In 1944, top British intelligence agent Lieutenant Colonel Robin “Tin Eye” Stephens took the trouble to write a top-secret report about Edward “Eddie” Arnold Chapman. This was finally declassified in 2005. The opening sentences of the report describe Chapman as “a man who likes—perhaps needs—to live on the fringes of society and has a strong desire to break its rules. He is driven by adventure and is often scornful of authority, with a talent for misbehavior.”
It was those less-than-salubrious qualities that allowed Chapman to become one of Britain’s most successful—and controversial—WWII double agents. Let’s take a closer look at 10 intriguing facts about Eddie Chapman.
10 A Plethora of Early Crimes
Edward Chapman was born in a village near the northern English city of Durham in 1914 into a home that was neither extremely poor nor particularly well off. School apparently didn’t suit him, and he often ditched class. An apparent shot at respectability came in 1932 when he joined the prestigious British Army regiment, the Coldstream Guards. But that didn’t last long—he ended up in military prison after deserting.
That was the first of many spells Chapman served in prison through the 1930s, with convictions for everything from robbery and fraud to lewd behavior and blackmail. Eventually, Chapman moved up the hierarchy of criminality and joined an elite band of safebreakers known as the Jelly Gang.
9 A Prince of the Underworld
It seems that Chapman had, at last, found his natural milieu. Tin Eye Stephens wrote that “The subject is a crook, but as a crook, he is by no means a failure,” adding, “In his own estimation [Chapman] is something of a prince of the underworld.” But Eddie’s position as criminal royalty came crashing down in Scotland. The police arrested him on suspicion of blowing up a safe in Edinburgh. Unwisely, the cops freed Chapman on bail, and he promptly absconded, fleeing south to Jersey, one of the Channel Islands. 
These islands in the English Channel are British Crown dependencies, a status they’ve enjoyed since 1066. However, the forces of law and order there didn’t take long to catch up with Chapman. Sticking to what he knew, Chapman did another safe-blowing job on the island, but he was arrested for that and tried in a Jersey court in March 1939.
8 A Nazi Invasion
Chapman was sentenced to two years in Jersey’s prison. The irrepressible rogue now managed to escape from jail a couple months into his sentence but was soon recaptured and sentenced to a further 12 months. Then in 1940, the Channel Islands had the unenviable distinction of being the only piece of British territory to be occupied by invading Nazis. Now Eddie was effectively a prisoner of the Germans. However, in 1941, he was released from prison.
Although he might now be free, life was hardly a breeze on Nazi-occupied Jersey. Chapman was compelled to scrape a living working with a gang of black marketeers, men he’d met in prison. But Chapman’s earnest wish was to find a way of getting back to England.
7 Vital Intelligence and Sabotage
The ever-resourceful Chapman hit upon a plan. He approached the German authorities and offered his services as a spy who would travel to Britain. From there, he could feed vital intelligence to his Nazi paymasters and perform acts of sabotage into the bargain. Incredibly enough, the Germans bought it, and Chapman had now become a Nazi spy. Or at least that’s what his masters believed.
In fact, the Nazis thought they’d found the ideal man for their purposes. He made no secret of his criminal history, and the Germans believed that he’d potentially be able to recruit more agents from among his underworld contacts. Plus, as a practiced safebreaker, Chapman already had a working knowledge of how to blow things up.
6 Chapman Becomes Fritzchen
In Nantes, the Germans gave Chapman a thorough grounding in the art of spying and sabotage. They gave him a codename, Fritzchen, which can be translated as “Little Fritz.” During his training with the Abwehr, the German secret service, Chapman was able to live the life of Riley. His handlers gave him generous supplies of money, alcohol, and food. As the year 1942 drew to a close, the Nazis decided that their new star agent was ready for action.
On December 16, Chapman boarded a plane bound for England, where he would be dropped by parachute near the city of Cambridge. His equipment included a suicide pill, a handgun, a radio, invisible ink, and a wad of cash. His mission was to cause as much damage as he could to the vital DeHavilland aircraft factory in Hatfield, not far north of London.
5 A Deep-Rooted Hatred of the Hun
Chapman’s plane successfully crossed the Channel to England. As expected, the German agent jumped from the plane, landing in the countryside. But what he did next was very far from what the Nazis had intended. Without delay, he surrendered himself to the police, who, in turn, handed him over to MI5. He was now held at Latchmere House in London, the facility run by Tin Eye Stephens, the senior security operative we met earlier.
Unsurprisingly, Stephens and his colleagues were initially deeply suspicious of this career criminal turned Nazi spy who now insisted he actually wanted to work for his own country. But eventually, Chapman convinced Stephens of his sincerity, and the spymaster wrote that his newly minted double agent “certainly has a deep-rooted hatred of the Hun.”
4 Fritzchen Becomes Zigzag
While Stephens was far from entirely flattering in his estimation of Chapman, one does sense a grudging admiration in the senior MI5 agent’s report. “Today, he is a German parachute spy; tomorrow, he will undertake a desperate hazard as an active double agent, the stake for which is his life.” And so Chapman agreed to travel back to Germany, now as a fully fledged double agent, with a new MI5 codename, Agent Zigzag. But there was a pressing problem that had to be solved first. The outcome of Chapman’s mission in England for the Germans.
The British had to show the Nazis that Chapman was a genuine agent for them. To do this, they needed to demonstrate that the mission to sabotage the DeHavilland factory had succeeded. Of course, they couldn’t literally blow up the vital factory. But they could pretend that it had been badly damaged.
3 The Iron Cross
In an inspired plan of subterfuge, MI5 set off some small explosions at the DeHavilland factory and brought in a top magician and illusionist called Jasper Maskelyne. He dressed the premises in canvas and debris to make it look like it had been seriously damaged. A story was planted in the British press reporting a damaging attack on the factory.
Chapman now traveled back to France via neutral Portugal, where Chapman was greeted as a hero by his Abwehr handlers. They paid him a handsome bonus for his successful mission. They even awarded him an Iron Cross, making him the only Briton ever to receive Germany’s highest military honor. Chapman also landed a rather easier job—instructing rookie agents in German-occupied Norway.
2 Nazi Missiles
The Germans found another mission for Chapman, reporting on damage wreaked by the Nazis’ V-1 and V-2 missiles that were raining down on southern England. After parachuting back into England, Chapman actually asked his MI5 handlers to send him back to Norway for more undercover work. But MI5 discovered that he’d been conducting an affair with a Norwegian woman, a member of the resistance there.
Chapman admitted that he’d told his girlfriend, Dagmar Lahlum, that he was a double agent. Sensibly enough, MI5 decided it was too risky to allow him to return to Norway.
1 A Handy Double Payday
So now Chapman was retired from his adventures as a double agent. Chapman was given a substantial pay-off by MI5 and allowed to keep the money given to him by the Abwehr, a handy double payday. He was also granted an unconditional pardon for his previous criminal offenses. He continued to live a life of some adventure, at times on the fringes of his old underworld habits. But he stayed out of jail for the rest of his life and died peacefully in 1997, aged 83.
A final word from “Tin Eye” Stephens. In his MI5 report, he wrote, “The story of Chapman is different. In fiction, it would be rejected as improbable.”