The Real James Bond

In the early years of the twentieth century, long before James Bond stepped onto the page, one man was at work as a new kind of spy. He crossed borders as easily as he changed names, slipped between governments and criminal networks, and dealt in secrets that could mobilise armies and shake empires. To some, he was a genius. To others, a liability waiting to be exposed. That man’s name, or so we’re told, was Sidney Reilly. He is often described as the real James Bond – the man whose nerve, charm, and audacity helped shape the modern image of the spy. But was Sidney Reilly truly the world’s first modern super-spy? How much of his legend was built on real intelligence work, and how much on stories he told about himself? And in the end, did Reilly master the world of espionage… or did it finally turn his own methods against him? This is a Short History Of the Real James Bond. A Noiser podcast production. Hosted by John Hopkins. With thanks to Andrew Cook, author of Ace of Spies: The True Story of Sidney Reilly. Written by Sean Coleman | Produced by Kate Simants | Production Assistant: Chris McDonald | Exec produced by Katrina Hughes | Sound supervisor: Tom Pink | Sound design by Oliver Sanders and George Tapp | Assembly edit by Anisha Deva | Compositions by Oliver Baines, Dorry Macaulay, Tom Pink | Mix & mastering: Cody Reynolds-Shaw Unlock the next two episodes of Short History Of… right now by subscribing to Noiser+. You’ll also get ad-free listening and early access to shows across the Noiser podcast network, including Real Survival Stories and Sherlock Holmes Short Stories. Just click the subscription banner at the top of the feed, or head to www.noiser.com/subscriptions to get started. ⁠A Short History of Ancient Rome⁠ - the debut book from the Noiser Network is out now! Discover the epic rise and fall of Rome like never before. Pick up your copy now at your local bookstore or visit ⁠⁠noiser.com/books⁠⁠ to learn more. Learn more about your ad choices. Visit podcastchoices.com/adchoices

• 0:01Speaker 00

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• 0:31Speaker 01

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• 0:40Speaker 01

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• 1:02Speaker 02

  It's March 1904, in Port Arthur, Manchuria, China.

• 1:08Speaker 02

  A Russian naval fortress rises out of the dark above the harbor, all concrete walls and iron gates. Searchlights rake slowly across the outer yard, then move on. Beyond them, warships sit at anchor, their guns pointed out to sea.

• 1:27Speaker 02

  At the base of the wall stands a slim man in a long, dark coat, collar turned up against the cold, his hat pulled low. He looks like an officer who belongs here, which is exactly the look he's trying to achieve.

• 1:42Speaker 02

  Waiting in the shadows, he counts the seconds between patrols, waiting for the perfect moment to strike.

• 1:50Speaker 02

  Out in the darkness, a bell rings aboard a ship.

• 1:55Speaker 02

  He takes a breath,

• 1:57Speaker 02

  checks the coast is clear, and makes his move. Stepping into the moonlight, he maintains an even pace as he approaches the service gate. The latch gives with a soft click, and he slips inside.

• 2:12Speaker 02

  The corridor beyond is narrow and poorly lit. A single electric bulb hums overhead as he strides towards a door which he finds unlocked, as he was assured it would be. Closing the door behind him, he crosses to a desk, sets his hat down carefully, and opens a drawer in which he finds a roll of confidential plans.

• 2:36Speaker 02

  As he spreads them across the table, the Russian Pacific Fleet reveals itself, laid out in front of him in precise lines. He memorizes what he can: the gun placements, the firing arcs, the fuel stores. Then opens a small notebook and swiftly sketches it all in his neat economical shorthand. He is a man used to working under pressure.

• 3:00Speaker 02

  But now, he hears a Russian voice in the corridor and footsteps approaching. There's nowhere to hide, but he doesn't rush.

• 3:09Speaker 02

  Instead, he calmly folds his copies, slips them inside his coat, and straightens the original plans.

• 3:17Speaker 02

  When the door opens, he is standing ready, irritation written plainly on his face.

• 3:25Speaker 02

  Surprised, the Russian demands to know who he is. The intruder answers calmly in a local accent that he's a courier here on late orders. He gestures at the paperwork as if it bores him, as if the delay is the greater crime. There is a pause as the Russian takes him in. The outfit is plausible, and the accent too. Finally, the guard nods and apologizes for disturbing him.

• 3:57Speaker 02

  Only as the door closes does the man smile briefly. He replaces the plans, retrieves his hat, and leaves.

• 4:05Speaker 02

  Climbing swiftly through an open window, he drops lightly into the yard below and walks away.

• 4:14Speaker 02

  Later, far from this harbour, men will read his notes and move fleets, money and lives because of them.

• 4:25Speaker 02

  But for now, the man disappears into the dark.

• 4:29Speaker 02

  His name, when it is finally spoken, will sound like something from a novel.

• 4:36Speaker 02

  His name is Riley. Sidney Reilly.

