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True Spies Episode 96: The Ace of Spies

Welcome to True Spies. Week by week, mission by mission you’ll hear the true stories behind the world’s greatest espionage operations. You’ll meet the people who navigate this secret world. What do they know? What are their secret skills? And what would you do in their position? This is True Spies Episode 96: The Ace of Spies.

NARRATOR: Question: how did one of the greatest spies of the 20th century survive and thrive for so long, in so many different conflict zones? Who was Britain’s Ace of Spies? 

SIDNEY REILLY: It’s addictive, the danger. I can’t deny it - the thrill of a checkpoint evaded, a husband bamboozled, an enemy deceived. It’s my weakness.

NARRATOR: Sidney Reilly is a legendary figure in espionage history, allegedly one of the real-life inspirations behind James Bond. One of several proto-Bonds we’ve profiled on True Spies, in fact. Reilly died nearly a century ago, and so the following is a recreation based on his memoirs and on several of his biographies. His words are spoken by an actor. Sidney was a master of deception and reinvention, so many details of his life are still disputed, even now. But a consensus has gradually emerged over much of his story. Including his role in the early days of Soviet Russia...

SIDNEY REILLY: That morning stays with me.

NARRATOR: 1918, a year after Russia’s communist revolution. Under Vladimir Lenin, the Bolshevik Party has taken over, promising to smash the power of the aristocracy and the bourgeoisie and end the oppression of the working class forever. On this morning, Reilly, a British agent, is in the small city of Klin, a few miles outside Moscow.

SIDNEY REILLY: I was on the platform at the railway station, just off the sleeper from Petrograd.

NARRATOR: Lenin’s hold on power at this time is far from certain, and so a ruthless crackdown is underway. Mass arrests, torture, summary executions. What the communists openly call their policy of 'Red Terror’.

SIDNEY REILLY: It was random, deliberately so. People knew that at any moment, they might disappear for any reason. And traveling between cities, using the railways, was, of course, an invitation to be scrutinized. I had just bought a copy of the Moscow papers from the kiosk and, as I suspected, they identified me as one of the most wanted men in Russia. Then I heard a commotion behind me. Down the platform, the crowds were parting. Over the heads of the families and factory workers, I could see the end of a long bayonet. A Bolshevik Commissar - or a political officer - and a Red Guard heading my way.

NARRATOR: The Soviet newspapers are filled with details of an anti-communist plot that Sidney is alleged to have masterminded. Further targets for Red Terror. 

SIDNEY REILLY: I put my hand in my coat and felt for my papers. Dug them out. So, to anyone reading those papers, I’m Comrade Relinsky, communist party member, and agent for the criminal investigation division of the Cheka.

NARRATOR: The Cheka - the feared secret police, the forerunner of the KGB.

SIDNEY REILLY: Always good to hide amongst the enemy. They were really good quality papers too, unlike some. The problem was that I wasn’t just Comrade Relinsky. Hidden in the lining of my suitcase were other papers identifying me by other names and other professions. A thorough search would be unwelcome.

NARRATOR: The blade of the bayonet is moving closer.

SIDNEY REILLY: Comrade Relinsky carried a weapon, obviously - all part of the look - so I reached for it. I have killed people when I’ve needed to, and sometimes when I haven’t. But only when the odds were in my favor. Here they were not. There was probably half the length of the platform to go before they reached me. I could already hear one poor fellow they’d grabbed. He was in tears, begging them to let him go. None of the passengers around me moved a muscle.

NARRATOR: Being seen to fear the Terror is as dangerous as opposing it.

SIDNEY REILLY: A decision was called for. I braced myself for action.

NARRATOR: Establishing when, and where Sidney Reilly was born has never been easy. For years biographers have disagreed about the simplest facts of his life. 

