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‘A Jedi shall not know hatred, nor fear… nor love.’ from Star Wars Episode II




The Rogue Spy Behind James Bond


Ian Fleming was a great admirer of Sidney Reilly, and several sources claim that Reilly was Flemings model for James Bond. Similarities are uncanny because of Reilly’s audacious real-life exploits, recalcitrant behaviour, mastery over women, fondness for gambling and the good life.


Reilly’s birth, death, age, paternity and education are shrouded in mystery, but 1874 and 1925 are accepted as the years of his birth and death. He was born Sigmund Georgievich Rosenblum, and though his passport claimed Tipperary (Ireland) as his birthplace, he was probably born near Odessa (southern Russia). Reilly was a pathological liar, cold-blooded killer, ice-cold conman, disloyal and recalcitrant spy, shameless opportunist, arms dealer, war-profiteer and a relentless womanizer. Much of what is known about him is of dubious origin, mainly because Reilly himself is the source and he habitually exaggerated his own achievements.


Realising that he was Jewish, he fled anti-semitic Russia after faking his own death. He emerged in Brazil under the name Pedro and after working several odd jobs he ended up working as a freelance secret service agent after he impressed a British major with sharp-shooting and an aptitude for languages. He was awarded a British passport, cash and passage to Britain. Either that or he landed up in Britain after robbing and assaulting two revolutionaries/couriers in France with the help of a Russian accomplice. In Britain he started selling “miracle” medicine.


Soon after he murdered his to-be wife’s husband while pretending to be a doctor and took her inheritance and last name. In 1901 at Port Arthur, Manchuria during the Russo-Japanese War, Reilly probably spied for Britain, Russia and Japan. With his marriage in trouble, he took a mistress – Anna, and soon fled. From there he landed up in South Africa and then in the Middle East (approx. 1905) after realizing the potential of oil. He wrested the development rights for oil from the Rothschilds and set the ball rolling for an organisation that has become known as British Petroleum.


In 1914 he was in Germany and secured a job for himself in the Krupps armaments factory from where he procured top-secret drawings and production schedules. When he was discovered he escaped leaving behind two dead security guards.


From there he went to Russia and set himself as a successful businessman and organized the St. Petersburg flying week. Using his position he got German visitors to confide secrets about aircraft engineering. German naval builders Blohm & Voss were convinced to make him their sole representative for exports to Russia, and his business acumen was so astute that his commercial ventures denied British interests a great deal of business. Nevertheless, Reilly became extremely wealthy and London was provided with detailed blueprints of Germany’s fleet. At this time it became apparent to his British paymasters that Reilly was supplying the same information to other nations, most probably Russia and France. Despite this they were unable to prevent or chastise him.


At this time though his marriage to Margaret Reilly was over but she refused to divorce him. That didn’t prevent him from bigamously marrying Countess Nadia Zalessky / Nadine Massino, ex-wife of a Russian minister. They had a volatile and disloyal marriage with mutual indiscretions on both sides. Soon after he set himself up in New York as an arms dealer and made a fortune for himself selling to the Russians vast amounts of ammunitions.


In America he was investigated by the FBI who ended up interviewing countless chorus girls, actresses and mistresses but didn’t manage to pin anything on him. From there he went on to Canada and eventually got himself a job with the SIS.


1917 saw him parachuting into Germany with false papers. He posed as a German officer and spent time in the mess overhearing whatever gossip or information he could. He even managed to attend a High Command conference in the presence of the Kaiser himself. After that Reilly set himself up as an officer’s driver. The officer was subsequently liquidated en route to a war council and Reilly took his place, coolly apologizing for the delay. He sat down taking notes of all battle plans which were forwarded to the British and saved their fleet from what could have been a crippling blow.


The next year he was in Russia trying to thwart an alliance between the Russians and Germans against the western front. He planned to kidnap Lenin and Trotsky and parade them in the streets in their underpants, subjecting them to public ridicule. Also on the agenda was an alternative government in Russia with Reilly himself as the Prime Minister. This became known as the ‘Reilly plot’. Unfortunately another anti-Bolshevik plot to kill Lenin failed and the police were on their guard. Reilly barely escaped the British consulate at St. Petersburg.


Disguised as a Russian peasant, Greek traveler and Turkish merchant, Reilly finally boarded a Dutch trading ship and reached London. There he divorced Countess Nadine Massino and started a relationship with a Caryll Houselander 30 years his junior. In 1923 he married Pepita Bobadilla who he met at a chance meeting, but remained determined to overthrow the Russian regime. He teamed up with another foe of Lenin and they tried to make contact with Russian rebels that went under the name of The Trust. Reilly went back to Russia to find out more about them and was never seen again in the west. Eventually it emerged that The Trust was a Soviet scheme to entice enemies of the state into the hands of the Russian police.


His wife at the time claimed that he was killed trying to cross into Russia from Finland, but she and the British and Russian governments believed him to be alive. Subsequently, Russian refugees claimed to have seen him in a Russian hospital, others said they saw him go insane after torture. Even under torture, Reilly made notes of Russian interrogation techniques on cigarette paper and hid them in the walls of his prison, hoping to use it to some advantage should he ever make it out. More sinister information came up writing Reilly off as a Russian agent helping to penetrate the British secret service and Foreign Office. Only unlocked KGB files can answer the last riddle.


Espionage and Spies at

Sun Tzu: The Art of War & Espionage

Reading Frederick Forsyth




AVENGER: Frederick Forsyth (including The Eichmann Rendition)


Refernces and further reading

-The World’s Greatest Spies and Spymasters: Roger Boar & Nigel Blundell (Octopus Books)


All Copyrights reserved by the Author/Publisher of the book.




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Reilly’s corpse

(Image: Wikipedia)

Reilly and Bond

(Images: Wikipedia)