rewarded Rosenblum with £1 , 500 , a British passport , and passage to Britain ; there , Pedro became Sidney Rosenblum . Andrew Cook asserts in " Ace of Spies : The True Story of Sidney Reilly " ( pg . 32 ) that evidence contradicts the Brazilian scenario , averring that the British expedition incident to be unsubstantiated . Cook states that the arrival of Sigmund Rosenblum in London in December 1895 was via France , and prompted by Rosenblum ' s unscrupulous acquisition of a large sum of money in Saint - Maur - des - Fossés , a residential suburb of Paris , necessitating a hasty flight . According to Cook ' s account , Rosenblum and Yan Voitek , a Russian accomplice , waylaid two Italian anarchists on 25 December 1895 , and robbed them of a substantial amount of revolutionary funds . One anarchist ' s throat was cut ; the other , Constant Della Cassa , died from knife wounds in Fontainebleau Hospital three days later . By the time Della Cassa ' s death appeared in the newspapers , police had learned that one of the assailants , whose physical description matched Rosenblum ' s , was already en route to England . Rosenblum ' s accomplice , Voitek , later related this incident as well as other dealings with Rosenblum to the British Secret Intelligence Service . Regardless of whether Sigmund Rosenblum arrived in England via Brazil or France , he resided at the Albert Mansions , an apartment block in Rosetta Street , Waterloo , London , in early 1896 . Now settled in England , Rosenblum created the Ozone Preparations Company , which peddled miracle cures . Because of his knowledge of languages , Rosenblum became a paid informant for the émigré intelligence network of William Melville , superintendent of Scotland Yard ' s Special Branch and , according to Cook , later the clandestine head of the British Secret Service Bureau , which was founded in 1909 . In London : 1890s . In 1897 , Rosenblum began a torrid affair with Margaret Thomas ( née Callaghan ) , the youthful wife of Reverend Hugh Thomas , shortly before the latter ' s death . Rosenblum first met Reverend Thomas in London via his Ozone Preparations Company . Thomas had a kidney inflammation and was intrigued by the miracle cures peddled by Rosenblum . Thomas introduced Rosenblum to his young wife at his Manor House , and an affair developed between the two over the next six months . On 4 March 1898 , Thomas altered his will and appointed Margaret as an executor . A week after the making of the new will , Reverend Thomas and his nurse arrived at Newhaven Harbour Station . On 12 March 1898 , in that same hotel , Rev . Thomas was found dead in his bed . A mysterious Dr . T . W . Andrew , who matched the physical description of Sigmund Rosenblum , appeared on the scene to certify Thomas ' death as generic influenza and , signing the relevant documents , proclaimed that there was no need for an inquest . Records indicate that no Dr . T . W . Andrew was in Great Britain circa 1897 . Margaret insisted that her husband ' s body be ready for burial 36 hours after his death . Six weeks later , she inherited roughly £800 , 000 . The Metropolitan Police did not investigate Dr . T . W . Andrew , nor did they investigate the nurse whom Margaret had hired , even though the nurse was previously linked to the arsenic poisoning of a former employer . Four months later , on 22 August 1898 , Rosenblum married Margaret Thomas . The two witnesses at the ceremony were Charles Richard Cross and Joseph Bell . Bell was an Admiralty clerk , while Cross was a government official . Both would eventually marry daughters of Henry Freeman Pannett , an associate of William Melville . The marriage brought the wealth which Rosenblum desired , but provided a pretext to discard his identity of Sigmund Rosenblum , and , with Melville ' s assistance , crafted a new identity : Sidney George Reilly . This new identity was the key to achieving his desire to return to Czarist Russia and voyage to the Far East . Tsarist Russia and the Far East . In June 1899 , the newly minted Sidney Reilly and his wife Margaret traveled to Czarist Russia using Reilly ' s new British passport — a cover identity purportedly created by William Melville . Margaret remained in St . Petersburg , while Reilly is alleged to have reconnoitred the Caucasus for its oil deposits and compiled a resource prospectus as part of " The Great Game . " He reported his findings to the British government , which paid him for completing the assignment . In early 1901 , Reilly and his wife voyaged from Port Said , Egypt , across the globe to the Far East . Shortly before the Russo - Japanese War , Reilly appeared in Port Arthur , Manchuria , as a double agent serving both the British and the Japanese interests . The Russian - controlled Port Arthur lay under the ever - darkening spectre of Japanese invasion , and Reilly and business partner Moisei ( Moses ) Akimovich Ginsburg turned the precarious situation to their benefit . They purchased enormous amounts of food , raw materials , medicine and coal , and made a small fortune as war profiteers . Reilly would have an even greater success in January 1904 , when he