Sidney Reilly

Sidney George Reilly (c. 1873 – c. 1925), commonly known as the "Ace of Spies", was a secret agent of the British Secret Service Bureau, the precursor to the modern British Secret Intelligence Service (MI6/SIS). He is alleged to have spied for at least four different powers.
Reilly's fame was created during the 1920s, in part by his friend, the British diplomat and journalist Sir Robert Bruce Lockhart, who publicised their thwarted operation to overthrow the Bolshevik regime in 1918. The London Evening Standard published in May 1931 a serial, headlined "Master Spy", imparting his exploits. Later Ian Fleming used Reilly as a model for James Bond. Today many historians consider Reilly to have been the first 20th-century "super-spy". Much of what is thought to be known about him could be false, however, as Reilly was a master of deception and most of his life is shrouded in legend.

The origins, identities and activities of Sidney Reilly have befuddled researchers and intelligence agencies for more than 100 years, and 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. He claimed to be the son of an Irish merchant seaman, an Irish clergyman, and an aristocratic landowner and habitué of the Imperial court of Tsar Alexander III of Russia. According to the Ukrainian newspaper Segodnya, he was born Zigmund Markovich Rozenblum (Rosenblum) on 24 March 1874 in Odessa, then a Black Sea port of the Russian Empire. His father, Mark, was a stockbroker, and shipping agent, and his mother came from an impoverished noble family.

Other sources claim that Reilly was born Georgy Rosenblum in Odessa on 24 March 1873 or 1874. However, in Ace of Spies: The True Story of Sidney Reilly (p. 28), Andrew Cook states that Reilly was born on 24 March 1873 in the Jewish Kherson gubernia of Tsarist Russia, as Salomon (Shlomo) Rosenblum, and that he 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 also speculation that he was the son of a merchant marine captain and the above-mentioned mother. Yet another source states that Sigmund Georgievich Rosen-blum (alias Sidney George Reilly), the only son of Pauline and Gregory Rosenblum, was born on 24 March 1874 into a wealthy Polish-Jewish family with an estate at Bielsk in the Grodno Province of Imperial Russia. His father was known locally as George rather than Gregory, hence Sigmund's patronymic Georgievich.

According to Rosenblum, in 1892 the Imperial Russian Secret Police arrested him for being a messenger for a revolutionary group, the Friends of Enlightenment. After he was released Grigory, his assumed father, told him that his mother was dead and that his 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 as a dock worker, a road mender, a plantation labourer and, in 1895, a 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 single-hand marksmanship, killed the attacking natives. Appropriately for a fantastic story, Major Fothergill rewarded Rosenblum with 1,500 pounds, 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 (p. 32) that the evidence contradicts this tale of Brazil. Cook states that the arrival of Sigmund Rosenblum in London in December 1895 was from France, and was 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 Britain. 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 Britain via Brazil or France, he resided at the Albert Mansions, an apartment block in Rosetta Street, Waterloo, London, in early 1896. Now settled in Britain, Rosenblum created the Ozone Preparations Company, which peddled patent medicines. 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 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 between the two happened over the next six months. On 4 March 1898, Thomas altered his will and appointed Margaret as an executor. A week after the new will was made, Reverend Thomas and his nurse arrived at Newhaven Harbour Station. On 12 March 1898 Rev. Thomas was found dead in his hotel room. A mysterious Dr. T. W. Andrew, whose physical description matched that of Sigmund Rosenblum, appeared on the scene to certify Thomas' death as generic influenza and after signing the relevant documents proclaimed that there was no need for an inquest. Records indicate that there was no one by the name of Dr. T. W. Andrew in Great Britain circa 1897.

Margaret insisted that her husband's body be ready for burial 36 hours after his death. 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, who 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 not only 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.

A ukiyoe print of the night attack on Port Arthur by the Japanese Navy. The surprise attack was allegedly made possible by the intelligence gathering of Sidney Reilly and Ho-Liang-Shung.

In June 1899, the newly endowed Sidney Reilly and his new wife Margaret travelled to Czarist Russia using Reilly's new (forged) British passport - a passport and a cover identity both purportedly created by William Melville. Margaret remained in St. Petersburg, while Reilly is alleged to have reconnoitered 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 the assignment. In early 1901, Reilly and his wife voyaged from Port Said, Egypt, to the Far East.

Shortly before the Russo-Japanese War, Reilly appeared in Port Arthur, Manchuria, as a double agent for the British and Japanese. The Russian-controlled Port Arthur lay under the ever-darkening specter of Japanese invasion, and Reilly and his 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 Liangshung 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 8 February – Tuesday 9 February). 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, Reilly voyaged to Imperial Japan in the company of an unknown mistress. If he did visit Japan, presumably to be paid for his espionage, he could not have stayed very long, for by June 1904 he appeared in Paris, France. During the brief time Reilly spent in Paris, he renewed his close acquaintance with William Melville, sometimes incorrectly described as the first director general of MI5, whom Reilly had last seen just prior to his 1899 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.

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 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 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 D'Arcy in the south of France and 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 Rothschilds and return to London to meet with the British Admiralty. Biographer Andrew Cook is skeptical 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. 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.

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, in January 1905, he arrived in St. Petersburg, Russia.

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 airplane 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.

According to Lockhart, when the German Kaiser was expanding the war machine of Imperial Germany in 1909, 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.

