Sidney Reilly
Sidney Reilly
Sidney Reilly German Passport September 1918.jpg
Sidney Reilly's 1918 German passport issued under the alias of George Bergmann.
Born c. 1873
Russian Empire
(now in Ukraine)
Died 5 November 1925
Possibly Moscow, RSFSR,
Soviet Union
Other names "Ace of Spies"
Spying career
Allegiance United Kingdom United Kingdom of Great Britain and Ireland
United Kingdom United Kingdom
Germany, Japan,[1]Russian Empire
Service United Kingdom Secret Service Bureau
Operation(s) Lockhart Plot[2]
D'Arcy Concession[3]
Zinoviev Letter[4]
Codename(s) ST1
Sidney Reilly
Allegiance United Kingdom United Kingdom
Service/branch  Royal Air Force
Rank Second Lieutenant
Unit Royal Flying Corps
Awards Military Cross

Sidney George Reilly MC (c. 1873 - 5 November 1925), commonly known as the "Ace of Spies," was a Russian-born adventurer and secret agent employed by the British Secret Service Bureau,[5] the precursor to the modern British Secret Intelligence Service (MI6/SIS).[6] During his lifetime, he is alleged to have spied for at least four different great powers.[7] Documentary evidence indicates he was involved in espionage activities in 1890s London among Russian émigré circles, in 1900s Manchuria on the eve of the Russo-Japanese War, and in an abortive 1918 coup d'etat against Vladimir Lenin's Bolshevik government in Moscow.

Following his disappearance in Soviet Russia in the mid-1920s, Reilly's friend, British diplomat and journalist Sir Robert Bruce Lockhart, publicised their 1918 operation to overthrow the Bolshevik regime.[8] Lockhart's 1932 book, Memoirs of a British Agent,[9] became an international best-seller and posthumously garnered global fame for Reilly. The memoirs retold the failed efforts by Reilly, Lockhart, and other conspirators to sabotage the Bolshevik revolution while still in its infancy.

Within five years of his capture and execution by Soviet agents in 1925, the press had turned Reilly into a household name, lauding him as a master spy and recounting his many espionage adventures. Contemporary newspapers dubbed him "the greatest spy in history" and "the Scarlet Pimpernel of Red Russia."[10] The London Evening Standard published an illustrated serial in May 1931, headlined "Master Spy," imparting his exploits. Later, writer Ian Fleming used Reilly as a model for James Bond in his novels of the 1950s and 1960s.[11] Today Reilly is considered to be "the dominating figure in the mythology of modern British espionage,"[12] as well as the first 20th-century "super-spy."[6]

Origins and youth

The true details about Sidney Reilly's origin, identity and exploits have eluded researchers and intelligence agencies for more than 100 years. Reilly himself told several versions of his origins to confuse and mislead investigators.[13] At different times in his life, Reilly disparately claimed to be the son of an Irish merchant seaman,[14] an Irish clergyman, and an aristocratic landowner and habitué of the Imperial court of the Emperor 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.[15]

Other sources claim that Reilly was born Georgy Rosenblum in Odessa on 24 March 1873.[16] In one account,[17] his birth name is given as Salomon (Shlomo) Rosenblum, and the Jewish Kherson gubernia of Tsarist Russia is given as his place of nativity.[17] 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.[17] There is also speculation that he was the son of a merchant marine captain and the aforementioned mother.

Yet another source states that Sigmund Georgievich Rosenblum,[12] 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.[18]

Travels abroad

According to Rosenblum's wife, the Imperial Russian Secret Police arrested him in 1892 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.[13] Renaming himself Sigmund Rosenblum, he faked his death in Odessa Harbour and stowed away aboard a British ship bound for South America.[16][19] In Brazil, young Rosenblum 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.[13] He allegedly saved both the expedition and the life of Major Charles Fothergill when hostile natives attacked them.[20] Rosenblum seized a British officer's pistol and, with single-hand marksmanship, killed the attacking natives.[19] Fothergill rewarded his bravery with 1,500 pounds, a British passport, and passage to Britain. There Pedro became Sidney Rosenblum.[16]

However, the record of evidence contradicts this tale of Brazil.[21] Cook states that the arrival of Rosenblum in London in December 1895 was from France, and was prompted by his unscrupulous acquisition of a large sum of money in Saint-Maur-des-Fossés, a residential suburb of Paris, necessitating a hasty flight.[21] According to this account, Rosenblum and Yan Voitek, a Polish 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.[21] 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 intelligence community.[21]

In London: 1890s

William Melville purportedly created the cover identity of Sidney Reilly for Rosenblum.

