Forget James Bond, Austin Powers, Jason Bourne… Today we’re looking at the person who I think is the greatest spy of all time.

And this one isn’t even fictional, although his story is so ridiculous that it’s hard to believe he isn’t. Actually, scratch that, it’s so ridiculous that were you to submit it as fiction, you’d probably get laughed out of the publishers for offering a story so ludicrously far-fetched.

So sit back, relax, and get ready for me to make your life seem comparatively very, very dull, as I tell you a thrilling tale of espionage, golden teeth, Nazi double-crossing and greyhound racing… which isn’t a sentence you get to say every day.

Before I get into the really juicy, spy-y bit, I should probably tell you a bit about the making of our unconventional war hero…

Edward ‘Eddie’ Chapman was born in County Durham, England in November 1914, slap bang in the midst of major international turmoil. Even from a very young age, he was never really one for following rules. He would often play truant from school to go to the cinema or the beach.

With his parents and teachers hoping it would straighten him out, Chapman was encouraged to join the military when he was 17. Despite earning himself quite a prestigious position as a guard at the Tower of London, rebellious Chapman soon realised that his priorities lay elsewhere… namely, with girls. You may notice this as a bit of a trend throughout this tale.

After just nine months with the army, Chapman abandoned his post and illegally absconded with a girl. When the army tracked him down two months later, he was sentenced to 84 days in a military prison. This was the first of many stints he ended up spending behind bars, but more on that later.

After his release from prison, Chapman returned to London. He scraped some cash together through a number of casual jobs, ranging from bartender to film extra, however he quickly wasted this away through his taste for fine alcohol and gambling.

It was around this time that Chapman received his first civilian prison sentence, having been caught forging a cheque. He was sentenced to two months in jail, by the end of which he’d made numerous inmate friends and had picked up a undeniable appetite for breaking the law.

It was then that Chapman turned to thievery. He joined a gang of safecrackers, with the deceptively sugar-coated nickname of the ‘Jelly Gang’, so-called because of their use of gelignite to explode the locks off safes and steal the contents inside.

He soon amassed a great fortune through his criminal activities and, during the 1930s, established a life as a wealthy playboy in London. He socialised with the upper-echelons of elite society, always with a girl on his arm and an expensive cocktail in his hand. He was known to be friends with popular celebrities, such as the actress and singer Marlene Dietrich and the flamboyant playwright and director Sir Noel Coward.

Over the next few years, Chapman spent various stints in prison, but never for very long, as he was always able to use his smooth charm to talk himself out of the most serious charges.

Nevertheless, by 1939, he had made himself an impressive number of authoritative enemies and had gained a reputation as an incredibly wanted man.

This didn’t really bother Chapman, though… in fact, he relished the chaos. He had grown up during an era of extreme political turbulence and – as should be no surprise considering his illegal exploits – had developed a highly anti-establishment viewpoint and disregard of Great Britain’s political and legal systems.

With the police on his back, Chapman fled to Jersey in the Channel Islands with his lover Betty Farmer.

One evening, when dining at a restaurant with Betty, Chapman spotted a police officer coming to arrest him and he did what any one of us would do in that situation: promptly dived out of the dining room window. That would be pretty damn cool in normal circumstances but, on this occasion… I’d be more tempted to say ‘painful’. The window was shut at the time. Ouch.

Sadly for Chapman, his daring and dramatic escape didn’t last all that long. Later that same night, he was arrested for attempting to commit a very slapdash burglary and immediately sentenced to two years in a Jersey prison.

During Chapman’s imprisonment, the Channel Islands were invaded by the Nazis. Spying an opportunity to improve his own situation, Chapman offered his services to the Germans, volunteering to turn traitor and work against Britain and her allies.

The German secret service – the Abwehr – accepted Chapman’s offer, impressed by his aforementioned hostility towards the British state, as well as the fact that he had lucrative contacts within the criminal underworld.

At the surprisingly luxurious Nazi base in La Bretonnière, France, the Abwehr spent a year training Chapman in numerous useful skills, such as the use of explosives, radio communication, secret codes and even parachute jumping.

Worryingly, Chapman struggled a bit with his parachuting lessons. One time he crash-landed and ended up breaking numerous teeth. Don’t feel too bad for him, though, because his oddly generous Nazi minders actually offered to replace his lost teeth with solid gold ones. I told you… this story is utterly bizarre.

On the 16th December 1942, Chapman was dropped by parachute into an English field, equipped with a radio, pistol, emergency cyanide capsule and £1000 (just over $800 at the time). Chapman – codenamed ‘Fritz’ – had been given a mission to sabotage the de Havilland aircraft factory at Hatfield, Hertfordshire, the base where the infamous Mosquito bomber plane was being manufactured.