SIDNEY REILLY: People say I've been born in many places, many nations, and many faiths. According to some, I'm the son of Polish-Russian Jews from Ukraine. Or should that be the Russian gentry from St Petersburg? It's hard to keep track. The answer I prefer is that I'm simply Sidney Reilly from Tipperary - son of an Irish merchant seaman. Or an Irish clergyman. Or a landowner. What would you prefer today? 

NARRATOR: Recent research shows that he was most likely born [Salomon] Shlomo Rosenblum in the 1870s, in or near Odessa in modern Ukraine, to a middle-class Jewish family. Odessa was then one of the most cosmopolitan cities in Europe - which may explain Sidney's mastery of languages - equally at home in Russian, English, French, and German, and his ability to pass as different nationalities.

SIDNEY REILLY: People tell me this accent isn’t strictly Tipperary but I’ve been away from Clonmel for a long time.

NARRATOR: We do know for certain that he left Russia early in his adult life, possibly to study chemistry in Germany. Or possibly because he fell out with his mother after discovering he was the illegitimate son of the family doctor. Or possibly to escape the violent anti-Semitic pogroms of Tsarist Russia. 

SIDNEY REILLY: The point is that a man has a right to reinvent himself. And I had the experience of doing that, long before I became an agent of any government.

NARRATOR: By the 1890s, he is recorded as Sidney Rosenblum, a freelance chemist in London producing homemade medicines and selling miracle cures, trading under the reassuringly scientific-sounding name of the Ozone Preparation Company.

SIDNEY REILLY: I have a background in chemistry and, I’d say, a good bedside manner. You know, so much of medicine is about helping the patient to relax, to trust in the treatment, to trust in you.

NARRATOR: In 1898, one of Sidney’s patients died suddenly. The Reverend Hugh Thomas is in his 60s and suffering from inflamed kidneys, which Sidney had been treating with some of his own patented remedies. Sidney has become a close friend of the Thomas family over the years - both of the Reverend and his much younger Irish wife, Margaret.

SIDNEY REILLY: It was tragic. I did everything I could for him, tried every cure at my disposal. But even my unique preparations could only do so much.

NARRATOR: Strangely, only one week before his death, Reverend Thomas arranged for his will to be drastically rewritten, making Margaret one of his executors for the first time.

SIDNEY REILLY: After the death, Margaret wanted a quick funeral and I’m sure that’s what Reverend Thomas would have wanted too. I believe he was buried within three days. Heart failure - quite tragic and unexpected. 

NARRATOR: No autopsy or inquest was ever carried out into the death. No record of the medicines supplied by Sidney survives. Margaret, meanwhile, inherited her husband’s entire estate, including two houses in London. A few months later, Margaret and Sidney were married. They later moved into one of the Thomas family’s London homes.

SIDNEY REILLY: It’s so funny how grief can bring people together.

NARRATOR: Around this time, the first signs of Sidney Reilly’s talents as an undercover agent begin to appear. He becomes a paid informant of Scotland Yard Special Branch - the forerunner of the Secret Service led by spymaster William Melville. If Special Branch is aware of Sidney’s history with Margaret and the Reverend Thomas, there is no record to show they took any interest. Sidney’s first assignment? To keep tabs on groups of politically active Russians in the capital.

SIDNEY REILLY: Melville had concerns that unhelpful political activity was brewing among the Russian emigres. Special Branch needed someone who could enter that world. It was similar to being a freelance chemist in fact. You had to identify the client, convince them you were to be trusted, establish your name. Then listening. I was good at it.

NARRATOR: According to some accounts, it is thanks to his work for Special Branch that he is first able to apply for and get a British passport under the new name of Sidney Reilly, born in southern Ireland - then still part of Great Britain. Someone in the government appears to have had ambitions for him. 

SIDNEY REILLY: I later did work in Spain, Italy, the Caucasus. It was an interesting time, a constant struggle between the great European powers. London needed someone who could blend in a way other agents couldn’t. I was proud to serve King and country. And, yes, I needed the money.

