Day: November 22, 2022

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It is altogether fitting that a new biography about Sidney Reilly, one of the most elusive master spies in modern history, should be a slim volume less than 200 pages long. Reilly, a British agent in Russia in the early days of the Bolshevik revolution, was so elusive that, along with his significant failures and a few successes, he probably will remain a mystery man forever. Obscurity may have been his greatest triumph.

Sidney Reilly (Unattributed photo from History Press UK)

Benny Morris has written this latest biography, Sidney Reilly: Master Spy, as part of a series from Yale University, Jewish Lives. A man named Reilly? Jewish Lives? Indeed, Reilly was born Rosenblum, perhaps his given name was Sigmund or Shlomo or Zalman or Salomon, Morris tells us. “He may have been born in Odessa, Ukraine—as the Soviets later determined—or in nearby Kherson, or in Russian-ruled Poland at Bendzin (near Auschwitz) or Pruzhany, on or around March 24, 1874 (though other versions have it that he came into this world in 1872).”  You get the idea. Reilly was hard to pin down.

The one thing apparently true but not absolutely confirmed was that he was shot and killed in a park in Moscow by a Bolshevik executioner on November 5, 1925. Events that brought Reilly, at times a full MI6 officer,  to that final day, imprisoned by the nascent Soviet intelligence services—and their need to kill him—are one aspect that makes his story worth telling again.

There are obvious contemporary overtones in the gamesmanship and double-dealing between the Soviet Russians and the West. As Morris concludes, Sidney Reilly would have been overjoyed at the fall of the Soviet Union in 1991; but he clearly would not have been friends with most of their successors, and certainly not Vladimir Putin.

Several biographies have been written about Reilly; one early one was The Adventures of Sidney Reilly, ghostwritten for Pepita Bobadilla, Reilly’s fourth and final wife (depending on how one tallies up the spy’s multiple liaisons). One influential work was the 1967 book Reilly: Ace of Spies, by Robin Bruce Lockhart, which in turn prompted a popular six-part BBC miniseries of the same name, starring Sam Neill.

Morris makes up for brevity with some scholarship that goes beyond previous attempts to write the definitive biography. He has plumbed details about Reilly’s life from every imaginable source—private letters and diaries, books, files at the U.S. and British National Archives, and, interestingly, dossiers of the Russian Federal Security Service, or FSB, modern day successor to the NKVD, the agency that ordered Reilly’s killing.

Reilly surfaced in the 1890s as a young agent of the Okhrana, the Russian monarchy’s secret police, for which he may have carried out assassinations. All the while, he developed a successful arms dealing business and considerable wealth while procuring guns for Czar Nicholas’s forces. During that period, he was not above making deals with Russian adversaries, such as the Japanese and the Germans, when the price was right. In 1896, he moved to London for a time and signed on with Scotland Yard’s superintendent, William Melville, who had established the Yard’s Special Branch intelligence unit (which eventually became MI5). It was Melville who probably renamed his up-and-coming polyglot spy—Reilly was fluent in Russian, English, French, and German (but possibly not Yiddish despite his background). He became Sidney George Reilly, an Irishman from the village of Clonmel, near Tipperary.

“In something of an in-joke,” writes Morris, a preeminent Israeli historian, “Reilly reportedly told a friend years later that Odessa, where some people were alleging that he had been born, was “a long, long way from Tipperary.”

Puzzle Pieces

In his admirable attempt to ferret out every last detail, Benny Morris’s narrative, brief though it is, sometimes feels like a jumble of names and encounters, not all of which are well grounded. The tale tracks Reilly’s world of business and spying from London to New York, to Canada, back to London, and frequent trips to the European continent before focusing on Moscow and Petrograd [now St. Petersburg] in the newly created Soviet state. Once again, the uncertainties are not Morris’s fault. Reilly did not leave a neat set of clues; he did everything he could to conceal his tracks, be it spurned lovers in every port, his MI6 bosses, or Soviet agents trying to hunt him down.

The best documented part of the story is Reilly’s attempt to  bring down the fledgling Bolshevik government that had overthrown Czar Nicholas II’s regime in 1917. Double agent, sometimes triple agent, Reilly tried to generate more British and international interest in a coup to overthrow Vladimir Lenin. In that plot, Reilly’s designs included the idea that he himself would take over as Russian prime minister in a post-Bolshevik government. He and his fellow coup plotters failed, of course. (There was a separate plot in which Fanny Kaplan of the Socialist Revolutionary Party shot and seriously wounded Lenin on August 30, 1918, but Reilly was not involved.) However, Reilly’s activities earned him the permanent enmity of Soviet intelligence and Lenin himself. He was sentenced to death in absentia in a Moscow trial after the failed coup attempt.

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But the Russian intelligence services finally succeeded in capturing Reilly seven years later. He had agreed to meet with members of an opposition group knowing there could be turncoats among them, but not knowing the organization was wholly a Soviet false flag operation, The Trust. On September 25, 1925, members of the group lured him across the Finnish border into Russia, ostensibly for high-powered meetings in Moscow to consolidate the opposition. Instead, Soviet police arrested him. Officials reminded him he had been under a death sentence for his attempts in 1918 to overthrow Lenin. Under torture, he did provide some information to his captors. “But most, if not all, of it was low-grade and likely already known” [to Soviet intelligence], writes Morris.

Author Benny Morris (Wikimedia Aude CC))

While Reilly’s execution is documented in Soviet archives, it is notable that stories emerged ever since that Reilly survived. In one version, he even became a KGB agent Morris writes, “indirectly training the Cambridge ‘moles’ of the 1930s-1950s, Kim Philby, Donald McLean, Guy Burgess, and Antony Blunt.”

There has never been proof of that, but it tracks with the fantastical story of Sidney Reilly, a legend in the history of British intelligence. 

“James Bond is just a piece of nonsense I dreamed up,” Morris writes, quoting Ian Fleming. “He’s not a Sidney Reilly.” 

The West could certainly use another like him today. Then again, maybe they have.

SpyTalk Contributing Editor Peter Eisner is an award-winning reporter and editor, formerly at The Washington Post, Newsday, and the Associated Press.