Will the Real Sidney Reilly Please Stand Up?

Welcome to Criminalia. I'm Maria Tremarquis and I'm Holly Frying. Many knew the man on the hot seat today as Sidney Riley, but he was born Sigmund Georgevitch Rosenbloom. Probably, in fact, most of what is known about him should probably be qualified as a Probably what else but a tangled web would you expect from the most accomplished spy in history. Though right much of what historians think they know about him may be false. Because Riley was a

master of deception. Siegmund Rosenbloom turned himself into a man with more than a dozen identities. He became a businessman and multi lingual Khan man whose real line of work

was espionage. By the beginning of the twentieth century, he was working as an agent for the British Intelligence Agency, assigned to spy on expat communities in Paris and London, with dispatches to Germany, the Russian Empire, and across the Far East, a European term referring to the geographical regions that include East and Southeast Asia, as well as the Russian Far East. Rosenbloom was born on March seventy four into a Polish Jewish family with an estate at Bielsk

in the Grodno Province of Imperial Russia. Grodno, now a city in western Belarus, is near the Polish and Lithuanian borders. He was the only son of Paulina and Gregory Rosenbloom, a pianist and contractor, respectively. Or maybe he wasn't. Some reports suggest he was born in eighteen seventy three in Odessa, Ukraine,

then part of the Russian Empire. Author Andrew Cook, in his book Ace of Spies The True Story of Sidney Riley, states that Riley was born on March seventy three as Solomon or Shlomo Rosenbloom in the Jewish care soon Berna of Imperial Russia. He writes that the man who called himself Sidney Riley was the illegitimate son of a woman named Paulina, who was Riley's acknowledged mother, and a doctor Mikhail Rosenbloom, the first cousin of Riley's presumed father, Gregory.

Is he right? There's always that? But though, isn't there? But uh so? Riley told several wildly different versions of his own origin story on purpose. As a spy, he always wanted to confuse and mislead other people. He would tell the story that he was the son of a merchant marine captain and his acknowledged true mother, Paulina. It's also said that he claimed to have been born to an Irish sea captain, or sometimes it was an Irish clergyman, or a habitue of the imperial court of Czar Alexander

the Third of Russia. Riley himself really liked to tell one particular origin story that historians know today just absolutely does not add up. His birth name, he claimed was Georgie, and he told this tale about his beginnings once while

attending a chemistry course in Vienna. He was called back to Odessa for his mother's funeral, and during the ceremony, as Riley told it, his uncle revealed that the child Georgie, was actually the result of an affair between his mother and a doctor rosen Bloom, a Jewish physician who had

treated her for an unknown condition. Riley claimed he chose to take the doctor's name, but recent evidence suggests that though Riley never wavered from his deception, and he told this story a lot, the doctor rosen Bloom in the original tale that he told was a fabrication. The doctor in question was Riley's uncle that he used as a character in his yarn. The whole thing was just false. He had borrowed from reality and twisted it into something new.

Riley's tale continued because he also claimed that he faked his death in Odessa's harbor and stowed away a board of ship bound for South America. He claimed to have saved three British officers on an expedition into the Amazon, who then offered him passage to England in gratitude. That would have happened right around, but there are no records to substantiate these claims. We do know, though, that Riley did arrive in England in and it wasn't long before

he became involved in clandestine affairs. Before the Russo Japanese War. He spied for, actually he spied for a few places. He's fined for both the British and Japanese. In Port Arthur. There he's still Russian plans for the Harvard Defenses, passing

them to the Japanese for a naval attack. When several British ship building firms discovered that Riley had gotten the contracts for the Germans instead of the British, they considered his actions to be bordering on treason, But that accusation felt at the side when the Admiralty began receiving copies of German naval plans. He'd posed as a welder in

the corrupt gun works, supposedly stealing German armament plans. But most, maybe all, of Riley's actual accomplishments are murky and controversial. So we're really not even going to talk about his assignments, not many of them, at least, because we'd be fighting with what might be act and what might be fiction. To talk about Riley is to talk about his legend. Some historians see him playing a double role in some events, such as selling munitions to both the Germans and the

Russians during the First World War. Historians have also established that Riley was entrusted by the British Secret Service with espionage and Russia through relationships he was able to develop through his miracle cure business. Uh, you did not mishear that that was his miracle cure business. And if you were not expecting that, neither were we. By eighteen ninety six,

Riley had also established himself as a consulting chemist. Within nine months of his company's launch, he became a fellow of the Chemistry Society and a member of the Institute of Chemistry. His business, though, was not what it appeared to be. He was manufacturing and distributing so called miracle cures to an unsuspecting public. Literally, he was a snake oil salesman. And that is how Ryle met his first wife.

