Deep Dive
Shownotes Transcript
Due to the nature of this episode, listener discretion is advised. This episode includes discussions of murder and assault. Consider this when deciding how and when you'll listen. To some, he was Mr. Constantine, a Greek merchant. Others called him Comrade Rylinski. Still more knew him as Mr. Masino, a Turkish businessman. And that was just in Moscow.
Sidney Riley used many names over his spy career. He was one of Britain's top secret agents, living in a world of cover-ups and classified operations. He had an early obsession with Napoleon, a man who risked everything for power. But his story makes you wonder, when you look behind the fake names, what else will you find hiding?
I'm Carter Roy, and this is Conspiracy Theories, a Spotify podcast. You can find us here every Wednesday, and be sure to check us out on Instagram at TheConspiracyPod. Stay with us.
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Hello there, I'm Mike Flanagan, and welcome to Spectre Vision Radio's production of Director's Commentary. Director's Commentary is a deep dive into a film through the eyes of the filmmaker or filmmakers who made it. It combines an in-depth interview format with a classic Director's Commentary track, the likes of which used to be common on physical media releases, but sadly are becoming more and more rare these days. Filmmakers talking about film with filmmakers. For people who love film.
and filmmakers. Sidney Riley had been awake for 36 hours straight, and his vision was beginning to blur. It was the middle of the night on September 2nd, 1918, and he had just arrived in Moscow. He was a fugitive from the Cheka, the Soviet secret police force that eventually became the KGB.
The Cheka had followed him from Petrograd, the Soviet capital, after Sidney's planned coup d'etat against Lenin and his Bolsheviks had been uncovered. Sidney's friends and contacts were already being arrested or killed. He needed to get out of Russia fast. If he were caught, he was certain to be executed as an enemy spy. But Sidney wasn't afraid. He was merely exhausted, and that was more dangerous than fear.
If he didn't get some rest, he would make a mistake. Mistakes could cost an agent his life. Sidney blinked hard, trying to focus as he looked up at the soot-covered brick walls, searching for familiar street names. Finally, he found one he recognized. He wasn't far from the house of a woman named Olga, who he had used as a cutout in the past.
According to Britain's Special Operations Executive Handbook, a cutout is an intermediary who forms the links between two agents or between an agent and the outside world. A cutout knows very little about the spy or his organization, will carry messages, and not undertake any subversive activity.
Sidney's womanizing was not merely for sexual gratification. It also gave him plenty of female cutouts willing to take risks for him without asking questions. He made it to Olga's apartment building and softly knocked on her door. She opened it and nearly burst into tears when she saw him. Sidney looked haggard and raw in his dirty suit, but made a gallant display of having returned to see her.
As she closed the door behind him, he breathed a sigh of relief. He was finally safe. But not for long. Sidney stayed with Olga on September 3rd and 4th, posing as Comrade Walensky, a member of the Soviet administration. This was how Olga knew him, and Sidney couldn't risk telling her the truth about his different names. A smart choice, because on September 5th, Olga was arrested by the Cheka.
The secret police were closing in on Sidney and Olga, terrified, was talking. The Comrade Rolinski legend was burned and the Cheka already knew his other aliases too. When the police raided Olga's apartment, Sidney himself was gone, meeting a contact from the British embassy named Captain George Hill.
Captain Hill was an official member of the embassy staff on a diplomatic visa, but he was also secretly an MI-1 agent gathering intel on the quickly deteriorating Soviet situation. Because of his dual missions, Captain Hill had an alias to use on his clandestine meetings. His second passport was under the name George Bergman.
If Hill would give Sidney that Bergman alias, he might be able to get out of Russia alive. Hill didn't need the fake passport to get home, after all. He could leave the country legally with the official embassy staff. Hill agreed to the scheme, and Sidney left the meeting carrying a new passport. There was only one problem. Sidney didn't have a beard, and George Bergman, according to his papers, did.
Sidney considered using a disguise, but it was too dangerous. If he was found wearing a fake beard, the Cheka would shoot first and ask questions later. And while Sidney had many ambitions, ending up in front of a Soviet firing squad was not among them. He would need to wait for his facial hair to grow out before crossing the border.
