Sidney Reilly

Sidney Reilly

Georgi Rosenblum, the only son of Hersh Yakov Rozenblium and his wife, Paulina Bramson, was born in Piotrków on 24th March 1874. He had two sisters, Elena and Mariam. His father was a contractor and a landowner. He was also active in the Jewish emancipation movement.

According to his biographer, Richard B. Spence, details of his education are uncertain. "Despite later claims, he did not attend Heidelberg or Cambridge universities or the Royal School of Mines. Nevertheless he demonstrated sufficient knowledge of chemistry to gain membership in the Chemical Society in 1896 and the Institute of Chemistry in 1897. He had an exceptional command of languages, including English, Russian, Polish, German, and French."

Giles Milton, who has researched his early life claims: "Both his parents were Jewish, although they had converted to Catholicism. Rosenblum fled Odessa in his late teens for reasons that remain obscure. No less obscure are the next two decades of his life. He would later spin tales about how he had been a cook, a dockworker, a railway engineer in India and a brothel doorman in Brazil, but there is no certainty that he did any of these jobs. He was also said to have worked as a spy for the Japanese government and there are many unverified stories of his early forays into espionage."

Rosenblum arrived in London in 1895. Three years later he married Margaret Callahan Thomas (1874–1933), a governess and the widow of the Revd Hugh Thomas. Richard B. Spence, the author of Trust No One: The Secret World of Sidney Reilly (2003) points out: "In 1899 he became Sidney George Reilly by receiving a passport in that name, though he never legally adopted it or became a British subject. A patron, possibly his entrée into British intelligence, was Sir Henry Hozier (1838–1907), powerful secretary of Lloyds connected to the War Office intelligence branch. With his strong Jewish features and accented English, Reilly was an unconvincing Englishman, but this became his favourite of many alternative identities." According to Brian Marriner Reilly "possessed passports in eleven different names."

Although based in London, Reilly spent most of his time in the Far East. In 1904 he began working for the trading firm M. A. Ginsburg & Company in Port Arthur, China. The author, Richard Deacon, has argued that he was working as a "double-agent serving both the British and the Japanese." In 1906 he moved to St Petersburg, where he became friendly with members of the revolutionary underground. It is believed that as well as working for the British he was also spying for the Tsarist regime. Deacon adds that: "He was certainly being well-paid as in 1906 he had a lavish apartment in St Petersburg, a splendid art collection and was a member of the most exclusive club in the city."

Sidney Reilly
Sidney Reilly as a young man

Reilly developed a reputation for womanising. Giles Milton, the author of Russian Roulette: How British Spies Thwarted Lenin's Global Plot (2013) has pointed out: "All accounts agree that he had a seductive charm, loving women as he loved himself. A string of mistresses would fall under his spell. Monogamy did not come naturally to Reilly and although he was usually fastidious in his choice of women, it did not prevent him from cavorting around London on one of his visits with a common tart named Plugger. How she acquired her nom de travail can only be imagined." His third wife, Pepita Burton, first met him in Berlin. "For a moment his eyes held mine and I felt a delicious thrill run through me."

Reilly then got a job working for German naval ship-builders. This enabled him to see and copy all blueprints and specifications of the latest German naval construction. These he passed to MI6. On the outbreak of the First World War Reilly went to New York City as a war contractor buying arms supplies for the Russians. Richard B. Spence has argued: "His ruthless business tactics earned him a fortune and many enemies." During this period he remained in contact with Mansfield Cumming via William Wiseman, his station chief in New York City.

After spending a short time in London in 1917, Reilly was smuggled into Germany and was given the task of discovering how close the country was to defeat. The Foreign Office's George Nevile Bland, has argued that Reilly was "a man of great courage... coupled with a somewhat unscrupulous temperament, making him a rather double edged tool". Another MI6 official, Norman Thwaites, described him as having a "swarthy complexion, a long straight nose, piercing eyes, clack hair brushed back from a forehead suggesting keen intelligence, a large mouth, figure slight, of medium height, always clothed immaculately, he was a man that impressed one with a sense of power." Thwaites added: "Not only had he charming manners, but he was a most agreeable companion with a fund of information in many spheres."

With the help of Norman Thwaites, on his return to England in October he joined the Royal Flying Corps as second lieutenant. Thwaites told Major John Scale, an MI6 agent, that Reilly would be a good person to work inside Russia. Scale took this information to Mansfield Smith-Cumming. He made enquiries and found that agents who had worked with him did not always agree with Thwaites. One agent said that Reilly "has made money since the beginning of the war through influence with corrupted members of the Russian purchasing commissions... and we consider him untrustworthy and unsuitable to work suggested." Another agent said that "Reilly was a shrewd businessman of undoubted ability but without patriotism or principles and therefore not recommended for any position which requires loyalty as he would not hesitate to use it to further his own commercial interests." Christopher Andrew, the author of Secret Service: The Making of the British Intelligence Community, argues that Winston Churchill supported Reilly's recruitment into MI6: "Reilly had a remarkable personal charisma and flair for intelligence work which was to win the admiration of both Cumming and Winston Churchill."

In April 1918, Mansfield Smith-Cumming, the head of MI6 sent Reilly to Russia. He joined a team that included the Robert Bruce Lockhart, the Head of Special Mission to the Soviet Government with the rank of acting British Consul-General, George Alexander Hill, Paul Dukes, Cudbert Thornhill, Ernest Boyce, Oswald Rayner and Stephen Alley. Xenophon Kalamatiano, the main American agent in Russia, also joined this conspiracy. The main objective of this group was to bring about the overthrow of the Bolshevik government. Reilly had a passionate hatred for communism. "Bolshevism had been baptised in the blood of the bourgeoise... its leaders were criminals, assassins, murderers, gunmen, desperadoes.... Over all, silent, secret, ferocious, menacing, hung the crimson shadow of the Cheka. The new masters were ruling in Russia."