and Chinese engineer acquaintance Ho - Liang - Shung allegedly stole the Port Arthur harbour defence plans for the Japanese Navy . Guided by these stolen plans , the Japanese Navy navigated through the Russian minefield protecting the harbour and launched a surprise attack on Port Arthur on the night of 8 – 9 February 1904 ( Monday February 8 - Tuesday February 9 ) . Yet the stolen plans did not help the Japanese much . More than 31 , 000 Russians ultimately perished defending Port Arthur , but Japanese losses were much higher , losses that nearly undermined their war effort . Historian Winfried Ludecke suggests that , upon leaving Port Arthur , Manchuria , Reilly voyaged to Imperial Japan in the company of an unknown mistress . If Reilly did visit Japan , presumably to be paid for his espionage , he could not have stayed very long , for by June 1904 Reilly appeared in Paris , France . During the brief time that Reilly spent in the city , he renewed his close acquaintance with William Melville , sometimes incorrectly described as the first Director General of MI5 , whom Reilly had last seen in 1899 just prior to his departure from London . Reilly ' s meeting with Melville is most significant , for within a matter of weeks Melville was to use Reilly ' s expertise in what would later become known as the D ' Arcy Affair . D ' Arcy Affair . In 1904 , the Board of the Admiralty projected that petroleum would supplant coal as the primary source of fuel for the Royal Navy . During their investigation , the British Admiralty learned that William Knox D ' Arcy — who later founded the Anglo - Persian Oil Company ( APOC ) in April 1909 — had obtained a valuable concession from the Persian government regarding the oil rights in southern Persia and that D ' Arcy was negotiating a similar concession from the Ottoman Empire for oil rights in Mesopotamia . The British Admiralty purportedly initiated efforts to entice D ' Arcy to sell his newly acquired oil rights to the British government rather than to the French de Rothschilds . In " Reilly : Ace of Spies " , Robin Bruce Lockhart repeats one of Reilly ' s oft - recited tales of how , at the British Admiralty ' s request , Reilly located William Knox D ' Arcy in the south of France and clandestinely approached him in disguise . According to Reilly , he boarded Lord de Rothschild ' s yacht attired as a Catholic priest and secretly persuaded D ' Arcy to terminate negotiations with the French Rothschilds and return to London to meet with the British Admiralty . Biographer Andrew Cook is sceptical about Reilly ' s involvement in the D ' Arcy Affair , for in February 1904 , Reilly was purportedly still in Port Arthur , Manchuria . Cook further claims that it was Reilly ' s intelligence chief , William Melville , and a British intelligence officer , Henry Curtis Bennett , who undertook the D ' Arcy assignment . Although the extent of his involvement in the D ' Arcy Affair is unknown , it has been verified that Reilly stayed in the French Riviera on the Côte d ' Azur after the incident — a location very near the Rothschild yacht . After conclusion of the D ' Arcy Affair , Reilly journeyed to Brussels , and shortly thereafter , in January 1905 , he arrived in St . Petersburg , Russia . An alternative scenario put forward in " The Prize " by Daniel Yergin has the Admiralty putting forward a " Syndicate of Patriots " to keep D ' Arcy ' s concession in British hands , apparently with the full and eager co - operation of D ' Arcy himself . Frankfurt International Air Show . In " Ace of Spies " , biographer Robin Bruce Lockhart recounts Reilly ' s alleged involvement in obtaining a newly developed German magneto at the first Frankfurt International Air Show ( " Internationale Luftschiffahrt - Ausstellung " ) in 1909 . According to Lockhart , on the fifth day of the air show a German plane lost control and crashed , killing the pilot . The plane ' s engine was alleged to have used a new type of magneto that was far ahead of other designs . Reilly and a British SIS agent posing as one of the exhibition pilots diverted public attention while they removed the magneto from the wreck and substituted another . The SIS agent quickly made detailed drawings of the German magneto , and when the engine had been removed to a hangar , the agent and Reilly managed to restore the original magneto . However , another biographer , Andrew Cook , has countered that this incident never happened . According to documents , no plane crashes occurred during the event . Stealing weapon plans . 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 . 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 . 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 . 