Sidney Reilly: Master Spy 
by Benny Morris.
Yale, 190 pp., £16.99, January, 978 0 300 24826 5
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On​ 7 May 1918, a man in Royal Flying Corps uniform presented himself at the gates of the Kremlin, claiming to be the personal emissary of the British prime minister, David Lloyd George, and demanding an audience with Lenin. He was persuasive enough to be let in and managed to talk his way as far as the chairman’s secretary, if not all the way to Lenin himself. Wary Bolshevik officials summoned the newly appointed British envoy in Moscow, R.H. Bruce Lockhart, to check the alleged emissary’s story. Lockhart had never heard of the man the Russians referred to as ‘Relli’, but he asked Ernest Boyce, Britain’s spy chief in Moscow, who told him that Sidney Reilly had been recently recruited by the Secret Intelligence Service. Lockhart and Reilly met soon afterwards, and Lockhart later described the encounter in his memoirs: ‘Although he was years older than me, I dressed him down like a schoolmaster and threatened to have him sent home. He took his wigging humbly but calmly and was so ingenious in his excuses that in the end he made me laugh.’

Sidney Reilly, the British spy who could charm almost anyone and talk his way out of (or into) almost anything, was born sometime in the early 1870s, probably in southern Ukraine (either Odesa or Kherson), probably with the name Sigmund Rosenblum. Benny Morris – whose excellent short biography of Reilly is part of Yale’s Jewish Lives series – is careful not to claim as fact anything about which there’s any doubt, and there’s a lot that’s doubtful in Reilly’s life. ‘Tracing the life of a spy is always difficult,’ Morris writes. ‘He operates in the shadows and most of what he does may never be consigned to paper.’ It doesn’t help that much of what has been consigned to paper was invented, by Reilly or others. But Morris is a scrupulous guide.

By the time he was in his teens, Sigmund (or Shlomo or Salomon or Georgi) was living in Odesa with his mother and one of his sisters, his parents having separated. (He seems to have had reason to believe that his mother’s husband wasn’t his biological father.) They spoke German and Polish at home, rather than Yiddish, and he went to a Russian-speaking school. He also learned English and French. He later claimed to have studied maths and physics at Odesa University, though he also said he studied chemistry in Vienna, and there’s no record of his having done either. It does seem certain that in 1893 he was arrested by the tsarist secret police, the Okhrana, on suspicion of belonging to a left-wing student organisation (if the suspicions were justified, it was Reilly’s only flirtation with socialism). He spent no longer than a week in prison, though it was solitary confinement in a windowless cell, and his mother died while he was inside. At her funeral one of his uncles, or so he later claimed, called him a ‘dirty little Jewish bastard’, and with no reason to stay in Odesa and every reason to leave, he set sail – possibly – for South America. Again, that was his story; no other records have been found that either confirm or disprove it.

In December 1895 he reappeared in Paris, where ‘he probably made some money by serving as an informant for the Okhrana.’ On Christmas Day, two anarchist couriers were robbed and murdered on a train to Fontainebleau. One of their assailants was said to have looked like Rosenblum. A few days later he was in London, with plenty of money to splash around. He took rooms in Lambeth, refreshed his wardrobe and found work as an art dealer with Wilfrid Voynich, a one-time Polish-Lithuanian revolutionary who had escaped from Siberia in 1890. Voynich would later open an antiquarian bookshop in Soho Square, and in 1912 acquired the mysterious, indecipherable 15th-century manuscript that now bears his name.* In 1902 Voynich married the novelist Ethel Boole (daughter of the mathematician and logician George Boole), but they were already living together in 1895. ‘It is likely that Ethel and Reilly became lovers,’ Morris writes, and the hero of her novel The Gadfly (1897) may have been based on him.

His science degrees (real or concocted) came in useful as he joined the Institute of Chemistry and got a job with the Electric Ozone Company. He set up a couple of patent medicine businesses, flogging a range of ‘Tibetan remedies’ and various opium, cocaine or alcohol-based cure-alls. He was also still – or again – working for the Okhrana, who gave him the codename ‘Khimik’, and he soon took up with the British security services too. The head of Scotland Yard’s Special Branch, William Melville, worked closely with the Okhrana’s top man in Paris, Petr Ivanovich Rachkovsky, whose many state-sanctioned crimes probably included overseeing the creation of the Protocols of the Elders of Zion. Morris thinks Melville wasn’t to know about Rachkovsky’s sideline in antisemitic propaganda, though it isn’t clear it would have been a deal-breaker if he had. In any case, the British head of counter-espionage was more than happy to hire the services of Okhrana agents, and Reilly signed on with Melville in 1896.