Sidney went underground for the next four days. As each day passed, his beard grew. So did his anxiety. He might get out of Russia, yes. But he had completely failed his mission. On these dark nights, Sidney felt deep pangs of fear. Fear that he would die without redeeming himself. Hopefully, the beard would give him that chance at redemption.
By September 8th, Sidney felt he could safely pass as George Bergman. He bought a ticket for an 8:30 p.m. train out of Moscow. And he had a stroke of luck. He shared his train compartment with a German diplomat. Sidney spoke fluent German and they had a lively conversation. When the Cheka boarded the train to check tickets, Sidney pretended to be part of the German diplomatic envoy and was left alone.
The train finally arrived in Petrograd, now known as St. Petersburg. Sidney knew his best bet was to head to Finland, which had just become independent from Russia, but he couldn't take a train across the Soviet border. Every passenger and passport would be inspected closely. He would have to go by sea.
It was uncomfortable, but safer. He paid a Dutch merchant captain 60,000 rubles, the last of his money, for passage on a small boat. After a dangerous stop in German-occupied Estonia, the boat docked in Helsinki, the capital of Finland. Sydney had escaped.
He made his way to the British Embassy, and by November 8th, 1918, Sidney was back at MI1 in London, wearing his customary tailored suit. Mansfield Cumming, the head of British intelligence codename C, was impressed by the amount of information Sidney had gleaned during his time in Russia, even if the plot to kill Lenin had been foiled. The spy master awarded Sidney the Military Cross,
one of Britain's highest honors. But the medal wasn't enough. Sidney couldn't accept failure. The Soviets reviled everything he admired, including wealth, education, and personal success. They'd taken over his homeland with their reign of tyranny, starving their citizens and executing dissidents. Even innocent women and children were put in work camps.
Plus, they'd foiled all Sidney's plans, embarrassed him. He was committed to ending the Soviet reign of terror, even at his own expense. Some things were more important than money. Sidney was now in his mid-forties and had a sense of greater purpose he had never felt before. He described this feeling in a letter, writing:
But the intelligence chief did not agree.
See told Sydney in no uncertain terms that it was not in the interest of the British Secret Service to sponsor his personal vendetta against the Soviets. Russia was still considered an ally, and there were other concerns in Europe. There would be no more missions against Lenin. Sydney, however, couldn't take no for an answer. On the surface, he calmly accepted See's verdict and agreed to continue working for MI1,
But he would continue pursuing his new mission on his own time. During his assignments for MI1 over the next four years, Sidney worked to create and financially support an expanding network of anti-Soviet contacts throughout Europe. See eventually took notice. By January of 1922, Sidney's support of the anti-Bolshevik movement was too public to ignore.
He was meeting known Russian agitators and bringing them to official events. And his personal vendetta was starting to affect his official duties, too. His intelligence reports were vague, unless they concerned Russian activities.
C knew Sidney had always put his own interests first, but this pattern of behavior was unacceptable. When, in 1921, Sidney asked for a British visa for a man named Boris Savinkoff, C denied the request. Savinkoff was a former high-level member of the Russian government who had fled to Paris. He was now an outspoken anti-Soviet leader.
Sidney wanted to bring him into MI1 as an asset, collecting information for the fight against communism. But C disagreed. Writing in a letter on February 1st, 1922, "The last thing in the world we should wish is to become embroiled in any way with Savinkov." Sidney was enraged. He felt betrayed.
Didn't his superior understand the threat the Soviets posed to freedom and the way of life he and all of Europe held dear? Sidney took matters into his own hands and went behind C's back to approach the passport office directly. This was the final straw. C fired him from the Secret Service. Sidney was horrified.
His famed career in British intelligence had reached an ignoble conclusion at the young age of 49. And on top of it, he had spent all his money supporting anti-Soviet propaganda efforts. Sidney Riley was no longer a wealthy playboy spy. He would have to reinvent himself to continue the fight. Coming up, Sidney finds a new way to sabotage the Russians. Now, back to the story.