• 4:49Speaker 02

  In the early years of the 20th century, long before James Bond stepped onto the page, one man was at work as a new kind of spy. He crossed borders as easily as he changed names, slipped between governments and criminal networks, and dealt in secrets that could mobilize armies and shake empires. To some, he was a genius; to others, a liability waiting to be exposed.

• 5:15Speaker 02

  That man's name, or so we're told, was Sidney Reilly. He's often described as the real James Bond, the man whose nerve, charm and audacity helped shape the modern image of the spy.

• 5:32Speaker 02

  But was Sidney Reilly truly the world's first modern super spy? How much of his legend was built on real intelligence work? And how much on stories he told about himself? And in the end, did Reilly master the world of espionage? Or did it finally turn his own methods against him?

• 5:53Speaker 02

  I'm John Hopkins. From the Noiser Podcast Network, this is A Short History of the Real James Bond.

• 6:10Speaker 02

  It's often said that Ian Fleming drew inspiration for James Bond from the exploits of a real-life spy called Sidney Reilly. This is undoubtedly the case. But the truth, as with so much in the Sidney Reilly story, is hard to pin down.

• 6:28Speaker 02

  By the time Fleming begins creating James Bond, Riley has already been dead for over 25 years, though his legend still circulates widely. His story has been told in newspapers, memoirs, and even in a popular cartoon strip. He is presented as an irresistible lone operator, charming allies, deceiving enemies, and living dangerously but lavishly.

• 6:55Speaker 02

  At a time when intelligence workers so far have been the slow, serious domain of diplomats and bureaucrats, the legend of Sidney Reilly suggests something far more glamorous. And for Ian Fleming, one day a famous author, but for now, a frustrated office worker, it is the perfect inspiration.

• 7:15Speaker 02

  Andrew Cook is the author of Ace of Spies: The True Story of Sidney Reilly.

• 7:21Speaker 03

  Who's the real James Bond? Well, despite what anyone says, Ian Fleming is the real James Bond. James Bond was just a fictitious alter ego that he created himself because he was bored to tears being stuck behind a desk in Whitehall during World War II, working for naval intelligence. He wanted to write a novel, or more than one novel, and ideally see that novel become a film. What he wanted to do was to create a spy superhero like the one he saw in The Evening Standard and that strip cartoon that he saw on a regular basis was called Master Spy. And it was the Sidney Reilly strip cartoon, and that was portraying Riley almost as like a Bond figure. If it wasn't for Riley, and more importantly, his fictitious alter ego,

• 8:05Speaker 03

  the Master Spy series in Beaverbrook Papers, Fleming might not have twigged on trying to create his own Sidney Reilly. And that's all James Bond was.

• 8:17Speaker 02

  The comic strip may have exaggerated Sidney Reilly's exploits, but it did not invent him entirely. Riley himself cultivated the image of the enigmatic master spy to perfection. But his life was a series of reinventions, aliases, and half-truths. Very little that we know of him can be taken as absolute fact. Only long after his death, as Cold War dossiers were declassified and new archives opened, has a clearer picture begun to emerge.

• 8:50Speaker 02

  Sidney Reilly is almost certainly born near modern-day Ukraine under the name of Shlomo Rosenblum sometime around the 1870s. From the very beginning, the facts blur. Even his parents, religion, and education are contested, with some claiming he is the product of an affair and that his biological father was not Russian Orthodox but Jewish. Though Riley himself tells different versions of his early life at different times, what is clear is that he comes of age at a time of deep unrest. These years in the Russian Empire are marked by poverty, political tension, and waves of violence.

• 9:32Speaker 03

  Life for folk in those days wasn't great, and it was even worse if you were Jewish. An awful lot of Jews left the Russian Empire in the late 19th century and went to Germany to escape pogroms, basically when mobs of Russians descend on a Jewish village and literally kill everybody.

• 9:51Speaker 02

  By the time he seeks safety by slipping out under a false name in the 1890s, it appears young Rosenblum has already learned that when things get dangerous, a new identity is a good form of protection.

• 10:04Speaker 02

  He arrives in London, having Germanified his name on his way through Europe.

• 10:09Speaker 03

  When he comes to the UK, he's Sigmund Rosenblum. He sets himself up as a company director, is a trained chemist. Whether or not he completed his degree is open to question, probably not is the answer. But he came over to this country and he got into what we call these days or back in the day, patent medicines, and he did very well.

• 10:31Speaker 02

  The patent medicine trade sits somewhere between science and salesmanship. Remedies for any ailment are branded boldly, tested lightly, and sold on confidence. Rosenbloom, with his training in chemistry and his gift for persuasion, proves adept at both.

• 10:50Speaker 03

  He could talk the hind leg of a donkey, and it wasn't just that he was extremely articulate. He was a manipulative person, almost to the extent that people wouldn't realise they were being manipulated. Some people have gone so far as to say he was a sociopath, he may well have been. But he was a very able person intellectually and in his ability to get what he wanted from people.