Regardless of whether 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.[22] Now settled in Britain, Rosenblum created the Ozone Preparations Company, which peddled patent medicines.[22] Because of his knowledge of languages, he 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.[23]

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.[24] Rosenblum first met Thomas in London via his Ozone Preparations Company.[25] 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 over the next six months, they began having an affair. On 4 March 1898, Thomas altered his will and appointed Margaret as an executrix. A week after the new will was made, Thomas and his nurse arrived at Newhaven Harbour Station. On 12 March 1898, Thomas was found dead in his hotel room.[26] A mysterious Dr. T. W. Andrew, whose physical description matched that of Sigmund Rosenblum, appeared to certify Thomas's 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.[27]

Margaret insisted that her husband's body be ready for burial 36 hours after his death.[28] 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.[28] Four months later, on 22 August 1898, Rosenblum married Margaret Thomas. The two witnesses at the ceremony were Charles Richard Cross, a government official, and Joseph Bell, an Admiralty clerk. 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; with Melville's assistance, he crafted a new identity: "Sidney George Reilly." This new identity was key to achieving his desire to return to Czarist Russia and voyage to the Far East.[29] It must be noted that Reilly "obtained his new identity and nationality without taking any legal steps to change his name and without making an official application for British citizenship, all of which suggests some type of official intervention" on his behalf.[30]

Czarist Russia and the Far East

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

In June 1899, the newly endowed Sidney Reilly and his wife Margaret traveled to Czarist Russia using Reilly's (forged) British passport -- a passport and a cover identity both purportedly created by William Melville.[33] While in St. Petersburg, he was approached by Japanese General Akashi Motojiro to work for the Japanese Secret Intelligence Services. As tensions between Russia and Japan were escalating towards war, Motojiro instructed Reilly to offer financial aid to Russian revolutionaries in exchange for information about the Russian Intelligence Services and, more importantly, to determine the strength of the Russian armed forces particularly in the Far East.[31][1] Accepting Motojiro's recruitment overtures, Reilly now became simultaneously an agent for both the British War Office and the Japanese Empire.[1] While his wife Margaret remained in St. Petersburg, Reilly allegedly 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.[16]

Shortly before the Russo-Japanese War, Reilly appeared in Port Arthur, Manchuria in the guise of a timber company owner.[34][12] At the time, he was still a double agent for the British and the Japanese governments.[13][34] The Russian-controlled Port Arthur lay under the ever-darkening spectre of a Japanese invasion, and Reilly and his business partner Moisei Akimovich Ginsburg turned the precarious situation to their benefit. By purchasing and reselling enormous amounts of foodstuffs, raw materials, medicine, and coal, they made a small fortune as war profiteers.[35]

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 by night 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). However, the stolen plans did not help the Japanese much. Despite ideal conditions for a surprise attack, their combat results were relatively poor. Although more than 31,000 Russians ultimately perished defending Port Arthur, Japanese losses were much higher, and these losses nearly undermined their war effort.[36]

According to writer Winfried Lüdecke, Reilly quickly became an obvious target of suspicion by Russian authorities at Port Arthur.[34] Thereafter, he discovered one of his business subordinates was an agent of Russian counter-espionage and chose to leave the region.[34] Upon departing Port Arthur, Reilly voyaged to Imperial Japan in the company of an unidentified woman where he was handsomely paid by the Japanese government for his prior intelligence services.[34] If he did a detour to Japan, presumably to be paid for his espionage, he could not have stayed very long, for by February 1905 he appeared in Paris, France.[37] By the time he had returned to Europe from the Far East, Reilly "had become a self-confident international adventurer" who was "fluent in several languages" and whose intelligence services were highly desired by various great powers.[12] At the same time, he was described as possessing "a foolhardy adventurous nature" with a tendency towards recklessness and prone to taking unnecessary risks.[14]

D'Arcy Concession

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.[16]

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 an Australian mining-engineer William Knox D'Arcy--who founded the Anglo-Persian Oil Company (APOC)--had obtained the valuable concession from the Mozaffar al-Din Shah Qajar regarding the oil rights in southern Persia.[10] D'Arcy was negotiating a similar concession from the Ottoman Empire for oil rights in Mesopotamia.[3] The Admiralty initiated efforts to entice D'Arcy to sell his newly acquired oil rights to the British Government rather than to the French de Rothschilds.[38][39]