In late 1922, Sidney Riley was 49 years old and no longer an operative for the British Secret Service. He had vowed to fight the Soviet menace at all costs, but his passion had taken a high toll. MI1 had fired him for insubordination. He had very little money, and though he had been a womanizer for so much of his life, he was now alone. So, he did the only thing he could think of,
He tried to rebuild his funds by turning to business. He traveled Europe using his charm and language skills to insert himself as a middleman into business deals. But it was a different kind of deal that really turned things around for Sidney. In December 1922, he met a 29-year-old actress named Pepita Bobadilla at the Hotel Adlon in Berlin. The petite brunette was a brilliant conversationalist who loved storytelling.
They quickly fell for each other. Five months later, on May 18th, 1923, they were married at a courthouse in London's Covent Garden. There seemed to be shades of Sidney's playboy, money-seeking habits to the marriage. Pepita was independently wealthy, with a significant inheritance from her first husband, not so different from Sidney's first wife, Margaret.
But Sidney's marriage to Pepita revealed a sensitive part of his personality. For the first time in his life, he stopped pursuing other women. Though Sidney and Pepita were able to live off her money for a while, Sidney was still set on rebuilding his own fortunes. He had to continue supporting his anti-Soviet network. And his efforts to land deals in Europe were flailing. But he had a promising lead in Paris.
In the spring of 1923, Boris Savinkov wrote to Sidney regarding an unspecified urgent matter. Sidney was exhilarated to hear something from his network, other than the ongoing requests for funds he didn't have. He wondered if Savinkov had a new plan to topple the ruthless Stalin, or perhaps he'd discovered some new intel that Sidney could use against the dictator.
For the first time in months, Sidney felt real hope and the familiar excitement of espionage. In July 1923, he and Pepita traveled to Paris. It was time for a new mission. Sidney met Savinkoff at the Chatham Hotel, a swanky establishment in Paris. Sidney felt right at home back in his luxurious game of cloak and dagger theatrics.
Then, Savinkov told Sydney about the Monarchist Union of Central Russia. It was an anti-Soviet underground collective within Russia itself, comprised of high-ranking members of the communist government. Savinkov had received letters and met several agents of the union, and he was convinced of their authenticity. This was their chance to marshal their expatriate forces against Stalin.
Sidney was stunned. A complete network of ranking Soviet officials ready and willing to overthrow the dictator? It was almost too good to be true. Sidney's espionage instincts kept him calm, even though they were a few years out of practice. He asked for proof of Savinkov's claims. Savinkov had a handwritten letter sent to him by a member of the Union. The signature was familiar to Sidney.
It was from an officer named Upperput. He was an old contact from Sidney's days in British intelligence. But it had been a long time since Sidney had heard from him. For all he knew, it could be a Soviet ruse. Sidney was concerned, but Savinkov was convinced. On August 20th, 1924, he crossed the border into the Soviet Union and met with his Union contacts.
But the very next day, Savinkov and his compatriots were arrested outside of Minsk by the OGPU, the secret police that would one day be called the KGB. On August 29th, Russian newspaper Izvestia began publishing details of Savinkov's trial and confession. Sydney followed the story closely, growing more agitated with each new detail.
By mid-September, it was obvious that Savinkov had given up names, dates, and plans. Sidney was furious with his old comrade for being so gullible, but more than anything, he was disappointed. Sidney felt like the spy world had left him behind. His contacts were outdated, and his instincts were dulled.
He was 50 years old, but felt even older. He had varicose veins in his legs and wore special elastic socks. Even his charm sounded paternalistic at his age. He was not the silk suit playboy he once was. Perhaps it was time to get out of the espionage world, permanently. Sidney and Pepita returned to New York. But even in business, Sidney met defeat.
His money was gone and his ambition wasn't going to put food on the table or buy his shirts and socks. And however depressed and destitute he might be, he still took pride in his appearance. The winter of 1924 was a dark, cold season for Sidney. He spent long nights wondering what had happened to his former glory as the ace of spies. Then, on January 24th, 1925,
The world of espionage reached out once more. A former British intelligence contact named Commander Boyce sent a ciphered letter to Sidney's business address in New York. When Sidney saw the signature, his excitement was palpable. The decoded letter said that the Monarchist Union of Central Russia was a genuine anti-Soviet group. And despite Savinkov's betrayal, they were still active.