• 11:13Speaker 02

  In London, he becomes close to a well-connected English clergyman, the Reverend Hugh Thomas, and his much younger wife Margaret. Reverend Thomas suffers from a serious kidney condition called Bright's disease. Rosenbloom presenting himself as medically knowledgeable frequents the household often, administering treatment to the reverend while growing increasingly close to Margaret. At the same time, Rosenbloom is moving in another circle altogether. London, at the turn of the century, is crowded with Russian exiles and political dissidents. Some are simply critics of the Tsar, but others are suspected of more extreme, even terrorist ambitions.

• 11:58Speaker 02

  William Melville, head of the special branch at Scotland Yard, is tasked with monitoring them. And it's at this point that a young exile by the name of Rosenbloom draws his eye.

• 12:11Speaker 03

  Rosenbloom, as he was at the time, was actively and almost openly associating with people that Scotland Yard were a bit concerned about. Rosenbloom was recruited by Melville effectively as an informant, keeping an eye and informing on people in revolutionary and radical circles in London.

• 12:34Speaker 02

  Charismatic young recruit proves himself observant and discreet. Qualities that make him very useful to Melville. Meanwhile, in the Thomas household, the reverend's condition now deteriorates rapidly. Almost certainly thanks to the ministrations of Rosenblum, who may be aided and abetted by Margaret herself. Just after writing a will bequeaving his entire estate to his wife, he dies.

• 13:03Speaker 02

  Though the circumstances and timing have prompted speculation ever since, Rosenblum swiftly marries the widow. Despite the uptick in wealth and social legitimacy, in 1898, he finds himself in trouble over some dubious business dealings. He needs to leave Britain quickly and turns to his contact at Scotland Yard for assistance. Melville comes up trumps, even going so far as to provide him with a new state-sanctioned identity.

• 13:33Speaker 03

  Melville found a birth certificate for a child who died at birth almost, and that was Sidney Reilly. He was given a passport and off he went with his new wife at the end of 1898.

• 13:45Speaker 02

  Sigmund Rosenblum disappears, and Sidney Riley leaves Britain with Margaret and her inheritance at his side.

• 14:01Speaker 00

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• 14:32Speaker 01

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• 14:59Speaker 02

  With his new passport and name in hand, Riley begins building his reputation. In the early years of the 20th century, he operates internationally, in ports, rail hubs, and industrial centers across Europe and Asia, as a broker and entrepreneur. And increasingly, he deals in information. Later, when establishing himself as a spy of note, Riley will tell dramatic stories of this period. Of slipping behind enemy lines, infiltrating naval installations, and playing dangerous games on the fringes of rival nations. As ever with Riley, the legend is embellished, but not entirely invented.

• 15:41Speaker 03

  We can actually place him in most of the places he claimed he was at. So whether that's in Manchuria, whether it's in Japan, whether it's in St. Petersburg...

• 15:55Speaker 02

  It's clear by this stage that Riley is comfortable moving in volatile regions at moments of geopolitical tension. In Manchuria in 1904, Russia and Japan edged towards conflict as they struggled for influence over Korea and northern China. As tensions mount, Riley moves among contractors, railway officials, and naval suppliers, exploiting his access on multiple sides to study the details that will matter when war breaks out. Apparently, in this time, he manages to secure sensitive information about Russian naval defenses and coastal positions, possibly even passing that intelligence to the Japanese.

• 16:36Speaker 02

  Even at this stage, Riley understands the value of secrets, how they can be acquired, packaged, and resold.

• 16:48Speaker 02

  By the early 1910s, he is spending significant time in Saint Petersburg. He is also accumulating wealth, not to mention an extensive Napoleonic art collection, through both legitimate and nefarious means. He may have married into money, but now he's building his own, and plenty of it.

• 17:10Speaker 02

  As Europe slides towards war in 1914, Riley and his wife relocate to New York, where he begins to dabble in arms procurement. Although naturally, he will later claim to have played a very different role in the war effort.

• 17:26Speaker 03

  Despite all his many stories about being behind German lines in the First World War, having met the Kaiser, posing as a German officer, all this palabaloo, not a word of it's true. The nearest he got to the front line in the First World War was when he was sitting in the cinemas of Manhattan watching the newsreels about what was happening in Europe. For most of World War I, he was living in the latter luxury in New York, more money than he knew what to do with. He was an arms salesman. He made the modern equivalent of millions, procuring arms for the Russians in the First World War, but all through the luxury of an armchair in a Fifth Avenue hotel.

• 18:09Speaker 02

  By 1917, Riley is prosperous and well-connected, moving in the same circles as financiers, diplomats, and arms dealers. He is just as fluid in his private life, entering relationships with other women. Inevitably, his marriage to Margaret, a partnership that once offered security and legitimacy, begins to fray. Fed by the admiration of others, Riley begins to build a mythology around himself as a suave, confident, international man of mystery. But that confidence is ruptured when Russia implodes.

• 18:49Speaker 02

  1917's February Revolution removes the Russian Tsar, but leaves a provisional government in place, so business can continue as normal. At first, Riley has no reason to panic. But eight months later, the October Revolution changes everything.