Jan Buikis, a Soviet agent, made contact with Francis Cromie, the naval attaché at the British Embassy, and requested a meeting with Robert Bruce Lockhart. On 14th August, 1918, Buikis and Colonel Eduard Berzin, met Lockhart. Berzin told Lockhart that there was serious disaffection among the Lettish troops and asked for money to finance an anti-Bolshevik coup. Lockhart, who described Berzin as "a tall powerfully-built man with clear-cut features and hard steely eyes" was impressed by Berzen. He told Lockhart that he was a senior commander of the Lettish (Latvian) regiments that had been protecting the Bolshevik Government ever since the revolution. Berzin insisted that these regiments had proved indispensable to Lenin, saving his regime from several attempted coups d'état.

Lockhart claimed that initially he was suspicious of Berzin but was convinced by a letter that had been sent by Cromie: "Always on my guard against agents provocateurs, I scrutinized the letter carefully. It was unmistakably from Cromie. The handwriting was his... The letter closed with a recommendation of Berzin as a man who might be able to render us some service." Lockhart also believed Berzin's claim that the Lativan regiments had lost all enthusiasm for protecting the Revolutionary Government and wanted to return to Latvia. Another agent involved in the plot, George Alexander Hill, also believed Berzin was telling the truth and the men were in the ideal position to overthrow the Bolshevik government: "The Letts were the corner stone and foundation of the Soviet government. They guarded the Kremlin, gold stock and the munitions."

On 17th August, 1918, Moisei Uritsky, the Commissar for Internal Affairs in the Northern Region, was assassinated by Leonid Kannegisser, a young military cadet. Anatoly Lunacharsky commented: "They killed him. They struck us a truly well-aimed blow. They picked out one of the most gifted and powerful of their enemies, one of the most gifted and powerful champions of the working class." The Soviet press published allegations that Uritsky had been killed because he was unravelling "the threads of an English conspiracy in Petrograd".

Despite these claims, Robert Bruce Lockhart continued with his plans to overthrow the Bolshevik government. He had a meeting with a senior intelligence agent based in the French Embassy. He was convinced that Berzin was genuine in his desire to overthrow the Bolsheviks and was willing to put up some of the money needed: "The Letts are Bolshevik servants because they have no other resort. They are foreign hirelings. Foreign hirelings serve for money. They are at the disposal of the highest bidder."

Lockhart asked Xenophon Kalamatiano to help arrange funds from America to pay for the overthrow of the Bolsheviks. Colonel Henri de Vertement, the leading French intelligence agent in Russia also contributed money for the venture. Over the next week, George Reilly, Ernest Boyce and George Alexander Hill had regular meetings with Colonel Eduard Berzin, where they planned the overthrow of the Bolsheviks. During this period they handed over 1,200,000 rubles. Unknown to MI6 this money was immediately handed over to Felix Dzerzhinsky, the head of Cheka. So also were the details of the British conspiracy.

Berzin told the agents that his troops had been to assigned to guard the theatre where the Soviet Central Executive Committee was to met. A plan was devised to arrest Lenin and Leon Trotsky at the meeting was to take place on 28th August, 1918. Robin Bruce Lockhart, the author of Reilly: Ace of Spies (1992) has argued: "Reilly's grand plan was to arrest all the Red leaders in one swoop on August 28th when a meeting of the Soviet Central Executive Committee was due to be held. Rather than execute them, Reilly intended to de-bag the Bolshevik hierarchy and with Lenin and Trotsky in front, to march them through the streets of Moscow bereft of trousers and underpants, shirt-tails flying in the breeze. They would then be imprisoned. Reilly maintained that it was better to destroy their power by ridicule than to make martyrs of the Bolshevik leaders by shooting them." Reilly's plan was eventually rejected and it was decided to execute the entire leadership of the Bolshevik Party.

Reilly later recalled: "At a given signal, the soldiers were to close the doors and cover all the people in the Theatre with their rifles, while a selected detachment was to secure the persons of Lenin and Trotsky... In case there was any hitch in the proceedings, in case the Soviets showed fight or the Letts proved nervous... the other conspirators and myself would carry grenades in our place of concealment behind the curtains." However, at the last moment, the Soviet Central Executive Committee meeting was postponed until 6th September.

On 31st August 1918 Dora Kaplan attempted to assassinate Lenin. It was claimed that this was part of the British conspiracy to overthrow the Bolshevik government and orders were issued by Felix Dzerzhinsky, the head of Cheka, to round up the agents based in British Embassy in Petrograd. The naval attaché, Francis Cromie was killed resisting arrest. According to Robin Bruce Lockhart: "The gallant Cromie had resisted to the last; with a Browning in each hand he had killed a commissar and wounded several Cheka thugs, before falling himself riddled with Red bullets. Kicked and trampled on, his body was thrown out of the second floor window."

Ernest Boyce and Robert Bruce Lockhart were both arrested but Sidney Reilly had a lucky escape. He arranged to meet Cromie that morning. He arrived at the British Embassy soon after Cromie had been killed: "The Embassy door had been battered off its hinges. The Embassy flag had been torn down. The Embassy had been carried by storm." Reilly now went into hiding and after paying 60,000 rubles to be smuggled out of Russia on board a Dutch freighter.