Now, the Secret Service needed someone to go into Russia to reestablish contact. The letter sender, Commander Boyce, was a fellow agent. And in fact, he had become the head of the MI-1 station in Helsinki, Finland. To Sydney, his credibility was without question. They wanted him back. And for a mission against the Soviets, no less. This was his chance for redemption.
Unfortunately, Sidney didn't know that Boyce hadn't conferred with London before sending his letter. Boyce wasn't inviting Sidney to join MI1 again. He was only using the old spy as an asset. This way, if something went wrong, Boyce wouldn't lose one of his own valuable agents. Sidney was expendable. Another vital correspondence from Boyce arrived on March 9th, 1925.
The text of the letter hinted that there was a secret note hidden on the paper itself. Sidney set down the letter with trepidation and went to find some iodine. According to declassified CIA documents, during the First World War, the Allies discovered that iodine vapor would turn all invisible inks brown. It worked by revealing where the paper's fibers had been altered with moisture.
As a former agent from the World War, Boyce knew Sidney would have experience with this type of communication and could reveal the secret message. He was right. Sidney held the letter over a saucer of the dark liquid iodine and another secret letter slowly appeared.
It was a message directly from the Union, and it gave Sidney the address of an agent named Nicholas Bunnikov, who was in close contact with the authors. Sidney was exhilarated. His old espionage techniques felt like a clandestine game he had almost forgotten how to play, but here he was on a new mission.
He expressed his happiness in a letter to Boyce, dated March 25th, 1925, the day after his birthday. "I was 51 yesterday and I want to do something worthwhile whilst I can. All the rest does not matter." Then he wrote a letter to Bunnikov to schedule a meeting with the Union. After months of waiting, Sidney finally received a telegram confirming that the Union was ready to meet him as soon as he could return to Europe.
This was all Sidney needed. He and Pepita departed New York on August 26, 1925. It was the last time Sidney would ever see America. Upon their return to Paris on September 3, Sidney and Pepita had dinner with Commander Boyce.
He was convinced the Union was still devoted to ending Stalin's rule. All the group needed was a strong leader to rally them to action. Sidney fancied himself as the perfect candidate. His old confidence was rising. It was dangerous. Sidney had been sentenced to death for the attempted coup against Lenin in 1918. If the OGPU caught him entering Russia, he'd be shot on sight.
But he believed his whole career, his whole life, had led him to this mission. From Odessa to China to Germany, Sidney had cultivated his espionage skills to lead the final charge against the Soviet menace. On Sunday, September 20th, Sidney made the Baltic Sea crossing to Helsinki. The trip was rough and Sidney felt ill.
His health wasn't up to these long, arduous journeys anymore. When he arrived, he dashed off a quick letter to Pepita, lamenting his pain. The next morning, he met Bunnikov for tea. Bunnikov had established a rendezvous with the Union representatives in the small town of Vyborg, not far from the Soviet border.
Given his past troubles with the OGPU, Sidney wouldn't actually have to cross over. He would stay safely within Finland's borders. He and Bunnikov boarded a train for Vyborg on September 25th, 1925. Sidney dressed his best for the meeting. He pulled up his new silk stockings and adjusted his yellow leather shoes. Then he ran a comb through his slick hair.
He wanted to impress as a dashing spy. But impressing the senior Union agent, Alexander Yakoshev, would take more than a dashing appearance. Yakoshev began the meeting by saying it was a pity that Sydney had traveled all this way but wouldn't visit the Union leaders in Moscow if only Sydney were not afraid of what had happened so many years ago. Sydney had doubts.
He knew the risks of crossing the border, and he had Pepita to think about now. But he also had the same hubris and confidence that had led him to undertake so many dangerous missions as a young man. Surely he could survive a short trip with his new assets? With a confident, excited grin, Sidney agreed to go to Moscow.