In Ace of Spies, Robin Bruce Lockhart recounts how Reilly, at the British Admiralty's request, located William D'Arcy at Cannes in the south of France and approached him in disguise. Attiring himself as a Catholic priest, Reilly gate-crashed the private discussions on board the Rothschild yacht on the pretext of collecting donations for a religious charity. He then secretly informed D'Arcy that the British could give him a better financial deal.[10] D'Arcy promptly terminated negotiations with the Rothschilds and returned to London to meet with the British Admiralty.[3] However, biographer Andrew Cook has questioned Reilly's involvement in the D'Arcy Affair since, in February 1904, Reilly might still have been in Port Arthur, Manchuria. Cook speculates that it was Reilly's intelligence chief, William Melville, and a British intelligence officer, Henry Curtis Bennett, who undertook the D'Arcy assignment.[40] An alternative scenario in The Prize by Daniel Yergin has the Admiralty creating 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.[39]

Though the extent of Reilly's involvement in this particular incident is uncertain, it has been verified that he stayed after the incident in the French Riviera on the Côte d'Azur, a location very near the Rothschild yacht.[41] At the conclusion of the D'Arcy Affair, Reilly journeyed to Brussels, and, in January 1905, he arrived in St. Petersburg, Russia.[41]

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 the attention of spectators 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.[38] However, later biographers such as Spence and Cook have countered that this incident is unsubstantiated.[42] There is no documentary evidence of any plane crashes occurring during the event.[40]

Stealing weapon plans

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 the plans for the weapons.[43] 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 to weld 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 plans.[43]

In the early morning hours, Reilly picked the lock of the office where the plans were kept and was discovered by the foreman whom he then strangled before completing the theft. From Essen, Reilly took a train to a safe house in Dortmund. Tearing the plans into four pieces, he mailed each separately so that if one were lost, the other three would still reveal the gist of the plans.[43] Biographer Cook questions the veracity of this incident but concedes that German factory records show a Karl Hahn was indeed employed by the Essen plant during this time and that a plant fire brigade existed.[44]

First World War activity

In earlier biographies by Winfried Lüdecke and Richard Deacon, Reilly is described as "living in Germany, as a spy, from 1917 till the end of 1918."[34] Likewise, Deacon asserts that Reilly had operated 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.[45] However, most later biographies concur that Reilly's activities in the United States between 1915 and 1918 precluded any such European escapades.[46] Historian Christopher Andrew notes that "Reilly spent most of the first two and a half years of the war in the United States."[46] Likewise, author Richard Spence in Trust No One states that Reilly lived in New York City for at least a year, 1914-15, where he engaged in arranging munitions sales to the Imperial German Army and its enemy the Imperial Russian Army.[47] However, when the United States entered the war in April 1917, Reilly's business became less profitable since his company was now prohibited from selling ammunition to the Germans and, after the Russian revolution occurred in October 1917, the Russians were no longer buying munitions. Faced with unexpected financial hardship, Reilly sought to resume his paid intelligence work for the British government while in New York City.[48]

This is confirmed by papers of Norman Thwaites, MI1c Head of Station in New York,[49] which contain evidence that Reilly approached Thwaites seeking espionage-related work in 1917-1918.[50] Formerly a private secretary to newspaper magnate Joseph Pulitzer and a police reporter for Pulitzer's The New York World,[49] Thwaites was keen on obtaining information concerning radical activities in the United States; in particular, investigating the Communist Labor Party of America's connections with Soviet Russia.[49] Consequently, under Thwaites' direction, Reilly presumably worked alongside a dozen other British intelligence operatives attached to the British mission at 44 Whitehall Street in New York City.[50][49] Although their ostensible mission was to coordinate with the U.S. government in regards to intelligence about the German Empire and Soviet Russia, the British agents also focused upon obtaining trade secrets and other commercial information related to American industrial companies for their British rivals.[49]

Thwaites was sufficiently impressed with Reilly's intelligence work in New York that he wrote him a letter of recommendation 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 enlisted the Royal Canadian Flying Corps.[51] Upon receiving a commission in the Royal Canadian Flying Corps, Reilly voyaged to London in 1918 where 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.[51] According to Reilly's wife Pepita Bobadilla, Reilly was sent to Russia to "counter the work being done there by German agents" who were supporting radical factions and "to discover and report on the general feeling."[5] Thus Reilly arrived on Russian soil via Murmansk prior to 5 April 1918. With the clandestine aid of General Mikhail Bronch-Bruyvech,[52] he assumed the role of a Bolshevik sympathizer.[53]

