Sidney Reilly; Greatest Spy

kaylarStarred Page By kaylar, 2nd Apr 2011 | Follow this author | RSS Feed
Posted in Wikinut>Guides>History

Coming as close as possible to the true story of Sidney Reilly, who was called the Ace of Spies

Who was he?

Everything you think you know about Sidney Riley is subject to disclaimer. This is because Riley was truly the 'Ace of Spies'.

He died in the field, so never lived long enough to write that memoir or even reach the stage where he could be partially honest, at least, about who he was.

What is Known, sort of;

Sholom Rosenbaum

He was born in March; either 1873 or 74 in the Ukraine. As a Jew, he had to be born in one of the gubernias, it is assumed the Kherson gubernia. His birth name may have been Salomon (Shlomo) or Gerogi Rosenblum.

It is claimed he was the illegitimate son of Paulina (Perla), his acknowledged mother, and Dr. Mikhail Abramovich Rosenblum, a first cousin of his putative father, Grigory (Hersh) Rosenblum.

Some claim his father was a sailor, a member of the merchant marines who is unknown to history.

What is understood was that as Jew he would learn Hebrew and use Yiddish (which is very much like German) in every day informal speech, as well as Russian.

In Russia

(To avoid confusion in the various names he used in this period, I will refer to him as 'R")

R claimed to have been arrested in 1892 by the Imperial Russian Secret Police for being a messenger for the Friends of Enlightenment revolutionary group.

He said, in one of the versions of his past, that upon release Grigory told him his mother was dead and true father was Mikhail.

R faked his death, adopted the name Sigmund Rosenblum and....

Story One

..... stowed away aboard a British ship bound for South America. This story continues with him arriving in Brazil, taking the name Pedro, and saving the life of a British Major who rewarded him with £1,500, a British passport, and passage to Britain where he became Sidney Rosenblum

Story Two

Sigmund Rosenblum arrived in London in December 1895 from France. According to this story he had murdered and robbed two Italian anarchists who were carrying a great deal of cash they had received from supporters.

What is Known.....

'R' arrived in England resided at the prestigious Albert Mansions, created the Ozone Preparations Company, which peddled miracle cures.

During this time, due to his knowledge of languages, Rosenblum became a paid informant for the émigré intelligence network of Scotland Yard's Special Branch and, later the the British Secret Service Bureau.

Becoming Reilly

In 1897, R began an affair with the wife of the elderly Reverend Hugh Thomas who had come to him for treatment of a kidney inflammation.

On March 4, 1898, Thomas altered his will and appointed his wife Margaret as an executor. A week after the making of the new will, Reverend Thomas and his nurse arrived at Newhaven Harbour Station. On March 12 Thomas was found dead in his bed.

Dr. T.W. Andrew, who matched the physical description of R, certified the death as generic influenza, signed the relevant documents, stating there was no need for an inquest.

There was no Dr. T.W. Andrew in Great Britain at the time..

Margaret inherited about £800,000. Four months later, on August 22, 1898 she married 'R' who now took the name of Sidney George Reilly.

In Manchuria

In June 1899 Sidney Reilly and Margaret traveled to Czarist Russia as British citizens. Margaret remained in St. Petersburg, while Reilly reconnoitered the Caucasus for oil deposits, compiling a prospectus for the British government which paid him.

In early 1901, Reilly and his wife had reached Egypt and then set sail to Japan, shortly before the Russo-Japanese War.

He became a double agent, serving both the British and Japanese interests.

Arriving in Port Arthur, which was controlled by the Russians, Reilly and Moisei (Moses) Akimovich Ginsburg purchased quantities of food, raw materials, medicine, and coal and were the epitome of war profiteers..

Perhaps True...

Perhaps true....

In January 1904, he and, Ho-Liang-Shung, stole the Port Arthur harbor defense plans for the Japanese Navy which enabled the Japanese Navy to navigate through the Russian minefield protecting the harbor.

There is a claim that after this, Reilly went to Imperial Japan with a mistress, but we know he arrived in Paris in June 1904 and met with William Melville who used Reilly's expertise in what would later become known as The D'Arcy Affair

D'Arcy Affair

In 1904, the Board of the Admiralty realised that petroleum would supplant coal. William Knox D'Arcy - who later founded the Anglo-Persian Oil Company (APOC) - had obtained valuable concession from the Persian government and was negotiating a similar concession from the Ottoman Empire for oil rights in Mesopotamia.