Reilly arrived back in London with another agent, George Alexander Hill, were asked to return to London in November 1918. Mansfield Smith-Cumming, the head of MI6 was very pleased with the information the two men had smuggled out of Russia and arranged for them to receive the Military Cross. Smith-Cumming then asked the men if they were willing to return to Russia. The main objective was to assess the prospects of the White Army led by General Anton Denikin against the Red Army in the Russian Civil War. The men agreeed but was shocked when they were told that their train bound for Odessa was departing in two hours. Hill and Reilly realised that it was a dangerous mission and if they were caught by the Bolsheviks they would be executed.

Reilly wrote to Robert Bruce Lockhart: "I told "C" (and I am anxious that you should know it too) that I consider that there is a very earnest obligation upon me to continue to serve - if my services can be made use of in the question of Russia and Bolshevism. I feel that I have no right to go back to the making of dollars until I have discharged my obligations. I also venture to think that the state should not lose my services. I would devote the rest of my wicked life to this kind of work.... I need not enlarge upon my motives to you; I am sure you will understand them and if you can do something I should feel grateful. I should like nothing better than to serve under you. I don't believe that the Russians can do anything against the Bolsheviks without our most active support. The salvation of Russia has become a most sacred duty which we owe to the untold thousands of Russian men and women who have sacrificed their lives because they trusted in the promise of our support."

Sidney Reilly
An unpublished cartoon of Sidney Reilly in 1919.

In 1921 Reilly became a business adviser to Brigadier Edward Louis Spears, who told Winston Churchill that he had received an attractive offer from "a big financial group interested in opening up Poland, the Ukraine and Rumania and in securing trade privileges in those countries for Great Britain". Spears recruited Reilly because of his wide experience of Eastern Europe. Spears later recalled that "Reilly accompanied me in the capacity of an able businessman which I certainly was not myself at the time." Spears warned Reilly about "the danger of dealing with shady people & mixing politics with business". A number of business ventures instigated by Reilly were not successful and on 2nd August, 1922, Spears sacked him.

In the 1923 General Election, the Labour Party won 191 seats. Although the Conservatives had 258, Ramsay MacDonald agreed to head a minority government, and therefore became the first member of the party to become Prime Minister. As MacDonald had to rely on the support of the Liberal Party, he was unable to get any socialist legislation passed by the House of Commons.

MI6 was appalled by the idea of a Prime Minister who was a socialist. As Gill Bennett pointed out in her book, Churchill's Man of Mystery (2009): "It was not just the intelligence community, but more precisely the community of an elite - senior officials in government departments, men in "the City", men in politics, men who controlled the Press - which was narrow, interconnected (sometimes intermarried) and mutually supportive. Many of these men... had been to the same schools and universities, and belonged to the same clubs. Feeling themselves part of a special and closed community, they exchanged confidences secure in the knowledge, as they thought, that they were protected by that community from indiscretion." Reilly now joined a conspiracy that was determined to overthrow the MacDonald government.

Reilly continued to take a close interest in events in Russia. He worked very closely with Boris Savinkov, a former terrorist with the Socialist Revolutionary Party but had been a member of the Provisional Government in 1917 and was close to Alexander Kerensky, the former prime minister of Russia. Savinkov was working with an anti-Bolshevik organization, Monarchist Union of Central Russia (also known as "The Trust"). As Richard Deacon, the author of A History of the Russian Secret Service (1972) pointed out: "Boris Savinkov... was given to understand that all the plotters inside Russia were waiting for was an assurance of massive support from the anti-Bolsheviks outside Russia. Soon Savinkov's own agents were being smuggled in and out of Russia." Savinkov asked Reilly to carry out investigations into "The Trust". Reilly contacted Ernest Boyce, the head of the Russian section of MI6. Boyce confirmed that the organization was apparently a movement of considerable power within Russia. Its agents had supplied valuable intelligence to the Secret Services of a number of anti-Bolshevik countries and was convinced that it was not under the control of Russian Secret Service.

Reilly contacted Winston Churchill, who he knew was a passionate supporter of intervention, and told him that Savinkov was the best man to coordinate an overthrow of the Bolsheviks. Reilly arranged for Churchill to meet Savinkov. Churchill agreed that that Savinkov was a man of greater stature than any of the other Russian expatriates and that he was the only man who might organize a successful counter-revolution. Prime Minister David Lloyd George had doubts about trying to overthrow the Bolsheviks: "Savinkov is no doubt a man of the future but I need Russia at the present moment, even if it must be the Bolsheviks. Savinkov can do nothing at the moment, but I am sure he will be called on in time to come. There are not many Russians like him."

The Foreign Office was unimpressed with Savinkov describing him as "most unreliable and crooked". Churchill replied that he thought that he "was a great man and a great Russian patriot, in spite of the terrible methods with which he has been associated". Churchill rejected the advice of his advisors on the grounds that "it is very difficult to judge the politics in any other country". With the agreement with Mansfield Smith-Cumming, the head of MI6, it was decided to send Savinkov back into Russia. Richard Deacon has argued that "It was not that he (Savinkov) did not realise there was a risk of deception, but that he had become desperate in his quest for a solution to the problem of defeating the Bolsheviks. His impatience caused him not merely to take a cautious gamble but to risk his life in the cause of counter-revolution."

Sidney Reilly
Sidney Reilly

In September 1924 MI5 intercepted a letter signed by Grigory Zinoviev, chairman of the Comintern in the Soviet Union, and Arthur McManus, the British representative on the committee. In the letter British communists were urged to promote revolution through acts of sedition. Hugh Sinclair, head of MI6, provided "five very good reasons" why he believed the letter was genuine. However, one of these reasons, that the letter came "direct from an agent in Moscow for a long time in our service, and of proved reliability" was incorrect. Vernon Kell, the head of MI5 and Sir Basil Thomson the head of Special Branch, were also convinced that the letter was genuine. Kell showed the letter to Ramsay MacDonald, the Labour Prime Minister. It was agreed that the letter should be kept secret but someone leaked news of the letter to the Times and the Daily Mail.