Unbeknownst to Chapman and his Nazi minders, the British secret services knew all about this plan. Via Ultra – decrypted german messages – they had overheard his training and knew Chapman’s name, intended target and date of departure.

They did, not, however, anticipate his first move upon landing in England that cold December morning.

Dishevelled from an uncomfortable flight and his trademark ‘bumpy’ skydive landing, Chapman brushed himself off and – bizarrely – marched straight to a police station to hand himself in.

He immediately offered to turn traitor against his Nazi heroes who – let’s not forget – put him up in a luxurious French base for a year, trained him, fed him and even gave him a shiny new set of 24-carat teeth.

The reasons behind Chapman’s decision to spy for MI5 are hard to guess. Did he really decide to help the British war effort out of a previously hidden sense of patriotic duty? Maybe he was just a chancer, spotting an opportunity to earn himself more money once he realised how valuable an asset he could be. Your guess is as good as mine.

One anonymous British military officer was later to remark that ‘Chapman loved himself, loved adventure and loved his country, probably in that order’.

Of course, MI5 didn’t just accept Chapman’s offer immediately. Initially, he was taken to a secret detention centre in West London to be interrogated by the formidable, monocle-wearing Lt Col Robin ‘Tin Eye’ Stephens. The interview went on for days, with Chapman’s story checked, double checked and then triple checked.

Eventually, it was determined that he was genuine, and was fully on the side of the British. Thus Agent Zigzag was born.

To avoid the suspicions of his German sponsors, Chapman had to at least look like he was trying to complete his mission to destroy the de Havilland factory.

An elaborate plan was therefore put into place, involving some players who you probably wouldn’t expect to be involved in wartime service. Utilising his contacts in the world of celebrity, Chapman and a team of movie set-designers – not to mention stage magician Jasper Maskelyne –  began creating one of the coolest ruses in history.

Using carefully-placed sheets and polystyrene rubble, Chapman’s team cleverly decorated the construction base so that – when viewed from above – it would give the appearance of having been obliterated by bombs. Perhaps surprisingly, this plan actually worked, and the Germans were successfully fooled into believing that Chapman had completed his first mission according to their plan.

He was then allocated a number of other tasks for the Nazis, all of which he ingeniously crafted ways of avoiding without arousing German suspicion.

For example, in 1944, one of his missions was to report on the locations of where German bombs had been landing. Instead of reporting back to his Nazi minders saying that their weapons were undershooting, he informed them that they were successfully hitting their central London target. Thus, he managed to get the Germans to adjust their fire to such a great extent, that they ended up aiming for uninhabited fields, on the outskirts of the city, no doubt saving countless lives.

The Germans came to love Chapman. They sent him to Norway to teach at a German spy school, rewarded him with a whopping 110,000 Reichsmarks (about the equivalent of $750,000 today) and his own personal yacht.

He was even awarded the Iron Cross by Hitler himself for his services to Nazi Germany, making him the first Englishman to receive such an award since the Franco-Prussian War of 1870-71.

And it wasn’t just the approval of his military associates that Chapman received. As I mentioned earlier, Chapman never seemed too shy with the ladies.

During the war, he had two fiancees, each from the different sides of the war: Englishwoman Freda Stevenson, who was the mother of his first child, Diane, and Norwegian Dagmar Lahlum, who actually turned out to be a member of the Norwegian resistance.

After the war ended, Chapman abandoned both of these women and instead married Betty Farmer, the woman who he last saw moments before diving out of that restaurant window in Jersey. Together, she and Chapman had a daughter, Suzanne.

As the second world war was winding to a close, Chapman’s favour with the British Intelligence waned a little. He became heavily involved in a scheme of dog doping for greyhound races, and also refused to cut ties with his former criminal associates.

Eventually, realising attempting to control Chapman wasn’t worth the effort they were putting in, MI5 dismissed him in November 1944. He was given a pardon for his pre-war activities, and also a healthy dismissal package.

He ended up enjoying a considerably well-off retirement, although he never quite quit the habit of committing the occasional crime here and there… once even becoming involved in an attempt to smuggle gold across the Mediterranean in 1950.

His war record helped him out though, and he never saw any serious ramifications for his post-war exploits.

After a long life and more adventure than most of us would see in a hundred lifetimes, Chapman died in December 1997, aged 83.

So was Eddie Chapman the greatest spy who ever lived? Or was he too much of a chancer, out for himself more than he was protecting his country?

Also, if you were interested in finding out more about this incredible story, check out historian Ben MacIntyre’s amazing book Agent Zigzag, which goes into more detail about the twists and turns of Chapman’s life.


Sources: MI5, Ben MacIntyre’s Agent Zigzag, BBC, The Independent, The Guardian, The Economist.