Chapter 1: Who was Sidney Reilly and why is he compared to James Bond?
It's March 1904 in Port Arthur, Manchuria, China. 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. 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. 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.
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. 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.
Instead, 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. Only 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. Later, 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. Sidney Riley.
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.
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Chapter 2: What were the early life and influences of Sidney Reilly?
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. It'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. 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. 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. Andrew 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.
If 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.
Only long after his death, as Cold War dossiers were declassified and new archives opened, has a clearer picture begun to emerge. Sidney 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.
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Chapter 3: How did Sidney Reilly become involved in espionage?
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. 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.
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. 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. 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.
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 bequeathing his entire estate to his wife, he dies.
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 contacts at Scotland Yard for assistance.
Melville comes up trumps, even going so far as to provide him with a new state-sanctioned identity.
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Chapter 4: What were Reilly's major exploits during the Russo-Japanese War?
As 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,
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 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.
Even at this stage, Riley understands the value of secrets, how they can be acquired, packaged, and resold. By 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 arms 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 hullabaloo, 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 lapper 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. Inevitably, his marriage to Margaret, a partnership that once offered security and legitimacy, begins to fray.
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Chapter 5: How did World War I impact Sidney Reilly's career?
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 Sea at Whitehall Court in London. And the next thing he knew, he was on the boat to Russia.
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. 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. 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. 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.
Yes, he did a good job. First and foremost, he worked for Mr. Sidney Riley, 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 Chequard, 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?
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?
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Chapter 6: What was the Lockhart Plot and how was Reilly involved?
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.
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. 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. They have brought not freedom, but merely tyranny with a different face. Now the crowd fall 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. She raises the gun. 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. 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. Lenin is caught as he stumbles. Blood seeps darkly through his jacket. He is pale but conscious, insisting through clenched teeth that he is alright. Fanny does not struggle as she is forced to the ground, wrists pinned, boots thudding 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. Lenin 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.
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Chapter 7: What led to Sidney Reilly's capture by the Bolsheviks?
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. 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 Dzerzhinsky, the head of the Chekhov, 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. 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.
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. Intelligence 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 Riley stays on the books till about 1922. He does earn the king's shilling doing the job they pay him to do, but his number one concern is Sidney George Riley.
Throughout the early 1920s, he drifts across Europe, inserting himself into émigré circles and anti-Bolshevik networks. He 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. With the days of slipping across borders with diamonds in his pocket well and truly over, his decadent lifestyle is catching up with him.
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Chapter 8: What is the legacy of Sidney Reilly and his connection to James Bond?
And when he bumps into her in the Hotel Adlon in Berlin, he thinks this might be useful for his awful financial state.
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.
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. Inside 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. Reilly? 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.
It 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. Besides, he's got out of tighter scrapes in the past.
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