The letter was published in these newspapers four days before the 1924 General Election and contributed to the defeat of MacDonald and the Labour Party. In a speech he made on 24th October, Ramsay MacDonald suggested he had been a victim of a political conspiracy: "I am also informed that the Conservative Headquarters had been spreading abroad for some days that... a mine was going to be sprung under our feet, and that the name of Zinoviev was to be associated with mine. Another Guy Fawkes - a new Gunpowder Plot... The letter might have originated anywhere. The staff of the Foreign Office up to the end of the week thought it was authentic... I have not seen the evidence yet. All I say is this, that it is a most suspicious circumstance that a certain newspaper and the headquarters of the Conservative Association seem to have had copies of it at the same time as the Foreign Office, and if that is true how can I avoid the suspicion - I will not say the conclusion - that the whole thing is a political plot?"

Sidney Reilly
Sidney Reilly

After the election it was claimed that Sidney Reilly and Arthur Maundy Gregory, had forged the letter. According to Christopher Andrew, the author of Secret Service: The Making of the British Intelligence Community (1985): "Reilly played an active part in ensuring that the letter was publicised. A copy of the Russian version of the letter has been discovered in what appears to be Reilly's handwriting, and there can scarcely have been another past or present SIS agent with so few scruples about exploiting it in the anti-Bolshevik cause." It later became clear that Major George Joseph Ball (1885-1961), a MI5 officer, played an important role in leaking it to the press.

Reilly had been less successful with his attempts to overthrow the Bolshevik government. Boris Savinkov went into Russia in Russia in August 1924. Soon afterwards Izvestia announced that Savinkov had been arrested. Over the next few months the newspaper announced that he had been condemned to death; sentence had been commuted to ten years' imprisonment and finally released. It was reported that he was living in a comfortable house in Loubianka Square. Savinkov wrote to Sidney Reilly, that he had changed his views of the Bolsheviks: "How many illusions and fairy tales have I buried here in the Loubianka! I have met men in the GPU whom I have known and trusted from my youth up and who are nearer to me than the chatter-boxes of the foreign delegation of the Social-Revolutionaries... I cannot deny that Russia is reborn."

Reilly believed the letter had been written by the GPU. A long letter appeared in The Morning Post on 8th September, 1924: "I claim the great privilege of being one of his most intimate friends and devoted followers, and on me devolves the sacred duty of vindicating his honour. Contrary to the affirmation of your correspondent, I was one of the very few who knew of his intention to penetrate into Soviet Russia. On receipt of a cable from him, I hurried back, at the beginning of July, from New York, where I was assisting my friend, Sir Paul Dukes, to translate and to prepare for publication Savinkov's latest book, The Black Horse. Every page of it is illuminated by Savinkov's transcendent love for his country and by his undying hatred of the Bolshevist tyrants. Since my arrival here on July 19th, I have spent every day with Savinkov up to August 10th, the day of his departure for the Russian frontier. I have been in his fullest confidence, and all his plans have been elaborated conjointly with me. His last hours in Paris were spent with me."

Boris Savinkov died on 7th May, 1925. According to the government he committed suicide by jumping from a window in the Lubyanka Prison. However, other sources claim that he was killed in prison by agents of the All-Union State Political Administration (GPU). Sidney Reilly insisted that Savinkov was murdered in August 1924: "Savinkov was killed when attempting to cross the Russian frontier and a mock trial, with one of their own agents as chief actor, was staged by the Cheka in Moscow behind closed doors."

Ernest Boyce, the MI6 station chief in Helsinki, wrote to Reilly asking him to meet the leaders of Monarchist Union of Central Russia in Moscow. Reilly replied: "Much as I am concerned about my own personal affairs which, as you know, are in a hellish state. I am, at any moment, if I see the right people and prospects of real action, prepared to chuck everything else and devote myself entirely to the Syndicate's interests. I was fifty-one yesterday and I want to do something worthwhile, while I can."

According to Keith Jeffery, the author of MI6: The History of the Secret Intelligence Service (2010), Boyce had sent Reilly into Russia without clearing the scheme with his superiors in London. "Boyce had to take some of the blame for the tragedy. Back in London, as recalled by Harry Carr, his assistant in Helsinki" he was "carpeted by the Chief for the role he had played in this unfortunate affair."

After a number of delays caused mainly by Reilly's debt-ridden business dealings, he met Ernest Boyce in Paris before crossing the Finnish border on 25th September 1925. At a house outside Moscow two days later he had a meeting with the leaders of MUCR, where he was arrested by the secret police. Reilly was told he would be executed because of his attempts to overthrow the Bolshevik government in 1918.

According to the Soviet account of his interrogation, on 13th October 1925, Reilly wrote to Felix Dzerzhinsky, head of Cheka, saying he was ready to cooperate and give full information on the British and American Intelligence Services. Sidney Reilly's appeal failed and he was executed on 5th November 1925.

Sidney Reilly
Sidney Reilly after his execution in 1925.

In 1938 Alexander Orlov, a senior figure in Cheka, fled to France. He later moved to the United States. FBI agent Edward P. Gazur, who interviewed Orlov, claims that Boyce was a double agent and was paid for information about British agents and was responsible for betraying Reilly. This was published for the first time in Gazur's book, Alexander Orlov: The FBI's KGB General (2001). Nigel West has argued that "the reason why this hasn't come out until now is that Orlov, who was not debriefed by British intelligence, never told anybody but Edward Gazur."

