How to Win at Monopoly

Here is a quick, sportsmanlike guide to killing your opponents in Monopoly. Many thanks are due to Phil Orbanes for permitting Book of Odds to develop probabilities based on his definitive guide, The Monopoly Companion, a vade mecum for players of all levels. The following tactics are derived from the Master himself. His book contains many more strategies.

These are just the basics:

Know your cards, beginning with Chance and Community Chest. These cards may look numerous, but in fact there are only 16 of each, and they may not be shuffled. With some serious mental effort, you can memorize which cards have been drawn, and deduce which are left—and since their contents are distributed unevenly, a canny player can take advantage of knowing what’s what. Of the 16 Chance cards, 10 move you to a new space, 3 impose fines (one of which is only for property holders), 2 give money, and 1 is the blessed “Get out of Jail Free” card.

Chance cards are likeliest to move your token to a new space. The odds a Chance card will:

Move you elsewhere: 1 in 1.6 (63%)

Fine you: 1 in 5.33

Give you cash: 1 in 8

Get you out of jail free: 1 in 16

Community Chest cards have a similar distribution, except they’re likeliest to give you cash. The odds a CC card will:

Give you cash: 1 in 1.78 (56%)

Fine you: 1 in 4 (one, again, only if you own buildings)

Move you elsewhere: 1 in 8

Get you out of jail free: 1 in 16

Know your dice. For the mathematically adroit, there are plenty more Monopoly probabilities to memorize, and the dice are a good starting place. The least likely rolls are 2 and 12: Out of 36 possible rolls, there’s only one way to roll each, making the odds of rolling a 2 or a 12 only 1 in 36. The likeliest roll is a 7—there are 6 ways to roll it: 1/6, 6/1, 2/5, 5/2, 3/4, and 4/3, making the odds you’ll roll it 1 in 6. Those are the same odds that you’ll roll doubles: For every six rolls of the dice, one is likely to come up with matching numbers, allowing you to roll again.

If you roll three doubles in a row, though, you go directly to Jail. The odds of that are 1 in 216.

Know your properties. The least landed-on property is Park Place. Take a look at the Monopoly board, and you’ll see why: It comes 7 spaces after Go Directly to Jail. Park Place is the space you’d be likeliest to go to next, if your token weren’t immediately incarcerated. It is, in other words, the space you are likeliest to be deprived of visiting—hence, the one you’re least likely to land on.

The dark purple spaces (Baltic and Mediterranean, just beyond GO) are the least visited color group as a whole. Buy them and build on them at will, of course—hotels there still pay big—but don’t expect other players to land on them more than 1 in 4.17 turns around the board.

Illinois Avenue is the most landed-upon single space. It and the two other orange properties are quite valuable—orange as a whole is the most visited color group: The odds are 1 in 2 that you’ll visit them for each trip around the board. Only railroads are visited more, but they don’t pay off nearly as much as a built-up orange property does. Rule of thumb: Buy orange if you can.

Cause a housing shortage. A little-known rule exists concerning the 32 green houses, and it can be used to an enterprising monopolizer’s advantage. It’s simple, really: If most or all green houses are currently in use, further building is restricted until some of those houses are given up and placed back in the bin. In intense play, it can be in your interest to build four houses on your spaces and then sit on them. If opponents want to buy houses toward a hard-hitting hotel, they can’t.

a) A color group is unowned, or partly owned only by you, OR

b) It prevents someone else from getting the whole color group—especially the orange group.

Know when to stay incarcerated. Believe it or not, jail time is occasionally preferable to freedom, despite what Bernard Madoff might say. Early in the game, it is best to cough up \$50 and get out of Jail immediately. But later in the game, when most properties have been bought and developed, it is actually advantageous to stay in Jail. It’s pretty self-explanatory, when you think about it: You spend three turns under the turnkey, cooling your heels, while your opponents circle the board, hopefully landing on your properties.

Use the speed die. This isn’t a tactic, so much as a method of expediting the end of the game. For decades, one of the most common and loudly trumpeted criticisms of Monopoly has been that it takes too long to end. Enter the speed die, a new addition to the game invented by Phil Orbanes himself. A third die, it makes gameplay faster, property purchasing easier, and allows you to move as many as 15 spaces in a single roll.

Be punishing, yet gracious. This Zen-like combo is Orbanes’ alpha and omega of Monopoly. The alpha, if you are truly out to win, is that you can’t take it easy on other players, even for a single turn. Be unrelenting. The dollar you don’t wring out of your opponent could be the dollar that brings them back into the game, and brings you down. It happens all the time, says Orbanes, a former judge for the World Monopoly Tournament. And then there’s the omega: Be gracious, be smooth, be a wheeler-dealer, but DO NOT be annoying or unsportsmanlike—your opponents will make it their top priority to watch you squirm. Mr. Orbanes gets the final word:

“Present yourself as the type of player others won’t mind losing to.”

Interview with Monopoly Expert Phil Orbanes

Phil Orbanes is former VP of Parker Brothers, Chief Judge for the US and World Monopoly Championships, and author of The Monopoly Companion. Click here for Part One of this interview.

Here’s something I’ve always wondered: Mr. Monopoly. Mr. Moneybags. Rich Uncle Pennybags. What’s his official name?

When the character was first created in 1936—and by the way, the artist who created him modeled his appearance on the iconic appearance of the nation’s most famous financier of the early 20th century, J.P. Morgan—he originally had no name. In 1946, he became Rich Uncle Pennybags. And that name stuck until the 1990’s when Hasbro did some research and determined that most people referred to him as “the Monopoly Man,” and at that point, they changed his name to Mr. Monopoly.

How has the game changed over time? I understand it had its start with a Georgist, who believed that no one had a right to own land. It was a way of illustrating the unfair practices of landlords.

