12 of History's Greatest Back Stabbers and their Dramatic Consequences

Eddie Chapman. Wikimedia

Eddie Chapman and the Germans

Eddie Chapman, AKA “Agent Zigzag” (1914 – 1997) was a safebreaker, thief, crook, and all around career criminal, who became the only Englishman ever awarded a German Iron Cross. It was ironic on many levels because he was also one of history’s most colorful double-crossers, and the false information he fed the Germans derailed the effectiveness of their “Vengeance Weapons”, and likely saved the lives of thousands of Londoners.

Raised in a dysfunctional family, Chapman was a delinquent from early on. He enlisted at age 17, but within a few months grew bored and deserted. When the army caught up with him, he was sentenced to a prison stint and a dishonorable discharge. After his release, he turned to fraud and crime to support a gambling habit and a taste for fine drinks.

When WW2 started, Chapman was hiding in Jersey in the Channel Islands from arrest warrants awaiting. A botched burglary earned him a two-year sentence in a Jersey prison, where the Germans found him when they captured the Channel Islands in 1940. He offered to work for them, so they freed and trained him in explosives, sabotage, and other clandestine skills, before parachuting him into Britain in 1942, tasked with destroying a bomber factory.

He was arrested soon after landing, however, and immediately accepted an offer to become a double agent – an easy choice, considering that the likeliest alternative would have been a hangman’s noose. Given the codename “Agent Zigzag”, a plan was concocted to fake the bomber factory’s destruction, which convinced the Germans and raised Chapman high in their esteem. From then on, his radio reports, carefully fed him by British intelligence, were treated as gospel by the Germans.

He was recalled and given a hero’s welcome by the Germans, and soon after D-Day, he was awarded an Iron Cross and sent back to Britain to report on the effectiveness of the German V1 and V2 rocket strikes on London. He set up shop, and under British control sent the Germans inflated figures about deaths from their rockets while deceiving them about their actual impact points, causing the Germans to shift their aim points, with the result that they tended to fall on lower population density parts of London, with correspondingly fewer casualties.

After the war, Chapman continued his colorful life, went into smuggling, moved to the colonies, started a farm, and in violation of the Official Secrets Act, got his exploits published in The Eddie Chapman Story (1953), Free Agent: Further Adventures of Eddie Chapman (1955), and The Real Eddie Chapman Story (1966), which collectively formed the basis of a 1967 movie, Triple Cross.