NARRATOR: In London, Reilly takes on the habits of a true British gentleman.

SIDNEY REILLY: For gentlemen's tailoring I recommend J. Daniels & Co. of Pall Mall. There’s something about their way with a tweed.

NARRATOR: Sidney’s superiors certainly don’t see him as one of their own. The head of the Secret Intelligence Service privately described him as being of the ‘Jewish-Jap type’ with ‘brown eyes deeply protruding and a sallow face’.

SIDNEY REILLY: Well, whatever anyone thought, the Service needed good Russian speakers. I think my longest assignment was several years in the Russian Far East - the Tsar’s Naval base at Port Arthur, on the border with Korea. Fascinating place.

NARRATOR: Sidney’s precise role in the Russian Far East will probably now never be known exactly. Well, why would it? He was a spy. According to some accounts he worked for both Japanese and British intelligence in Port Arthur helping them come to grips with the growing might of the Russian Navy. He may even have facilitated a daring raid by Japanese warships on the Port itself. 

SIDNEY REILLY: It’s fair to say I left the Far East in a hurry.

NARRATOR: Reilly next appears in Paris in 1904. By this time he and Margaret are living apart. And here he is tasked by his handlers with a crucial mission.

SIDNEY REILLY: I received a telegram, telling me through the usual codes that I was wanted for an urgent interview at the embassy in the 8th Arrondissement. Melville - my handler - always enjoyed the theater of these meetings: “How are you, dear boy?” The glass of Port and so on. 

NARRATOR: Something has come up that has got Sidney’s bosses in London scared.

SIDNEY REILLY: His exact words were: “You see Sidney, it’s to do with the dreadnoughts.” At that time every warship in the world - give or take- ran on coal. Including His Majesty’s Royal Navy. But the way things were going, more and more were going to be powered by oil. It simply works better. And the great oil deposits of the world were regrettably, inconveniently, outside the confines of the British Empire. He told me: “We will have to go and get it ourselves, dear boy.”

NARRATOR: One of the great oil deposits is located in Persia - modern-day Iran. A businessman named William Knox D'Arcy has purchased the right to extract the oil from the cash-strapped Shah of Iran. And now D’Arcy is threatening to sell that right to the highest international bidder. Melville explains that D’Arcy is known to be discussing selling up to the Rothschild banking family, not to the British government. 

SIDNEY REILLY: So, would I be able to go and discover quite what the Rothschilds are offering Mr. D’Arcy, and what he is likely to need to be persuaded otherwise?

NARRATOR: It’s probably Reilly’s biggest assignment yet.

SIDNEY REILLY: I immediately took a train to the French Riviera where the Rothschilds were based. Very sensibly they had decided to conduct negotiations onboard their own very well-appointed yacht. No doubt to impress Mr. D’Arcy and to keep him away from prying eyes. I remember standing on the waterfront in Cannes watching that enormous yacht floating out in the harbor and thinking: “The future of the British Empire might be being decided on that thing at this very moment.” At moments such as this, I pride myself on a certain decisiveness. A very simple plan came to me.

NARRATOR: A day or two later, the Rothschilds receive a surprise visitor on board the yacht.

SIDNEY REILLY: I can tell you I’ve spent enough time amongst the very rich to know that they expect to be plagued by charitable requests but also that those requests are most successful when they appeal to their vanity as great men.

NARRATOR: The visitor is a priest fundraising for a local orphanage.

SIDNEY REILLY: Apparently there had been some confusion and the Reverend’s invitation to come onboard had been mislaid. But by then I was already in the middle of the harbor, in my little rowing boat, alongside their beautiful yacht. The staff was quite firm at first but when they saw the dog collar, the rosary, the literature about the little orphans a message was put through.

NARRATOR: And the response comes back, a reluctant ‘yes’, the priest may indeed come aboard and discreetly approach the guests after lunch.