The British Admiralty wanted D'Arcy to sell his newly acquired oil rights to the British Government rather than to the French de Rothschilds

The Story Goes

The Story goes;

according to Reilly, he boarded Lord de Rothschild's yacht attired as a Catholic priest and secretly persuaded D'Arcy to terminate negotiations with the French Rothschilds and return to London to meet with the British Admiralty .

But it might be....

Just a story as at the time Reilly would have still been in Manchuria.

Reilly did stay in the French Riviera on the Côte d'Azur after the D'Arcy affair, near the Rothschild yacht.

Another Story

The German's had developed a magneto which they were displaying at the first Frankfurt International Air Show in 1909.

A German plane crashed, killing the pilot. The engine had the magneto. Reilly and a British SIS agent posing as a pilot diverted attention while they removed the magneto from the wreck and substituted another. The SIS agent made detailed drawings, and then when the wreckage was in a hangar, the agent and Reilly restored the original magneto


this never happened.

And Another Story

The Brits knew nothing about the types of weapons being forged inside Germany's war plants. Reilly was sent to find out..

He arrived in Essen, Germany, in 1909 posing as a Baltic shipyard worker by the name of Karl Hahn. He gained a low-level position then joined the plant fire brigade.

He persuaded its foreman that a blueprint of the plant was necessary for safety. He was successful and the schematics were lodged in the foreman's office for members of the fire brigade to consult.

Reilly used lock-picks to break into the foreman's office, was discovered, strangled the foreman, took a train to Dortmund to a safe house, tore the plans into four pieces, mailing each separately.

Or this never happened.

The Facts suggest....

According to some sources Reilly' was living in New York between 1914 - 1915 selling munitions to both the Germans and Russians.

There is evidence that Reilly approached Norman Thwaites, MI1c Head of Station in New York, seeking a job in 1917-1918. Thwaites wrote a letter of recommendation to Mansfield Cumming, head of MI1c and told Reilly to visit Toronto to obtain a military commission.

This would explain why Reilly joined the Royal Canadian Flying Corps.

Officially Sworn In

On Reilly's return to London in 1918, Mansfield Cumming formally swore Lieutenant Reilly into service as a staff Case Officer in His Majesty's Secret Intelligence Service (SIS), then sent him on Counter-Bolshevik operations in Germany and Russia.

Clearly this would be a perfect deployment for him, as he appeared to be the upper class Brit, Sidney Riley, not the Russian/German speaking Shlomo Rosenbaum.

Now here's the quandary...

Did the Allies launch a clandestine operation to overthrow the Bolsheviks?

The 'Coup'

What we know:

In May 1918, Robert Bruce Lockhart was an agent of the British Secret Intelligence Service. Reilly repeatedly met with Boris Savinkov, the head of the counter-revolutionary Union for the Defense of the Fatherland and Freedom (UDFF), such group supported with SIS funds.

Members of the Latvian Riflemen who were disillusioned were directed to Captain Cromie, a British naval attaché, and Mr. Constantine, a Turkish merchant (actually Reilly).

The Latvians were entrusted with the security of the Kremlin.

Reilly planned a coup, drawing up a list of Soviet military leaders to assume power at the fall of the Bolshevik government.

An Allied force landed on August 4, 1918, at Arkhangelsk, Russia, beginning Operation Archangel. Its objective was actually to prevent the German Empire from obtaining Allied military supplies stored in the region.

Responding to this incursion, the Bolsheviks raided the British diplomatic mission on August 5 where Reilly was having a meeting with the anti-Bolshevik forces. Somehow it escaped the notice of the raiders.

The coup was set for the first week of September during a meeting of the Council of People's Commissars and the Moscow Soviet at the Bolshoi Theatre.

Everything turned horribly wrong.

Horribly Wrong

A military cadet shot and killed Moisei Uritsky, the head of the Petrograd Cheka, (the police) On the same day, Fanya Kaplan, a member of the Socialist Revolutionary Party, shot and wounded Lenin.

The Cheka clamped down on all possible opponents.

Thousands were seized and executed. Using lists supplied by undercover agents, the Cheka arrested those involved in Reilly's pending coup, raiding the British Embassy, killing Cromie, Reilly's accomplice.

Lockhart was arrested, but later released in exchange for Litvinov, a diplomat who had been arrested in London in a reprisal.

