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Sydney Reilly

Sydney Reilly Cover Image

K.A. Bachus

Model Spy

In Cetus Wedge, the second book of the Charlemagne Files, Frank Cardova mentions the subjects of the first two articles in this series. First, I introduced Felix Dzerzhinsky, who founded the Cheka and conducted the Red Terror. Today’s topic is his most famous adversary, Sidney Reilly.

Like his nemesis Dzerzhinsky, Reilly was probably Polish. He told so many variations of his origin story that it is difficult to tell which is true. Even the year of his birth is uncertain, anywhere from 1873 to 1875, but the day is consistently reported to be March 24. He was most likely born Sigmund Georgievich Rosenblum in Odessa, perhaps the biological son of a doctor who was a cousin of Grigory Rosenblum, his acknowledged father. The family was wealthy and well-connected in Polish nationalist circles.

In his youth, Sidney participated in revolutionary groups but was already playing double games both for and against the Tsarist secret police, the Okhrana. His talent for subterfuge and information gathering eventually earned him a British passport and he began his formal espionage career working for Scotland Yard’s Special Branch. From there, he became an agent of the fledgling British Secret Intelligence Service. He was an expert assassin, and was often described as being reckless.

Reilly was a key element in several convoluted plots during the first decades of the twentieth century, most notably an abortive coup attempt against the Bolsheviks in 1918. He managed to escape with his life, but returned to coordinate another plot in1925. His contacts betrayed him at the Finnish border. Stalin himself ordered his execution outside Moscow on November 5, 1925. Reilly’s capture was part of a counterespionage operation devised by Felix Dzerzhinsky known as The Trust. It will be the subject of the next article.

Sidney Reilly was popular with women and married several, not always waiting until a previous marriage ended. He is said to have been the inspiration behind the early James Bond stories by Ian Fleming. An acclaimed 1980s miniseries, Reilly, Ace of Spies stars Sam Neil as Sidney Reilly. He is described in R.H. Bruce Lockhart’s Memoirs of a British Agent.