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Close-up of Monopoly board game txking/Shutterstock

A computer played Monopoly over 300 million times — here's the mathematically best way to win

Monopoly has been a part of family life in America for over 100 years, sometimes bringing parents and children together, but just as often causing an argumentative schism when one family member bankrupts the other. If you’re a player who finds themselves too often cashing in your houses and hotels to pay rent, a new experiment could help you become your family’s rich Uncle Pennybags.

Perfect Play had a computer play more than 312 million games of Monopoly against itself, coding eight classic strategies into player models and running a tournament. The best of those digital players won 43% of the games it faced. At the other end of the spectrum, the worst won just 3% of the time.

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The first player type bought everything it lands on. Another, even more aggressive, player never kept cash, mortgaging properties to buy even more. The saver, the third player type, always kept cash on hand. And the three-houses player never exceeded that number of additions to their property.

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Specific player types made up the remaining players. One only wanted properties on the cheap side of the board. Another only wanted properties on the second half. A third picky player focused exclusively on railroads and utilities. And the final player bought any sort of property, but refused to ever trade them.

What it takes to win

Victory on a consistent basis was the result of players making one or more of four mistakes, Perfect Play said.

Players who are too picky about what they buy tend to lose. If you land on a property and you have the cash, buy it. Don’t want it? Another player might and that could be something you can leverage later in the game.

While hoarding cash isn’t a bad idea in this real-world economy, it’s a bad idea in Monopoly. Players who chose a strategy of liquidity over investment rarely won the game.

Housing costs might take a big bite out of your cash on hand, but you still want to max out your real estate holdings on your properties. Get to three houses fast and mortgage properties to do it if you have to.

Finally, don’t be close minded to trades with other players. Refusing to trade puts you at a disadvantage that can ultimately cost you the game.

And if you have to choose a certain property group, it said, fight for the orange properties—St. James Place, Tennessee Avenue, and New York Avenue.

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The legend of Monopoly

Monopoly is a game that can teach a lot of economic lessons to players, including the value of real estate. The legend of the game is that it was developed by an unemployed salesman named Charles Darrow during the depression, somewhere around 1935. That’s not quite true.

A Quaker named Lizzie Magie, in fact, created the game in 1904 to showcase the evils of property ownership. (The original title was “The Landlord’s Game”.) Magie was a supporter of the Quaker tax reformer Henry George and the game focused on players extorting others.

It was a hit in the Quaker community – a big one. One enthusiastic fan was a hotelier named Charles Todd, who would sometimes play with his guests. One regular visitor was (you guessed it) Charles Darrow, who asked Todd to write up the rules for him.

Once the game took off, Parker Bros. learned its true origins and had to do some damage control. It bought the rights for $500 from Maggie, who believed her original game – and its philosophies - would be distributed. And it was – well, for a couple hundred copies at least before it was discontinued. Turns out people had more fun with Darrow’s tweaks to the game.

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Chris Morris Contributing Writer

Chris Morris is a US based veteran journalist with more than 35 years of experience at many of the biggest digital news outlets. In addition to his activities as a writer, reporter and editor, Chris is also a frequent moderator and speaker at major conferences, including CES and South by Southwest.

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