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, Cook in chapter 6 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 City 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 facts that by April 1917 the United States had entered the war and by October the Russians had undergone a revolution and were out of the war, made Reilly's munitions business far less profitable since his company would be 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.

From the London Evening Standard's Master Spy serial: Reilly, disguised as a member of the Cheka, bluffs his way through a Red Army checkpoint.

The endeavour to depose the Bolshevik Government and assassinate Vladimir 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 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 being prepared, an Allied force landed on 4 August 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 5 August, 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 in 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 was arrested at Otten's flat with the papers she was carrying for Reilly.

On 3 September, 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 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 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 return debriefing, the British Secret Intelligence Service and the Foreign Office again sent Reilly and Hill to South 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. At that time, the region was home to a variety of anti-Bolshevik. They travelled in the guise of British merchants, with appropriate credentials provided by the Department of Overseas Trade. Over the next six weeks or so, Reilly prepared 12 despatches which reported on various aspects of the situation in South Russia and were delivered personally by Hill to the Foreign Office in London. 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 the Ukraine; and the economic situation. In his opinion, the future course of events in this region would depend not only on the interaction of these factors with each other, but 'above all upon Allied attitude towards them...'. Reilly advocated Allied assistance to organise South Russia into a suitable "'placed'armes" for decisive advance against Petlurism and Bolchevism'. In his opinion:

 "The military Allied assistance required for this would be comparatively small as proved by recent events in Odessa. Landing parties in the ports and detachments assisting Volunteer Army on lines of communication would probably be sufficient." 

Reilly's reference to events in Odessa concerned the successful landing there on 18 December 1918 of troops from the French 156th Division commanded by General Borius, who managed to wrest control of the city from the Petlyurists with the assistance of a small contingent of Volunteers.

Urgent as the need for Allied military assistance to the Volunteer Army was in Reilly's estimation, he regarded economic assistance for South Russia as 'even more pressing ...'. Manufactured goods were so scarce in this region that he considered any moderate contribution from the Allies would have a most beneficial effect. Otherwise, apart from echoing a certain General Poole's suggestion for a British or Anglo-French Commission to control merchant shipping engaged in trading activities in the Black Sea, Reilly did not offer any solutions to what he called a state of 'general economic chaos' in South Russia. Reilly found White officials, who had been given the job of helping the Russian economy get better, 'helpless' in coming to terms with 'the colossal disaster which has overtaken Russia's finances, ... and unable to frame anything, approaching even an outline, of a financial policy'. But he supported their request for the Allies to print '500 Million roubles of Nicholas money of all denominations' for the Special Council as a matter of urgency, with the justification that 'although one realizes the fundamental futility of this remedy, one must agree with them that for the moment this is the only remedy'. Lack of funds was one reason offered by Reilly to explain the Whites' blatant inactivity in the propaganda field. They were also said to be lacking paper and printing presses needed for the preparation of propaganda material. Reilly claimed that the Special Council had come to appreciate fully the benefits of propaganda.

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 Foreign 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:

• In the Second Boer War he disguised himself as a Russian arms merchant to spy on Dutch weapons shipments to the Boers.
• He procured Persian oil concessions for the British Admiralty, the so-called D'Arcy Affair.
• In the disguise of a timber company owner, he gathered information on the Russian military presence in Port Arthur, Manchuria, and reported to the Kempeitai, the Japanese secret police.
• He spied on the Krupp armaments plant in Germany.
• He volunteered for the Royal Flying Corps in Canada at the start of the First World War.
• He seduced the wife of a Russian minister to obtain information about German weapons shipments to Russia.
• During the First World War, he donned a German officer's uniform and attended a German Army High Command meeting.
• He saved British diplomats in Brazil.
• He attempted, but failed, to engineer the downfall of the Russian Bolshevik government.

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 the First World War. 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 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 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, Nelly Louise "Pepita" Burton, known professionally as Pepita Bobadilla, actress and widow of Haddon Chambers, dramatist, married Sidney Reilly at a civil Registry Office on Henrietta Street, in Covent Garden, Central London, with Captain Hill acting as a 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.

Following execution in a forest near Moscow, the alleged corpse of Sidney Reilly (Salomon Rosenblum) was photographed in OGPU headquarters by Soviet personnel on or around 5 November 1925.

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. In his book The Gulag Archipelago, Alexandr Solzhenitsyn says that Richard Ohola, a Finnish Red Guard, was “a participant in the capture of British agent Sidney Reilly.” (In the biographical glossary appended to that work, Solzhenitsyn says that Reilly was “killed while crossing the Soviet-Finnish border.”) 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, he in turn was analysing and documenting their techniques. The diary was a detailed record of OGPU interrogation techniques, 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 5 November 1925. Eyewitness Boris Gudz claimed the execution was supervised by an OGPU officer, Grigory Feduleev; while 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 rumours about his survival. Some, for example, speculated that Reilly had defected and became an adviser to Soviet intelligence.

Reilly: Ace of Spies

Sam Neill portraying Sidney Reilly in the TV miniseries Reilly, Ace of Spies (1983).

In 1983, a television miniseries, Reilly, Ace of Spies, 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. Significantly, the theme music for the 1983 television mini-series is essentially a piece of The Gadfly Suite (Op. 97a) by Dmitri Shostakovich.