Monopoly’s Secret History: From Anti-Landlord Protest to WWII Escape Kit

1904. That’s the year the game that became Monopoly was patented, 31 years before Parker Brothers sold a single box, and not by the man on the box.

More than a decade ago, Book of Odds interviewed Philip Orbanes, the leading historian of the game. Orbanes spent years as Senior Vice President for Research and Development at Parker Brothers and has served as Chief Judge at the U.S. National and World Monopoly tournaments, a role he has held since 1979. Below are the stories he told us, re-checked against the record, including one famous number that doesn’t survive the check.

It started as a protest against landlords

Monopoly’s first designer was Lizzie Magie, a follower of the economist Henry George, who built her game to show how land rent concentrates wealth. She designed it around 1902–03 and play-tested it in the single-tax community of Arden, Delaware. On January 5, 1904, she received U.S. patent no. 748,626 for The Landlord’s Game, and after no publisher bit, she released it herself in 1906.

Her design introduced the feature that still defines the game: a “continuous path” board with no fixed start or finish. The patent drawing already includes railroad spaces, a Go to Jail instruction, and a Public Park space that anticipates Free Parking.

The game spread hand to hand for three decades. Quaker players added Atlantic City street names and fixed property prices, and it was one of these homemade versions that Charles Darrow learned from a friend and later sold to Parker Brothers. Darrow received his own Monopoly patent on December 31, 1935, and Parker Brothers soon bought Magie’s patent as well, locking up control of the game.

Who is the man in the top hat?

He didn’t exist in Darrow’s version. The mustachioed tycoon first showed up on Chance and Community Chest cards in U.S. editions in 1936, drawn by artist Daniel Fox, whose role was forgotten until one of Fox’s grandchildren contacted Orbanes in 2013.

He also went nameless for a decade. He got his first name in 1946, when Parker Brothers put him on the box of a spin-off game called Rich Uncle. That’s where “Rich Uncle Pennybags” comes from. He moved into the logo itself, popping out of the second “O,” in 1985, and Hasbro officially renamed him Mr. Monopoly in the late 1990s. Sources give 1998 or 1999.

His look is usually described as loosely based on financier J.P. Morgan, which is what Orbanes told us too. Not everyone agrees: some fan histories point instead to banker Otto Kahn. Nobody has produced a design brief that settles it.

Too capitalist for dictators

A game about cornering property markets made authoritarian governments nervous.

In Germany, the most expensive address on the first German edition was Schwanenwerder, a wealthy island in Berlin’s Havel river, and Joseph Goebbels bought property on that same island just as the game hit the market. He paid 270,000 Reichsmarks in 1936 for the house of Deutsche Bank chairman Oscar Schlitter. Orbanes told us the regime disliked the association and that Hitler Youth picketed shops selling the game. Whether the Nazis formally banned Monopoly is less clear. A 2022 Berliner Zeitung investigation treats the ban as an open question rather than established fact.

Elsewhere, Mussolini objected to the game being produced in Italy. In the Soviet bloc, Monopoly was played underground, irritating Soviet officials who saw it as a tool of capitalism.

The escape kit hidden in the box

The best story is also the truest, in outline at least.

During World War II, Britain’s escape-and-evasion service, MI9, needed a way to get maps to captured airmen. Maps printed on silk were ideal: light, quiet and hard to destroy. John Waddington Ltd. happened to be both the British firm that had mastered printing on silk and the British licensee for Monopoly. British intelligence officer Clayton Hutton designed and distributed the special sets. Later, America’s MIS-X ran a similar program.

Doctored sets reportedly concealed silk maps, compasses, file parts and real currency under the play money. What the popular version gets wrong:

They didn’t come from the Red Cross. Escape aids were sent through private and often fictitious organizations, such as the “Licensed Victuallers Prisoner Relief Fund,” and never in Red Cross parcels, so Germany would have no excuse to block the real aid.
The maps didn’t show safe houses. MI9 assumed some maps would fall into German hands, so marking safe houses would have been reckless.

The famous number, re-checked

You’ve probably seen the claim: of roughly 35,000 Allied POWs who escaped, about a third were helped by rigged Monopoly sets. It appears across forums, email chains and history blogs, usually word for word, and even careful retellings hedge that it is only “claimed”.

We couldn’t find a primary source for the one-third figure. In our original interview, Orbanes said something more modest: no accurate records were kept of how many prisoners owed their escape to Monopoly. The rigged sets were real. The one-in-three figure isn’t documented anywhere.

Book of Odds verdict: The odds a WWII escape involved a Monopoly board are unknown, and anyone quoting “one in three” is repeating a chain letter, not a record.

Why Monopoly never ends

Magie’s continuous path is why games drag on: there’s no finish line, only bankruptcy. House rules make it worse. Putting fines under Free Parking, for example, injects cash back into the game, the opposite of what the rules intend. Orbanes told us he designed the third “speed die” specifically to shorten games by getting properties bought faster.

For the math behind winning, including which properties get landed on most and when to stay in jail, see How to Win at Monopoly, by the Odds.

How we checked: We re-verified every claim from our original interview with Philip Orbanes against patent records, published histories and fact-checks. Where sources disagree (the rename year, the ban, Mr. Monopoly’s model), we say so. Last checked: September 2026.

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