• 19:07Speaker 03

  What happened? Well, Bolsheviks came along and seized power and closed down the country. You know, you couldn't get into Russia if you were an outsider. So all of a sudden, Riley's in panic mode. He's got an extremely valuable art collection, and the Bolsheviks have just literally slammed the door in terms of Russia. How's he gonna get back and rescue his fortune, or part of his fortune, in Russia? The only way he can think to get in there is to go and volunteer himself to the British Armed Forces and suggest that, you know, he's fluent in Russian. Of course, he's Russian, but he's masquerading as an Irishman.

• 19:46Speaker 02

  His marriage to Margaret, now fading from his story, he crosses without her from the United States into Canada and presents himself at a British recruitment station in Toronto. With the war entering its final phase, his offer to do his bit arrives late. But when he casually mentions that he speaks fluent Russian, the paperwork finds its way onto a desk far away.

• 20:12Speaker 03

  Now, that was music to the ears of people in London. They could count on one hand the number of reliable intelligence people they had who could speak Russian and could masquerade as being Russians themselves if it came down to it.

• 20:25Speaker 02

  Britain urgently needs men who can enter revolutionary Russia and discover what's happening inside the new Bolshevik regime. Riley is ambitious, multilingual, already experienced in arms dealing and politics. He is exactly what they need.

• 20:45Speaker 02

  And of course, his name is not entirely unfamiliar in London. Some in the intelligence world, like William Melville, remember him as an effective informant from years before. Officials in MI1C, the foreowner of MI6, review his file and find a shady past, questionable business dealings, and irregularities around his identity.

• 21:08Speaker 03

  Under normal circumstances, you wouldn't have touched this guy with a barge pole. But they didn't really have a choice, they were desperate for people. They brought him over to London, he had a brief interview with C at Whitehall Court in London, and the next thing he knew, he was on the boat to Russia.

• 21:26Speaker 02

  Riley is dispatched to revolutionary Russia with clear instructions to report to Moscow and find out what the new Bolshevik government is really thinking. He is given funds, a bag of diamonds for leverage, and a simple brief to assess whether Russia really intends to pull out of the war.

• 21:45Speaker 02

  But he doesn't follow his orders. Instead of heading straight to Moscow, Riley vanishes. With his bosses apparently clueless of his whereabouts, he detours to Petrograd, the former St Petersburg, to recover his Napoleonic art collection, which later resurfaces in New York.

• 22:05Speaker 02

  Even on his first official mission, Riley appears to place self-interest above national service. Eventually, though, he does arrive in Moscow and gets to work. The task is intelligence gathering in its purest form: digging around, talking to people, sorting truth from rhetoric. The Bolsheviks speak of withdrawal from the war, but are they serious or are they posturing? He operates alongside the British diplomat Robert Bruce Lockhart, who is attempting to answer the same questions through formal channels. Lockhart works the drawing rooms, while Riley operates in the shadows, cultivating contacts, probing loyalties, and testing who might be persuaded.

• 22:50Speaker 02

  By that time, the Bolsheviks' new, secret police, the Cheka, are already active in the city. Suspicion is everywhere, and foreigners are being closely watched. Yet, for all his self-interest, Riley does produce results.

• 23:05Speaker 03

  Yes, he did a good job. First and foremost, he worked for Mr Sidney Reilly, and secondly, he worked for MI-1C. He did basically do what they asked him to do when he had a bit of spare time on his hands. And of course, he sends back reports about people that he'd met that were working for the Cheka, working civil servants, party members, people in Bolshevik circles, about what was really in their minds. Were they really going to pull out of the First World War? If they did, would they actually still pick up a rifle if the Germans nudged into Ukraine, for example?

• 23:43Speaker 02

  London is getting answers out of their man in Moscow, but those answers are troubling. If Russia does pull out of the war, German forces can redeploy west, and the balance of the war could shift dramatically. Though Lockhart continues to negotiate, behind closed doors, something more radical emerges. What if this new Bolshevik government could be toppled before it consolidates power?

• 24:08Speaker 02

  Riley embraces the idea with open arms. No longer merely gathering intelligence, he and his associates begin exploring the possibility of bringing about a regime change. They hope to replace Lenin's government with one willing to resume the war alongside the Allies, and in doing so, reopen Russia to the West.

• 24:29Speaker 02

  The plot that takes shape is breathtakingly reckless. Guards are to be bribed and strategic buildings seized. Loyal military units will either be persuaded or bought, and if necessary, Lenin himself will be eliminated.

• 24:48Speaker 02

  Riley throws himself into it, convinced that boldness will succeed where diplomacy has failed.

• 24:53Speaker 03

  Books call it the Lockhart plot. Lockhart was tenuously involved, but you might more accurately call it the Riley plot. So he was up to his eyes in that.

• 25:04Speaker 02

  By late summer 1918, the conspiracy is gathering momentum, but also drawing attention from potentially dangerous eyes. Then, in the dying days of the summer, everything accelerates dramatically. It is the evening of the 30th of August 1918, outside the Mikkelsen Engineering Factory in Moscow. As another shift ends, weary workers spill from the building, heavy boots scraping across the yard floor. Instead of filing out through the factory gates tonight, however, the workers linger in the yard.

