Sidney Reilly – The Greatest Spy in the annuals of Espionage

Sidney Reilly has had few if any peers in the annuals of espionage. Born Georgi Rosenblum, a Jew, in Odessa in 1873, Sidney was an adventurer par excellence. His story is a testament to his laudable courage and overweening chutzpah. Like most spies, they are the only source of their often vaulting claims as the facts are mostly unsubstantiatable from other sources.

In spite of his Russian heritage, Sidney Reilly was imbued with a sense of duty to the British. Be that as it may but Sidney was an incorrigible rogue with perhaps a misguided sense of duty. Unlike the outdated British Secret Service, still wedded to a bygone era of chivalry and fair-play, Sidney obtained the results that they required through a ruthless uncompromising streak even if it meant breaking a number of female hearts or even killing in the process. Dubbed the Ace of Spies, Reilly’s sobriquet was apt.

Reilly combines espionage with a torrid affair

Sidney’s first assignment for the Scotland Yard’s Special Branch under William Melville was to establish the extent of the Russian oil reserves in Baku near the Caspian Sea. After being interned by the Russians, he convinced Margaret Thomas, the youthful wife of Reverend Hugh Thomas, that she should stay overnight in his room in order that he could make an escape.

Margaret Thomas, Reilly's first wife as far as is known

Margaret Thomas, Reilly’s first wife as far as is known

When the ruse was uncovered by the Russians, both Margaret and her husband were imprisoned for their part in aiding and abetting Sidney’s escape. This affair scandalised British society not only due to Sidney impugning a woman’s honour but for killing a Russian during his escape.

Back in England, Margaret and Sidney commenced a torrid affair while her cuckold husband lay sick in bed. Sidney was the opposite of Margaret’s husband in every way – young, suave and a womaniser. It is unknown whether they jointly or she alone conspired to have the executor of Reverend Thomas’ will amended. What transpired will never be established for Margaret’s husband died soon thereafter but what is known is that a mysterious Dr Andrews – who is suspected of being none other than Sidney Reilly himself – certified that he had died of influenza but it is strongly suspected that he was in fact poisoned.

The £800,000 pay-out from the insurance policy made the newly married couple, instantly fabulously wealthy.

Russian naval vessels


Reilly as a Shipping Agent

In order to distance himself from his past, Rosenblum settled on Sidney Reilly as his name. His irrefutable logic was that no nations had any squabbles with the Irish. For his services to the British, the newly minted Reilly was even provided with a British passport for his next mission.

This time Sidney was playing for higher stakes. As a double agent – acting for both England and the Japanese – he was bound for Port Arthur in Manchuria in the Orient. With his “disguise” as a Shipping Agent, he and a Chinese engineer acquaintance Ho Liangshung allegedly stole the Port Arthur harbour defence plans at the behest of the Japanese Navy. Guided by these stolen plans, the Japanese Navy was able to navigate through the Russian minefield protecting the harbour. A surprise attack was launched on Port Arthur by the Japanese on the night of 8–9 February 1904 destroying the Russian fleet lying at anchor.


Port Arthur

Port Arthur

Again Sidney escaped unscathed.


Reilly as a Catholic Priest

Next Reilly was to re-appear in Paris where he was persuaded to assist the British in purchasing concessions to oil in the Middle East in what became would become known as the D’Arcy Affair.



With the introduction of the new class of battleship to the British fleet – the Dreadnought – [literally meaning to fear nothing] farsighted naval officers realised the importance of oil to power their steam turbines.

D’Arcy was an Australian oil engineer who had purchased the rights to oil in the Middle East and who was now attempting to on-sell these rights to the French in the form of the Rothschild’s.

According to Reilly, he boarded Lord de Rothschild’s yacht at Antibes on the Cote de Azure attired as a Catholic priest and secretly persuaded D’Arcy to terminate negotiations with the Rothschilds and return to London to meet with the British Admiralty.



In the interim Margaret had absconded with her lover together with all their savings. Reilly’s ill-gotten gains were no more.

Reilly as a shipyard welder

Impecunious and in search of adventure, yet again he consented to assisting the British Intelligence Services. With the Germans under von Tirpitz involved in a ship building program to compete in the Dreadnought derby, the British was naturally intrigued as to their armament and capability. Reilly was tasked with replacing the floundering British naval agent already in situ, and to obtain the desired information.

Being a multi-linguist, Reilly obtained work as a welder at the Blohm & Voss shipyard on the island of Kuhnwerder near the Free and Hanseatic City of Hamburg. Ironically Blohm & Voss now known as Blohm + Voss – without the ampersand – has recently been purchased by Star Capital of the UK.

The brazen Herr Fricker – Reilly’s alias – found accommodation in the same gasthaus as Goschen, the British naval spy. With Basil Zarharoff, a consultant for Vickers, offering him a substantial sum of money for a copy of the actual plans of the ships, Reilly was playing for higher stakes. Goschen was dispensable in this process. Herr Fricker wrangled an appointment to be in charge of a fire team after he had miraculously extinguished a blaze that undoubtedly he himself had ignited.

Bismark leaving Blohm & Voss shipyard

Bismark leaving Blohm & Voss shipyard

By means of this ruse Reilly managed to have the buildings’ fire plans relocated to the same office as the ship’s plans. Herr Friker escaped with the plans but not before Goschen was forced to commit suicide after being unmasked as a British spy.

Reilly and the Blohm & Voss Contract

Sidney decided to return to his mother country, Russia but instead of the sunny Odessa on the Black Sea it was to the snow bound St Petersburg [to be changed to Petrograd in 1914, Leningrad in 1924 & finally St Petersburg again in 1991]. At this stage in its history, it was the seat of government in Russia.

