In short
The episode argues that Sidney (Sydney) George Reilly—often called “the real James Bond”—inspired Ian Fleming’s James Bond, while also stressing that Reilly’s legend is partly exaggerated and hard to verify.
Guest backgrounds
Andrew Cook, author of Ace of Spies: The True Story of Sidney Riley, discusses Fleming’s inspirations and Reilly’s historical record.
Key claims
Reilly likely began life near modern Ukraine as Shlomo Rosenblum (c. 1870s), reinvented himself through aliases, and used charm and manipulation. Fleming’s James Bond is presented as a desk-bound Naval Intelligence writer’s “super spy” fantasy shaped by the Master Spy comic strip featuring a Riley-like figure. Reilly worked for British intelligence (MI1C/forerunner of MI6), but may have been self-interested and possibly involved in the “Lockhart plot,” which the episode suggests may have been a Cheka trap. Reilly was arrested by Soviet security, interrogated at Lubyanka, and executed in November 1925.
Notable examples
Reilly’s 1904 Manchuria naval-plan theft; his 1917 claim of war heroics contrasted with evidence he stayed in New York; the 1918 Lenin assassination attempt by Fanny Kaplan leading to crackdown; and Reilly’s 1925 border arrest near Finland after meeting “The Trust.”
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Intriguing Life of Sidney Riley
0:07 to 0:38
Discover the early life and espionage tactics of Sidney Riley, the man often called the real James Bond.
“That's why drivers have enjoyed Progressive's Name Your Price tool for years.”
The Intriguing Life of Sidney Riley
0:56 to 6:04
Discover the early life and espionage tactics of Sidney Riley, the man often called the real James Bond.
“A Russian naval fortress rises out of the dark above the harbor, all concrete walls and iron gates.”
Riley's Influence on James Bond
6:04 to 8:10
Explore how Ian Fleming drew inspiration from Sidney Riley's life to create James Bond.
“But the truth, as with so much in the Sidney Riley story is hard to pin down.”
Riley's Reinventions and Deceptions
8:10 to 14:14
Learn about Sidney Riley's aliases, manipulations, and the blurred lines of his identity.
“The comic strip may have exaggerated Sidney Riley's exploits, but it did not invent him entirely.”
The Early Life of Sidney Riley
14:50 to 28:01
Exploring the life of Sidney Riley as he builds his reputation.
“With his new passport and name in hand, Riley begins building his reputation.”
The Assassination Attempt on Lenin
28:01 to 31:20
Learn about the dramatic moment when an assassination attempt on Lenin leads to a series of political consequences.
“Lenin jerks, his body folding slightly at the waist.”
The Rise and Fall of Sidney Reilly
31:20 to 38:11
Explore the life of Sidney Reilly, his espionage activities, and his encounters with the Bolshevik regime.
“Canva, the thing that makes anything a thing.”
Riley's Dangerous Decision
38:11 to 42:01
Discuss Riley's risky choice to infiltrate a Soviet anti-Bolshevik organization and the consequences that follow.
“And right now, he's getting encouragement on the home front to take a closer look at the trust organization too.”
The Arrest and Fate of Sidney Riley
42:01 to 45:40
Explore the dramatic events leading to Sidney Riley's capture and execution.
“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 onto a very good thing indeed.”
The Myth of Sidney Riley
45:41 to 48:09
Learn how Riley's life transformed into myth after his death and its impact on espionage lore.
“It will be decades before the Cold War thaws and documents get declassified that explain the truth.”
Show all 11 chapters
Riley's Legacy in James Bond
48:10 to 49:34
Discover how Sidney Riley inspired the character of James Bond and influenced Ian Fleming's work.
“And though the man has long since gone to his grave, the myth has proved harder to kill.”
Transcript
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1:29He looks like an officer who belongs here, which is exactly the look he's trying to achieve. Waiting in the shadows, he counts the seconds between patrols, waiting for the perfect moment to strike. Out in the darkness, a bell rings aboard a ship. He takes a breath, 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. 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.
2:17Closing 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. 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. But now he hears a Russian voice in the corridor and footsteps approaching. There's nowhere to hide, but he doesn't rush.
3:02Instead, he calmly folds his copies, slips them inside his coat, and straightens the original plans. When the door opens, he is standing ready, irritation written plainly on his face. 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.
3:50Only as the door closes does the man smile briefly He replaces the plans, retrieves his hat and leaves Climbing swiftly through an open window He drops lightly into the yard below And walks away
4:08Later, far from this harbor Men will read his notes and move fleets, money, and lives because of them. But for now, the man disappears into the dark. His name, when it is finally spoken, will sound like something from a novel. His name is Riley. Sydney Riley.
4:42In 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. That man's name, or so we're told, was Sidney Riley. He's often described as the real James Bond. The man whose nerve, charm, and audacity helped shape the modern image of the spy.