© , September 1997 - April 2014

Primary Sources

(1) Christopher Andrew, Secret Service: The Making of the British Intelligence Community (1985)

Cumming's most remarkable, though not his most reliable, agent was Sidney Reilly in St Petersburg, the dominating figure in the mythology of modern British espionage. Reilly, it has been claimed, "wielded more power, authority and influence than any other spy", was an expert assassin "by poisoning, stabbing, shooting and throttling", and possessed "eleven passports and a wife to go with each". The reality, though far less sensational, is still remarkable. Reilly was born Sigmund Georgievich Rosenblum in 1874, the only son of a rich Jewish landowner and contractor in Russian Poland. Some time in the 1890s he left home, broke off all contact with his family, and emigrated to London. At the turn of the century, having changed his name to Reilly, he moved to Port Arthur, the base of the Russian Far Eastern Fleet, where he worked first as partner in a firm of timber merchants, then as manager of the Danish Compagnie Est-Asiatique. By the time Reilly returned to London on the eve of the Russo-Japanese War in 1904, he had become a self-confident international adventurer, fluent in several languages, already weaving around his cosmopolitan career a web of fantasy which has since ensnared most of those who write about him. "He had", writes his most recent biographer, "passed his test with the SIS with flying colours, and they decided that they had a most promising recruit on their hands, who merited very special training". Not the least problem with this romantic view of Reilly's intelligence initiation is that SIS did not yet exist. It is quite possible, though there is no proof, that Reilly did provide NID with intelligence on the Russian Far Eastern Fleet during his years in Port Arthur. But it is scarcely possible that his unusual experience of higher education over the next few years was specially devised as a training programme by NID. In 1904-5 he successfully completed a year's course in electrical engineering in the Royal School of Mines. In October 1905 he went up to Trinity College, Cambridge, as an "advanced student" but left two or three years later without taking any degree.

(2) Giles Milton, Russian Roulette: How British Spies Thwarted Lenin's Global Plot (2013)

There was a darker side to Reilly's personality, one that was to haunt Mansfield Cumming for many years. He was a compulsive gambler and a reckless one to boot. He spent his money with great ostentation, staking all on a hand of cards.

What struck everyone was Reilly's vaunting ambition. He detested the Bolsheviks and was already dreaming of toppling Lenin's government. When he had come to consider who might replace Lenin, he looked no further than the mirror.

"Behind all Reilly's efforts lay the conviction that some day he was destined to bring Russia out of the slough and chaos of Communism," wrote Norman Thwaites. "He believed that he would do for Russia what Napoleon did for France."

Reilly had long identified himself with Napoleon. It was an alarming comparison in one who was preoccupied with turning fantasy into reality. Such was his fascination with his historical hero that he amassed a large collection of memorabilia - a collection he would eventually sell for the considerable sum of $100,000.

Cumming had been fully briefed on Reilly's dubious background when he called him in for a meeting on 15 March 1918. His interviews with potential agents were usually cordial but perfunctory and there is no reason to doubt that his meeting with Reilly was any different. He must surely have asked him about his contacts in Russia and his political affiliations, but the content of their conversation remains unknown for Cumming recorded only a brief mention of their encounter in his diary. He found Reilly charming, yet he clearly had concerns. "Very clever," he wrote, "very doubtful - has been everywhere and done everything."

His resourcefulness was an important point in his favour: Reilly was exceptionally good at adapting himself to unfamiliar surroundings. Hector Bywater said that "the good intelligence man had to dig himself in and stick it, bearing loneliness and fear and excitement and triumph in complete silence."

Reilly fitted this mould so exactly that Cumming was prepared to turn a blind eye to Reilly's defects and send him into Russia, although he confessed that employing him was "a great gamble".

"He will take out £500 in notes and £750 in diamonds, which are at a premium," wrote Cumming in his diary.
The British government were playing with high stakes: Reilly was being given the modern equivalent of £50,000.

Ten days after his meeting with Mansfield Cumming, Reilly - now bearing the codename STl (the ST stood for the Stockholm bureau) - was en route to Bolshevik Russia. The plan was for him to enter the country at the port of Archangel and then make his way overland to Moscow, the new capital.

Cumming contacted his operatives in Vologda, 300 miles to the south of Archangel, and informed them of the imminent arrival of Reilly. "A Jewish-Jap type," was how he described him, "brown eyes very protruding, deeply lined sallow face, may be bearded, height five foot nine inches.".

Cumming added that he "carries code message of identification ... ask him what his business is and he will answer: "Diamond Buying." This bogus occupation was rendered more believable by the fact that he was carrying sixteen large diamonds.

Reilly was not travelling incognito on the first stage of his journey. Shortly before leaving London, he had been issued with an official business visa by Maxim Litvinoff, the Bolshevik government's sole representative in London. He was one of a small group of emigres who had remained in England after the two Russian revolutions of 1917. Now, he found himself playing a role similar to that of Robert Bruce Lockhart.

Litvinoff was wholly ignorant of the fact that Reilly was being sent to Russia as a spy. Nor did he know that Reilly detested Lenin's new regime. He took Reilly at face value and believed his claim to be a bona fide businessman who was keen to serve the new Bolshevik government.

Reilly's independent spirit got the better of him before he even arrived at his destination. Instead of disembarking at Archangel, as Cumming had requested, he left the ship at Murmansk. He may have done this because he knew there was a direct train to Petrograd, but it meant that he immediately drew attention to himself. The port was being guarded by a small team of British marines who had been sent to prevent the stockpile of Allied munitions from falling into German hands. These marines promptly arrested Reilly and locked him up in HMS Glory until they had completed their investigations.