St Petersburg

St Petersburg

In the interim, the Russians had also joined the naval arm’s race. Tenders were requested from all the famous shipyards including Vickers of Britain and Blohm & Voss of Germany. Reilly contrived by various devious underhand means to obtain a 51% stake in a Russian Consortium which represented none other than Reilly’s old nemesis, Blohm & Voss [Never written as Blohm and Voss] .

The ultimate winner was Blohm & Voss and with it Reilly had made yet another huge fortune. Foolishly he fell in love with a married woman and in order to satisfy honour, a huge settlement had to be paid. It was not as if Reilly was ever short of lovers as there was an interminable succession of them, including it is rumoured his half-sister Anna who subsequently committed suicide.

Reilly’s bid for Power

Reilly final piece de resistance, if it may be termed that, was his decision to oppose the Bolshevik’s Orwellian Regime in 1918 and replace it with a government with himself as the head thereof. Like all of Reilly’s stakes, they were delicately poised but in all the other affairs, he himself was strictly in control. Given his presence of mind and forceful character, he was able to control events.



Not so this time.

With the ruthless Cheka – meaning Death to Spies – under Felix Dzerzhinsky, a Polish aristocrat turned communist, apprehending suspects & torturing them, all secrets were rapidly known to the Bolsheviks.

When Vladimir Ilyich Ulyanov alias Lenin got wind of a plot to overthrow their tyrannical regime, he postponed the Party Conference by ten days. This would afford the Cheka the necessary opportunity to establish the facts and apprehend the traitors.

The success of this counter revolution depended upon a number of actions all occurring simultaneously. One key Russian role player was Boris Savinkov, formerly in Kerensky’s provisional government, who would lead an uprising of the UDMF comprising several thousand Russian fighters.

Felix Dzerzhinsky

Felix Dzerzhinsky

Ilyich Lenin unwisely deemed that the Latvian troops were the Praetorian Guard of the Bolsheviks. As such they were entrusted with the security of the Kremlin. In June 1918 , disillusioned members of the Latvian troops began appearing in anti-Bolshevik circles in Petrograd – formerly St Petersburg – and were eventually directed to Captain Crommie, a British naval attaché, and Mr. Constantine, a Turkish merchant who was unsurprisingly was actually Reilly. These disaffected troops were encouraged to revolt at a pre-arranged signal

The final of the trio of measures was direct assistance by the British military which would land two divisions of troops at Archangel.

Boris Savinkov

Boris Savinkov

On the same day, Fanya Kaplan, a member of the Socialist Revolutionary Party, shot and wounded Lenin as he left a meeting at the Michelson factory in Moscow. In the immediate aftermath of this attempted assassination, the Cheka used these events to implicate any malcontents in a grand conspiracy that warranted a full-scale campaign dubbed the “Red Terror”. Thousands of political opponents and dissidents were seized and executed. Using lists supplied by undercover agents, the Cheka arrested those involved in Reilly’s pending coup. They raided the British Embassy in Petrograd and killed Cromie, Reilly’s accomplice, who put up an armed resistance.

Reilly was fortunate to escape with his life.

Reilly’s denouement and swansong

In September 1925 undercover agents of the OGPU, the intelligence successor to the Cheka, lured Reilly to Russia ostensibly to meet the supposed anti-Communist organization The Trust. In reality this OGPU deception netted Reilly as he crossed the Finnish Border. The Soviets then transported him to the Lubyanka Prison in Moscow where he was interrogated.

Lubyanka Prison

Lubyanka Prison

Having been found guilty in absentia in 1919 and sentenced to death, this warrant was executed on Guy Fawkes Day 1925.

Reilly unmasked

Reilly’s life is more gripping than a James Bond spy novel. It possesses most of the same ingredients – wanton women, miraculous escapes and stylish clothes, cars and houses. Of course this was underpinned by vast hordes of money much of it ill-gotten as the British Intelligence Service was rather miserly in this respect.

Sidney Reilly in disguise

Sidney Reilly in disguise

Whilst much of the detail of these operations cannot be established with any degree of certainty, the broad outline is known and is verifiable

Amongst the many questions that I personally would like to pose to Reilly is how many fortunes did he manage to squander, did he really love his first wife Margaret or was she a gateway to ill-gotten wealth and finally was he ever scared.

Certainly Reilly has been acknowledged as the greatest accomplished and successful spy ever to have lived.

It was only hubris and his sense of invincibility, a feeling of imperviousness that led him to attempt one final mission.

Or perhaps it was the side-effects of withdrawal from the spying addiction that affected his judgement.

Whatever it was, The Trust could not be trusted and he paid the ultimate penalty – his life.


  1. How times have changed. Secret Service under Scotland Yard!Being a linguist will be helpfull to any spy.Sydney was able to blend in (different hats such as shipping agent, welder etc) which is another strong career characteristic.
    The saying, “no honour amongst thieves” comes to mind with the unmarking of Goschen as a British spy.
    I wonder, are the more successful spies the ones that get exposed/caught or, the ones that work tirelessly and retire without any fanfare?

    • The British Secret Services were only established in the early 1900s.
      Sidney Reilly led such a full life that I was only able to capture the briefest essence of his life

  2. As compelling as this account is, it’s almost completely incorrect. The stories that the author recalls seem to be a mix of Lockhart’s 1967 biography about Reilly and the ITV Show Reilly, Ace of Spies. Thus, the author can’t be faulted for getting the facts wrong. However, Lockhart’s biography has been proven to be must made up as Lockhart got his stories from Reilly himself who was a complete liar. Reilly was more con man than spy, even if his life was colorful.


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