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 . World War I activity . One of Reilly ' s claims is that he was a secret agent behind German lines , and that he allegedly attended a German High Command conference { see below } ; however , see Cook { Chapter 6 } , which effectively debunks this by revealing Reilly ' s activities between 1915 and 1918 { reference only } . According to author Richard Spence in " Trust No One " , Reilly lived in New York for at least a year , 1914 – 15 , where he engaged in arranging munitions sales to both the Germans and the Imperial Russian Army . This is confirmed by papers of Norman Thwaites , MI1c Head of Station in New York , wherein has been found evidence that Reilly approached Thwaites seeking a job in 1917 – 1918 . Thwaites was reportedly impressed with Reilly , and wrote a letter of recommendation for him to Mansfield Cumming , head of MI1c . It was also Thwaites who recommended that Reilly first visit Toronto to obtain a military commission , which is why Reilly joined the Royal Canadian Flying Corps . The fact that ( by April 1917 ) the U . S . was now in the war and ( by October ) the Russians were out of the war made Reilly ' s munitions business far less profitable since his company would then have been prohibited from selling ammunition to the Germans and the Russians were no longer buying . Sometime during 1916 – 1918 , Reilly reportedly received a commission in the Royal Canadian Flying Corps , and according to Spence , upon his return to London in 1918 , Mansfield Cumming formally swore Lieutenant Reilly into service as a staff Case Officer in His Majesty ' s Secret Intelligence Service ( SIS ) , prior to dispatching Reilly on counter - Bolshevik operations in Germany and Russia . Ambassadors ' plot . 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 . In May 1918 , Robert Bruce Lockhart ( BBC 2011 ) , an agent of the British Secret Intelligence Service , and Reilly repeatedly met with Boris Savinkov , head of the counter - revolutionary Union for the Defence of the Motherland and Freedom ( UDMF ) . 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 UDMF consisting of several thousand Russian fighters . Lockhart and Reilly then contacted anti - Bolshevik groups 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 . 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 , UDMF officials , and Lockhart . On 17 August , 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 . On 30 August , a military cadet shot and killed Moisei Uritsky , head of the Petrograd Cheka . On the 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 . On 3 September , the aborted coup was sensationalised 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 8 November . 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 . Within a 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 . Career with British intelligence . Throughout his life , Sidney Reilly maintained a close yet tempestuous relationship with the British intelligence community . In 1896 , Reilly was recruited by Superintendent William Melville for the émigré intelligence network of Scotland Yard ' s Special Branch . Through his close relationship with Melville , Reilly would be employed as a secret agent for the Secret Service Bureau , which the War Office created in October 1909 . In 1918 , Reilly began to work for MI1 ( c ) , an early designation for the British Secret Intelligence Service , under Sir Mansfield Smith - Cumming . Reilly was allegedly trained by the latter organization and sent to Moscow in March 1918 to assassinate Vladimir Ilyich Lenin or attempt to overthrow the Bolsheviks . He had to escape after the Cheka unravelled the so - called Lockhart Plot against the Bolshevik government . Reilly told various tales about his espionage deeds and adventurous exploits . According to Reilly , he earned and lost several fortunes in his lifetime and had many wives and mistresses . He claimed that : British intelligence adhered to its policy of publicly saying nothing about anything . Yet Reilly ' s espionage successes did garner indirect recognition . After a formal recommendation by Sir Mansfield " C " Smith - Cumming , Reilly , who had been commissioned into the Royal Flying Corps in 1917 , was awarded the Military Cross on 22 January 1919 , " for distinguished services rendered in connection with military operations in the field . " Cook claims the medal was bestowed due to Reilly ' s anti - Bolshevik operations in southern Russia , but espionage historian Richard Deacon states the award was given for Reilly ' s clandestine activities in World War I . Reilly had allegedly parachuted behind German lines on a number of occasions . Once , disguised as a German officer , he spent three weeks inside the German Empire ( Deutsches Reich ) gathering information about the next planned thrust against the Allies . Deacon asserts in " History of the Russian Secret Service " that in April 1912 , Reilly was an Ochrana agent with the task of befriending and profiling Sir Basil Zaharoff , the international arms salesman and representative of Vickers - Armstrong Munitions Ltd . Another Reilly biographer , Richard B . Spence , claims in " Trust No One : The Secret World Of Sidney Reilly " that during this assignment Reilly learned " " le systeme " " from Zaharoff . To Zaharoff , " " le systeme " " was the strategy of playing all sides against each other in order to maximise financial profit . Cook counters in " Ace of Spies : The True Story of Sidney Reilly " ( pg . 