How an Intelligence Officer Used Monopoly to Free POWs

What got Christopher Clayton Hutton his job as an intelligence officer at MI9 wasn’t anything on his professional resume. His career as a journalist, his work in Hollywood publicity departments, and his stint as a pilot in the Royal Air Force during the First World War mattered little to the War Office when he applied in 1939. “My passport to the whole curious business,” he recounted 22 years later in his autobiography, Official Secret, “had been a casual reference to my thwarted efforts to get the better of Harry Houdini, the world’s greatest escapologist.”

During his interview, Hutton—or Clutty, as he was called—recounted to Major J.H. Russell how, on April 29, 1915, he had written to the legendary showman, challenging him to escape from a box built on stage, in full view of the audience, by the master carpenter of his father’s timber mill company. “You enter immediately,” Hutton wrote, “we … nail down the lid, securely rope up the box, and defy you to escape without demolishing same.”

Houdini accepted, with one condition: that he be allowed to visit the timber mill and meet the carpenter. Hutton, then just 20, arranged the meeting—not realizing, until much later, that Houdini had used the time to bribe the woodworker. In exchange for a mere £3 (less than $5), the carpenter agreed to build the box in such a way that, once Houdini was inside and the box was concealed behind a curtain, it would be easy for the famous escape artist to push one end off using just his feet, then nail it back on properly while the orchestra at the performance played especially loudly.

Though he’d always been interested in show business, Hutton told Russell that the Houdini incident marked the beginning of an obsession with magic. “Magicians, illusionists, escapeologists in particular—they all fascinate me,” Hutton said.

“You may be the very man we want,” Russell replied. “We’re looking for a showman with an interest in escapology.” And just like that, Hutton was hired.

Hutton’s job, he learned that day, would be to build and conceal tools that would allow Allied prisoners of war to escape German POW camps. Over the course of World War II, 232,000 Western Allies (and 5.7 million Soviet soldiers) were imprisoned in the camps, most of which were located in Eastern Germany and Austria, making for a long and difficult route back home. The prisoners, Hutton’s superior told him, were being instructed to try to escape, with the hope that they would be able to divert German soldiers from the front. Clutty was given the rank of lieutenant and told to get to work.

It quickly became clear that Clutty had no respect for rules or boundaries. He often employed unorthodox methods, and stepped on plenty of toes, to get things done. “This officer is eccentric,” his commanding officer wrote to a provost marshal. “He cannot be expected to comply with ordinary service discipline, but he is far too valuable for his services to be lost to this department.” Hutton and his team regularly churned out impressive devices to aid POWs in their escape attempts, including flying boots with hollow heels that held knives, maps, a compass, and a file—and could also be transformed into civilian shoes; a telescope disguised as a cigarette holder; and compasses so tiny they could be hidden on the backs of buttons.

But as ingenious as Hutton’s concealments were, the Germans inevitably figured them out. All of them, that is, but one. This particular scheme that Clutty had hatched wouldn’t come to light until the documents were declassified four decades after the end of the war: With the help of a Leeds-based manufacturing company, Hutton hid escape kits for POWs in unassuming, ordinary-looking Monopoly games.

MAPS AND MONOPOLY

Monopoly first made its way to the UK in 1935, just a few months after Parker Brothers purchased it from Charles Darrow. Not long after, the company shipped the game overseas to its U.K. partners, John Waddington Limited, a printing and packaging company that was beginning to make the move into games. “The Waddingtons were so taken by Monopoly that they immediately licensed it in December 1935,” Philip Orbanes, a Monopoly historian at Parker Brothers and author of three books about the game, tells mental_floss. “They adapted it to the market by changing the street names to appropriate streets in London.” The game, released in 1936, was an immediate hit in England.

In its original role as a printing company, Waddingtons was responsible for creating the silk play bills that were presented to the Royal Family at command performances. This had required the company to perfect the process of printing on silk, which its workers had accomplished by stretching the material and adding a gummy substance called pectin to the ink to keep it from running. The innovation made the printing of highly detailed silk escape maps—which didn’t rustle like paper maps, were impervious to dirt and water, and didn’t distort—possible, and the company was already making thousands for MI9, which were sewn into airmen’s uniforms. It was a perfect solution if an airman somehow managed to evade capture. But what about the men who ended up in POW camps?

From the collection of Philip E. Orbanes. Click to enlarge.

Clutty knew that games were allowed into camps; the Germans believed they provided a diversion for POWs whose main activity was trying to figure out how they could escape. And then inspiration struck: Most of his devices could only conceal one tiny tool, but a game with a large board could hide a silk map, a small compass, a Gigli saw, and a file. Waddingtons made silk maps—and Monopoly. The game was large enough for what he wanted, and the fake money could conceal the real money that POWs on the run would need. It was perfect for Hutton’s all-in-one escape kit.