SIDNEY REILLY: After I entered, I was careful not to go immediately to Mr. D’Arcy, although I spotted him easily enough across the drawing room. He was deep in conversation with one of the Rothschild lieutenants. I knew his face. I’d studied photos of them all.

NARRATOR: The challenge was now to detach D’Arcy from the rest of the group without causing undue suspicion. There would only be limited time to make contact. 

SIDNEY REILLY: I circled. I’m pleased to say the poor orphans brought out some surprisingly generous cash donations from the other guests. Eventually, I got tired of waiting. I broke into D’Arcy’s conversation quite firmly, and I asked whether he might spare a minute or two for the less fortunate. He seemed startled but let himself be led to one side. On the cover of the pamphlet I pushed into his hands there was a small note informing him that I was acting on behalf of His Majesty’s government and that London would be prepared to double whatever offer was being presented by the Rothschilds.

NARRATOR: If D’Arcy wanted to expose Reilly, this was his moment.

SIDNEY REILLY: To his credit, he took it very calmly. I asked whether he would care to meet me that evening to inspect the orphanage in person. He replied that he would find that intriguing. 

NARRATOR: In fact, Reilly was lying again. There was no guarantee from London to double the Rothschilds’ offer - particularly as it was impossible to say what that offer would eventually be.

SIDNEY REILLY: I had to let him down gently on that point when we met that evening in Cannes. Nevertheless, he agreed to hold off from signing any deal for 10 days to give us time to put together a counter-offer.

NARRATOR: Melville was impressed. Later that year, D’Arcy signed an agreement with a consortium organized by the British government giving Britain access to the oil fields. Oil was struck a few years later, a breakthrough that led to the creation of the Anglo-Persian Oil Company, later known as British Petroleum or BP.

SIDNEY REILLY: Most gratifying. I’m afraid the orphanage donations didn’t last long. I had a bad run at the casino in Nice a little while after.

NARRATOR: We’re back in Russia. Petrograd - or St Petersburg, 1918. Over a decade has passed since the D’Arcy affair on the yacht. This is the beginning of Reilly’s greatest mission. At the Moscow Grand Theater, Lenin takes the stage. The theater is packed.

SIDNEY REILLY: Whatever one thinks of the Bolsheviks - and I regard them, generally, as frankly the scum of the earth - I will say that they do have a sense of occasion. Behind Lenin’s lectern, there was a huge, crude, dramatic tableau showing the triumph of the Russian proletariat. All framed by flags, slogans, and red stars. Yes, they were right to hold this event in a theater.

NARRATOR: Reilly is at an event for Communist Party members and officials, a coming together of the Party to learn from the leadership.

SIDNEY REILLY: A contact had smuggled me in. This was around the time I started using papers identifying me as Comrade Relinsky, a member of the Cheka.

NARRATOR: You’ll remember Reilly’s ‘Comrade Relinsky’ disguise from the beginning of this episode. And I will say that it was also extraordinary to see Lenin up close. Very different from reading his words, yes. The inflections. The big sweeping arm gestures, the chin jutting forward. The sense of one man’s charisma just filling that theater. Almost inspirational. But also, quite mad. Every word of it. The early years of Lenin’s rule see the emergence of a fledging police state, arbitrary arrests, torture, disappearances. And it coincides with starvation and food shortages in every major Russian city.

SIDNEY REILLY: The contrast between Lenin's words to his followers, his promises of justice and progress, and the death and suffering on the streets just outside? Unspeakable. 

NARRATOR: Reilly is now a veteran agent, in his mid-40s, one of the more experienced in the British Secret Service. And he has been entrusted with a crucial mission. The Communist Revolution in Russia is less than a year old and London is deeply worried. Russia had been Britain’s military ally against Germany in World War One. But under Lenin, they have made peace with their old enemy. Reilly’s mission is to gather intelligence on the likelihood that Russia could be persuaded to rejoin the war against Germany.