And on that thought, we're going to take a break for a word from our sponsor, and when we're back, we'll talk about how Riley's personal relationships were as murky as his work. Welcome back to CRIMINALLYA Let's talk about how Sigmund Rosenbloom got his first British passport allegedly in Riley met year old Margaret Thomas. The short version of the story is that he married the widow Margaret Thomas at the Holborn Registry office in London on August, but

there's a whole lot more to it than that. There are many versions and many tales of Riley the Womanizer. Many historians believe Riley and Margaret had an affair while she was married to sixty three year old Reverend Hugh Thomas. Riley and the Reverend met in London through Riley's Ozone Preparations company, which peddled all sorts of fake cures. The reverend had kidney inflammation, which was reportedly attributed to Bright's disease, and he was intrigued by the cures Riley could offer him.

Thomas introduced Riley to Margaret at his manor house, and an affair developed between the two over the next few months. On March four, the Reverend updated his will and appointed Margaret as executor. A week after finalizing that new will, Reverend Thomas traveled with his nurse to the new Haven Harbor Station hotel. On March twelve, in that same hotel,

the reverend was found dead in his room. No one, it seems, could remember any specific details, but there had been a doctor, doctor T. W Andrew, who matched the physical description of Sidney Riley, who had appeared at the hotel to certify Thomas's death as influenza. Among the documents he signed was one claiming that there was no need for an inquest. Records indicate that no one calling themselves

Dr T w Andrew existed in the British Empire. In or around about six weeks later, Margaret inherited roughly eight hundred thousand pounds. The Metropolitan Police, whom Riley may or may not have been connected to, did not try to locate or investigate a doctor T. W Andrew, nor did they investigate the nurse who Margaret had hired to care for her husband, even though the nurse was previously linked to the arsenic poisoning of a former patient. A few

months later, on August, Riley and Margaret got married. Giles Milton, the author of Russian Roulette, How British Spies Thwarted Lennon's global Plot, has quote All accounts agree that he had a seductive charm, loving women as he loved himself, a string of mistresses would fall under his spell. Monogamy did not come naturally to Riley, and although he was usually fastidious in his choice of women, it did not prevent him from cavorting around London on one of his visits

with a common tart named Plugger. Margaret was the first of an unverifiable number of Riley's wives and mistresses. Estimates suggests he may have had three or four wives and at least six regular mistresses. His relationships are as elusive to pin down as his work. At least two of Riley's marriages were witnessed by members of the British Secret Intelligence Service, who knew that they were big amous, but said nothing because they too were involved in the deception.

He once entertained the wife of the assistant to a Russian minister, a woman named Nadine Messino. Not long after she met Riley, he reportedly planted stories in Russian newspapers claiming that his wife, Margaret, had died in a train crash, and he then paid Nadine's husband a large sum of money to divorce her. Nadine and Riley married in New York City in nineteen sixteen, Margaret, though had not died

and Riley was committing bigamy. In nineteen Riley and Nadine divorced, and although Riley was still legally married to Margaret, in two he committed bigamy again when he married a young actress named Pepita Bobadilla Nelly Louise Burton. Pepita described their first meeting in Berlin, quote, for a moment, his eyes held mine and I felt a delicious drill run through me. And that's the thing about Riley. Through the accounts of those who knew him, we know that Riley's character definitely

left an impression. He was suave, self confident, and charming. It said he was generous with his friends, he enjoyed gambling, both with his money and with his life, but he could also be cold and pragmatic, capable of using any means necessary to get what he wanted. On his personal stationary was the motto mundo no la fetus, which translates as put no faith in the world, or even more simply, trust no one. According to Richard B. Spence, the author

of Trust No One. The Secret World of Sydney Riley, Riley was a quote, mercenary of a rather specialized sort, a freelance entrepreneur in the business of information and influence. Commenting on his own character, Riley was known to describe himself as quote a practical man. But back to Margaret.

There were many women. But marrying Margaret gave Riley the wealth that he had desired at a time when he really needed it for travel, and it also provided a pretext to discard his identity of Sigmund Rosenblue for a fresh new I Wish origin story. Marriage helped him craft the identity of Sydney George Riley. Riley was a surname in Margaret's family, or maybe it wasn't marriage that had anything to do with that first passport of questionable origin.