It was fortunate that another of Cumming's operatives, Stephen Alley, happened to be in Murmansk at the time. The soldiers summoned Alley on board and asked for his opinion of this strange new arrival. "His passport was very doubtful and his name was spelt REILLI," wrote Alley. "This, together with the fact that he was obviously not an Irishman, caused his arrest."

But Reilly was able to provide proof of his status. He uncorked a bottle of medicine and produced a minuscule message written in code. Alley immediately recognised it as a code of the Secret Intelligence Service and Reilly was released. He was free to continue his onward journey.

Alley himself was travelling in the other direction, returning to London under something of a cloud. He had been fired by Cumming for reasons that remain obscure: Alley would later make the sensational claim that he had been sacked for failing to carry out an order to assassinate Joseph Stalin, already a member of Lenin's inner circle.

"I didn't always obey orders," he admitted. "Once I was asked to rub out Stalin. Never did like the chap much ... [but] the idea of walking into his office and killing him offended me."

Reilly was supposed to head directly to Moscow. Instead, he took the train to Petrograd in order to make contact with a number of old friends who might prove of use to him. He had not visited the city since 1915 and found that much had changed. War and revolution had left deep scars on the population and an air of decay hung like a stinking pall over the city's imperial boulevards.

"The streets were dirty, reeking, squalid. Houses here and there lay in ruins. No attempt was made to clean the streets, which were strewn with litter and garbage."

When Reilly had visited three years previously, queues for bread had been a fact of daily life. "Now... the bread queues were still there, but there was no food at all."

More alarming was the presence of the newly founded Cheka, whose officers seemed to lurk on every street corner.

"There was no police except for the secret police," wrote Reilly, "which held the country in thrall." It was testimony to Dzerzhinsky's efficiency as head of the Cheka that it was already a malign presence in everyone's lives, despite having been established just three months earlier.

Reilly took care not to draw attention to himself, for the last thing he wanted was to make his presence known to Lenin's secret police. He made his way to the house of an old friend, Yelena Boyuzhovskaya, hoping that he was not yet being tracked. He confessed to being in a`cold bath of perspiration' when he finally reached her apartment.

"Watching that I was not observed, I slipped into the house. It might have been a necropolis I entered, and my footfall awoke a thousand echoes". He was delighted to find Yelena at home; she gave him a friendly welcome.

Reilly had equipped himself for many different eventualities during his time in Russia. He had entered the country on a genuine passport and intended to remain as Sidney Reilly for as long as was possible. But he was also prepared to change his identity and live in disguise if and when that became necessary.

He began perfecting several different personas while staying at Yelena's apartment. He was to have two principal identities, one for Moscow and one for Petrograd. In Petrograd, he would pose as a Levantine merchant named Konstantine Markovich Massino. The Massino name was adopted from his second wife, Nadine: it perfectly suited the polyglot merchant he was pretending to be.

He was so proud of this Massino disguise that he had himself photographed for posterity. With his luxuriant beard and oil-slicked hair he looked the picture of a prosperous Levantine entrepreneur.

(3) Richard Deacon, Spyclopaedia (1987)

At the age of nineteen he discovered that he was not his father's son at all, but the product of an illicit union between his mother and a Jewish doctor from Vienna. It is not surprising, therefore, that Reilly told different stories about his origins, even to people who thought they knew him well. Many years later, when having his passport endorsed while working for the British, he was asked, "How comes it, Mr Reilly, that you yourself admitted several times you were born in Odessa?" "There was a war and I came over to fight for England," replied Reilly. "I had to have a British passport and therefore a British birthplace, and you see, from Odessa, it's a long, long way to Tipperary!"

After discovering his true identity Reilly left his family and stowed away on a British ship bound for South America. There followed a variety of jobs as docker, road-mender and plantation worker, but finally he became cook to a British expeditionary party in Brazil, led by Major Fothergill of the British Secret Service. From about 1896 onwards, he was firmly involved in international espionage. At first he was no more than a freelance agent for the British, but shortly before the Russo-Japanese War he turned up in the Far East as a double-agent serving both the British and the Japanese. Suddenly he went off to China and lived in a lamasery for several months, allegedly becoming a Buddhist. Then he returned to Russia and, while still working for the British, is alleged to have started spying for the Tsarist regime. He was certainly being well paid as in 1906 he had a lavish apartment in St Petersburg, a splendid art collection and was a member of the most exclusive club in the city. At this time, of course, Britain and Russia were allies so that this did not mean that he was double-crossing the British. But he had almost certainly double-crossed the Japanese to whom he had previously sold information about Russia.

Reilly frequently acted on his own initiative. For example, when working as a welder in Krupp's arms factory in Germany before World War I, he not only stole plans of the factory, but killed two watchmen in making his getaway. Then he got the job as sole agent in Russia for a firm of German naval ship-builders. By this means he managed to see and copy all blueprints and specifications of the latest German naval construction. These he passed back to Britain.

(4) Sidney Reilly, letter to Robert Bruce Lockhart (December, 1918)

I told "C" (and I am anxious that you should know it too) that I consider that there is a very earnest obligation upon me to continue to serve - if my services can be made use of in the question of Russia and Bolshevism. I feel that I have no right to go back to the making of dollars until I have discharged my obligations. I also venture to think that the state should not lose my services. I would devote the rest of my wicked life to this kind of work. "C" promised to see the F.O. about all this.

I need not enlarge upon my motives to you; I am sure you will understand them and if you can do something I should feel grateful. I should like nothing better than to serve under you.

I don't believe that the Russians can do anything against the Bolsheviks without our most active support. The salvation of Russia has become a most sacred duty which we owe to the untold thousands of Russian men and women who have sacrificed their lives because they trusted in the promise of our support.