5:25But was Sidney Riley 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 Riley master the world of espionage? Or did it finally turn his own methods against him? I'm John Hopkins. From the Noiser Podcast Network, this is a short history of the real James Bond.
6:03It's often said that Ian Fleming drew inspiration for James Bond from the exploits of a real-life spy called Sidney Riley. This is undoubtedly the case. But the truth, as with so much in the Sidney Riley story is hard to pin down.
6:21By 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. At a time when intelligence work has so far been the slow, serious domain of diplomats and bureaucrats, the legend of Sidney Riley 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.
7:09Andrew Cook is the author of Ace of Spies The True Story of Sidney Riley 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 Riley strip cartoon and that was portraying Riley almost as like a Bond figure.
7:53If it wasn't for Riley and more importantly his fictitious alter ego, the Master Spy series in Beaverbrook Papers, Fleming might not have twigged on trying to create his own Sidney Riley, and that's all James Bond was. The comic strip may have exaggerated Sidney Riley'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. But only long after his death, as Cold War dossiers were declassified and new archives opened, has a clearer picture begun to emerge.
8:43Sidney Riley 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. Life for folk in those days wasn't great, and it was even worse if you were Jewish.
9:30An 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. 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. He arrives in London, having Germanified his name on his way through Europe. When he comes to the UK, he's Sigmund Rosenblum. He sets himself up as a company director. He's a trained chemist. Whether or not he completed his degree is open to question.
10:12Probably 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. The patent medicine trade sits somewhere between science and salesmanship. Remedies for any ailment are branded boldly, tested lightly, and sold on confidence. Rosenblum, with his training in chemistry and his gift for persuasion, proves adept at both. 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 realize they were being manipulated.
10:55Some people have gone so far as to say he was a sociopath. They may well have been. But he was a very able person intellectually and in his ability to get what he wanted from people. 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. Rosenblum presenting himself as medically knowledgeable frequents the household often, administering treatment to the reverend while growing increasingly close to Margaret. At the same time, Rosenblum is moving in another circle altogether.
11:36London, 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. 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 Rosenblum draws his eye. Rosenblum, as he was at the time, was actively and almost openly associating with people that Scotland Yard were a bit concerned about Rosenblum was recruited by Melville effectively as an informant keeping an eye and informing on people in revolutionary and radical circles in London
12:28Charismatic 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, bequeathing his entire estate to his wife, he dies.
12:56Though 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. Melville found a birth certificate for a child who died at birth almost, and that was Sidney Riley. He was given a passport and off he went with his new wife at the end of 1898.
13:39Sigmund Rosenblum disappears and Sidney Riley leaves Britain with Margaret and her inheritance at his side.
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15:26As ever with Riley, the legend is embellished, but not entirely invented. 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.
15:45It'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 edge towards conflict as they struggle 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.
16:26Even at this stage, Riley understands the value of secrets, how they can be acquired, packaged, and resold.
16:38By the early 1910s, He is spending significant time in St. 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 is building his own, and plenty of it. As Europe slides towards war in 1914, Riley and his wife relocate to New York, where he begins to dabble in alms procurement. Although naturally, he will later claim to have played a very different role in the war effort. 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 pala bala, not a word of it is true.
17:29The 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 lap of 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. 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.
18:14Inevitably, 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.
18:401917'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 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 up. 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 going to get back and rescue his fortune or part of his fortune in Russia?
19:21The 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.
19:36His 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. 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. Britain urgently needs men who can enter revolutionary Russia and discover what's happening inside the new Bolshevik regime.
20:23Riley is ambitious, multilingual, already experienced in arms dealing and politics. He is exactly what they need.
20:35And 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 forerunner of MI6, review his file and find a shady past, questionable business dealings and irregularities around his identity. 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.
21:16Riley 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. 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. Even on his first official mission, Riley appears to place self-interest above national service.
22:02Eventually, 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.
22:40By 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, Reilly does produce results. Yes, he did a good job. First and foremost, he worked for Mr. Sidney Reilly, and secondly, he worked for MI1C. 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 with Chekar working civil servants, party members, people in Bolshevik circles about what was really in their minds.
23:21Were 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? 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? 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.
24:09They 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. 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.
24:38Riley throws himself into it, convinced that boldness will succeed where diplomacy has failed. 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. 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.
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25:14It 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. 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.
25:59Noticeably, 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. To Fanny, he is the man who has strangled it She was just 16 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.
26:56They have brought not freedom, but merely tyranny with a different face.
27:05Now the crowd falls silent as Lenin hastily mounts a small platform to speak. Production must increase, he says. Discipline must hold. The revolution depends on factories like this one. The workers lean in to catch his words. Some nod, a few clap when he finishes. His audience already dissipating, Lenin steps down from the platform and turns towards the waiting car. 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. Her quarry is only a few paces away now, framed by workers shifting aside to let him pass.
27:55She raises the gun.