SIDNEY REILLY: That was my original mission. But as I sat watching Lenin, I began to conceive of a very different, more ambitious plan. What if one day, something serious were to happen in a theater like this? Because gathered in front of me were not just the communist leadership but also their entire upper bureaucracy. What if the soldiers guarding the exits on my left and right were to turn on their new masters? And what if we were to smother the entire idea of communism, Bolshevism in its cot, once and for all? It had been a shock returning to Petersburg for the first time since the Revolution. Before the war, I remembered a glittering European city, bars, gentleman's clubs, theaters, and opera houses. Shops filled with food from across Europe. Now? All gone. Desperate shortages for all but the most senior party members. Even the long queues for bread that had appeared early in the war had vanished. There was nothing left to queue for. In much of the city, all running water had stopped. The stench in summer was overwhelming. And what grew alongside this deprivation was a sense of perpetual fear of the Red Guards, the commissars, and the Cheka. But most of all, fear of each other. Neighbor denouncing neighbor, friend denouncing friend. What if there were a way to end all that with a single blow?

NARRATOR: Reilly puts his plan for a coup to his contact at the British Embassy, a young embassy official called Bruce Lockhart. Reilly claims he is given a green light - although that will later be disputed by London. 

SIDNEY REILLY: It’s true the embassy wanted to be kept at arm's length but they nodded it through in principle.

NARRATOR: Reilly’s plan requires several elements - first, a strike force.

SIDNEY REILLY: Call it a spear point to take physical control. My sources suggested that the Bolshevik’s support amongst their own military was wavering, above all due to the food shortages. In fact, it seemed that only the Latvian regiments were still considered reliable. They had lost their homeland to Germany and so had nowhere to go if Lenin were to fall. I learned that Lenin and Trotsky’s personal bodyguards were always comprised solely of members of these regiments. But I suspected that even their loyalty to the Party might be undermined. I met Colonel Berzin, one of the three senior-most Latvian officers. He had a family to feed. And, with money from London, I was able to put him and his troops on our payroll.

NARRATOR: Second, intelligence from within the regime.

SIDNEY REILLY: By this point, cities like Petersburg and Moscow were being ruled mainly through fear. Now that is a medicine that only works in small doses. And the patient was beginning to reject the treatment. Many Russians were sick of communism. There were, of course, true believers, true Bolsheviks. But these tended to be opportunists - illiterate factory workers suddenly given a taste of power. Or a chambermaid who found herself living in her former employer’s apartment. To manage the country, the Leninists still needed the help of professionals, the old bourgeoisie. Some of my most useful sources swore loyalty to the Soviet Union but were secretly only too happy to risk everything to support our plans. An example? There was a charming young ballerina I had begun to get to know who also happened to share a flat with two young actresses. One of their brothers was the Bolshevik military chief of staff. A man who was also only too happy to betray the revolution. London received a stream of top-secret military documents as a result. Quite soon my network began to grow - dozens, hundreds, and eventually thousands of people who were pledged to the cause if we could first eliminate the Bolshevik leadership. 

NARRATOR: Of course, having this many people signed up for a subversive organization is, in itself, a risk.

SIDNEY REILLY: It never felt too difficult to turn these people - and that perhaps was the root of my own downfall. I operated the ‘five’ system. Each member of a cell would only ever know the names of four other counter-revolutionaries. Only I possessed the names and addresses of every member - and even I had not met them all. But I was quite aware that I was taking every one of their lives into my hands.

NARRATOR: And finally, a moment of vulnerability.

SIDNEY REILLY: In early August, the same young actress brought me some remarkable news. She had learned that Lenin and Trotsky would be addressing the Grand Committee of the Soviet Union in a few weeks’ time. And the venue would be the very same Grand Theater where I had first heard Lenin speak. The head and shoulders of Bolshevism gathered together in a single space, guarded by troops from the Latvian regiments. Irresistible.

NARRATOR: Lockhart at the British Embassy is aware of the plan. Reilly also moves to inform staff at the embassies of Britain’s allies - the US and France.

