Considered by many the greatest spy in history. His heroic missions, quick thinking and love for the ladies made him the prototype for spies.
Born Sigmund Georgievich Rosenblum in Odessa, Russia in 1874, the son of a rich Jewish landowner. Was educated briefly through grade school but was largely self-taught from thereon. Over the years, became proficient as a linguist, learning to speak at least seven languages fluently.
Left Russia at the age of 19, stowing away on a ship and traveling to Brazil. Worked in Brazil in various occupations, including as a dishwasher, a cook and a bouncer.
Served as part of an expedition through the jungle in Brazil, working as a cook for a group of British explorers. The group was attacked by cannibals and Reilly bravely grabbed a revolver and shot several of the attackers dead, driving off the rest. The grateful explorers invited Reilly to return with them to England. Impressed with his language skills, they steered him in the direction of the intelligence community.
Was very popular with the ladies. carrying on several affairs. Had a brief affair with noted author Ethel Voynick. Later began an affair with Margaret Callahan, the young wife of Reverend Hugh Thomas. Reilly had met Reverend THomas advising him on cures for his kidney information. When Thomas was found dead in his room at the Newhaven Harbour Station hotel. Apparently, a person claiming to be a doctor named T.W.Andrew, who bore a strong resemblance to Reilly, certified the death as a result of generic influenza and ordered no inquest be held. Despite the fact that there was no record of a doctor by that name in Great Britain at the time, Thomas’ wife Margaret inherited about £800,000. Reilly subsequently married her on August 22, 1898. At this time, he discarded the name Sigmund Rosenblum and became known as Sidney George Reilly. Was granted British citizenship soon thereafter.
Was sent by NID to Holland during the Boer War where he was to gather information on the armaments shipments being sent to South Africa. Used his innate ability for disguise to assume identities and assumed the role of a Russian arms purchaser. Under this guise, he put himself in a position to inspect the arms development at certain Dutch facilities. Once again, he returned to Britain with valuable information, impressing his superiors. He enjoyed similar success on a number of other assignments and became known within NID as one of the top agent within the agency.
Had a natural flair for his assignments, cool-headed, creative and brave. A master of disguise, he also possessed remarkable acting skills, allowing him to don almost any persona. He also possessed a confidence and bravery that prompted him to accept even the most dangerous and impossible assignments.
Was allocated large blocks of cash to use to bribe officials and informants. Was also afforded a hefty salary, allowing him to enjoy a life of luxury outside of his dangerous work and enjoyed the company of numerous women. It was said of him that he had as many wives as he had forged passports (which were numerous, indeed). He used his charm as a method for obtaining information from the wives of important officials.
While in the service of England, Reilly’s true loyalty was to himself and his bank account. He would go to any extreme to accomplish the most dangerous mission so far as it would enhance his position, thereby prompting his superiors to call on him again. His willingness to risk life and limb was what made him so attractive as an agent to NID. it should also have alerted the agency to his willingness to to do anything for money, a trait that would make him a prime target to be recruited by a rival intelligence service.
Was sent to Port Arthur, Manchuria, a naval base for the Russian Far Eastern fleet. Accompanied by his wife, he was provided with an enormous bank account, the funds from which he purchased an interest in a small timber company as well as a Danish company (for whom he served as a manager). In reality, these were covers for his real business, spying on the Russian naval assets in Port Arthur. Reilly observed and recorded the positions and schedules of Russian warships as well as assessments of their armaments, crews and capabilities. He even drew sketches of the ships and the port. Reilly sent this information back to England, but was believed by some to have also had financial dealings with Russian and Japanese intelligence officers.
Was brought into the Secret intelligence Service (later known as MI6) in 1909 and served under Captain Mansfield Smith-Cumming. While SIS and NID were pleased with Reilly’s capabilities and results, Smith-Cumming said of Reilly “[H}e is a man of indomitable courage, a genius as an agent, but a sinister man who I could never bring myself wholly to trust.”
Was sent to Essen, Germany in 1909 to monitor the vast growth of the German war machine. He devised a cover as a Baltic shipyard worker named Karl Khan secured a job as a welder in a Krupp armaments plant. His plan was the photograph the plant and its production output, but he realized that the drawing office was heavily guarded during the day. Instead he volunteered for the fire brigade which worked during the night shift. A few nights later, he strangled the head of the night security detail and incapacitated another security officer, thereby gaining access to the drawing room. In true Reilly fashion, rather than bothering with photographing the plans, he simply stole them, hopped a train and then a boat and evaded German agents as he escaped back to England.