28:00The 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. 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.
28:31Lenin 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. Fanny does not struggle as she is forced to the ground, wrists pinned, boots studding around her. And though she has not killed Lenin, the echo of her shots will travel far beyond the factory gates. Hers will not be the only arrest that comes from this.
29:08Lenin survives the attack, but by nightfall, Moscow already feels different. Sidney Riley 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. 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.
29:54Among 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. 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. 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 Dziński, the head of the Checar, 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.
30:36They 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.
31:19Whatever needs to be done for your thing, Canva can make it an even better and bigger thing. Canva, the thing that makes anything a thing. 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. In the aftermath of the failed coup and the deepening Russian Civil War, espionage begins to evolve. The improvisational, personality-driven spycraft of the pre-war years gives way to something colder and more structured.
32:09Intelligence services that once relied on colorful adventurers now prefer disciplined officers who follow instructions. And though Sidney Riley has certainly never been one of those, For now, he is too experienced and too knowledgeable to be discarded immediately. Even after the war, they kept him on for two or three years, which was actually quite unusual. But Reilly 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 Reilly. Throughout the early 1920s, he drifts across Europe, inserting himself into émigré circles and anti-Bolshevik networks.
32:51He cultivates wealthy backers and displaced Russian aristocrats who still believe the revolution can be undone. 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.
33:16With the days of slipping across borders with diamonds in his pocket well and truly over, his decadent lifestyle is catching up with him. 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 War, as 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.
33:57He'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? And so, despite never having officially divorced his first wife, Margaret, Riley looks again for an advantageous marriage.
34:22In Berlin, he meets a young woman calling herself Pepita Bobadilla. 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. 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.
35:03When he married Pepita Bobadilla, he marries her effectively because her husband, Hayden Chambers, has just died and left her a lot of money. And when he bumps into her in the Hotel Adlon in Berlin, he thinks this might be useful for his awful financial state.
35:23For 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. 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. But then word reaches him of something extraordinary.
36:02Inside Soviet Russia, an underground anti-Bolshevik organization 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. 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 ruble to rub together. So they meet Riley and 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?
36:38You'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.
37:06It is an extraordinary proposition. 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.
37:55Besides, he's got out of tighter scrapes in the past. 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 organization too. A couple of Riley's intelligence colleagues or former intelligence colleagues were saying, well, we really need to find out a little bit more about this trust organization. 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.
38:39But you're not working for us anymore, Sydney. Why don't you do this? Despite his reservations, Riley convinces himself that the opportunity outweighs the risk. and in 1925, he makes the decision to meet them.
38:57Initially, 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.
39:34So 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, I'm not going to do that. And they said, hold on a minute, you're Sidney Riley. 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.
40:04He 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. 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.
40:35It is the 25th of September, 1925, near the Soviet-Finnish border.
40:45Sidney Riley steps out of the safe house into the brittle light of early autumn. The air is cool and crisp, and he pulls his coat closer around him as he crosses to the waiting car. In the trees beyond, a crow calls. Settling into the back seat, as the vehicle pulls away from the house and onto the narrow forest road, he watches birch trees streak past in white and gold.
41:13And as they travel back towards the border with Finland, he lights a cigarette and reviews the past couple of days in his mind.
41:24His 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. 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 has all felt organized, structured, and reassuringly real. 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 onto a very good thing indeed.
42:15Now 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. 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.
43:03Cold 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
43:22Riley 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.
43:44At 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. And there is a rumor that Riley is one of the people who is shot crossing the border. Of course he wasn't. In reality, he is taken to the Lubyanka, where he is interrogated for weeks. He's put in a cell, cell 73, 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.
44:42Now, 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 going to happen. Sadly, for Riley, his time is up. Britton does not ride to his rescue. And on the 25th of November 1925, he is driven out to some woods where he is executed. 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 pato and the same sort of seduction that he used when trying to get information out of people for intelligence purposes.
45:32And he was very good at it. But as I say, every dog has his day. And unfortunately, that was the 25th of November 1925. There is no formal announcement of his execution. Sidney Riley 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.
46:10In the intervening years, without confirmation of his demise, rumors 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, though much of his biography was drafted by another colleague who'd known Riley in the early days and had taken his tales of daring do at face value.
47:00In 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 Riley, 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. But the template for him was already in circulation in the shape of Sidney Riley. The impeccably dressed, lone operative, fluent in danger, always one step ahead.
47:49The 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. James Bond survives every mission. Sidney Riley did not. And though the man has long since gone to his grave, the myth has proved harder to kill. How do you describe somebody like Sidney Riley? He was a one-off. He was an enigma within an enigma.
48:35He wasn't a likable person. It 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. 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.
49:23But I think, yes, that's unintentionally Sidney Riley'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.
49:46Next time on Short History of, we'll bring you a short history of the Haitian Revolution. 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.
From the publisher
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
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