• 25:48Speaker 02

  They have been told that their leader, Vladimir Ilyich Lenin, will address them here, and now they must wait patiently for his arrival. Fanny Kapler, a slight, frail-looking woman in her late twenties, stands slightly aside from the rest. Her coat is plain, her face gaunt, and her posture rigid. Noticeably, she doesn't push forward with the others as the motorcade arrives. As the door of his car swings open, Lenin steps down onto the gravel, compact and purposeful, his cap pulled low, his jacket buttoned tight. To most of the workers, he is the architect of a new world.

• 26:30Speaker 02

  To Fanny, he is the man who has strangled it. She was just sixteen when she was first involved in a violent plot against a Tsarist official in Kiev, a representative of the old regime she believed was killing Russia. The years of hard labor that followed her trial damaged her body, but sharpened her belief that Russia must be remade. When the Tsarists fell, she thought her sacrifice had meant something. But these Bolsheviks have outlawed her party, silenced dissent, and crushed rival revolutionaries. They have brought not freedom, but merely tyranny with a different face.

• 27:15Speaker 02

  Now the crowd falls silent, as Lenin hastily mounts a small platform to speak.

• 27:21Speaker 02

  "Production must increase," he says. "Discipline must hold. The revolution depends on factories like this one."

• 27:29Speaker 02

  The workers lean in to catch his words. Some nod, a few clap when he finishes.

• 27:36Speaker 02

  His audience already dissipating, Lenin steps down from the platform and turns towards the waiting car.

• 27:43Speaker 02

  Fanny takes her cue. Moving slowly, deliberately, like someone whose fate is already decided, she slips her hand into her coat pocket and grips the revolver, heavy and cold.

• 27:57Speaker 02

  Her quarry is only a few paces away now, framed by workers shifting aside to let him pass.

• 28:05Speaker 02

  She raises the gun.

• 28:10Speaker 02

  The first shot splits the air, but for an instant, the yard holds its breath, as if the sound has not yet been understood. Then she fires again.

• 28:21Speaker 02

  Lenin jerks, his body folding slightly at the waist. With the third shot, panic detonates across the yard. Most workers scatter, but others lunge towards Fanny, grabbing her arms, wrenching the weapon from her grasp, before she can fire again.

• 28:41Speaker 02

  Lenin is caught as he stumbles. Blood seeps darkly through his jacket. He is pale but conscious, insisting through clenched teeth that he is all right.

• 28:54Speaker 02

  Fanny does not struggle, as she is forced to the ground, wrists pinned, boots studding around her.

• 29:02Speaker 02

  And though she has not killed Lenin, the echo of her shots will travel far beyond the factory gates.

• 29:09Speaker 02

  Hers will not be the only arrest that comes from this.

• 29:18Speaker 02

  Lenin survives the attack, but by nightfall, Moscow already feels different. Sidney Reilly quickly learns what has happened, as word spreads through party offices and factory floors alike, that the revolution has been targeted. Within hours, the Bolshevik leadership frames the shooting as part of a wider assault on the regime. The Cheka respond with urgency, drawing on lists already compiled from suspicions long entertained and grievances carefully noted.

• 29:49Speaker 02

  In truth, Fanny Kaplan acted alone. She had no connection to the British or French missions in Moscow. But in the charged atmosphere that follows, the Cheka move against foreign nationals already under scrutiny for counter-revolutionary intrigue. Among those detained is Robert Bruce Lockhart. He is taken to the notoriously brutal Cheka headquarters at the Lubyanka for interrogation, before being held under guard in the Kremlin itself.

• 30:19Speaker 02

  The so-called Lockhart plot, with Riley at its heart, collapses before it can be launched. But once again, all is not as it seems.

• 30:29Speaker 03

  A lot of people would argue, and I'm pretty convinced of this myself, it was never a real plot. It was actually started by Dzhinsky, the head of the Cheka, and it was designed at a time of maximum peril to the Bolsheviks, because they were on the edge. It could have gone either way for them. They could have been pushed out at that time. They'd only been in power a short period of time, and their regime didn't have deep roots. So, the quick solution is to create a number of fictitious conspiracies and plots, and see how many anti-Bolsheviks come running to sign up to it. And that's exactly what happened in 1918.

• 31:10Speaker 00

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• 31:40Speaker 01

  Born from the intensity of a night in the Eternal City. Introducing Born in Roma Fragrances by Valentino. Feminine perfume Donna Born in Roma features juicy black currant, central jasmine, soft cashmerin, and warm vanilla. Masculine-leaning but unisex Womo has notes of fresh violet leaf, aromatic sage, green vetiver, and mineral salt. Shop holiday gifts at macy's.com.

• 32:09Speaker 02

  Whether Riley is one of the architects of a reckless coup, or the unwitting participant in a trap carefully laid by the Cheka itself, remains a matter of debate. What is certain is that with the net tightening, Riley's time in Moscow has run out. He slips beyond Russia's grasp by the skin of his teeth. But the world he leaves behind is changing fast.

