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.

Buy properties when…

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.”

Click here for part one of an interview with Phil Orbanes.

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