Soon afterwards he met Margaret Thomas, the much younger Irish wife of a rich Welsh clergyman. Reverend Thomas died in March 1898, leaving his estate to his pregnant widow. In August that year, no longer pregnant, she married Sigmund Rosenblum at Holborn Register Office. The following summer, in part to escape an investigation by the Russian authorities into a gang of ruble counterfeiters he was involved with, he got a British passport in the name of Sidney Reilly and presumably left the country, disappearing from the record until he resurfaced five thousand miles to the east, at Port Arthur, in 1901. He got a job with a firm that supplied the Russian navy, while also (possibly, probably) keeping an eye on the tsar’s Pacific fleet for his spymasters in London. Margaret went with him but after a few months she returned to Europe alone, to a sanatorium in Belgium, to be treated for alcoholism. Reilly began a relationship with a woman called Anne (surname unknown, possibly a colleague). He left Port Arthur at the outbreak of the Russo-Japanese War in 1904. Anne may have gone with him (they may even have got married) but she soon drops out of view and he’s making his peripatetic, priapic way back to Paris, via Shanghai, Manila and Rio de Janeiro, with an American woman called Irene Dawson – or so her husband complained when he filed for divorce a few years later.

From Paris – where he boasted that he’d played a key role in securing a British claim to oil exploration concessions in Persia – Reilly went to St Petersburg, arriving in October 1905, soon after the end of the Russo-Japanese War. Morris writes that ‘the Revolution of 1905 … was winding down’ and the tsar ‘reasserting control’, though there’s more than a flicker of hindsight to that view: the thousands of workers who took to the streets of Moscow in December didn’t think it was over. Still, Reilly doesn’t seem to have been involved with the revolution on either side, and Morris’s story jumps ahead four years to 1909, when Reilly got into the business of importing French aircraft to Russia. He also worked as a middleman for a German shipbuilding company in its dealings with the tsarist government, while ‘no doubt’ keeping London informed of Russia’s arrangements. His love life didn’t get any less complicated, either: he began an affair with Nadine Petrovna, whose husband was a staff officer at the Ministry of the Navy. Meanwhile, Margaret – who briefly joined Reilly in St Petersburg, ‘against his wishes’ – refused to divorce him.

Reilly and Petrovna were on holiday in the South of France when Gavrilo Princip assassinated Archduke Franz Ferdinand in Sarajevo. On hearing the news, ‘Reilly immediately understood the business implications and rushed off to St Petersburg,’ Morris writes, ‘leaving Nadine literally stranded on the beach.’ When war broke out two months later, he went to America – by way of Vladivostok and Japan – with a commission from the Russian military to buy arms. He set up shop in New York, with an office on Broadway, arranging deals between US armaments firms and the Russian government while skimming off a generous commission for himself. By 1917 he had made more than $2 million (the equivalent of at least ten times as much today), though he seems to have spent the money as fast as he accumulated it. Petrovna joined him in February 1915. She didn’t have a visa and Reilly was in danger of being prosecuted under the Mann Act on suspicion of white slavery, but the police agreed not to charge him if they got married. The marriage seems to have been largely one of (in)convenience: Reilly had a ‘string of affairs’ with a series of dancers and actresses.

Morris’s principal source for Reilly’s escapades in New York during the First World War, including his sexual relationships, are papers in the archive of the US Bureau of Investigation, which suspected him of being a German spy and in September 1918 raided his offices but didn’t find any incriminating evidence. ‘The bureau’s investigation,’ Morris writes, ‘was overlaid with a clear patina of antisemitism.’ Reilly probably continued to supply information to the British intelligence services but otherwise any skulduggery he got up to in New York was directed at thwarting his competitors in the arms trade. German agents were active in the United States as saboteurs, destroying factories and warehouses where weapons and ammunition were being manufactured or stored for shipping to Europe. Following a blast on the night of 29 July 1916, ‘shells flew through the air, windows shattered throughout lower Manhattan, burglar alarms went off, water mains burst, telephone lines went dead and Brooklyn Bridge swayed … The various explosions apparently cost Reilly a number of serious commissions.’