(5) Max Egremont, Under Two Flags (1997)

Boris Savinkov introduced Spears to the spy Sidney Reilly. Born Rosenblum of Jewish ancestry in Odessa, Reilly had worked as a businessman in St Petersburg. After the revolution, he showed courage on behalf of his British paymasters even if some of his ideas were impractical; one of these was to debag Lenin and Trotsky and parade the humiliated pair through the streets. Reilly worshipped Napoleon and was both intensely secretive and wildly boastful. He had been with Denikin's forces in south Russia and, when Spears first met him, supported Savinkov, Spears became cautious about believing a man who claimed to have been attached to the German staff during the war...

Sidney Reilly was a difficult associate. Spears now had an office in London which the spy used when he was there; in October the telephone was cut off because Reilly had not paid the bill, there were exorbitant claims for expenses and the spy was rude when these were challenged. "I won't stand cheek," Spears said. He warned Reilly of "the danger of dealing with shady people & mixing politics with business". Reilly had damaged his position in Prague by identifying himself with Savinkov, "who is now out of favour there". The disadvantage of the spy, he decided, was the company he kept: "he is not careful enough."

(6) Giles Milton, Russian Roulette: How British Spies Thwarted Lenin's Global Plot (2013)

Reilly marched up to the Kremlin gates in full dress uniform and informed the sentries that he was the personal emissary of Prime Minister David Lloyd George. He demanded to see Lenin.

It must have been a convincing act, for he was immediately granted entry and taken to meet one of Lenin's senior aides. However, no sooner was he inside the building than the Bolshevik officials manning the gates immediately began investigating the identity of this uninvited emissary.

Reilly's presence in Moscow was as yet unknown to the skeleton staff of the British Embassy. Robert Bruce Lockhart was taken by surprise when, at six o'clock that evening, he received a telephone call from Lev Karakhan, the Deputy Commissar for Foreign Affairs.

The commissar had an extraordinary story to recount. "That afternoon," he told Lockhart, "a British officer had walked boldly up to the Kremlin gate and had demanded to see Lenin."

Karakhan provided Lockhart with a few more details before asking if the man was an impostor. Lockhart was as perplexed as the commissar and asked to know more. He was told that the man's name "was Relli".

This meant nothing to Lockhart. "I nearly blurted out that he must be a Russian masquerading as an Englishman, or else a madman."

But he knew that Mansfield Cumming was intending to send new agents into Russia and he chose to bite his tongue. "Bitter experience ... had taught me to be prepared for almost any surprise and, without betraying my amazement, I told Karachin (sic) that I would inquire into the matter."

There was only one man who could tell him more. Ernest Boyce was now working as Cumming's principal agent in Moscow and he was also the link man with the main Stockholm bureau. Lockhart was sure that he would know the identity of this mystery individual.

Boyce was nonplussed when Lockhart recounted the story of Reilly's visit to the Kremlin. He calmly replied that, "the man was a new agent, who had just come out from England."

Lockhart was furious that he had not been pre-warned and "blew up in a storm of indignation." He insisted that Reilly come to the embassy on the following day in order to explain himself.

Reilly agreed to meet with Lockhart but made no apologies for his actions. Indeed, he expressed his surprise that Lockhart was so angry. "The sheer audacity of the man took my breath away... "fumed Lockhart, "although he was years older than me, I dressed him down like a schoolmaster and threatened to have him sent home."

Reilly, who was forty-five years of age, was amused to be ticked off by a man fourteen years his junior. He had already warmed to Lockhart and now used his natural charm to placate him. "He took his wigging humbly but calmly and was so ingenious in his excuses that in the end he made me laugh."

Lockhart was, by his own admission, captivated by the human chameleon seated opposite him. Reilly was the person he secretly wished to be. "The man who had thrust himself so dramatically into my life was Sidney Reilly, the mystery man of the British secret service," he would later write in his memoirs, "and known today to the outside world as the master spy of Britain." Reilly's methods, he said, "were on a grand scale which compelled my imagination."

Reilly returned to the Kremlin two days later, this time with his friend Grammatikov in tow. He was granted an audience with General Mikhail Bonch-Bruevich, Director of the Bolshevik's Supreme Military Council and "the brain centre of the entire Bolshevik organisation."

Reilly was at his loquacious best. He painted himself as a Bolshevik sympathiser, telling the general that he was "very interested in Bolshevism, the triumph of which had brought me back to Russia."

This was "quite true", noted Reilly in his memoirs; although he had obviously not come back to celebrate the triumph.
Reilly was anxious to discover two key pieces of information from the general. First, he wanted to know the state of relations between Germany and Russia now that the two countries were no longer at war. Secondly, he wanted to know if there were any divisions in the Bolshevik leadership.

He soon discovered that the leadership was split from top to bottom on the very issue of peace with Germany. The general himself was furious with the concessions that his fellow Bolsheviks had made to the German high command. Dropping his guard, he confessed to Reilly his fears that the Foreign Commissar, Georgy Chicherin, had been "bought by the Germans."

Reilly had been accorded a private glimpse into the rival factions that already existed in the new regime. One of his aims was to push Russia back to war. He now knew that this was not a forlorn hope: several senior Bolshevik commissars wanted to do the same.

Over the weeks to come, Reilly went out of his way to court the general. He quickly saw the benefit of cultivating contacts within the regime, commissars who could provide access to Lenin's inner circle.

"Nobody could be more officious on our behalf than Bruevich," wrote Reilly. He even supplied Reilly with a pass that enabled him to attend a meeting of the Soviets in the Grand Theatre.