104 ) that there is no evidence of any relationship between Reilly and Zaharoff . According to Cook , Reilly was more of a con artist . Reilly claimed to have been employed by the British Secret Intelligence Service since the 1890s , but he did not volunteer his services nor was he accepted as an agent until 15 March 1918 , and was effectively fired in 1921 because of his tendency to be a rogue operative . Nevertheless , Reilly 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 . On 18 May 1923 , Pepita Bobadilla , an actress and the widow of Haddon Chambers , dramatist , married Sidney Reilly at the Registrar Office in Henrietta Street , Covent Garden , Captain Hill acting as witness . Author Michael Kettle has claimed in " Sidney Reilly : The True Story of the World ' s Greatest Spy " ( pg . 121 ) that despite having been fired by SIS , Reilly possibly was involved with Sir Stewart Graham Menzies in the forging of the " The Zinoviev Letter " in 1924 . Death . In September 1925 , undercover agents of the OGPU , the intelligence successor of the Cheka , lured Reilly to Bolshevik Russia , ostensibly to meet the supposed anti - Communist organization The Trust — in reality , an OGPU deception existing under the code name Operation Trust . At the Russian border , Reilly was introduced to undercover OGPU agents posing as senior Trust representatives from Moscow . One of these undercover Soviet agents , Alexander Yakushev ( Александр Александрович Якушев ) , later recalled the meeting : After Reilly crossed the Finnish border , the Soviets captured , transported , and interrogated him at Lubyanka Prison . On arrival , Reilly was taken to the office of Roman Pilar , a Soviet official who the previous year had arrested and ordered the execution of Boris Savinkov , a close friend of Reilly . Pilar reminded Reilly that he had been sentenced to death by a 1918 Soviet tribunal for his participation in a counter - revolutionary plot against the Bolshevik government . While Reilly was being interrogated , the Soviets publicly claimed that he had been shot trying to cross the Finnish border . Historians debate whether Reilly was tortured while in OGPU custody . Cook contends that Reilly was not tortured other than psychologically by mock execution scenarios designed to shake the resolve of prisoners . During OGPU interrogation , Reilly maintained his charade of being a British subject born in Clonmel , Ireland , and would not reveal any intelligence matters . While facing such daily interrogation , Reilly kept a diary in his cell of tiny handwritten notes on cigarette papers which he hid in the plasterwork of a cell wall . While his Soviet captors were interrogating Reilly , Reilly in turn was analysing and documenting their techniques . The diary was a detailed record of OGPU , and Reilly was understandably confident that such unique documentation would , if he escaped , be of interest to the British SIS . After Reilly ' s death , Soviet guards discovered the diary in Reilly ' s cell , and photographic enhancements were made by OGPU technicians . According to British intelligence documents released in 2000 , Reilly was executed in a forest near Moscow on Wednesday November 5 , 1925 . According to eyewitness Boris Gudz , the execution of Sidney Reilly was supervised by an OGPU officer , Grigory Feduleev ; another OGPU officer , George Syroezhkin , fired the final shot into Reilly ' s chest . Gudz also confirmed that the order to kill Reilly came from Stalin directly . After Reilly ' s death there were various rumors about his survival . Some , for example , speculated that Reilly had defected and became an adviser to Soviet intelligence . Fictional portrayals . Ace of Spies . In 1983 , a television mini - series , " " , dramatised the historical adventures of Reilly . The programme won the 1984 BAFTA TV Award . Reilly was portrayed by actor Sam Neill . Leo McKern portrayed Sir Basil Zaharoff . The series was based on Robin Bruce Lockhart ' s book , " Ace of Spies " , which was adapted by Troy Kennedy Martin . James Bond . 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 . " The Gadfly " . According to Lockhart , while in London in 1895 Reilly encountered noted author Ethel Lilian Voynich . Voynich was a well - known figure in the late Victorian literary scene and in Russian émigré circles ( and married to sometime Polish revolutionary Wilfrid Voynich ) . Lockhart claims that Reilly and Voynich had a sexual liaison and voyaged to Italy together . During this dalliance , Reilly allegedly " bared his soul " to Ethel and revealed to her the peculiar story of his youth in Russia . After their affair had concluded , Voynich published in 1897 " The Gadfly " , her critically acclaimed novel whose central character , Arthur Burton , was allegedly based on Reilly ' s early life . Cook , however , disputes Lockhart ' s romanticised version of events and asserts that Reilly was not Voynich ' s inspiration . According to Cook , Reilly may have been merely investigating Voynich ' s radical , pro - émigré activities and reporting to William Melville of the Metropolitan Police Special Branch . See also . People Events Organizations External links . Sidney Reilly