Sidney Reilly: James Bond, IRL, srsly.

I watched Casino Royale, my first James Bond movie ever, this weekend.  Someone told me Ian Fleming based Bond on a real spy, so I did a little digging. With pleasure, I bring you Sidney Reilly, the real life James Bond.

Spoiler alert: He doesn't look like Roger Moore, 1979.
Spoiler alert: He doesn’t look like Roger Moore, 1979.

A high-roller playboy who was as smart as he was cunning, English spy Sidney Reilly was actually…Ukranian.* As far as what we know for sure about his early life, he was almost certainly illegitimate, almost certainly Jewish, and almost certainly up for anything. He said he went to University of Heidelberg,* he said he went to Cambridge,* he said his dad was an Irish merchant*– long story short, he said a lot of things, but most of them were not true. This is probably unsurprising to you if you’ve seen any James Bond movies or are familiar with the general outline of the job description of “spy.” Anyway, Sidney Reilly was not his real name, since that’s not really a thing Russian people are generally named. It was probably Georgi Rosenblum.*

We start knowing things for sure around 1892.

He faked his own death at an early age, stowed away on a ship for Brazil, and got out of the general vicinity of Russia as fast as he could. There’s a pretty incredible story that says Reilly saved some high-level British army types from cannibal tribes in the Amazon and in return for saving their lives, they arranged a British passport for him. This is about as plausible as John Smith/Pocahontas narrative Disney used, which is to say “not at all.” More accurately, Reilly befriended some Englishmen in Brazil and they helped him get papers.  In 1896, regardless of how it came to pass, he moves to England and sets himself up as a chemist. Now things get really, really fun.

He had a lot of affairs (again, not surprising if you are familiar with any James Bond lore whatsoever), but one in particular set him up as Sidney Reilly, International Man of Mystery. He had a torrid affair with a one Margaret Callahan, the young wife of an old man.

Halle, who, now?

And what an affair it was. They fall in love (well, at least she did). She convinces her elderly husband to rewrite his will and strangely, he dies a week later of the “flu”*, despite the fact he is using all the drugs his helpful pharmacist Solomon Rosenblum has prescribed.

A doctor who is about ‘ye high and dark haired (yep) comes to sign the papers saying that there’s no need for an inquest, all is fine, move along, nothing to see here. The Jolly Pharmacist and the Widow Callahan marry a few weeks later, he gets permanent British citizenship for real, and he discards the name Sigmund Rosenblum and becomes Sidney George Reilly, Englishman. Rich Englishman. Rich Englishman with a really hot wife. Hey, guy’s gotta have a plan, and his was “marry this pretty lady come hell or high water and then get my friend William Melville, Scotland Yard, to sign some papers and make me English.”

The pair move to Manchuria and Sid gets into the import/export business. He’s making a killing, and things are overall going pretty well. It’s early 1904 and since you maybe weren’t paying attention in AP World History, Japan invades Russia. Melville (yeah, this is “M”, y’all) needs someone who speaks Russian, English, and maybe some other languages to help get information back to the UK to help navigate this and other crises.


They really need somebody. Sidney J. Reilly was that somebody.

He gets to work, sets himself up in Saint Petersburg in 1904, and gets some stuff done.  He leaves Margaret, which might have been expected, but they never divorce. He has a great number of dalliances and a few more marriages (not even already being married slows SJR down), and makes up some more facts about himself that aren’t even remotely true.

The next fifteen years see him parachuting in to Germany, running guns across Canada, escaping certain execution at Bolshevik hands approximately 16,000 times, and going to a lot of parties, shows, exhibitions, and other fun gatherings.

There’s pretty damning evidence that he was working both sides of the aisle (come on, this guy’s a grifter, basically; his loyalty is to his bank account only), but he brought MI6 the information they wanted, and he made a killing doing so. Despite Scotland Yard’s knowledge that this guy was pretty untrustworthy, they still trusted him enough to put him in charge of assassinating Lenin and Stalin. He didn’t do it, not wanting to make martyrs of them, but perhaps that would have been to his advantage. In 1925, Reilly crossed the Finnish border into Russian and was caught. It’s kind of  an odd story how it all unfolded, but he was executed by personal order of Josef Stalin before anyone back in London could intervene.

It’s hard to separate fact from fiction with this guy, in large part because he so believed his own tall tales. Suffice to say, he was an exceptionally bright light, but also probably suffering from narcissism and a lousy husband/countryman. Ian Fleming, it would seem, polished that turd just a little bit before immortalizing him in print.

So did you know about this guy? Got any good stories? Which Bond movie should I watch next?

2 Replies to “Sidney Reilly: James Bond, IRL, srsly.”

  1. So even though the movie (discounting the awful Woody Allen parody) Casino Royale was the 21st made, it was actually the first James Bond novel. I’ve read a handful of the original Ian Fleming novels and CR was, by far, my favorite. Not only did I find the tense baccarat (not poker) scenes fascinating, but for a reader the more emotionally vulnerable and troubled James Bond fresh out of 00 training comes out of the pages more readily than the cool killer we all know. I think the movie did an excellent job of rebooting the franchise with this green Bond (on screen and actor) and opened the door for Quantum of Solace and, particularly, Skyfall to wrap up the Bond backstory that no one ever saw in the films of the 60’s to now.

    That being said, I think the next Bond movies you choose to watch should be the old ones. True, Skyfall sets up the new age of old-style Bond like no other; but in order to recognize all the awesome details that are colliding together, you have to know the old movies. Dr. No, Goldfinger, Thunderball, Moonraker, and The Man With the Golden Gun are some of the most iconic original films, but you really can’t go wrong pre-Pierce Brosnan.

    1. Thanks for the recommendations! We had a copy lying around for reasons I don’t quite fathom, but I’ll seek out the older ones for sure! Maybe the stories for this summer…

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