On March 26, 1941, Hutton discussed the matter with the company's chairman, Victor Watson, then followed up with a letter that same day, which read, in part:

Dear Mr. Watson, Reference our conversation today. I am sending you, under separate cover, as many maps as I have in stock of the following: Norway and Sweden Germany Italy I shall be glad if you will make up games on the lines discussed today containing the maps as follows: One game must contain Norway, Sweden, and Germany. One game must contain N. France, Germany, and frontiers. One game must contain Italy. I am also sending you a packet of small metal instruments. I should be glad if in each game you could manage to secrete one of these. I want as varied an assortment containing these articles as possible. You had then better send me 100/200 games on the straight. In those that are faked, you must give me some distinguishing clue and also state what they contain.

Waddingtons put just a few workers on the project, secluding them in a small room, where they used cookie cutter-like dies to punch compartments exactly the size of the items into the Monopoly boards—which were then an eighth of an inch thick, compared to today’s twelfth of an inch—before gluing the game board decal over it. When their job was done, the board was indistinguishable from one a regular citizen might buy in a store.

Courtesy of Philip E. Orbanes. Click to enlarge.

GETTING THE GAMES INTO THE CAMPS

After designing his ingenious escape aids, Clutty’s greatest challenge was figuring out how to actually get them into the camps. He couldn’t use Red Cross packages, and monthly personal packages sent to POWs by family and friends were out, too. “I had no doubt that if the Germans discovered an illegal item in a ‘family’ parcel, they would have no compunction about withdrawing the privilege altogether,” Clutty wrote in Open Secret.

But Hutton knew that hundreds of organizations were sending care packages to POWs, and he decided to use that to his advantage. “We would hide our escape aids in parcels containing games, sports equipment, musical instruments, books, and articles of clothing,” he wrote. “We knew that these voluntary gifts, designed for the comfort and entertainment of the prisoners, were flooding the camps from hundreds of sources … There was no valid reason why we should not take cover behind this multiplicity of well-wishers.”

He and his team created a bunch of bogus organizations using the addresses of blitzed buildings. A printer made letterheads for the organizations “littered with quotations that we hoped would act both as clues and as an inspiration to the prisoners,” Clutty wrote. “One obvious quotation was from St. Matthew, Chapter 7: ‘Ask and it shall be given you; seek and ye shall find; knock and it shall be opened unto you.’” To make their packages as authentic looking as possible, the team wrapped the parcels that supposedly came from Liverpool organizations, for example, in sheets from the Liverpool Echo.

To see if their packages were getting through, Hutton and his team enclosed “a printed card of acknowledgement on which the contents were enumerated. All the prisoner had to do was to tick off each article as received and return the card,” which was slightly bigger than the one used by the Red Cross, allowing for easy sorting by the censors. After sending out the first batch—which contained no contraband—the team waited and waited to receive cards. “We grew more and more depressed,” Hutton wrote, “telling ourselves gloomily that the Jerries had confiscated the lot and we should hear no more about the matter.”

But then, three months after they’d sent their packages, a card came in—then another, and another. The packages had gotten through! It was time to send through a batch that wasn’t entirely legitimate. “These plans of mine were greeted on all sides with complete skepticism,” Hutton wrote. “Even Major Crockatt said to me as the first 13 loaded parcels were sent, ‘They will never get through in 100 years.’” But Crockatt was wrong. Everything, even the fake material, had been delivered: “We had our entree into the camps.”

SENDING A MESSAGE

Getting the games into the camps was just one part of getting the tools to the POWs. Clutty also had to make sure that the prisoners knew what they were receiving. Clever messages that hinted at what was hidden inside the packages weren't enough; Clutty decided to train at least two members of every Air Force squadron in the art of sending hidden messages concealed in ordinary looking letters addressed to Mom and Dad.

When the trained men mailed letters back to the UK, those letters were intercepted and given to intelligence officers, who steamed them open and took a look at the date. “If it was written out, M-A-Y 3rd, the letter was simply resealed, and it went to whatever relative it was addressed to,” Orbanes says. “But if the letter’s date was numerical—three slash five slash '43—that said ‘there’s a message in this letter.’” The intelligence officer would then multiply the number of letters in the first two words to determine how many words were in the message. If the first two words were “how nice,” for example, then the officer would multiply three by four to get 12 words. “Then,” Orbanes says, “there was a technique by which he could pick out the words in the letter and write out the message.”