Ambassadors' plot

The attempt to assassinate Vladimir Lenin and depose the Bolshevik government is considered by biographers to be Reilly's most daring scheme.[55][56] The Ambassadors' Plot, later misnamed in the press as the Lockhart-Reilly Plot, has sparked considerable debate over the years: Did the Allies launch a clandestine operation to overthrow the Bolsheviks and, if so, did Felix Dzerzhinsky's Cheka uncover the plot at the eleventh hour or did they know of the conspiracy from the outset?[55] At the time, the American Consul-General DeWitt Clinton Poole and others publicly insisted the Cheka secretly orchestrated the conspiracy from beginning to end and that Reilly was a Bolshevik agent provocateur.[57][58][59] Later, Robert Bruce Lockhart would state that he was "not to this day sure of the extent of Reilly's responsibility for the disastrous turn of events."[5]

In May 1918, Reilly, Lockhart, and other agents of the British Secret Intelligence Service[60] repeatedly met Boris Savinkov, head of the counter-revolutionary Union for the Defence of the Motherland and Freedom (UDMF).[61] Savinkov had been Deputy War Minister in the Provisional Government of Alexander Fyodorovich Kerensky, and a key opponent of the Bolsheviks.[62] A former Socialist Revolutionary Party member, Savinkov had formed the UDMF consisting of several thousand Russian fighters.[62] Lockhart, Reilly, and others then contacted anti-Bolshevik groups linked to Savinkov and Socialist Revolutionary Party cells linked to Savinkov's friend Maximilian Filonenko. Lockhart, Reilly, and others supported these factions with SIS funds.[60] They also liaisoned with the intelligence operatives of the French and U.S. consuls in Moscow.[63][64]

In June, disillusioned elements of Colonel Eduard Berzin's Latvian Riflemen began appearing in anti-Bolshevik circles in Petrograd and were eventually directed to a British naval attaché Captain Francis Cromie and his assistant Mr. Constantine, a Turkish merchant who was actually Reilly.[64] At the time, Cromie purportedly represented the British Naval Intelligence Division and oversaw its operations in northern Russia.[65] As Berzin's Latvians were deemed the Praetorian Guard of the Bolsheviks and entrusted with the security of both Lenin and the Kremlin, Reilly and others believed their participation in the pending coup to be vital. With the aid of the Latvian Rifleman, the Allied agents hoped to "seize both Lenin and Trotsky at a meeting to take place in the first week of September."[5] Reilly arranged a meeting between Lockhart and the Latvians at the British mission in Moscow. At this stage, Cromie,[65] Lockhart, Reilly, and other Allied agents planned a coup against the Bolshevik government and drew up a list of Soviet military leaders ready to assume responsibilities on its demise.[66] Their objective was to capture or kill Lenin and Trotsky, to establish a provisional government, and to extinguish Bolshevism.[5] Lenin and Trotsky, they reasoned, "were Bolshevism," and nothing else in their movement had "substance or permanence."[5] Consequently, "if he could get them into [their] hands there would be nothing of consequence left of Sovietism."[5]

It was during this chaotic time of plots and counter-plots that Reilly and Lockhart became further acquainted.[59] Lockhart later posthumously described him as "a man of great energy and personal charm, very attractive to women and very ambitious. I had not a very high opinion of his intelligence. His knowledge covered many subjects, from politics to art, but it was superficial. On the other hand, his courage and indifference to danger were superb."[59] Throughout their backroom intrigues in Moscow, Lockhart never openly questioned Reilly's loyalty to the Allies, although he privately wondered if Reilly had made a secret bargain with Colonel Berzin and his Latvian Riflemen to later seize power for themselves.[59] In Lockhart's estimation, Reilly was a limitless "man cast in the Napoleonic mold" and, if their counter-revolutionary coup had succeeded, "the prospect of playing a lone hand [using the Latvian Riflemen] may have inspired him with a Napoleonic design" to become the head of any new government.[59]

While Allied agents prepared their coup in Moscow, an Allied force landed on 4 August 1918, at Arkhangelsk, Russia, beginning a famous military expedition dubbed Operation Archangel. Its professed 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.[66]

