5 November: This Day in Mystery

5 November 1925
Sidney Reilly - the British espionage agent known as the Ace of Spies - is executed by the Soviets on this day.

Froom Wikipedia.com
Lieutenant Sidney George Reilly, MC (c. March 24, 1873/1874 – November 5, 1925), famously known as the Ace of Spies, was a Jewish Russian-born adventurer and secret agent employed by Scotland Yard, the British Secret Service Bureau and later the Secret Intelligence Service (SIS). He is alleged to have spied for at least four nations. His notoriety during the 1920s was created in part by his friend, British diplomat and journalist Sir Robert Bruce Lockhart, who sensationalised their thwarted operation to overthrow the Bolshevik government in 1918.

After Reilly's death, the London Evening Standard published in May, 1931, a Master Spy serial glorifying his exploits. Later, Ian Fleming would use Reilly as a model for James Bond. Today, many historians consider Reilly to be the first 20th century super-spy. Much of what is thought to be known about him could be false, as Reilly was a master of deception, and most of his life is shrouded in legend

Death
In September 1925, undercover agents of the OGPU, the intelligence successor of the Cheka, lured Reilly to Bolshevik Russia, ostensibly to meet the supposed anti-Communist organization The Trust—in reality, an OGPU deception existing under the code name Operation Trust. At the Russian border, Reilly was introduced to undercover OGPU agents posing as senior Trust representatives from Moscow. One of these undercover Soviet agents, Alexander Yakushev, later recalled the meeting:
“The first impression of [Sidney Reilly] is unpleasant. His dark eyes expressed something biting and cruel; his lower lip drooped deeply and was too slick—the neat black hair, the demonstratively elegant suit. [...] Everything in his manner expressed something haughtily indifferent to his surroundings.”

After Reilly crossed the Finnish border, the Soviets captured, transported, and interrogated him at Lubyanka Prison. On arrival, Reilly was taken to the office of Roman Pilar, a Soviet official who the previous year had arrested and ordered the execution of Boris Savinkov, a close friend of Reilly. Pilar reminded Reilly that he had been sentenced to death by a 1918 Soviet tribunal for his participation in a counter-revolutionary plot against the Bolshevik government. While Reilly was being interrogated, the Soviets publicly claimed that he had been shot trying to cross the Finnish border.

Historians debate whether Reilly was tortured while in OGPU custody. Cook contends that Reilly was not tortured other than psychologically by mock execution scenarios designed to shake the resolve of prisoners. During OGPU interrogation, Reilly maintained his charade of being a British subject born in Clonmel, Ireland, and would not reveal any intelligence matters.[6] While facing such daily interrogation, Reilly kept a diary in his cell of tiny handwritten notes on cigarette papers which he hid in the plasterwork of a cell wall. While his Soviet captors were interrogating Reilly, Reilly in turn was analysing and documenting their techniques. The diary was a detailed record of OGPU interrogation techniques, and Reilly was understandably confident that such unique documentation would, if he escaped, be of interest to the British SIS. After Reilly's death, Soviet guards discovered the diary in Reilly's cell, and photographic enhancements were made by OGPU technicians.

Reilly was executed in a forest near Moscow on November 5, 1925; British intelligence documents released in 2000 confirm this. According to eyewitness Boris Gudz, the execution of Sidney Reilly was supervised by an OGPU officer, Grigory Feduleev; another OGPU officer, George Syroezhkin, fired the final shot into Reilly's chest.

After the death of Reilly, there were various rumors about his survival. Some, for example, speculated that Reilly had defected and became an adviser to Soviet intelligence.