SIDNEY REILLY: There was an unfortunate incident there. As I was briefing the French consul on our plans we were interrupted - and I believe overheard - by a young French journalist, a gentleman who was known for his socialist sympathies. Had it been possible, I might have disposed of him myself. But his disappearance would only invite further attention.

NARRATOR: The plan for the attack is meticulous.

SIDNEY REILLY: Once Lenin and Trotsky were on the stage, I would signal to the Latvians to lock the doors and turn their rifles on the audience. Then with a group of riflemen alongside me, we would take the stage, and arrest Lenin, Trotsky, and the leaders of the Revolution in front of their followers. I was determined that violence would only be used if unavoidable - not for sentimental reasons. Violence creates martyrs. Instead, I had a rather original plan of my own. The entire leadership would be taken into custody and then marched through the streets of Moscow without their trousers. Yes - in their underwear. I wanted them… not dead, but a laughing stock. We would then invite anti-communist forces into Moscow to establish order. And if the Bolsheviks in the theater resisted? Well, I was prepared to die. Every member of our party would be carrying grenades. In a packed theater, the effect would be considerable.

NARRATOR: Six weeks before the meeting at the theater, something begins to change.

SIDNEY REILLY: I was in Petersburg traveling on foot between safe houses when I realized something unwelcome was happening. I was being followed. A tall fellow, not particularly good at his job. He fell for some of my simpler tricks - like double backing and suddenly crossing the street. Now being tailed is not itself unusual for a foreign national in Russia. But so soon before our event? It made me uneasy.

NARRATOR: A month before the event, one of Reilly’s safe houses in Petersburg is raided by the Cheka.

SIDNEY REILLY: Similar. None of our supporters were caught, and no incriminating documents were discovered. But it was concerning. 

NARRATOR: Then, three weeks before the attack, Reilly calls his trusted second in command, using a secret private phone line.

SIDNEY REILLY: I’ll never forget how his voice sounded. He spoke slowly - very slowly - and refused to acknowledge me when I introduced myself under a code name. Then, in Russian, he said this: “The doctors have operated too early. The patient’s condition is serious.” I reached his apartment soon after, taking care to observe it carefully from the outside before entering. When I arrived, he was frantically burning documents in the fireplace. He explained that, independent of us, a young anti-communist army officer had assassinated the head of the Petersburg Cheka. He was seeking revenge for the execution of his male lover, we discovered later. In response to that assassination, raids and mass arrests were spreading through all the major cities.

NARRATOR: What would you do if you were in Sidney’s position? Call off the theater attack? Use your embassy contacts to flee the country? Or stay and try to hold your network together long enough to have a shot at bringing down the regime?

SIDNEY REILLY: I didn’t consider running. Perhaps it was vanity but I had a vision of myself on that stage looking Lenin in the eye as I handcuffed him. 

NARRATOR: Reilly goes to ground, moving from safe house to safe house. 

SIDNEY REILLY: Always with my revolver by my side. Never staying more than a day in one place. I was often an unwelcome guest. Some well-meaning supporter who had agreed to join our network in easier times would receive a knock on the door - me.

NARRATOR: And the assassination attempts from other anti-regime groups continue. Lenin was severely injured in a pistol attack in August. The Cheka are ordered to implement the first Red Terror to stamp out any opposition.

SIDNEY REILLY: You could say our real mistake was to underestimate quite how many Russians wanted to shoot a Bolshevik at that time. Around then, I was walking through central Moscow in uniform as Comrade Relinsky, Cheka member, criminal division. All at once, I began to hear the sound of multiple motor cars. Now, only the Red Guards and the Cheka still retained access to petrol so the sound of any motor vehicle was greeted with concern by most people. They were driving at high speed toward the embassy district. And I followed. In front of the steps of the British Embassy, they had something like 10 bodies laid out on the pavement - all Red Guards or Cheka officers. Above them, the British Union Flag torn off its flagpole, the front door smashed off its hinges. Smoke rising from one of the windows. And, all around, cars of more Cheka officers driving in, guns drawn to provide reinforcements.