Within days of the February Revolution breaking out in Russia, Reilly went to Toronto to enlist in the Royal Flying Corps and in August 1917 arrived in Arkhangelsk. Two months later he went to an aviation conference in Petrograd where he met a British SIS officer, George Hill. After the October Revolution the pair of them wasted no time in ‘cultivating and corrupting’ Bolshevik officials, or trying to. Early in 1918 Reilly went to London to apply for a job with the SIS. He was vetted by MI5, who reported that he had been born in Ireland and ‘spent much of his time dining or taking coffee at the Savoy and the Ritz’. SIS officers in New York told their London colleagues that Reilly was ‘a shrewd businessman of undoubted ability but without patriotism or principles’. They supported his recruitment. He went to see the head of the service, Sir Mansfield Cumming (aka ‘C’), on 15 March. Less than two months later he was knocking on the door of the Kremlin, asking for Lenin.

Until this point Reilly seems to have been motivated less by loyalty to any particular country, ideology or person than by a promiscuous combination of money, sex, thrill-seeking and a strong survival instinct. He doesn’t appear to have borne grudges: his early imprisonment by the Okhrana didn’t prevent him from later working for them; it’s possible they recruited him while they had him locked up in Odesa. After the Russian Revolution, however, and especially after the Treaty of Brest-Litovsk in March 1918 brought Russia out of the war against Germany, he committed himself wholeheartedly – recklessly, quixotically – to the anti-Bolshevik cause. Soon after Reilly’s ineffectual ‘dressing-down’ by Lockhart for his shenanigans at the Kremlin, the two men became co-conspirators in a scheme to bring down the Bolshevik government.

Opinions differ as to which of them – if either – was the more responsible for their joint plan. Morris refers to it as ‘the Reilly Plot’ or ‘the Reilly-Lockhart operation’; it’s also known as ‘the Ambassadors’ Plot’ or ‘the Lockhart Plot’. Reilly is a secondary character in Jonathan Schneer’s The Lockhart Plot; Neal Ascherson, reviewing the book in the LRB (5 November 2020), describes him as an ‘ungraspable rogue’. Schneer gives a detailed account of the plot and its failure. In brief, it turned on subverting the regiments of Latvian soldiers who were responsible for guarding key sites in Petrograd and Moscow. Reilly handed over hundreds of thousands of rubles (supplied by the British, American and French governments) to the apparently disaffected Latvian officers he thought he’d recruited who in fact turned out to be Cheka agents. In August 1918 Lockhart was among the thousands of suspected enemies of the state swept up in the crackdown that initiated the Red Terror. In his diary he described the Lubyanka as ‘very wet and beastly’. He was released in October and returned to London. Reilly, meanwhile, sentenced to death in absentia by a Russian court, had slipped away. He evaded arrest for weeks and eventually escaped to Helsinki by tugboat, more convinced than ever that the ‘salvation of Russia’ from the Bolsheviks, as he wrote to Lockhart, was a ‘most sacred duty’.

In December 1918 Reilly and Hill got themselves sent by the SIS to the northern Black Sea coast. It took them two weeks to travel from London to Odesa via Paris, Marseille, Malta, Istanbul and Sevastopol. ‘The situation in southern Russia in December 1918,’ Morris writes, ‘was infinitely complicated … Following the defeat of the Central Powers, most of Ukraine was loosely (though only for a few months) held by local Ukrainian nationalist forces, with the south-eastern corner occupied by White Russians or foreign troops (French, British and Greek).’ Reilly wrote to London from Odesa urging support for General Denikin’s White Russian forces. He didn’t let on to anyone that he had once lived in the city, though he may have ‘displayed a moment of weakness’ in front of Hill ‘when he halted by a house he recognised from his childhood’. The British consul general in Odesa, Picton Bagge, observed that Reilly ‘gets on extremely well with the Russians’, but doesn’t seem to have suspected that he was anything but an ‘Irish-born British officer’, certainly not an Odesan-born Jew: Bagge’s dispatches ‘occasionally slid into antisemitic gossip’ but he had nothing but praise for Reilly. Reilly, in turn, doesn’t seem to have been much troubled by Denikin’s antisemitism, or by the anti-Jewish pogroms carried out by the White Russian troops under Denikin’s command. Or rather, if he was, he didn’t convey his concerns to the SIS or the Foreign Office.