On 17 August 2018, Reilly conducted meetings between Latvian regimental leaders and liaisoned with Captain George Alexander Hill, another multilingual British agent operating in Russia.[67] 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.[66] On 30 August, Boris Savinkov and Maximilian Filonenko ordered a military cadet named Leonid Kannegisser--Filonenko's cousin--to shoot and kill Moisei Uritsky, head of the Petrograd Cheka.[68] Uritsky had been the second most powerful man in the city after Grigory Zinoviev, the leader of the Petrograd Soviet, and his murder was seen as a blow to both the Cheka and the entire Bolshevik leadership.[65] After killing Uritsky, a panicked Kannegisser sought refuge either at the English Club[65] or at the British mission where Cromie resided and where Savinkov and Filonenko may have been temporarily in hiding.[69][70] Regardless of whether he fled to the English Club or to the British consulate, Kannegisser was compelled to leave the premises and, after having donned a long overcoat, he fled into the city streets where he was apprehended by Red Guards.

On the same day, Fanya Kaplan--a former anarchist who was now a member of the Socialist Revolutionary Party[71]--shot and wounded Lenin as he departed the Michelson arms factory in Moscow.[71] As Lenin exited the building and before he entered his motor car, Kaplan called out to him. When Lenin turned towards her, she fired three shots with a Browning pistol.[72] One bullet narrowly missed Lenin's heart and penetrated his lung, while the other bullet lodged in his neck near the jugular vein.[68] Due to the severity of these wounds, Lenin was not expected to survive.[68][65] The attack was widely covered in the Russian press, generating much sympathy for Lenin and boosting his popularity.[73] As a consequence of this assassination attempt, however, the meeting between Lenin and Trotsky--where the bribed soldiery would seize them on behalf of the Allies--was postponed.[5] Although it is still unknown if Kaplan either was part of the Ambassadors' Plot or was even responsible for the assassination attempt on Lenin,[74] the murder of Uritsky and the failed assassination of Lenin were used by Dzerzhinsky's Cheka to implicate any malcontents and foreigners in a grand conspiracy that warranted a full-scale reprisal campaign: the "Red Terror".[75] Thousands of political opponents were seized and "mass executions took place across the city, at Khodynskoe field, Petrovsky Park and the Butyrki prison, all in the north of the city, as well as in the Cheka headquarters at Lubyanka."[75] The extent of the Chekist reprisal likely foiled much of the ongoing plans by Cromie, Lockhart, Reilly, Savinkov, Filonenko, and other conspirators.[66][65]

Using lists supplied by undercover agents, the Cheka proceeded to clear out the "nests of conspirators" in the foreign embassies and, in doing so, they arrested key figures vital to the impending coup.[65][5] On 31 August 1918, believing Savinkov and Filonenko were hiding in the British consulate,[69][70] a Cheka detachment raided the British consulate in Petrograd and killed Cromie who put up an armed resistance.[76][69][70] Immediately prior to his death, it is possible that Cromie may have been trying to communicate with other conspirators and to give instructions to accelerate their planned coup.[65] Before the Cheka detachment stormed the consulate, Cromie burned key correspondence pertaining to the coup.[65] According to press reports, he made a valiant last stand on the first floor of the consulate armed only with a revolver.[76] In close quarters combat, he dispatched three Cheka soldiers before he was in turn killed and his corpse mutilated.[76][69] Eyewitnesses, such as the sister-in-law of Red Cross nurse Mary Britnieva, asserted that Cromie was shot by Cheka guards while retreating down the consulate's grand staircase.[77] The Cheka detachment searched the building and, with their rifle butts, repelled the diplomatic staff from getting close to the corpse of Captain Cromie, which the Chekist soldiers had looted and trampled.[65] The Cheka detachment then arrested over forty persons who had sought refuge within the British consulate, as well as seized weapon caches and compromising documents which they claimed implicated the consular staff in the imminent coup attempt.[76][63] Cromie's death was publicly "depicted as a measure of self-defence by the Bolshevik agents, who had been forced to return his fire."[63]

From the Evening Standard's Master Spy serial: Reilly, attired as a Cheka officer, bluffs through a Red Army checkpoint.
From the Evening Standards Master Spy serial: Reilly, attired as a Cheka officer, bluffs through a Red Army checkpoint.