He crossed into the Soviet Union with Yakoshev on September 25, 1925. It was the last time anyone verifiably saw Sidney Riley alive. Coming up, Sidney's final days in Moscow are shrouded in mystery. Now, back to the story. 51-year-old Sidney Riley crossed the Soviet border on September 25, 1925.
intending to meet with high-level members of the Monarchist Union of Central Russia, a group of alleged anti-Soviet agents hiding within the ranks of Joseph Stalin's tyrannical government. He promptly disappeared. On September 30th, the first reports appeared that something had gone wrong with Sidney's mission. There was a small notice in the Soviet newspaper Izvestia that read:
On the night of September 28th, 29th, four smugglers attempted to cross the Finnish frontier. Two were killed, one was taken prisoner, and the fourth, mortally wounded, died on the way to Leningrad. September 28th was the night Sidney was supposed to return to Finland. As soon as the story was published, rumors began flying that one of the so-called smugglers was him.
Meanwhile, Pepita was waiting for her husband in Hamburg. She was growing more anxious by the hour. She'd heard nothing from him since he arrived in Vyborg on September 22nd. Then she received a new letter from Sidney. He had left the note with Nicholas Bunnikoff before he crossed the border, to be delivered to Pepita only if something were to happen to him. The letter expressed Sidney's deep love and commitment to his wife.
It was unusual for him to write his feelings with such clarity and vulnerability. As Pepita read through her husband's final letter, she began to sob. He wrote, "My most beloved, my sweetheart, I am doing what I must do with the absolute inner assurance that you would approve. You are in my thoughts always, and your love will protect me. I love you beyond all words. Sidney."
Bunnikov sent off the parting note once he was sure Sidney was dead. The last sign of life was a short postcard from Sidney to Commander Boyce, dated September 27th, stating, "All was well." When the British government inquired, the Soviets confirmed the wanted spy had been shot while escaping arrest at the border, just as the newspapers had said.
By the end of 1925, an obituary appeared in the London papers saying: "On the 28th of September, killed near the village of Alekul, Russia by OGPU troops, Captain Sidney George Riley, beloved husband of Pepita Riley." But Sidney Riley was still alive. Sidney hadn't been shot at the Finnish border.
Yakoshev had brought him to Moscow, where they met with several of the alleged Union officers, discussing plans to subvert the government. On September 28, 1925, Sidney and Yakoshev were ready to return to the border just as planned. They slipped into the backseat of a car and drove to the train station. As Sidney adjusted his coat to settle in for the ride, Yakoshev slapped a pair of handcuffs around his wrists.
Suddenly, the driver sped off down the street, driving deeper into Moscow city center. Sidney told Yakishev this must be a misunderstanding. But Yakishev was silent until the car slammed to a stop in front of an enormous brick building. They had brought Sidney to Lubyanka prison, an infamous dungeon for dissenters and enemies of the state. Many people who went in never came out. The union had been a scam.
It was a front for the Soviet secret police, a long con developed in 1921 to entrap enemy agents, and the ace of spies had been at the top of their wanted list. Sidney's desperation to prove himself, to return to his status as ace of spies, had led him right into their trap. Sidney was held at Lubyanka for several weeks after his arrest.
He was never tortured, but he was interrogated often. By October 7th, 1925, the Soviets had a statement from Sidney that outlined his entire career of espionage in Russia. But Sidney refused to reveal any specific names or details of his current network. He didn't give his captors any information they could use in their hunt. This was going to be Sidney's last stand.
He managed to string along the Soviet interrogators until the end of October, but then they gave him an ultimatum. He would turn over details of his network or face the consequences. Sidney's response was simple. He said, "I am unable to agree." After this, Sidney began to keep a scattered diary written in pencil on torn cigarette papers.
He wasn't able to write much, but he wanted to keep track of the days. He was certain he didn't have many of them left. On Friday, October 30th, 1925, Sidney's journal entry said, "The execution will take place immediately. They gave me one hour." Sidney collected his things into a small package for Pepita. Then he smoked the last of his cigarettes and waited.
When the executioner returned, offering one last chance for Sidney to reveal names, he refused. Sidney was handcuffed and left in his cell for a few minutes. He heard the executioner loading his machine gun in the corridor. Sidney was resigned to his fate. But he didn't feel fear.
He thought about his long career, about Pepita, and about the decisions that had brought him here to this cold, dark cell in Moscow. And then the executioners returned. They took Sidney to a car and drove him out into the countryside. Now Sidney's heart was racing. He was being driven to his death, and there was no escape. Suddenly, the driver brought the car to a halt
He said there was something wrong with the radiator. They would have to turn back. Sidney was put back in his cell and told his execution had been postponed until tomorrow. That night, Sidney wrote in his diary, was terrible and full of nightmares. As he huddled in the dark, looking at a small photo of Pepita, Sidney finally broke. He began to cry and said a prayer. The Soviet trick had worked.
