Sidney Reilly

Lieutenant Sidney George Reilly, MC (c. 24 March 1873 – 5 November 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 fame 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

“[Sidney Reilly's role] is one of the unsolved riddles about the Russo-Japanese War.
—Ian H. Nish”

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 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 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, 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 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.

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 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 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 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.

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; however, see Cook Template:Chapter 6, which effectively debunks this by revealing Reilly's activities between 1915 and 1918 Template: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 fact that (by April 1917) the US 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

“In 1918, behind-the-scenes helpers such as [...] Sidney Reilly, the erstwhile Russian double agent who was operating on Britain's behalf, were involved in the formulation and execution of various attempts to snatch both Russia and the [Romanov family] from the Bolsheviks.
— Shay McNeal, historical researcher on Russian history and contributor to BBC”

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 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 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 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 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 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 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 World War I.
• He seduced the wife of a Russian minister to obtain information about German weapons shipments to Russia.
• During World War I, 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 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.

"Reilly was dropped by plane many times behind the German lines; sometimes in Belgium, sometimes in Germany, sometimes disguised as a peasant, sometimes as a German officer or soldier, when he usually carried forged papers to indicate he had been wounded and was on sick-leave from the front. In this way he was able to move throughout Germany with complete freedom."

Robin Bruce Lockhart, Reilly: Ace of Spies, p. 71.

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:

“The first impression of [Sidney Reilly] is unpleasant. His dark eyes expressed something biting and cruel; his lower lip drooped deeply and was too slick—the neat black hair, the demonstratively elegant suit. [...] Everything in his manner expressed something haughtily indifferent to his surroundings.”

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 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. 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, 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.