Meanwhile, Lockhart was arrested by Dzerzhinsky's Cheka and transported under guard to Lubyanka Prison.[68] During a tense interview with a pistol-wielding Cheka officer, he was asked "Do you know the Kaplan woman?" and "Where is Reilly?"[68] When queried about the coup, Lockhart and other British nationals dismissed the mere idea as nonsense.[60] Afterwards, Lockhart was placed in the same holding cell as Fanya Kaplan whom their watchful Cheka jailers hoped might betray some sign of recognizing Lockhart or other British agents.[78] However, while confined together, Kaplan showed no sign of recognition towards Lockhart or anyone else.[78] When it became clear that Kaplan would not implicate any accomplices, she was executed in the Kremlin's Alexander Garden on 3 September 1918, with a bullet to the back of the head.[72] Her corpse was bundled into a rusted iron barrel and set alight.[72] Lockhart was later released and deported in exchange for Maxim Litvinov, an unofficial Soviet attaché in London who had been arrested by the British government as a form of diplomatic reprisal.[79] In stark contrast to Lockhart's good fortune, "imprisonment, torture to compel confession, [and] death were the swift rewards of many who had been implicated" in the imminent coup against Lenin's government.[5] Yelizaveta Otten, Reilly's chief courier "with whom he was romantically involved,"[80] was arrested as well as his other mistress Olga Starzheskaya.[53] After interrogation, Starzheskaya was reportedly later executed.[53] Another courier, Maria Fride, likewise was arrested at Otten's flat with an intelligence communiqué that she was carrying for Reilly.[81][66]

On 3 September 1918, the aborted coup was sensationalized by the Russian press.[63] Outraged headlines denounced the Allied representatives and other foreigners in Moscow as "Anglo-French Bandits."[63] Reilly was identified as a key suspect, and a dragnet ensued. Reilly "was hunted through days and nights as he had never been hunted before."[5] The Cheka raided his assumed refuge, but Reilly avoided capture and met Captain Hill while in hiding. Hill proposed that Reilly exfiltrate Russia via the Ukraine using their network of British agents for safe houses and assistance. For unknown reasons, 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 with the aid of local Baltic smugglers.[82] He arrived unscathed in London on 8 November.[82]

While safely in England, Reilly, Lockhart, and others were tried in absentia before the Supreme Revolutionary Tribunal in a proceeding which opened 25 November 1918.[83] Approximately twenty defendants faced charges in the trial, most of whom had worked for the Americans or the British in Moscow. The case was prosecuted by Nikolai Krylenko, an exponent of the theory that political considerations, rather than criminal guilt or innocence, should decide a case's outcome.[83] Krylenko's case concluded on 3 December 1918, with two defendants sentenced to be shot and various others sentenced to terms of prison or forced labor for terms up to five years.[83] Thus, the day before Reilly met Sir Mansfield Smith-Cumming ("C") in London for 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.[83][84] The 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 Dzerzhinsky's OGPU in 1925.[83][85]

Activities from 1919 to 1923

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.[86] At that time, the region was home to a variety of anti-Bolsheviks. 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 twelve dispatches which reported on various aspects of the situation in South Russia (now Ukraine) 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 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 (now Ukraine) into a suitable "'placed'armes" for decisive advance against Petlurism and Bolshevism'. 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."[87]

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.[87]

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.[87]

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.[88][5]

Alleged Execution

According to Reilly's wife Pepita Bobadilla, Reilly was perpetually determined "to return to Russia to see if he could not find and succor some of his friends whom he believed to be still alive. This he did in 1925--and never came back."[5] 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.[89][90] 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 Alexandrovich Yakushev, later recalled the meeting:

After execution, the alleged corpse of Reilly was photographed in OGPU headquarters circa 5 November 1925.

Reilly was brought across the border by Toivo Vähä, a former Finnish Red Guard fighter who now served the Cheka. Vähä took Reilly over the Sestra River to the Soviet side and handed him to the Cheka officers.[92][93] After Reilly crossed the Finnish border, the Soviets captured, transported, and interrogated him at Lubyanka Prison. (In his book The Gulag Archipelago, Alexandr Solzhenitsyn states 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.[94] 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.[95]

Reilly was executed in a forest near Moscow on Thursday, 5 November 1925.[96] 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. For example, both Reilly's wife Pepita Bobadilla and Robert Bruce Lockhart's son claimed to possess evidence indicating that Reilly was still alive as late as 1932.[5][10] Others speculated that Reilly had defected and became an adviser to Soviet intelligence.

Career with British intelligence

Reilly in later years.

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.[23] In 1918, Reilly began to work for MI1(c), an early designation[23] 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.[60] He had to escape after the Cheka unraveled the so-called Lockhart Plot against the Bolshevik government. Later biographies contain numerous tales about his espionage deeds. It has been claimed that:

British intelligence adhered to its policy of publicly saying nothing about anything.[7] 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."[98] Most later biographers claim the medal was bestowed due to Reilly's anti-Bolshevik operations in southern Russia.