Author Richard B. Spence writes of the Riley name quote in eight he became Sydney George Riley by receiving a passport in that name, though he never legally adopted it or became a British subject a patron. Possibly his way into British intelligence was Sir Henry Josier, powerful Secretary of Lords connected to the War Office Intelligence branch. With his strong Jewish features and accented English Riley was an unconvincing Englishman,

but this became his favorite of many alternative identities. Riley's new British passport could also have been a cover identity created by William Melville, who was the first chief of the British Secrets Ervice Bureau, which was the precursor to m I five. According to True Prime author Brian Mariner, and we definitely believe this Riley quote possessed passports in eleven different names. Allegedly he spied for at least four countries,

and we think that number is higher than four. Secret Intelligence Service Captain Mansfield Smith coming one set of Riley that he was quote a man of indomitable courage, a genius as an agent, but a sinister man who I could never bring myself to holy trust. It's believed that as well as working for the British government, Riley was

also spying for the Czarist regime of Imperial Russia. The newly named Sidney Riley, with his new bride, moved to St. Petersburg, where he immediately became friendly with members of the revolutionary underground. Richard Deacon, author of a history of the Russian Secret Service, writes that quote he was certainly being well paid. As of nineteen o six, he had a lavish apart mean in St. Petersburg, a splendid art collection, and was a

member of the most exclusive club in the city. Although still married, Margaret becomes less of a character in Riley's story. Around this time. She remained in St. Petersburg while Riley went on assignments from the British Secret Service Bureau. One early assignment, it's reported, was to survey the Caucuses for its oil deposits, compile a resource perspectus, and report the

findings to the British government. Such the life of a burgeoning spy, Riley, who spoke several languages, including German, used his linguistic skills to join the German army on the Western Front. After the First World War broke out in nineteen fourteen, Great Britain received detailed information from him on German troops which he sent. It said by carrier pigeon, we are going to take a quick break here for

a word from our sponsor. Many modern historians consider Riley to be the first twentieth century super spy, but was he the inspiration for the character James Bond? Welcome Back to criminalia. Let's talk about Riley's arrest and execution and how he may have been undermined by another British agent. Riley returned to Russia in the aftermath of the Bolshevik Revolution in an attempt to both give aid to anti Bolsheviks and to top of Vladimir Lenin, the head of

the Bolshevik Party. The most often cited plan is this he had prepared a covert plot to use the disillusioned guards protecting the Kremlin to kill key figures in the Soviet government, including Lenin, at a meeting at the Bolshoi Theater. In a twist of fate, his preparations were undermined by another assassination attempt on Lenin, this by Fanny Kaplan, which triggered the Red Terror that resulted in the deaths of

hundreds of thousands of suspected counter revolutionaries. Once news reached the press, Riley was vilified as a key conspirator and he was sentenced to death in absentia. A man hunt was ordered, but Riley had vanished by the time the secret police reached to St. Petersburg apartment. Riley escaped through Finland, but he was lured back to Russia by a faith organization created by the Joint State Political Directorate to capture him.

The Joint State Political Directorate, or o g p U as it was called, was the intelligence and State Security Service and secret police of the Soviet Union from nine to nine thirty four. Earnest Boys, the British Secret Intelligence Service station chief in Helsinki, wrote to Riley asking him if he would meet the leaders of the Monarchist Union of Central Russia, a right wing nationalist organization out of Moscow.

Riley replied, quote, much as I am concerned about my own personal affairs, which as you know, are in a hellish state, I am, at any moment, if I see the right people and prospects of real action, prepared to check everything else and devote myself entirely to the syndicate's interests. I was fifty one yesterday and I want to do something worthwhile while I can. He met with Boys in

Paris before crossing the Finish border on September. Two days later, during that meeting in a safe house outside of Moscow, he was arrested by the Russian secret police for his attempts to overthrow the Bolshevik government. Riley had been one percent convinced that he would be meeting with the leaders of an anti Bolshevik group. There were claims that Boyce was a double agent and had been paid for information about British intelligence agents, but this, like other stories, has

many versions. In this version of Riley's life story, Voice may have been responsible for betraying him through a counter intelligence operation run by Soviet agents. That operation, called Operation Trust, ran from nineteen twenty one to nineteen twenty six, and it was created specifically to tease out the man the Soviet intelligence groups considered their most formidable enemy, and that

was British agent Sydney Riley. Riley was brought to the Yanka prison in Moscow, and the man incarcerated in Cell seventy three was kept a closely guarded secret. According to the Soviet account of his interrogation, Riley wasn't physically tortured, but he was subjected to severe psychological torture, including a mock execution, an act that terrified him enough to possibly

sign a confession. Though he was willing to give full information on the British and American intelligence services, Riley's appeal failed. Riley was regularly taken from the Lebyanka prison after dark and driven to the Soko Niki district for walks in the woods. Riley was always dressed in the uniform of the Soviet Secret Police for these outings. He was a secret prisoner, so all of this was so that his

movements could be concealed. By November four, it was decided that Riley had nothing left to give, and it was believed that the longer he remained alive, the greater the chance word of his incarceration would leak out. Stalin it said, Quote anticipated this situation and ordered his execution on the evening of November five, thinking that he was going for another walk in the woods. Riley was shot in the

