How To Win Monopoly

By on February 19, 2013

How To Win Monopoly
After the 2008 financial crisis, studying the fundamentals of capitalism is more relevant than ever. And what better way to learn about the ins and outs of this solidly free market economic theory than learning how to win Monopoly? The goal of the game, as you likely know, is to bankrupt your opponents and win by owning the most properties and having the most cash. This isn’t exactly how real-life economics works, but delving into Rich Uncle Pennybags’ strategy of Monopoly—yes, strategy, ignoring the massive misconception that this game is purely one of luck—can help you topple your opponents before they quit out of boredom (according to this fascinating article from The Daily Beast, the longest game of Monopoly ever recorded was 70 days!).

Getting Started

Remember the real world advice that says you should always “make your money work for you”? It applies here as well! Cash in hand is the worst way to monopolize the board in your favor, so the first step to winning is buying every property you can. Of course, some Monopoly strategists say this is a bad idea because you should be saving that cash for properties within a specific color group, but the trick is buying up everything you can and holding as little cash as possible (but never $0) because not only is the return on investment greater than what you’ll be paying upfront, this tactic will also give you more leverage to trade properties later on in the game.

Study in Human Psychology

In their pursuit of the capitalistic payoff, many people tend to neglect the human element when playing Monopoly. Think it’s all just luck and number crunching? Not quite—studying how your opponents manage their cash and properties can give you valuable insight to how they’ll act later on in the game. Are they cash hoarders? Are they going for the same properties as you? How do they maximize their own profitability in early stages of the game? Studying these aspects can give you an edge over your opponents, as well as facilitate trading of properties if/when you decide to do so.

Railroads and Utilities

Monopoly experts are divided on the issue of the Railroads. They do have consistent payouts and while they’re undoubtedly useful if you own all four (or 1 or 2, just to prevent another player from owning a Railroad monopoly), it’s generally better to buy them early and trade them later on for another property in a color group in which you’re trying to monopolize.

Utilities…aren’t too useful. Only go for these if they’re up for auction. Otherwise, you’ll see that your profits here pale in comparison to the rest of your portfolio as the game plays out.

Which Color?

Mathematicians and Monopoly enthusiasts agree that orange properties are the best to own (and monopolize). Not only do they have a higher frequency of visitors (who’ll be paying you rent), but the immediate returns on house developments are greater, too.

What about the low-end dark purples? Baltic and the Mediterranean cost little upfront, but the cheap investment is going to cost you: they have the worst ROI until you get four houses on them and you won’t have as many visitors in comparison to the orange properties.

The green properties don’t get much traffic either, though they have the greatest expected return on investment, long-term. The only problem is squandering your excess cash on houses for properties few people land on. What about the dark blue Park Place and Broadway? While the rent may seem attractive, they also don’t get much traffic and are quite expensive to develop beyond a single house. That’s not to say you shouldn’t try to acquire these properties; just take it under serious consideration when it comes time to choose between the $400 Broadway or two, $200-something orange properties.

Houses and Hotels

After most or all of the properties on the board are under some form of ownership, it’s up to the owners to decide what to do with them. Trade them? Or maximize profitability by building on them (in cases where you control the color group)? It may seem obvious to go all-out in getting a hotel on your properties, but let’s be a little more strategic here: the opportunity cost for getting another house tends to go up after the first and third. What this means is that the cost of developing your property is likely higher than what your return on investment will be, short-term. There’s also the issue of house shortages; why upgrade to a hotel when you can diminish the availability of houses for your opponents to acquire for their own monopolies?

Mortgaging Properties

Short on cash? Mortgage your property and the bank will lend you half its value. While this does take time to pay back, this will give you a surplus of capital to use in the further development of your other properties (an investment that will pay off in dividends once your opponents start landing on your properties more often).


What was once deemed the dreaded “Go to jail” card in Chance can actually prove beneficial to you if you’re further along in the game. If there are still properties to be bought, pay the fine and get out as soon as you can. But if you’re in a mature game, staying in jail for a few turns while the other players duke it out Hunger Games style (okay, perhaps not so drastic) and lose money to each other while you’re avoiding paying them rent can be a solid strategy.


Games of Monopoly don’t have to drag on forever. Strategic investing, trading, and mortgaging can give you the upper hand over your opponents and ultimately lead you to be the monopolistic force in the victory seat.

Photo Credit: Mark J P & Mike_fleming 

Kelly Kehoe

About Kelly Kehoe

Kelly Kehoe is a full time college student and personal finance writer. In her free time she competes in speech and debate and writes fiction. Follow Kelly @kellypkehoe or on Google+.

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