Deacon asserts in History of the Russian Secret Service that in April 1912, Reilly was an Ochrana double agent with the task of befriending and profiling Sir Basil Zaharoff, the international arms salesman and representative of Vickers-Armstrong Munitions Ltd.[100] Another Reilly biographer, Richard Spence, claims that during this assignment Reilly learned "le systeme" from Zaharoff -- the strategy of playing all sides against each other in order to maximise financial profit.[101] Cook counters in Ace of Spies: The True Story of Sidney Reilly that there is scant evidence of any relationship between Reilly and Zaharoff.[102] Furthermore, Cook asserts Reilly's SIS-specific career has been greatly embellished as he wasn't accepted as an agent until 15 March 1918. He was then discharged in 1921 because of his tendency to be a rogue operative. Nevertheless, Cook concedes that 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.

Circa 1924, according to Winfried Lüdecke and author Michael Kettle, Reilly was likely involved with Sir Stewart Graham Menzies in the forging of the Zinoviev letter.[103][4] Writing in 1929--only four years after Reilly's death--Lüdecke noted that Reilly's transmission of "the famous Zinoviev letter assumed a world-wide political importance, for its publication in the British press brought about the fall of the [Ramsay] Macdonald ministry, frustrated the realization of the proposed Anglo-Russian commercial treaty, and, as a final result, led to the signing of the treaties of Locarno, in virtue of which the other states of Europe presented, under the leadership of Britain, a united front against Soviet Russia."[4]

Fictional portrayals

Reilly: Ace of Spies

Sam Neill portraying 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. Directed by Martin Campbell and Jim Goddard, the program 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. In a review of the program, Michael Billington of The New York Times noted that "pinning Reilly down in 12 hours of television is difficult precisely because he was such an enigma: an alleged radical, yet one who helped to bring down Britain's first Labor government in 1924 by means of a forged letter, supposedly from the Bolshevik leader Zinoviev, instructing the British Communists to form cells in the armed forces; a Lothario and two-time bigamist who was yet never betrayed by any of the women he was involved with; an avid collector of Napoleona who wanted to be the power behind the throne rather than to rule himself."[10]

James Bond

In Ian Fleming, The Man Behind James Bond by Andrew Lycett, Sidney Reilly is listed as an inspiration for James Bond.[104] 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.[105] Lockhart had worked with Reilly in Russia in 1918, where they became embroiled in an SIS-backed plot to overthrow Lenin's Bolshevik government.[46] 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.[105] When queried on whether Reilly's colorful life had directly inspired Bond, Ian Fleming replied: "James Bond is just a piece of nonsense I dreamed up. He's not a Sidney Reilly, you know."[10]

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.[6] 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.[106] The theme music for the 1983 television mini-series is essentially a piece of The Gadfly Suite (Op. 97a) by Dmitri Shostakovich.