This allowed intelligence officers and POWs to communicate back and forth. POWs reported on conditions in the camp, and what they might need to escape—and intelligence officers let them know when special packages were coming their way. “The code user in the camp would eventually get a letter back from ‘Mom or Dad’ that would contain a secret message, and it would tell them when to expect the shipment and what the parcels might look like,” Orbanes says. The contents of Clutty's escape kits could be modified based on requests from code users.

Courtesy of Philip E. Orbanes. Click to enlarge.

Because keeping the secret of how escape tools were getting into the camps was paramount, only a few men ever knew how it was happening. Each POW camp had an escape committee that would receive the items, destroy the method of delivery by burning it in the barracks stove, and hide the tools away in false walls. “Ninety-nine percent of all the POWs had no idea of how the tools were getting into the camps,” Orbanes says. “If you and your buddies had a plan for an escape, you would go to the escape committee and present your idea. And if it was approved, they would issue you the tools you needed. So the POWs got what they needed to effectuate their plan, but they never knew how the tools got into the camp.”

THE AMERICAN EFFORT

When the United States entered the war, after the Japanese attacked Pearl Harbor on December 7, 1941, Hutton was tasked with training his American counterpart, Captain Robley Winfrey, in the art of concealing escape tools in ordinary looking stuff. Winfrey, a civil engineering professor at Iowa State, took a leave of absence to join the Army when the U.S. entered the war; he set up a large, secret operation, Military Intelligence Services—Escape and Evasion Section (MIS-X), on the grounds of Mount Vernon in Virginia. Winfrey came up with a number of ideas to supplement Hutton’s, and it wasn’t long before MIS-X was sending out Monopoly boards loaded with escape tools, too.

But Winfrey’s operation differed from Hutton’s in one very important way: He didn’t have a factory that was making complete escape kit boards for him. Instead, he had to send MIS-X staffers in civilian clothes to stores to buy the games. “They would bring the games back to their facility and steam off the gameboard labels,” Orbanes says. “Then they would cut the compartments in, put in the particular escape tools that they wanted inside that game, and then re-apply the label—they actually had to reverse engineer the glue that Parker used.” Not even Parker Brothers knew their boards were being doctored.

GAME OVER

The Germans had discovered a number of Clutty and Winfrey’s concealments, so the duo always had to be one step ahead of the enemy. When the Germans realized that the cribbage boards prisoners were receiving actually contained radio parts, Winfrey began hiding the parts in the cores of baseballs; it took four baseballs to conceal enough parts to build one radio. Table tennis, Snakes & Ladders, chess sets, and playing cards were used to get escape tools and maps into POW camps.

When the war ended in September 1945, there was just one escape kit the Germans hadn’t discovered: Monopoly. None of the modified boards survived—the POWs had to destroy the boards that came into the camps, and MI9 and MIS-X destroyed whatever was left at the end of the war—and the role the game played wouldn’t be revealed until 1985, when British intelligence declassified documents related to Clutty’s work in MI9. MIS-X’s use of the game wasn’t revealed until 1990, when a member of that team was granted permission to tell his story.

According to Orbanes, at least 744 airmen escaped with aids created by Hutton and Winfrey. One of them was an American officer, Lieutenant David Bowling, who was a prisoner at Stalag Luft III, 100 miles southeast of Berlin. In late 1943, he responded to a commanding officer’s request for a solo escape attempt—which, if Bowling was recaptured, was punishable by death. “Leaders inside the camp had learned that the SS was attempting to wrest control of POW camps from the Luftwaffe,” Orbanes says. “With the war turning against the Germans, the SS proposed executing all POWs in order to free the security forces to bolster the front lines. This possibility had to be communicated quickly to Allied Command in England.”

Bowling spoke German well, and was issued civilian clothing, a forged ID, and a train schedule. He also traveled with German money, a silk map, a tiny compass, wire cutters, and a Gigli saw, which most likely came from a Monopoly game.

A few nights after getting the orders, Bowling waited until lights out at 10 p.m., crawled to the wire, and cut his way through, making his way to Sagan, about 10 miles away, where, the next morning, he boarded a train heading toward Switzerland, according to his map. “For days, Bowling guided his movements by his compass and map,” Orbanes says. “At times, he had to cut through fence wire to avoid walking across fields and remain hidden in woods.” Bowling eventually made it to Zurich and relayed the urgent message.

Were there more attempts like Bowling’s? Most definitely. But we’ll never know for sure just how many—most of the records, British and American, were destroyed just after the war ended. Says Orbanes, “These were better kept secrets than the Manhattan Project.”