• 32:34Speaker 02

  In the aftermath of the failed coup and the deepening Russian civil war, espionage begins to evolve. The improvisational, personality-driven spy craft of the pre-war years gives way to something colder and more structured. Intelligence services that once relied on colorful adventurers now prefer disciplined officers who follow instructions. And though Sidney Reilly has certainly never been one of those, for now, he is too experienced and too knowledgeable to be discarded immediately.

• 33:05Speaker 03

  Even after the war, they kept him on for two or three years, which was actually quite unusual. But Riley stays on the books till about 1922. He does earn the King's Shilling during the job they pay him to do, but his number-one concern is Sidney George Riley.

• 33:22Speaker 02

  Throughout the early 1920s, he drifts across Europe, inserting himself into emigre circles and anti-Bolshevik networks. He cultivates wealthy backers and displaced Russian aristocrats who still believe the revolution can be undone.

• 33:39Speaker 02

  But as the Bolsheviks consolidate power and the Red Army strengthens, Western governments grow cautious about further exploits in Russia. The political will to intervene drains away, and with it goes the need for men like Riley.

• 33:56Speaker 02

  With the days of slipping across borders with diamonds in his pocket well and truly over, his decadent lifestyle is catching up with him.

• 34:05Speaker 03

  By this time, by the way, he's got big debts. He made an absolute fortune in St Petersburg and he made an even bigger fortune during the First World Wars, an arms dealer in the States. But like a lot of people who make massive fortunes very quickly, he's not very good at looking after it. He spends it quicker than he earns it, and he's living this luxury lifestyle. I mean, that's about the only probably tangible comparison to James Bond in that era. He's living in five-star hotels, drinking champagne like it's going out of fashion, digging into caviar. He's got a luxury lifestyle that most people would just pass out at hearing about. So is it no surprise that he's not penniless, but he's got big money problems by the early 1920s?

• 34:49Speaker 02

  And so, despite never having officially divorced his first wife, Margaret, Riley looks again for an advantageous marriage.

• 35:02Speaker 02

  In Berlin, he meets a young woman calling herself Pepita Bobedilla. Seemingly glamorous, exotic and wealthy, in reality, she is as much a reinvention as Riley himself. Her real name is Nellie Chambers, from Blackburn, Lancashire. Though it is true that she is a widow newly in possession of a good deal of money.

• 35:24Speaker 03

  He was a serial bigamist, that was another one of his money-making approaches. Sometimes he married or associated with women from an intelligence point of view. But Margaret, who he married in 1898, almost certainly murdered her husband. He inherited an absolute fortune from her, indirectly from him. When he married Pepita Bobadia, he marries her effectively because her husband Hayden Chambers has just died and left her a lot of money. And when he bumped into her in the Hotel Adlon in Berlin, he thinks this might be useful for his awful financial state.

• 36:03Speaker 02

  For a time, Pepita's money ensures the hotels remain grand and the champagne continues to flow. But by the mid 1920s, Riley is entangled in financial disputes with creditors, mounting bills, and legal claims over failed ventures. The fortunes he once made so effortlessly are no longer being replenished.

• 36:23Speaker 03

  He can't control his lifestyle. He's still spending money like there's no tomorrow, but there is no tomorrow because there's no today. He's not actually earning anything like what he was earning before. And if his legal cases go wrong, he's going to owe even more.

• 36:37Speaker 02

  But then word reaches him of something extraordinary.

• 36:42Speaker 02

  Inside Soviet Russia, an underground anti-Bolshevik organisation is said to be operating at the highest levels, calling itself The Trust. It has a role for Riley that could put him back on the map.

• 36:56Speaker 03

  What's the offer? The offer is, we're dissidents within Russia, we're fighting the Bolsheviks. The only problem is we haven't got a rub all to rub together. So they meet Riley, and to cut a very long story short, they say to him, there are an awful lot of works of art, priceless works of art in Russia. They're in galleries and museums, no security, all the rest of it. Why don't you come over here, Mr Riley? You're a great leader. Come over here, lead us, we'll break into these museums and we'll fence all the stuff to you. You auction it in America. Obviously, you're going to have a very large finder's fee, but you send the money back to us and we'll buy arms and ammunition and bribe people and all the rest of it with this money. So he was seduced by this amazing offer of literally the modern equivalent of absolute millions by pillaging Russian art.

• 37:46Speaker 02

  It is an extraordinary proposition.

• 37:50Speaker 02

  Priceless Russian art idling in museums with no security. A covert anti-Bolshevik network waiting for leadership. Money enough to fund a counter-revolution and to restore Riley's own fortunes in the process. On paper, it is almost too good to be true. Now, Riley is not a fool. He knows the risks. He knows Soviet Russia is no place for carelessness. And he knows that honey traps have been used in the past to lure other intelligence officers to their deaths. This could be another example of that Soviet cunning. And yet Riley is not like other agents. He has spent his life believing that he can see the angles others miss and that he can navigate danger where others would falter.