The forerunner of Monopoly was entitled “The Landlord’s Game.” It was patented by Elizabeth Magie Phillips in Washington, DC, back in 1903, and she had a very strong political reason for developing her game. It was similar to Monopoly only in that it had 40 spaces at the perimeter of the game board—the idea of the “continuous path” that you followed round and round. She did have spaces on her board that were properties, and she did have railroads and she had a jail and “Go To Jail” and the equivalent of GO, which was called “Mother Earth.”

What it did not have are the rules allowing properties to be monopolized and developed. Those were actually created by college students a few years later.

Charles Darrow, an unemployed radiator repairman in Philadelphia, came across a handmade version that friends had, and he realized there was something great about this game. He gave it the look and the feel and the styling that we know today. And that look and feel and styling did not change at all from 1935, when Parker Brothers acquired it, until 2008 when a few tweaks were made to the game board to make it a universal board that’s the same now worldwide.

That “continuous path” can make for very long games. Like circumnavigating the Earth, you don’t come to the end, you just begin again.

There were three or four reasons why Parker Brothers initially said no to Monopoly, and one of them was just that: that the game did not have a clear ending. Most games in that era, the 1930’s, had a definite start state and a definite finish.

Not so with Monopoly. But over time, Monopoly grew out of being just a game for the purpose of winning; it became a social experience. And that meant that players actually wanted to see it last a long time so that you continued to socialize and just relax over the table.

One of the ways that’s accomplished is by placing under Free Parking all of the penalties that are being collected by the bank. So, instead of the bank keeping the \$100 that you just paid because you drew a Community Chest card telling you to, that \$100 is slipped under Free Parking and whoever lands there next gets your \$100 plus any other money that’s been accumulating there. It’s fun, but also completely contrary to the purpose of the game, which is to bankrupt your opponents as quickly as possible.

Now in a new edition of the game there’s the speed die you invented?

The speed die is now standard in all the basic Monopoly games sold around the world. We use the speed die to very good effect in the Championship.

The speed die came into being because I was challenged to come up with a solution to what many people feel is the major problem with Monopoly in the 21st century—and that’s how long it takes to play. Another reason for the length ties right into your theme of odds and probabilities, and that is that when you’re just at the mercy of two dice, very often many properties stay in the bank for an inordinate period of time, which means those color-groups can’t be formed and there’s less trade. So you can spend an hour or more just trying to get the properties into play before anybody can start to comfortably make deals.

Well, the purpose of the speed die is to overcome that problem, and it does it by making sure that all the properties get landed on and purchased early in the game, and immediately thereafter all the big rents come into play so you bring about the conclusion of the game—bankrupting your opponents.

What are some of the more exotic editions you are aware of?

There are well over 200 so-called localized editions, you know, California Monopoly, I Love Lucy Monopoly, Star Wars Monopoly. Those are officially licensed by Parker Brothers. There are also any number of unofficial so-called “-opoly” games. But some of the ones I like best are the unofficial versions that were made behind the Iron Curtain before communism came crashing down in Eastern Europe. And the reason that I particularly have a fondness for them is that the Russians banned Monopoly behind the Iron Curtain. They felt that it was a screaming endorsement of capitalism, and they didn’t want their people to be associated with it. Well, that just made the people behind the Iron Curtain even more desirous to play Monopoly, so a lot of cottage industries developed where informal versions were made and sold on the black market.

And Nazi Germany did not particularly like Monopoly.

There’s truth to that. The reason for that was that the German licensee, in 1936, happened to name the most valuable space on the board after an island in a canal in Berlin where many wealthy people lived, including some of the most famous Nazi officials. The Nazis were trying to project themselves as being of the people, and not being taken by riches and things like that, so they didn’t like the fact that their favorite place to live was associated with the highest-priced space on the Monopoly board. And they actually encouraged the Hitler Youth to picket in front of shops that sold the game. So the manufacturer was never told to stop making it, but consumers were fearful of buying it.

The greatest irony of all is that, during the war, a good chunk of the inventory was in a warehouse that—by accident—the British Royal Air Force destroyed. Most of the early copies of Monopoly in Germany disappeared in that one bombing raid.

And other games, like chess, are so old that any early anecdotes must be lost in time.

My favorite Monopoly story is how Monopoly was used to help prisoners of war escape in World War II. This was a top secret project of MI9, the British Secret Service. MI9 was responsible for helping prisoners to escape. They began to arm every airman with a silk map of the area where they would be flying, so if they were shot down they would have a map, marked with some locations where partisans would help them get back to England.

The reasons why silk was the preferred material were manifold. First, it was very lightweight. Second, it folds very nicely without creases. Third, it’s waterproof. And fourth, if you take it out at night, it doesn’t rustle and give your location away. So silk escape maps became standard for British airmen.

The company that made the silk escape maps, John Waddington Ltd., happened to be the same printer that was making Monopoly, and very quickly the British Secret Service realized that they could use Monopoly to smuggle escape tools and currency to prisoners of war. Then the prisoners would have the means to get out of these camps. They had a very small number of artisans in a locked room, who would carve openings in the Monopoly game board before the label was put on, and press into the openings low-profile compasses, files, and of course the silk escape map.

Then the board would be finished and go into a game, where real currency had been hidden under the Monopoly currency, and those games were given to the Red Cross to deliver to specific prisoner-of-war camps—so that the maps inside matched up to the area of the camp. The Germans were not inspecting packages that came in through the Red Cross for prisoners because they had become dependent on food delivered by the Red Cross to meet the Geneva minimum standards of nutrition for prisoners of war.

Although the project was kept secret for 50 years, and no accurate records were kept on how many prisoners owed their escape to Monopoly, what we do know is that 35,000 prisoners escaped successfully and got back to England.