With England still interested in Germany’s naval and military capabilities, Reilly was sent to Russia where he pose as an armament distributor. Believing that aerial reconnaissance would provide the best opportunity for seeing and assessing the strength of the German fleet, he used his burgeoning bank account to sponsor air races for Russian aviators. In addition to establishing him as a member of the social elite, it also enabled him cover for flying over areas of the Baltic Sea, photographic German vessels. Through his newfound social connections, Reilly was introduced toa man named Massino, the assistant to the Russian Minister of Marine. Reilly seduced Massino’s wife, Nadine, who confided that a German company, Blohm & Voss, were seeking to win the contracts to rebuild the Russian fleet. Reilly bought a small company (Mendrochovich & Lubersky) and pursuaded Massino to convince Blohm & Voss to name his company as their St. Petersburg agents. After Blohm& Vos was awardrd the contracts to rebuild the Russian fleet, they sent copies of all of their designs to Reilly’s firm, the designs having been based on the German fleet. Before he turned the plans over to the Russian Minister of Marine, he made a full set of photographic copies, which he sent back to England.
Was able to reach an agreement with SIS so that any profits he earned through his “cover” businesses were kept by him. Reilly became very wealthy through his SIS funded endeavors.
Enjoying Russia, he stayed, living a life of luxury and social prominence. He purchased a small palace where he entertained Nadine Massino and a bevy of other beautiful women. Eventually he planted stories in Russian newspapers claiming his wife Margaret had died in a train crash. He then paid Massino a large sum of money to divorce Nadine, whom Reilly eventually married in New York City in 1916.
Was engaged by Russia to purchase arms for its war effort. Reilly purchased arms from the United States and from Japan.
Was assigned a new mission at the behest of British Prime Minister David Lloyd George. With the Russian government in tatters (after the overthrow of Czar Nicholas) Alexander Kerensky had taken control of the government as the new Prime Minister and was struggling to keep Russian in the fight of World War I. Ultimately, the Bolsheviks overthrew the Russian government and under the revolution’s leader Vladimir Lenin, signed a peace treaty with the Germans in 1918. Reilly, in cooperation with Robert Bruce Lockhart, the British general counsel to Russia, attempted to overthrow the new Russian (Bolshevik) government in order to bring Russia back into the war.
Was assigned to a new mission for England, sent to Germany again, this time to assess German army strength and movements. Speaking German fluently, he actually joined the German army and served on the Western front, while sending detailed assessments of German troop plans back to England via carrier pigeons.
Claimed to have impersonated the Chief of Staff to Rupert of Bavaria, thereby gaining access to planning conferences of the German high command, information of great importance that he passed back to London.
Tried to deal directly with Lenin, turning up at the Kremlin gates, demanding to see the Russian leader (infuriating Lockhart in so doing).
Decided the best way to cause the overthrow of the Russian government was to assassinate Lenin. Began to plot his assassination and bribed two of Lenin’s bodyguards, who agreed to help him. He also began consolidating factions of anti-Bolsheviks to take part in the plot and compiled a list of Russian military leaders to take over after the fall of the Bolshevik government.
Before Reilly could act, Lenin was shot by a woman, Fanya “Dora” Kaplan. Lenin survived and after Kaplan was executed, the Bolsheviks began to search for a plot and tracked down the two guards Reilly had bribed. They cooperated and identified Reilly as well as Lockhart. Reilly eventually escaped on a Dutch freighter. Nonetheless, he was tried in absentia and was convicted of conspiracy against the Bolshevik government and against the life of Vladimir Lenin. He was sentenced to death.
Despite his failure, his flight and his death sentence, Reilly was convinced that he could still Lenin and overthrow the Bolshevik government, begging Smith-Cumming to send him back in. The SIS chief declined. Nonplussed, Reilly endeavored to carry out his own mission.
Formed an alliance with anti-Communist Boris Sakinov, the head of the counter-revolutionary Union for the Defense of the Fatherland and Freedom. Sakinov was able to gain a following of 30,000 anti-Bolshevik troops. Unfortunately anit-Bolshevik forces within Russia were soundly defeated before Sakinov could lead his troops into the country. Despite this, Sakinov was elated to find other pro-pro-Monarchist anti-Bolsheviks in Paris who agreed to fund his counter-revolution. The Monarchist Union of Central Russia (also known as the Trust) sent his to Russia to meet with underground Trust sympathizers.
In truth, the Trust a front group, created by the Bolsheviks under the guidance of Feliks Dzerzhinsky (OGPU). Months later, Reily was introduced to “Trust” members and led him also going to Russia to meet with the Trust’s council leaders. Upon crossing the Finnish border, he was arrested on February 27, 1925 and taken to Lubyanka Prison where he was interrogated.
Was notified that the death sentence against him was to be carried out. Reilly, according to Soviet reports, tried to barter with Dzerzhinsky, promising to pass along British and American intelligence secrets in return for his life. It was to no avail.
Was executed by firing squad on November 5, 1925 outside of Moscow and buried in an unmarked grave.