Sidney Reilly

Sidney Reilly was the most extraordinary man I ever met.” Sir Robert Bruce Lockhart

Sidney George Reilly, MC was a British spy who worked for the British Secret Intelligence Service (SIS/MI6) in the early 20th century. According to some sources, he was born as Zigmund Markovich Rozenblum in Odessa, Ukraine, in 1873 or 1874. He studied chemistry in Vienna and then moved to Brazil, where he met some British Army intelligence officers who recommended him to the SIS in London. He operated in various countries, but he is best known for his activities in Russia.

Much about Reilly is murky. Other sources claim that he was sent to Russia as an agent of the Crown by William Melville, one of the pioneers of British intelligence. He also allegedly spied for Germany and Japan before joining the SIS. He changed his name to Sidney George Reilly in 1899 and claimed to have Irish origins.

The source of the claim that Reilly was sent to Russia by William Melville is a book by Robin Bruce Lockhart, who was Reilly’s friend and colleague in the SIS. Lockhart based his account on Reilly’s own memoirs, which are considered unreliable and exaggerated by many historians. Other sources suggest that Reilly went to Russia on his own initiative, seeking business opportunities and adventure. He may have spied for various countries, but there is no conclusive evidence that he worked for the British intelligence before 1918.

Reilly is widely regarded as one of the most daring and successful agents in the history of espionage, although many of the romanticized stories about him may be of his own creation. He was involved in many audacious and dangerous missions. He earned the nickname “Ace of Spies” for his remarkable achievements and skills. He was known for his charisma, cunning, and ruthlessness. He was married several times and had numerous affairs. He met his end in 1925, when he was captured and executed by the Soviet secret police. but his legend lived on in the media and popular culture.

Notable Activities

Reilly was a mysterious and controversial figure. He traveled around the world, using different names and identities, and was involved in various political and espionage activities.

In 1904, Reilly infiltrated the Russian naval base in Port Arthur, Manchuria, and obtained valuable information about the fortifications and the fleet before the Russo-Japanese War. He also helped the Japanese agents to sabotage the Russian ships. Port Arthur was a strategic port that Russia had leased from China and had turned into a naval base with a powerful fleet and strong defenses. However, the Russian forces were caught off guard by a surprise attack from the Japanese navy on 8-9 February1904, which marked the beginning of the war. Reilly, who was posing as a British merchant, used his contacts and skills to gain access to the port and spy on the Russian activities. He reported his findings to the Japanese intelligence and provided them with maps and plans of the port. He also assisted them in planting explosives on some of the Russian ships, which caused further damage to their naval power. Reilly’s actions contributed to the Japanese victory in the siege of Port Arthur, which lasted for five months and ended with the surrender of the Russian garrison on 2 January 1905.

Cropped 1918 German passport photo of famous spy Sidney Reilly. This passport was issued under his alias of “George Bergmann.”

One of his most remarkable feats was in 1914, when he obtained a copy of the German naval expansion plan from a German shipbuilder in St. Petersburg, Russia, and alerted the British authorities about the threat of a naval arms race. This information was crucial for the British naval strategy in World War I, as it revealed the German ambitions to challenge the British supremacy at sea. Reilly used his charm, cunning, and disguise skills to infiltrate the German shipbuilder’s office and copy the documents without being detected. He then escaped to London with the help of his contacts in the Russian secret police.

He is best known for his role in the failed plot to overthrow the Bolshevik regime in Russia in 1918, In 1918, Reilly participated in a plot to overthrow the Bolshevik regime in Moscow, along with Robert Bruce Lockhart, a British diplomat who also worked for the SIS. They planned to assassinate Lenin and other Soviet leaders, and to incite a revolt among the anti-Bolshevik forces. He tried to bribe some Soviet officials and military officers to stage a coup and restore a pro-British government in Russia. However, the plot was foiled by the Cheka, the Soviet secret police, who arrested several of Reilly’s accomplices and uncovered his identity. Reilly managed to escape from Russia with the help of his lover, actress Pepita Bobadilla. He spent the next few years in various countries, engaging in espionage and business activities.

Pepita Bobadilla was an actress who claimed to be from South America but was actually born Nelly Louise Burton in England. She had been married to playwright Haddon Chambers before meeting Reilly in Berlin in 1922. She helped Reilly escape from Russia after his failed coup attempt, but their relationship did not last long. She divorced Chambers and married Reilly in 1923, but they separated soon after. She later remarried. She died in 1973.

Many of Reilly’s fellow conspirators in the Lenin plot were either executed or imprisoned by the Bolsheviks. Robert Bruce Lockhart was arrested by the Cheka and accused of being part of the plot. He was exchanged for Maxim Litvinov, a Soviet diplomat held by Britain. Boris Savinkov, a Russian revolutionary who led the anti-Bolshevik forces in Moscow was captured by the Cheka and sentenced to death but committed suicide in prison. Sidney Georgevich, a British agent who worked with Reilly in Russia, was betrayed by one of his contacts and shot by the Cheka. George Hill, another British agent who worked with Reilly in Russia, was wounded during an ambush by the Cheka and later died of his injuries.

The Lubyanka building in Moscow, where Riley was taken after his arrest by the Soviet OGPU secret police in 1925. © A.Savin, WikiCommons

In 1925, Reilly returned to Soviet Russia for one last mission, hoping to gather intelligence on the Soviet military and industrial capabilities. He was obsessed with overthrowing the Soviet government and believed that there was a secret anti-Bolshevik organization inside Russia, called the Trust, that could help him achieve his goal. The Trust, however, was a clever deception operation by the OGPU (the successor to Cheka) that was designed to attract and neutralize foreign agents and dissidents. Reilly fell for the bait and contacted the Trust through its representatives in Europe. He was invited to cross the border into Russia and meet with some of the Trust’s leaders. He accepted the offer and traveled to Finland, where he was met by a Trust agent named Fyodor. Fyodor escorted him to a remote forest cabin, where he claimed that they would wait for a car to take them to Moscow. In reality, Fyodor was an OGPU officer, and the cabin was surrounded by Soviet troops. Reilly realized too late that he had walked into a trap. He was captured, taken to the Lubyanka prison and interrogated, before being shot on 5 November 1925 in a forest near Moscow, according to documents released by British intelligence in 2000. His body was buried in an unmarked grave. The order to kill Reilly came directly from Stalin.

An Inspiration

Reilly is widely regarded as one of the main inspirations for Ian Fleming’s fictional character James Bond, the suave and sophisticated agent 007. Fleming learned about Reilly’s exploits from his friend and colleague Robert Bruce Lockhart, who had worked with Reilly in Russia and who wrote a biographical book on him called Reilly: Ace of Spies. Fleming also borrowed some aspects of Reilly’s personality, appearance, and lifestyle for his creation of Bond, such as his preference for fine clothes, cars, and drinks, his skill with languages and weapons, and his cold-blooded attitude towards his enemies.

A dominating figure in the mythology of intelligence, Sydney Reilly was a man who lived by his own rules, and who helped change the course of history with his actions. His legacy lives on in books, films, and TV shows.

*The views and opinions expressed on this website are solely those of the original authors and contributors. These views and opinions do not necessarily represent those of Spotter Up Magazine, the administrative staff, and/or any/all contributors to this site.

By Eugene Nielsen

Eugene Nielsen owns and runs a private intelligence and security consulting firm. He has a BA degree from the University of California, Santa Barbara in Political Science. His byline has appeared on over 1,500 articles published in major national and international journals and magazines. He was on Contributing Staff of SWAT Magazine for over 20 years.

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