• 38:35Speaker 02

  Besides, he's got out of tighter scrapes in the past.

• 38:39Speaker 02

  But perhaps the biggest factor clouding his judgment is that he really needs this to be real. He needs the money, but he also needs to feel relevant again. And right now, he's getting encouragement on the home front to take a closer look at the Trust Organisation too.

• 38:57Speaker 03

  A couple of Riley's intelligence colleagues or former intelligence colleagues are saying, "Well, we really need to find out a little bit more about this Trust Organisation. We can't do it because we're now very short of staff. The government cuts in the 20s and the government's mood isn't really, as I say, to go sending people into Russia and start prodding hornets' nests and ruffling feathers. But you're not working for us anymore, Sidney. Why don't you do this?"

• 39:24Speaker 02

  Despite his reservations, Riley convinces himself that the opportunity outweighs the risk. And in 1925, he makes the decision to meet them.

• 39:37Speaker 02

  Initially, he is cautious. Riley insists he has no intention of wandering blindly into Soviet territory, where he could potentially be arrested or worse. He is a busy man. If there is to be any cooperation between them, it can be discussed safely on neutral ground. The Trust agrees. They invite him to meet in Finland, near the border with Russia, for a discreet conversation. No risk and no commitments. It is exactly the sort of compromise a careful operator would offer. So, reassured, Riley agrees.

• 40:14Speaker 03

  So he flies off to Finland. They wine and dine him and whatever. They sit around the table talking about him. And then, they know him, they've read him, as it were. And in the last resort, they say to him, "Well, come on, just cross the border for a couple of days. What harm is it going to do? People have forgotten all about you now." And he says, "No, no, no, I'm not going to do that, not going to do that." And they said, "Hold on a minute, you're Sidney Reilly. You're this superhero guy. Are you really telling us you're frightened to cross the border just for a day?" And his pride gets the better of him.

• 40:44Speaker 02

  He crosses into Soviet Russia, still fearing the worst. But his contacts are true to their word, and no arrests take place. Riley spends a couple of days looking at the operation on the ground and meeting other members of the group.

• 40:59Speaker 02

  And by the time he's preparing to leave, he has seen enough to convince him that the Trust is a genuine group of anti-Bolshevik dissidents intent on regime change.

• 41:15Speaker 02

  It is the 25th of September, 1925, near the Soviet-Finish border.

• 41:24Speaker 02

  Sidney Reilly steps out of the safe house into the brittle light of early autumn.

• 41:30Speaker 02

  The air is cool and crisp, and he pulls his coat closer around him as he crosses to the waiting car.

• 41:37Speaker 02

  In the trees beyond, a crow calls. Settling into the backseat, as the vehicle pulls away from the house and onto the narrow forest road, he watches birch trees streak past in white and gold.

• 41:53Speaker 02

  And as they travel back towards the border with Finland, he lights a cigarette. And reviews the past couple of days in his mind.

• 42:04Speaker 02

  His trip out here has unfolded almost too neatly. He's had meetings in dimly lit rooms with men introduced as railway officials, military officers, administrators. They've all been, they claim, quietly opposed to the Bolsheviks.

• 42:22Speaker 02

  In those meetings, a plan has taken shape to liberate a number of precious artworks from Russian galleries, with roots sketched in pencil and onward black market networks described with persuasive detail. It is all felt organized, structured, and reassuringly real.

• 42:41Speaker 02

  He's been on high alert for anything that might suggest he's being tricked, but with no evidence to that effect, he can only conclude that he's on to a very good thing indeed.

• 42:55Speaker 02

  Now as the car approaches a small border settlement, Riley leans forward and asks the driver to make a quick stop at a postbox. The car slows to a halt, and Riley jumps out, strides over to send a postcard, then heads back to the car. Climbing in, he smiles. The border is minutes away, and the safety of Finland lies beyond that. Then Berlin, then London.

• 43:23Speaker 02

  He waits for the driver to get moving again, but just as he's sitting back and thinking of home, another car pulls alongside him. The doors on both sides of the car are flung open. And Riley is hauled bodily from the vehicle by three burly officers of the Russian security services.

• 43:43Speaker 02

  Cold steel closes around his wrists, locking his arms together. He's bundled into their car, which accelerates away from the border and back down the road towards the interior.

• 44:02Speaker 02

  Riley sits in the back as the cold inevitable realization dawns that his friends in the trust group were secret police all along. It was nothing more than an elaborate trap and he, Sidney Riley, the great manipulator, walked right into it.

• 44:26Speaker 00

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• 44:56Speaker 01

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• 45:24Speaker 02

  At the time of his arrest, the Russians believe they have caught the master spy who has slipped their grasp before. Worried that his connections in MI6 will send more agents to look for him if it turns out he has been taken in Russia, they put out a story that a couple of Westerners have been shot crossing the border.

• 45:45Speaker 03

  And there is a rumor that Riley is one of the people who is shot crossing the border. Of course he wasn't.