Reilly sent a series of reports to Mansfield Cumming detailing the strengths and weaknesses of the Bolshevik leadership.

He admitted that their seizure of power was almost complete and that they were the "only real power in Russia". Yet he also revealed that the political opposition was growing in strength. "If properly supported," he wrote, "it will finally lead to the overthrow of the Bolsheviks."

Reilly proposed a twin-pronged strategy for dealing with Russia. The most immediate objective was to safeguard the stockpiles of Allied weaponry in the ports in Northern Russia. This would necessitate the landing of significant numbers of British troops, something that could only be done with the co-operation of the Bolsheviks.

At the same time, Reilly recommended funding the opposition movement with the long-term aim of toppling Lenin's government. "It may mean an expenditure of possibly one million pounds," he told Cumming, "and part of this may have to be expended without any real guarantee of ultimate success."

Reilly never received the one million pounds. It was far too much money for a country still at war. But his advice about safeguarding the Allied weaponry in the White Sea ports certainly struck a chord. There was a growing feeling in Whitehall that military intervention might be the only way of preventing the revolutionary government from playing fast and loose with the stockpile of munitions.

(7) Giles Milton, Russian Roulette: How British Spies Thwarted Lenin's Global Plot (2013)

The stage was set for a dramatic power struggle, one which was witnessed by three key people: Arthur Ransome, Robert Bruce Lockhart and Sidney Reilly. All of them were present at a raucous political forum that took place at Moscow's Bolshoi Theatre on 4 July 1918.

The Fifth Congress of the Soviets was intended to provide a platform for political debate, but it presented Lenin with a serious problem. A third of the elected delegates were not Bolsheviks: rather, they were Lenin's political rivals - Socialist Revolutionaries - who stood in total opposition to peace with Germany. Now, they saw their chance to attack Lenin in public.

Robert Bruce Lockhart had been granted permission to attend the Congress as an observer. He arrived early at the theatre and was alarmed to notice that `every entrance, every corridor, is guarded by troops of Lettish [Latvian] soldiers, armed to the teeth with rifle, pistol and hand-grenade.' These troops were mercenaries, paid by the Bolsheviks to protect them from potential troublemakers.

The initial assault on Lenin was led by the leader of the Social Revolutionary party, Maria Spiridonova. With her neatly coiffed hair and pince-nez, she looked like a prim schoolmistress. But she was a schoolmistress with a ruthless streak. She denounced Lenin in a torrent of invective, accusing him of using the peasantry for his own political ends.
She then swung her gaze around to the peasant delegates in the theatre and harangued them for allowing themselves to be used as political pawns. "In Lenin's philosophy," she shouted in her high, shrill voice, "you are only dung - only manure."

Her speech provoked wild applause from the auditorium. "Pandemonium ensues," wrote Lockhart. "Brawny peasants stand up in their seats and shake their fists at the Bolsheviks. Trotsky pushes himself forward and tries to speak. He is howled down and his face blenches with impotent rage."

Arthur Ransome had joined Lockhart in the theatre and was equally impressed by the spectacle unfolding before him. He described Spiridonova as "looking like a nursery governess rapt into uncontrollable frenzy" and he listened enraptured as she "poured out a rhythmic, screaming denunciation of the Brest-Litovsk treaty."

Lenin sniffed at the danger: he faced the real risk of losing the support of the crowd. If so, the entire future of his revolution stood in jeopardy. Aware that only his oratory could pacify the rabble, he rose to his feet and delivered a highly skilful response that cast a spell over Spiridonova's supporters. Not for the first time, Ransome and Lockhart were witness to Lenin's hypnotic charm. Like a magician, he was able to transfix the crowd that had been baying for his blood just moments before.

"Gradually," wrote Lockhart, "the sheer personality of the man and the overwhelming superiority of his dialectics conquer his audience, who listen spell-bound until the speech ends in a wild outburst of cheering."

Lockhart knew that he was witness to an unequal political battle. He also knew that the final showdown between these political enemies was certain to have dramatic consequences.

(8) Desmond Morton, memo to Bertie Maw (31st January, 1922)

Reilly is not a member of our office and does not serve C (Mansfield Cumming) in that he is not receiving any pay from us. He worked at one time during the war in Russia for C's organisation and is now undoubtedly of a certain use to us. We do not altogether know what to make of him. There is no doubt that Reilly is a political intriguer of no mean class, and therefore it is infinitely better for us to keep in with him, whereby he tells us a great deal of what he is doing, than to quarrel with him when we should hear nothing of his activities... he is at the moment Boris Savinkoff's right hand man. In fact, some people might almost say he is Boris Savinkoff. As such he has undoubted importance. In addition to the above, Reilly is of course a very clever man, indeed with means of finding out information all over the world. Whatever may be Reilly's faults, I personally would stake my reputation that he is not anti-British, at the moment at any rate, and never has been. He is an astute commercial man out for himself, and really genuinely hates the Bolsheviks. That is about all one can say of him.

(9) Sidney Reilly, letter to Ernest Boyce (March 1925)

Much as I am concerned about my own personal affairs which, as you know, are in a hellish state. I am, at any moment, if I see the right people and prospects of real action, prepared to chuck everything else and devote myself entirely to the Syndicate's interests. I was fifty-one yesterday and I want to do something worthwhile, while I can.

(10) Sidney Reilly, letter to Felix Dzerzhinsky (October, 1925)

After prolonged deliberation, I express willingness to give you complete and open acknowledgement and information on matters of interest to the OGPU concerning the organization and personnel of the British Intelligence Service and, so far as I know it, similar information on American Intelligence and likewise about Russian emigres with whom I have had business.