On this date in 1925, legendary British spy — and subsequent James Bond inspiration — Sidney Reilly was shot in a forest outside Moscow for his efforts to overthrow the Soviet government.

Fact blends insensibly into fiction in Reilly‘s biography; much of what is known or believed about him is conjectural or colored by his posthumous valorization, such the 1967 book Reilly: Ace of Spies written by [the son of] his onetime cloak-and-dagger collaborator Robin Bruce Lockhart — who was himself a close friend of Bond author Ian Fleming.

However, even at the word of less sensational biographers — such as Andrew Cook — Reilly lived a life almost too extraordinary for belief.

A Jewish child of tsarist Russia born in what is now the Ukraine, Reilly claimed to have escaped Odessa by faking his death and hopping a ship bound for Brazil. Like much of Reilly’s life, the story is unverifiable, but by hook or by crook — and possibly by way of a murder in France — he arrived in London in 1895, hitched himself to a wealthy woman a few months after the suspicious death of her husband (discarding the inconvenient surname Rosenblum in the process), and became entangled with British intelligence.

In the first decade of the 20th century, he apparently spied promiscuously on England’s imperial rivals Germany and Russia, though the particulars are disputed. He arrived in Port Arthur, Russia, shortly before the outbreak of the Russo-Japanese War and may have provided the Japanese fleet intelligence enabling it to navigate the mined harbor — in addition to a copious side business in war profiteering. He may also have had a hand in capturing British oil concessions in Persia and reconnoitering behind German lines during World War I.

Like his fictional heir 007, he gambled often and left a string of lovers and mistresses in his wake. His true allegiances, and the extent to which his exploits were inflated or outright fabricated, are debated to this day.

The adventures that brought both death and fame were his machinations to overthrow the Bolshevik government in the fraught early months after Lenin took power. A planned coup d’etat in September 1918 came to grief and Reilly fled Russia steps ahead of the authorities, who subsequently condemned him to death in absentia.

Notwithstanding the sentence, which had been ruthlessly visited on his less-fortunate conspirators, Reilly was lured back to the USSR in 1925 by the Soviet counterintelligence project Operation Trust. Intending to meet anti-Bolshevik agitators, he was instead arrested at the border and tortured at the infamous Lubyanka Prison, where he kept notes on cigarette papers about enemy interrogation techniques for the eventuality of an escape or release that never came.

Part of the Themed Set: Spies.

On this day..

• 1959: Guenther Podola
• 1849: Pierre Dudragne, avarice
• 2009: Xu Wei, Jilin gangster
• 1974: Beqir Balluku, Albanian Minister of Defence
• 1607: Jan Le Loup, Maastricht werewolf
• 1915: Louis Bundy, "I would like to have shown the world what I could do"
• 1864: Four Confederate soldiers, under Burbridge's Order 59
• 1556: Hemu
• Executioner-in-Chief: a tour of U.S. Presidents and the death penalty
• 1927: Alfredo Jauregui, Bolivian lottery winner
• 1978: 12 coup plotters in Yemen
• 555: Rusticus and John
• 2009: Khristian Oliver, Bible basher
• 1941: Arndt Pekurinen, conscientious objector
• Themed Set: Spies