Oddlet: Sidney Reilly · 1 min read
Jun 1, 2026
The Spy Who Wanted to Pants Lenin
A British spy once tried to topple the Bolshevik Revolution without firing a shot — his actual plan involved Lenin, Trotsky, and a tailoring problem.
Sidney Reilly, born Sigmund Rosenblum somewhere in the Russian Empire around 1873, was British agent ST1, the man Ian Fleming kept insisting James Bond was not based on. He spoke seven languages. He carried eleven passports. His personal stationery bore the motto Mundo Nulla Fides, Trust no one. The first wife brought £800,000 and a dead husband whose death certificate was signed by a Dr. T. W. Andrew, whom biographers suspect was Reilly.
In the summer of 1918, in Moscow, Reilly devised a plan to end the Bolshevik Revolution. He would not shoot Lenin and Trotsky. Martyrs were bad publicity. He would, in the precise words of his biographer, march them through the streets bereft of trousers and underpants, shirt-tails flying in the breeze. Power destroyed by ridicule. The plot was funded with 1.2 million rubles of British money.
His private collection ran to 1,049 Napoleonic items: a lock of the Emperor's hair, the purple satin from his funeral casket, six silver-handled knives from St Helena. He told colleagues he would do for Russia what Napoleon had done for France. What his colleagues made of this is not recorded.
The Latvian colonel he handed the 1.2 million rubles to was a Cheka double agent. The trouser money went straight to the Soviet secret police.
Seven years later, the same secret police shot him in a forest outside Moscow.
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- Encyclopædia Britannica — Sidney George Reilly — Covers birth as Sigmund Rosenblum in Odessa on 24 March 1874, British SIS career, pre-WWI intelligence work, 1918 Moscow mission, and September 1925 border re-crossing leading to arrest and execution
- Wikipedia — Sidney Reilly — Most detailed publicly accessible biography: variant names and birth dates, marriage to Margaret Thomas, Melville/SIS recruitment, 1918 Lockhart Plot, marriages including the bigamous 1923 marriage to Pepita Bobadilla, Zinoviev Letter, Operation Trust capture, and 5 November 1925 execution
- Executed Today — 1925: Sidney Reilly — Detailed account of capture, Lubyanka interrogation, torture, execution in a forest outside Moscow, and burial of remains in a pit on the Lubyanka grounds
- Warfare History Network — The Mysterious Sidney Reilly — Covers identity disputes, ST1 agent number, pre-WWI operations, wives, the 'underclothes' quote, the 'Window' border crossing, 'Prisoner #73,' and 2002 confirmation by former OGPU colonel Boris Gudz
- Spartacus Educational — Sidney Reilly — Detailed dates: 25 September 1925 Finnish border crossing, 13 October 1925 arrest, Reilly's text appeal to Dzerzhinsky, coordination with Eduard Berzin and Boris Savinkov, historian Christopher Andrew quote on Reilly and the Zinoviev Letter
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