Sidney Reilly
By Benny Morris
Yale University Press, £16.99

Yale University Press’s Jewish Lives series is a splendid initiative: short (fewer than 200 pages) biographies of the greatest names in Jewish life and thought since Moses. Plucking names at random, you’ll find Rabbi Akiva, Moshe Dayan, Albert Einstein, Maimonides — you get the idea.

Whether Sidney Reilly, born Sigmund (or possibly Shlomo) Rosenblum in Odessa in 1874 (or possibly 1872), belongs in such exalted company is questionable. He would certainly have thought he did: at various times he compared himself favourably to Napoleon and Jesus. Others may beg to differ.

He did everything in his power to deny his Jewishness, though fooling nobody at all as far as one can see, and his life, though dramatic, was essentially a failure.

His name lives on because he was said to have been the greatest secret agent of his generation, working mainly in Russia in the turbulent years between 1905 and 1925, when he was executed by the Bolsheviks. He is even said to have been the model for James Bond.

sidney reilly By Benny Morris

The principal similarity between the two is that Reilly was a tremendous womaniser, although, unlike Bond, he was always getting married: the final headcount of wives is uncertain.

He was cosmopolitan — speaking several languages fluently — imaginative, daring and mysterious, the ideal qualities for an agent. He fancied himself as a businessman and indeed made a lot of money at various times, all of which he spent on gambling and high living.

His main employer was MI6, by whom he was recruited after he fetched up in London aged 20, escaping from the Russian secret police.He took the name Reilly in 1899, later claiming to have been born in a village in Tipperary. He made his reputation by buying arms for Russia in New York during the First World War, gleaning invaluable intelligence about German arms deals which he passed on to MI6 — and possibly others.

Back in London, Mansfield Cumming — “C”, the agency’s legendary first director — sent him on many important missions but Reilly never shook off the aura of shadiness and duplicity. Indeed, Cumming described him as “a man of indomitable courage, a genius as an agent but a sinister man whom I could never bring myself wholly to trust”.

Reilly’s boldest act as an agent was to try to topple the Bolshevik government in the newly created Soviet Union in 1918.

Working with Britain’s agent in Moscow, RHB Lockhart, he set up a network of conspirators, but it was infiltrated from the start by the secret police, the Cheka. Reilly planned to assassinate Lenin, Trotsky and other Bolshevik leaders at a meeting in the Bolshoi Theatre, a suitable dramatic setting. Lenin was indeed shot and severely wounded by the Jewish revolutionary Fanny Kaplan but the Cheka smashed the network before the coup could be staged.

Although under sentence of death, Reilly evaded capture, lying low in a brothel among other safe houses before getting away by ship to Helsinki.

Cut loose by MI6 in 1920, he resurrected his business career while plotting with anti-Bolshevik exiles as a freelance agent.

His luck finally ran out in 1925 when he was lured back into Russia by a supposed monarchist group that was in reality run by the Cheka. It was almost as if he had a death wish. He was interrogated at length until being taken out and shot. He was still only in his early forties.

Benny Morris, as one would expect from such a distinguished historian, has produced an excellent summary of a tumultuous period, full of colourful and exotic figures. But one of them remains elusive: Reilly himself. What motivated him? Why was he so desperate to shed his Jewish identity? What made Sigmund/Sidney run? We’re none the wiser at the end.