The psychological torture technique, which spy historian Andrew Cook called "the mock execution," was meant to bring a captive up to the moment of their death and then grant reprieve. The scared captive would then give in to their interrogators in order to prolong their life. Sidney agreed to tell the OGPU anything they wanted to know. But he didn't have specifics about current MI-1 operations in the Soviet Union.
He'd been fired four years ago. His value to the Soviets was dwindling, and Sidney knew it. His final journal entry was dated on the night of November 4th. He wrote, "Very weak. Feel at ease about my death." By November 4th, the OGPU recognized that Sidney had no more information to provide, and the Soviet government couldn't risk keeping a British spy captive indefinitely.
If rumors got out, it could cause a diplomatic crisis. The order to kill Sidney came from Stalin himself. At 8:00 p.m. on November 5th, 1925, four OGPU officers collected Sidney from his cell and escorted him out for his evening walk. This was typical, as Sidney was often allowed out into the nearby Sokolniki Park for exercise. A little after 8:45 p.m.,
The driver stopped the car and claimed he needed to repair an issue with the car. Two of the officers suggested they stretch their legs while they waited. As they walked away from the car, one of the officers, Ibrahim Abisalof, dropped back a few paces. Abisalof fired a single shot that struck Sidney in the back. He fell without a sound and the other officer fired one more round into his chest.
They waited 15 minutes to make sure Sidney was dead. Then they drove to a nearby morgue where a doctor and photographer were waiting. They took three pictures of Sidney's corpse, then placed him in a coffin. On November 9th, 1925, Sidney was buried in the interior courtyard of the prison. The ace of spies was no more. At least...
That was the story a single KGB officer revealed years later. But there are other contradictory stories about Sidney's fate. Years later, Soviet defectors reported that a British spy was still being held in Nubianka prison. Other agents said Sidney himself had defected to the Soviets in 1925 and was happily living in Russia.
In 1929, two MI1 informants claimed to have spotted Sidney in Berlin and Paris that year. Or perhaps, as the official Soviet story claimed, he was shot while trying to illegally cross the Finnish border. The mystery surrounding his death has never fully been resolved, but it only serves to heighten the intrigue of Sidney Riley, Gentleman Spy.
Pepita's efforts also ensured Sidney's legacy survived. She published her husband's memoirs, a short series of journal entries written by Sidney, along with Pepita's own recollections of their time together. Many of these stories seemed grandiose and improbable, but the book attracted attention in London's literary circles. Winston Churchill himself read the account to ensure Sidney's widow hadn't revealed any discreet stuff.
Pepita lived until 1973, surviving off the proceeds from the book. Sidney's exploits survived him in fiction, too. After learning of Sidney's personality in Escapades, Sir Ian Fleming developed the hero spy character James Bond in a series of best-selling novels.
Today, Bond remains one of the most well-known fictional spies of all time, thanks to the extremely popular film adaptations of Fleming's books. But the story's never quite lived up to the real man, proud, passionate, and dashing as he was, even in his many dark moments. As Fleming once wrote, "Bond is just a bit of fiction I made up. He's no Sidney Riley."
Thank you for listening to Conspiracy Theories, a Spotify podcast. Be sure to check us out on Instagram at The Conspiracy Pod. For more information on Sidney Riley, amongst the many sources we used, we found Britain's Master Spy: The Adventures of Sidney Riley, a narrative written by himself, edited and completed by his wife, by Sidney Riley and Pepita Bobadilla, extremely helpful to our research.
Until next time, remember, the truth isn't always the best story. And the official story isn't always the truth.
Conspiracy Theories is a Spotify podcast. This episode was written by Andrew Messer, with writing assistance by Kate Gallagher, fact-checked by Haley Milliken, and sound designed by Trent Williamson, with production assistance by Ron Shapiro, Carly Madden, and Freddie Beckley. Our head of production is Nick Johnson, and Spencer Howard is our post-production supervisor. I'm your host, Carter Roy.
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