back as he walked away from the car. A few years after Riley's death, in May of n one, the London Evening Standard published what they call a master Spy cereal, in which they read articles glorifying Riley's exploits. That twenty years after his execution, a young naval officer named Ian Fleming was working with the Director of Naval Intelligence during

the Second World War. While doing his work coordinating Allied espionage and occupied Europe, Fleming discovered the legend of a spy code named ST One in the archives, and ST One was that's right, Sidney Riley. Years later, Fleming admitted to a friend that his character James Bond was largely based on Riley, but even so, he said, quote, James Bond is just a piece of nonsense I dreamed up. He's not Sidney Riley. You know. Today many historians consider

Riley to be the first twentieth century super spy. In the century since his death, the truth of his life is still quite difficult to distinguish from the lies that he told. His reputation, though, has held fast among members of the intelligence community. One former British Secret intel Leigant Service officer stated quote he was very, very good, a bit of a crook, you could almost say, certainly sharp practice,

but as an agent he was superb. While Agent Double O seven may have accomplished his assignments with the gadgets provided by the creative and innovative character of Q, we can't confirm if he drank a Martini shaken not stirred. World War One spy Sidney Riley's accomplishments were due to his cunning, his wits, his appeal among women, and a

complete lack of a moral compass. There's a pretty obvious connection as we walk into the perfecty poor with James Bond and alcohol, right obviously, yes, yes, for anyone who doesn't know, James Bond's martini, which is called a vesper, was a made up drink. It was not like a drink he was plucking out of historical drink books. That is a made up drink, the books in the films.

That drink, in case you're curious, was three ounces of jim, one ounce of vodka, a half ounce of Lillt blanc or driver mouth, and then a lemon peel for garnish. It's a lot of alcohol, yes, and I thought, let's do that, but we're gonna do it a little bit differently, and we're switching ours up in a way that James Bond would probably be horrified by. I love to horrify a made up person. So here we go. We are calling this Riley's vesper, and it's really a very close one.

So it's the three ounces of gin, one ounce of vodka. Please drink responsibly. This is a lot of drink. Instead of that driver mouth, we're going to do grapefruit liqueur. Here because that yeah, you still get like a bright kind of cutting flavor, but it's nice and it's got a juiciness to it. I would bump that up from half an ounce to more like three quarters because it just helps balance out all of that gin and vodka.

And I would almost like do this and pour it into two glasses and share it with somebody, because that's that's a lot of liquor, a lot of it's almost five ounces of just spirit at that point. And then do your lemon peel or I did one in prep for this to test it, where I did a lemon and a grapefruit peel and I expressed a little of each on top and stuck him on a cute pick and made a cute thing. You are going to shake this like the Dickens in a shaker with ice the

point for that shake and not stir. To say, when you shake it, you're getting more dilution of all of that alcohol a little bit because some of the ice will break down and it will water it down a little bit, which you do actually want in some occasions. And then some people like to double strain of martini like this. You can if you want. I just did it.

Once into a pre chilled glass, because that that very cold glass is going to keep this tasting nice and crisp for you, and not that, oh, that just tastes like a lot of alcohol. It's really fascinating how temperature shifts your perception of flavor when it comes to alcohol. It's a good one, but it is very much like

a heavy hitter. The one thing that my my beloved noted when he and I were testing this was that the smell of the grapefruit actually for him countered that heavy punch of alcohol, like just that aroma of it really like it does something else to your palate, and he found it to not be as biting as like just drinking that much straight alcohol. So the mock tail for this is very different, obviously because this thing is all alcohol, but it's also very fun. It's very easy. Also,

you're just gonna use grapefruit syrup. You can pre buy it. You can also make grapefruit sorr it pretty easily, and then you can add either club soda or ginger ale to it and just make a beautiful grape fruit soda.

If you are not opposed to using bidders, because they do have a slight minuscule alcohol content, a couple of dashes of angist or Bidders did something very cool in this, and it made it like a really yummy drink that kind of has that little bit of bite of an actual alcoholic cocktail, but instead it is well mocktail a refresher. Grapefruit is another flavor that I used to dislike, and I have come around on I'm still not gonna eat a grapefruit, but if you mix it with vodka, I'll

do it. I was about to say, I'm actually not gonna eat a half of a grapefruit, but I love when it shows up in things, and I do love the sentiments beautiful. So uh, that is Riley's vesper And like I said, I don't know if you drank him. I don't think James Bond would like this version, but I like it and I hope you do too. Thank you so much for spending this time with us while we talk about superspies and treason this week. We will be right back here next week with more treason and

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