NARRATOR: As part of the Red Terror, soldiers and Chekists have stormed the British Embassy. A British naval intelligence officer had died trying to hold them back with his pistol, giving staff time to destroy documents. The gunbattle had been intense.

SIDNEY REILLY: Standing there, surrounded by the Cheka, I had to maintain my pose as a passionate Bolshevik. But inside, I recognized that this might be the end. With the embassy in ruins, I was cut off from any easy escape from Russia or even access to funds. And who knew what incriminating evidence might be found in that building by Lenin’s troops? The mission had to change to save what was left of our network. And, if I could, myself too.

NARRATOR: In fact, we now know the network was already deeply compromised. Colonel Berzin, the Latvian commander who had promised to support the coup, was a Cheka informant. And the French journalist who had overhead the plans had also spoken to the Cheka. A net was closing around Sidney. 

SIDNEY REILLY: It was a few weeks after that, that I found myself on the platform at Klin Station with a bayonet and a Bolshevik commissar coming towards me on the platform. The newspapers in my hand confirmed that I was now one of the Most Wanted men in Russia.

NARRATOR: The commissar is about 100 yards away now. Sidney is disguised as Comrade Relinsky, a Cheka officer. But will the illusion hold?

SIDNEY REILLY: My Cheka officer’s revolver was loaded in a holster under my coat. There were only two Bolsheviks approaching and I would have the benefit of surprise. But no. Instead, I took two steps smartly forward to the edge of the platform, and slipped down onto the tracks, under the waiting train. None of the passengers on the platform reacted. No doubt many envied me. I crouched down and I began moving beneath the carriages, getting as far I could away from the station concourse. To my surprise, I was far from the only one - here and there were little knots of other huddled figures. Each with their own reasons to avoid a conversation with a Commissar.

NARRATOR: It’s not the safest place of refuge. The train is due to depart for Moscow at some point soon. 

SIDNEY REILLY: I could, I suppose, have crossed to the opposite platform but then I would still have had to pass the checkpoint at the station exit. So, I began to move faster under the train. Eventually, I saw what I was looking for - a little patch of trees and undergrowth just past the end of the station platform. Timing is crucial in these situations. As the whistle blew, I made a leap and landed in the bushes. I didn’t wait to find out if I’d been seen. From there I scrambled through a fence, and I was away into the back alleys.

NARRATOR: Comrade Relinsky is no more.

SIDNEY REILLY: A swap of clothes, different papers in my jacket pocket and there. In his place, stood Mr. Constantine, a Greek-speaking businessman from the Levant, resident in Moscow, with a firmly supportive view of the Revolution. I hitched a ride on a farmer’s cart heading towards Moscow.

NARRATOR: Sidney escapes Russia a few months later, smuggled aboard a Dutch cargo ship. He is unable to save many of those he’d recruited from falling victim to the Terror. Many of the people who gave him shelter died at the hands of the Cheka. The ballerina and actresses in St Petersburg are among them. According to one account, eight different women questioned by the Cheka claimed to have been married to Sidney. The Soviet Union sentences Sidney Reilly and Bruce Lockhart - his British embassy contact - to death in absentia. If either entered Russian territory they could be shot on sight which makes the final chapter in this story all the stranger. Seven years later, in the mid-1920s, Sidney is contacted by Ernest Boyce, a former British intelligence service chief in Moscow.

SIDNEY REILLY: By then I was living in New York and had left the espionage game. I married again. It had become a habit. I was trying to make it in business but times were hard.

NARRATOR: The letter from Boyce is in thinly veiled code. It speaks of a group of ‘Californians’ who are keen to meet Sidney, and who bring news of a potential major business concern, which ‘may affect European markets. Would he be interested in becoming involved?