See also


  1. ^ a b c Deacon 1987, p. 77.
  2. ^ a b c McNeal 2002, p. 137.
  3. ^ a b c d Spence 2002, pp. 57-59.
  4. ^ a b c Ludecke 1929, p. 107.
  5. ^ a b c d e f g h i j k l m n New York Times 1933.
  6. ^ a b c Robin Bruce Lockhart, Reilly: Ace of Spies; 1986, Hippocrene Books, ISBN 0-88029-072-2.
  7. ^ a b Deacon 1987, pp. 133-136.
  8. ^ Spence 2002, Chapter 8: The Russian Question.
  9. ^ Lockhart 1932.
  10. ^ a b c d e f g Billington 1984.
  11. ^ Lycett 1996, pp. 118,132.
  12. ^ a b c d e f Andrew 1986, p. 83.
  13. ^ a b c d e Deacon 1987, p. 134.
  14. ^ a b Ludecke 1929, p. 105.
  15. ^ Segodnya 2007.
  16. ^ a b c d e Lockhart 1986
  17. ^ a b c Cook 2004, p. 28.
  18. ^ Ainsworth 1998, p. 1447.
  19. ^ a b Cook 2004, pp. 26-27.
  20. ^ Spence 2002, p. 12.
  21. ^ a b c d Cook 2004, pp. 32-33.
  22. ^ a b Cook 2004, p. 34.
  23. ^ a b c SIS Website 2007.
  24. ^ Spence 2002, pp. 28-39.
  25. ^ Spence 2002, p. 24.
  26. ^ Spence 2002, p. 30.
  27. ^ Spence 2002, p. 37.
  28. ^ a b Cook 2004, pp. 15-18.
  29. ^ Cook 2004, p. 44.
  30. ^ Spence 1995, p. 92.
  31. ^ a b Cook 2004, p. 56.
  32. ^ Nish 2014.
  33. ^ Cook 2004, pp. 44-50.
  34. ^ a b c d e f Ludecke 1929, p. 106.
  35. ^ Spence 2002, pp. 40-55.
  36. ^ Cook 2004, pp. 59-60.
  37. ^ Spence 2002, p. 61.
  38. ^ a b Lockhart, 1986.
  39. ^ a b Yergin 1991, p. 140.
  40. ^ a b Cook 2004, p. 78.
  41. ^ a b Cook 2004, pp. 64-68.
  42. ^ Spence 2002, p. 92.
  43. ^ a b c Lockhart 1967
  44. ^ Cook 2004, pp. 276-277.
  45. ^ Deacon 1987, p. 135.
  46. ^ a b c Andrew 1986, p. 214.
  47. ^ Spence 2002, Chapter 6: War on the Manhattan Front.
  48. ^ Andrew 1986.
  49. ^ a b c d e Hicks 1920.
  50. ^ a b Spence 2002, pp. 150-151.
  51. ^ a b Spence 2002, pp. 172-173, 185-186.
  52. ^ Spence 2002, pp. 195.
  53. ^ a b c McNeal 2002, p. 81.
  54. ^ McNeal 2018.
  55. ^ a b Spence 2002, pp. 187-191.
  56. ^ McNeal 2002, p. 121.
  57. ^ Long 1995.
  58. ^ Debo 1971.
  59. ^ a b c d e Lockhart 1932, pp. 277, 322-323.
  60. ^ a b c d Thomson 2011.
  61. ^ McNeal 2002, pp. 105-106.
  62. ^ a b McNeal 2002, p. 234.
  63. ^ a b c d e Lockhart 1932, p. 322.
  64. ^ a b Cook 2004, pp. 162-164.
  65. ^ a b c d e f g h i j Ferguson 2010, pp. 1-5, Prologue.
  66. ^ a b c d e Cook 2004, pp. 166-169.
  67. ^ Kitchen.
  68. ^ a b c d e Lockhart 1932, p. 317-318.
  69. ^ a b c d Brooklyn Eagle 1918.
  70. ^ a b c Washington Post 1918.
  71. ^ a b Brooke 2006, p. 74.
  72. ^ a b c Donaldson & Donaldson 1980, p. 221.
  73. ^ Volkogonov 1994, pp. 222, 231.
  74. ^ Gransden 1993: "In 1993, Russia's Security Ministry raised doubts about the conviction and execution of Fanny Kaplan."
  75. ^ a b Brooke 2006, p. 75.
  76. ^ a b c d New York Times 1918, pp. 1,6.
  77. ^ Britnieva 1934, pp. 77-86.
  78. ^ a b Lockhart 1932, p. 320.
  79. ^ Lockhart 1932, p. 330.
  80. ^ Spence 2002, p. 209.
  81. ^ Spence 2002, p. 234.
  82. ^ a b Spence 2002, p. 240.
  83. ^ a b c d e Service 2012, pp. 164-165.
  84. ^ Spence 2002, p. 236.
  85. ^ Spence 2002, p. 453.
  86. ^ Spence 2002, pp. 247-251.
  87. ^ a b c Ainsworth 1998, pp. 1447-1470.
  88. ^ Bobadilla & Reilly 1986, p. 110.
  89. ^ Deacon 1987, p. 136.
  90. ^ Grant 1986, pp. 51-77.
  91. ^ Cook 2004, p. 238.
  92. ^ Ristolainen 2009.
  93. ^ Kotakallio 2016, p. 142.
  94. ^ Spence 2002, pp. 455-456.
  95. ^ Cook 2004, p. 250.
  96. ^ Cook 2004, pp. 258-259.
  97. ^ a b Corry 1984.
  98. ^ a b Cook 2004, p. 188.
  99. ^ Lockhart 1984, p. 71.
  100. ^ Deacon 1972, pp. 144,175.
  101. ^ Spence 2002, pp. 25-26.
  102. ^ Cook 2004, pp. 104.
  103. ^ Kettle 1986, p. 121.
  104. ^ Lycett 1996, pp. 118, 132.
  105. ^ a b Cook 2004, p. 12.
  106. ^ Cook 2004, p. 39.


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