Elizaveta Otten, Reilly's chief courier and mistress was arrested as well as his other mistress Olga Starzheskaya and Maria Fride.

By September 3, Reilly was identified as a leader. He escaped Russia with a German passport, in a railway car reserved for the German Embassy. In Kronstadt, Reilly sailed by ship to Helsinki and reached Stockholm. He arrived in London on November 8


During his life, he often claimed;

he earned and lost several fortunes in his lifetime and had many wives and mistresses.

This seems to be true.

He claimed that:

In the Second Boer War he disguised himself as a Russian arms merchant to spy on Dutch weapons shipments to the Boers....

This remains to be proven.

He procured Persian oil concessions for the British Admiralty, the so-called D'Arcy Affair.

This is partially true.

• In the disguise of a timber company owner, he gathered information on the Russian military presence in Port Arthur, Manchuria, and reported to the Kempeitai, the Japanese secret police.

This may be true

• He spied on the Krupp armaments plant in Germany.

This may be true

• He volunteered for the Royal Flying Corps in Canada at the start of World War I.

This is true

• He seduced the wife of a Russian minister to obtain information about German weapons shipments to Russia.

This is possible

• During World War I, he donned a German officer's uniform and attended a German Army High Command meeting.

This may be a story

• He saved British diplomats in Brazil.

This may be a story

• He attempted, but failed, to engineer the downfall of the Russian Bolshevik government.

This is probably true.

The End

In September 1925, undercover agents of the OGPU, the intelligence successor of the Cheka, lured Reilly to Bolshevik Russia.

He was captured, transported, and interrogated at Lubyanka Prison. There is debate as to
whether Reilly was tortured.

Reilly maintained his charade of being a British subject born in Clonmel, Ireland, and would not reveal any intelligence matters

He was executed in a forest near Moscow on November 5, 1925.

In Fiction......

Does he sound like James Bond?

This isn't an accident;

Reilly's friend, former diplomat and journalist Sir Robert Bruce Lockhart, was a close acquaintance of Ian Fleming and recounted many of Reilly's adventures.

James Bond, like Reilly was multi-lingual, fond of fine living, a compulsive gambler who had many lovers.

Sidney Reilly was a legend in the British Secret Service.


Bolshevics, Bolsheviks, Britian, Ian Fleming, James Bond, Jewish, Mi-1, Odessa, Rosenbaum, Russian, Spy, Spying

Meet the author

author avatar kaylar
I am passionate about history, culture, current events, science and law

Share this page

moderator Mark Gordon Brown moderated this page.
If you have any complaints about this content, please let us know


author avatar kaylar
3rd Apr 2011 (#)

still cheesed off

Reply to this comment

author avatar Jerry Walch
3rd Apr 2011 (#)

Cheesed off about what?

Reply to this comment

author avatar kaylar
3rd Apr 2011 (#)

topic discussed on MB

Reply to this comment

author avatar Rathnashikamani
3rd Apr 2011 (#)

Ace write up on an ace spy. Amazing facts!

Reply to this comment

author avatar Mark Gordon Brown
3rd Apr 2011 (#)

Must have been a good spy I have never heard of him!

Reply to this comment

author avatar kaylar
3rd Apr 2011 (#)

There was a miniseries about him; Reilly; Ace of Spies, in the early '80s and a number of books were written in the 30s and continuing.

He had so many legends and was so able to pass as everything from a Turkish businessman to a Baltic factory worker, to a member of the Brit Upper Class.

Reply to this comment

author avatar Denise O
4th Apr 2011 (#)

Kaylar just a fine piece my friend. I love learning some thing new every day, thank you for helping me. Great read. Thank you for sharing.:)

Reply to this comment

author avatar kaylar
4th Apr 2011 (#)

you're very welcome

Reply to this comment

author avatar JohnH
4th Apr 2011 (#)

well written... I enjoyed it, fact and fiction, and you did this so well.

Reply to this comment

author avatar kaylar
4th Apr 2011 (#)

It was hard, because for every 'fact' there was a 'fallacy' so I tried to be as accurate as I could

Reply to this comment

author avatar Aileen Tecson
8th Apr 2011 (#)

Good to know about this person remarkable character :-)

Reply to this comment

author avatar kaylar
8th Apr 2011 (#)

He was quite remarkable, his ability to take on personas and be believable.

Reply to this comment

Add a comment
Can't login?