SIDNEY REILLY: ‘Californians’ was our term for Russians. And ‘business concern’ meant a political movement. 

NARRATOR: In other words: Would he like to meet a new group who were preparing to attempt to overthrow communism?

SIDNEY REILLY: They promised to bring a poem by Omar Khayyam to the meeting so that would have been another basis for a coded message. I was intrigued.

NARRATOR: The underground group calls itself ‘The Trust’ and they bring news of growing discontent across the Soviet Union. For the first time since Sidney’s network, a large number of powerful people are committed to ending the tyranny of the Communist Party.

SIDNEY REILLY: Of course, I was skeptical. I thought they weren’t to be trusted. It seemed too obvious a way for Moscow to bait its hook for me.

But the more I spoke to my old contacts and read their analysis the more intrigued I became. It reminded me so strongly of what we had built in 1918.

NARRATOR: The courtship by letter continues. The Trust suggests a face-to-face meeting at Vyborg in Finland, just across from the Russian border. Sidney buys a ticket back to Britain and then on to Finland. The meeting is set. 

SIDNEY REILLY: It was good to be back in the old world again. And to speak Russian again, and to hear it spoken. The Trust had even smuggled two of their operatives over the border to meet me in Finland. They insisted that with their network that kind of border crossing was safe and easy. I was impressed.

NARRATOR: One of the Trust’s operatives, using the name Alexander, has a suggestion.

SIDNEY REILLY: It was after dinner, we had begun the toasts with vodka. And he began speaking about how this meeting was so unfortunate. Something like: "What a shame it would be for you to have traveled all this way from America to stop here, only at the threshold. And for you not to dare to take the final step." And everyone went very quiet. But he carried on: "What a shame. When there are so many of our colleagues who would find it inspirational to meet the great Sidney Reilly. Who would learn so much from our conversations? But I understand you do not dare to cross that line.” I thought hard. And I have never been a coward.

NARRATOR: Before making his impromptu trip into Russia with the Trust, Sidney writes a letter to his new wife, Pepita. It explains where he is traveling to for a few days, and says there is almost certainly no risk at all in the journey. And if he should be detained for any reason, it will only be for a short while - a week or two. Sidney Reilly was never seen outside of Russia again. Archives from the Russian secret service show that after crossing the border with Sidney, Alexander and the other agents maintained the fiction that they belonged to an anti-communist group for some time, hoping to provoke Sidney into giving away valuable information. Then, at an appointed time, the handcuffs went on, and he was taken by car to the dreaded Lubyanka prison in Moscow. The Trust organization had played its role. Sidney Reilly was eventually shot in the back after months of interrogation, mock executions, and psychological torture. His execution was never publicly acknowledged by the USSR and remains disputed by some to this day.

SIDNEY REILLY: I always found danger addictive. And I never was a coward.

NARRATOR: There are many books on the life of Sidney Reilly - many with deeply conflicting theories as to who he was and what he did. For this episode, we made use of Robin Bruce Lockhart’s Reilly: Ace of Spies and Andrew Cook’s Ace of Spies: The True Story of Sidney Reilly. Reilly’s own account of his work in the Soviet Union is available as Adventures of a British Master Spy: The Memoirs of Sidney Reilly. I’m Vanessa Kirby. We all have valuable spy skills, and our experts are here to help you discover yours. Get an authentic assessment of your spy skills, created by a former Head of Training at British Intelligence, now at SPYSCAPE.com.

Guest Bio

Sidney George Reilly - known as The Ace of Spies - was a Russian-born secret agent employed by Scotland Yard's Special Branch and later by the Foreign Section of the British Secret Service Bureau in the 1890s. He is believed to have spied for four powers and was involved in an abortive 1918 coup d'état against Vladimir Lenin's Bolshevik government in Moscow. Reilly disappeared in Soviet Russia in the mid-1920s.

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