Hill and Reilly left Odesa in March 1919: ‘May I respectfully suggest that I be ordered to return home as my further stay here is a waste of time.’ They joined the British delegation at the Paris Peace Conference, under orders from the SIS to ‘hold [them]selves in readiness to give expert information’ on southern Russia and more generally to ‘observe what was happening’. Morris suggests that Reilly ‘spent most of his time … in nightclubs and cabarets, or gambling’. His only contribution to the conference that has left any trace in the record was the undermining of American efforts to involve the Soviets in the treaty negotiations.

Reilly’s​ last mission for the SIS was to Warsaw in the autumn of 1920, as the Polish-Soviet War was coming to an end. He made contact there with Boris Savinkov, who had been a minister in Kerensky’s provisional government for a couple of months in 1917 and then an inveterate plotter of failed attempts against the Bolsheviks, with a hand in the Reilly-Lockhart operation in 1918. Reilly considered Savinkov ‘the only man outside of Russia worth talking to and worth supporting’, but the FO thought him ‘unreliable and crooked’. British foreign policy was shifting towards rapprochement with the Soviets, and Reilly’s implacable anti-Bolshevism was one reason the SIS decided to let him go, though Morris suggests that establishment antisemitism also played a part, and Britain was in any case reducing its spying operations across Europe in the years after the war.

Released from his obligations to the British government, Reilly went freelance, with a series of unsuccessful money-making schemes (tobacco, radium, patent medicines again), a new wife (the actress Pepita Bobadilla, born Nelly Louise Burton) and a renewed commitment to helping Savinkov overthrow the Russian government. They got involved with the Monarchist Union of Central Russia, aka the Trust, a false flag operation set up by the Cheka, who persuaded Savinkov to return to Russia. He was arrested near Minsk on 20 August 1924 and put on trial a week later, his death sentence commuted after he announced in court that ‘I unconditionally recognise Soviet power and none besides.’ Reilly was horrified, but all the more determined to continue the struggle.

Savinkov’s arrest apparently didn’t lead Reilly to wonder if the Trust might not after all be the anti-Bolshevik outfit it claimed to be. In the autumn of 1925 – with the unofficial encouragement of Ernest Boyce, now stationed in Helsinki – he met with Trust agents in the Finnish capital, who pressed him to go to Russia to meet their superiors. He wrote his last letter to Pepita from Finland on 25 September: ‘It is absolutely necessary that I should go for three days to St Petersburg and Moscow … I would not have undertaken this trip unless it was absolutely essential, and if I was not convinced that there is practically no risk attached to it.’ It was the same trap they had laid for Savinkov, and Reilly fell right into it. He was arrested in Moscow and taken to the Lubyanka. When he didn’t reappear, Pepita travelled to Helsinki in search of news, to be told by a Trust operative that he had been shot by Soviet soldiers on the Finnish border on 28 September. She repeated the story to the Times, which reported his death in its edition of 15 December. In fact he had spent the month of October being interrogated by the OGPU, the successor to the Cheka. According to some accounts he flipped and became a Soviet spy, perhaps even working for them – in total secrecy – until 1944. But there seems little reason not to believe the OGPU files, according to which Reilly was executed by counterintelligence agents in a park in Moscow on the evening of 5 November 1925.

Within months of leaving New York in 1917, Morris writes, ‘Reilly was to position himself on the very cusp of changing the course of history.’ But he didn’t: his first and subsequent attempts to overthrow the Bolsheviks all failed. And, as Morris concedes, ‘Reilly’s reporting from southern Russia had little effect on policy or history’ either. Ian Fleming once said that ‘James Bond is just a piece of nonsense I dreamed up. He’s not a Sidney Reilly, you know.’ But it’s just as true that Sidney Reilly wasn’t James Bond: in Fleming’s novels (and even more in the films based on them), 007’s individual actions make all the difference. Bond’s secret missions save the world, or at least preserve the status quo. Yet even on Morris’s Reilly-centred account, it isn’t clear that the course of early 20th-century history would have run any differently if Sidney Reilly had never existed, or if Sigmund Rosenblum had never left Odesa. To the extent that Reilly resembles a figure in a spy novel, he’s less like Fleming’s creation – his promiscuity and enjoyment of the high life aside – than one of Eric Ambler’s characters: occupying the murky hinterland between espionage, diplomacy and business; crossing and recrossing Europe’s borders even as they shifted under his feet, adopting a new name and a new nationality as he went; carried remorselessly along on the currents of history however hard he tried covertly to direct them.

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