The "Get Out of Jail Free" card in Monopoly took on a literal meaning during World War II. British intelligence smuggled real escape tools—maps, compasses, files, and actual foreign currency—inside specially modified Monopoly games sent to Allied prisoners in Nazi camps. And the Germans never figured it out.
In 1941, thousands of British airmen were being shot down over Nazi-occupied Europe and held in German POW camps. MI9, the branch of British intelligence responsible for escape and evasion, faced a problem: how do you get escape materials to prisoners when every package is searched?
The answer came from an unlikely source. John Waddington Ltd., a British company that manufactured Monopoly games in the UK, also happened to be one of the only firms in Britain that could print on silk. Silk maps were perfect for escapes—they didn't tear, didn't dissolve in water, and most importantly, didn't make noise when unfolded. Paper maps rustled and could alert guards.
MI9 approached Waddington with a top-secret proposal: create modified Monopoly games that could smuggle escape kits into German POW camps. In a secure, secret workshop, sworn-to-secrecy employees began producing special game boards with hidden compartments carved into them before the paper surface was glued on top.
Inside these compartments, they hid: silk maps customized for each region showing escape routes and safe houses, tiny magnetic compasses hidden in game tokens, metal files disguised as playing pieces, and real German, Italian, and French currency slipped underneath the Monopoly money. The modified boards were the exact same weight and thickness as regular games to avoid suspicion.
But how would prisoners know which games contained escape kits? Each modified game was marked with a tiny red dot on the "Free Parking" space—designed to look like a printing error. Additional codes told prisoners which region the map covered: a period after "Marylebone Station" meant Italy, after "Mayfair" meant Germany, after "Free Parking" meant Northern France.
The Germans allowed POWs to receive packages from humanitarian organizations, viewing games and pastimes as harmless distractions that kept prisoners occupied. MI9 created fake charities with names like "Licensed Victuallers' Sports Association" and "Prisoners Leisure Hours Fund" to send the games. They deliberately used return addresses from bombed-out London streets to avoid German investigation.
Before RAF aircrews left on missions, they were briefed about the Monopoly escape kits. If captured, they knew to watch for care packages from these specific fake charities and look for the red dot marking. Secret codes embedded in letters from "mum and dad" would alert them when a special game was on its way.
Once prisoners extracted the escape materials, they were instructed to destroy the game immediately to prevent the Germans from discovering the scheme. This is why no examples of these modified Monopoly sets survive today—every single one was deliberately destroyed during or after the war to protect the secret.
The operation was so successful that historians estimate these Monopoly games helped hundreds, possibly thousands, of Allied POWs successfully escape from German camps. By the end of the war, over 35,000 Allied prisoners had escaped—and while there's no way to know exactly how many used Monopoly maps, intelligence officers confirmed the games played a vital role.
The most remarkable part? The Germans never figured it out. Right up until the end of the war, Nazi prison guards had no idea that the innocent board games they allowed into camps were sophisticated escape kits. They saw Monopoly as a way to keep prisoners docile and occupied—never suspecting it was literally helping them break free.
After the war, everyone involved—including the escaped prisoners—was sworn to secrecy. All remaining modified games were destroyed so the technique could potentially be used again in future conflicts. The story didn't become public until 2007, when the surviving Waddington craftsmen were finally honored for their work.
So the next time you land on "Free Parking" or pick up a "Get Out of Jail Free" card, remember: for hundreds of Allied prisoners during WWII, Monopoly wasn't just a game—it was literal freedom hidden in plain sight.