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."
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. 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.
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." George Alexander Hill, another agent based in Petrograd, also believed Berzin was telling the truth and 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."
Sidney Reilly and Ernest Boyce were brought into the conspiracy. Over the next week Hill, Reilly and Boyce were having regular meetings with Berzin, where they planned the overthrow of the Bolsheviks. During this period they handed over 1,200,000 rubles. Some of this money came from the American and French governments. Unknown to MI6 this money was immediately handed over to Felix Dzerzhinsky. 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 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."
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."
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?"
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.
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."