• 45:52Speaker 02

  In reality, he is taken to the Lubyanka where he is interrogated for weeks.

• 45:58Speaker 03

  He's put in a cell, cell seventy-three, for weeks on end. He's given some drugs and all the rest of it. We've got a pretty good idea what they were asking him, because he kept cigarette papers, and he wrote down in very, very tiny handwriting on these cigarette papers what he was being asked, and allegedly what his replies were and all the rest of it. Now, he thought at the time, and it's very sad, I guess, in a way, a bit of sentimentality, he genuinely believed that he just had to hold out as long as possible and good old Britain would find some way of rescuing him. But that was never, ever gonna happen.

• 46:39Speaker 02

  Sadly for Riley, his time is up.

• 46:43Speaker 02

  Britain does not ride to his rescue. And on the twenty-fifth of November, nineteen twenty-five, he is driven out to some woods, where he is executed.

• 46:53Speaker 03

  Quite a sad old story. You know, he'd manipulated more people than you could throw a stick at. Particularly women. I mean, all the talk about the countless mistresses and women and vigorous wives and all the rest of it. It was the same sort of pateau and the same sort of seduction that he used when trying to get information out of people for intelligence purposes, and he was very good at it. But as I say, every dog has his day, and unfortunately, that was the twenty-fifth of November, nineteen twenty-five.

• 47:20Speaker 02

  There is no formal announcement of his execution. Sidney Reilly simply disappears. It will be decades before the Cold War thaws and documents get declassified that explain the truth. But eventually, something resembling a clearer story emerges of his life, his operations for military intelligence, his arrest, interrogation, complete with those scribbled notes on cigarette papers, and his death.

• 47:51Speaker 02

  In the intervening years, without confirmation of his demise, rumours begin to build. Some claim he has escaped again. Others insist he is still operating somewhere in Europe, under yet another name. Some even claim he has been turned, and is now working for the KGB. The silence around his death gets filled with myth, as those who knew him, or simply heard of him, share stories and embellish the tales he had already polished in his own lifetime. The title "Ace of Spies" begins to circulate, half-ironic at first, then becoming more admiring and reverent as it takes hold. His former colleague, Robert Bruce Lockhart, publishes his own account of Revolutionary Moscow, although much of his biography was drafted by another colleague

• 48:35Speaker 02

  who'd known Riley in the early days, and had taken his tales of daring do at face value. In Lockhart's book, Riley appears as a daring, shadowy figure, part conspirator, part romantic adventurer. Soon, in the Evening Standard newspaper, a comic strip called "Master Spy" dramatizes the exploits of a thinly veiled version of Sidney Reilly, a glamorous, resourceful spy, outwitting enemies across Europe. Among its readers is a young naval intelligence officer, named Ian Fleming. Fleming would later insist that James Bond was a composite character, drawn from many men he encountered during the war.

• 49:16Speaker 02

  But the template for him was already in circulation, in the shape of Sidney Reilly, the impeccably dressed, lone operative, fluent in danger, always one step ahead. The truth, as ever with Riley, is less tidy. He was brilliant, opportunistic, manipulative, often self-serving, at times courageous, and at times reckless. But he was not the unflappable superhero of later fiction. He was a man operating in a chaotic world, exploiting its fractures for personal gain, until the system he tried to outplay closed around him.

• 49:56Speaker 02

  James Bond survives every mission. Sidney Reilly did not. And though the man has long since gone to his grave, the myth has proved harder to kill.

• 50:07Speaker 03

  How do you describe somebody like Sidney Reilly? He was a one-off. He was an enigma within an enigma. He wasn't a likable person. He was almost certainly a murderer several times over. And that wasn't in the field of combat or espionage. That was killing his first wife's husband. There was another death of a flatmate in St Petersburg, I think in 1911, which enabled Riley to get his hands on this guy's money. He's a confidence man. He is an espionage agent. But he is just 110% a fascinating and magnetic character. Without a shadow of a doubt, his story found its way into Ian Fleming's head, and it never left Ian Fleming's head.

• 50:51Speaker 03

  And I think it inspired Fleming to create James Bond. And Fleming then went forward and hoovered up all kinds of stories and characteristics to graft into the James Bond character. But I think, yes, that's unintentionally Sidney Reilly's biggest epitaph, that he more than possibly lit the flames within Ian Fleming's very, very creative mind that led to the creation of James Bond.

• 51:26Speaker 02

  Next time on Short History, we'll bring you a short history of the Haitian Revolution.

• 51:32Speaker 04

  And poverty ensues. Instability ensues. And this is directly because of the punishments of the other world powers who did not want a free, black republic. They did not want that in their hemisphere, whether that was the American hemisphere or the Western hemisphere in general. And he has paid the price and continues to pay.

• 51:55Speaker 02

  That's next time. You can listen to the next two episodes of Short History of right now, without waiting and without adverts, by subscribing to Noiser Plus. Just hit the link in the episode description or head to www-noiser.com/subscriptions to unlock more episodes today.

• 52:14Speaker 00

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