5 Ian Fleming
Yes, that’s right, the creator of James Bond himself had a good deal of Bond-esque flair! And he also had a background in British military intelligence. Fleming attended prestigious schools and, as a young man, excelled at athletics. In his early 20s, he lived in Austria, Germany, and even in the USSR for a time. He also conducted numerous affairs with several women. His “training” to become a real life 007 was almost complete! With the outbreak of WWII, Fleming joined the Royal Navy in an intelligence capacity and was soon helping to plan special operations. One of the missions he helped orchestrate was called Operation Golden Eye. Go figure.
4 Michael Vickers
If Michael A. Vickers passed you by on the streets of Washington DC, you might not look twice at this sixty year old fellow. But the current Under Secretary of Defense for Intelligence is a badass of the highest order. Vickers joined the army’s Special Forces at age 20, and was soon made a commissioned officer. After nearly a decade and a half, he moved to CIA paramilitary operations with that agency’s secretive Special Activities Division. We will never know most of what Vickers did in the field, but we do know that this soldier/spy has a BA from the U of AL, an MBA from Wharton and a Ph. D from Johns Hopkins, so he can likely destroy you in a heated debate as easily as he can kill you with a thimble.
3 F. F. E. Yeo-Thomas
This guy’s name lets you know he’s not messing around even before you know a thing about him! Forest Fredrick Edward Yeo-Thomas was the name this Englishman’s parents bestowed upon him. To the British military intelligence, he was The Seahorse. To the Gestapo, Yeo-Thomas was The White Rabbit. Too young by a year for WWI, he joined the Polish fight against the USSR in 1919. He was captured by Soviets and strangled a guard in order to escape, thus avoiding execution. During WWII, he parachuted into occupied France numerous times, working with the Resistance. Captured by the Germans in early 1944, Yeo-Thomas spent much of the rest of the war escaping and being recaptured.
2 Robert de la Rochefoucauld
Before Count Rochefoucauld served for decades as the beloved mayor of a town in France, he was serving the British Special Forces as goddamn badass. Rochefoucauld slipped out of German-occupied France and made his way via Spain to England, where he soon trained to parachute, use explosives and kill in a variety of ways. Rochefoucauld then began a series of daring missions in which the series of events usually went this way: 1. Parachute into France. 2. Blow something up. 3. Get captured by Nazis. 4. Outsmart and/or kill captors. 5. Escape back to England via disguise and/or submarine. 6. Repeat.
1 Sir William Stephenson
Of this man Ian Fleming once said: “James Bond is a highly romanticized version of a true spy. The real thing is William Stephenson.” When the creator of James Bond essentially says “You’re James Bond,” you win at life. Canadian by birth, Stephenson spent much of his youth raised by a foster family from Iceland. During WWI, he made his way to England and eventually joined the Royal Flying Corp, becoming a double ace with 12 confirmed aerial victories before he himself was shot down over France. He escaped a POW camp in October of 1918. Between WWI and WWII, thanks to a marriage and a series of inventions and patents, including one that sent images over wireless frequencies, Stephenson was rich and well-connected. He knew many international businessman and thus knew of Germany’s military buildup in the 30s, information he passed on to British military and intelligence authorities. During WWI, under the codename Intrepid, Stephenson was essentially tasked with creating a network of intelligence operatives spread out across the Western Hemisphere. He worked closely with US officials as well as with the governments of more than a dozen other countries in helping organize as many allied covert operators as possible. In many ways, he was the father of the modern spy.