The Ultimate Monopoly Strategy Guide

Caleb Compton
12 min readNov 16, 2020

Transcript:

What’s up designers, and welcome back to Rempton Games. First, I want to apologize for not uploading in a while. I am completing my Master’s degree this semester, and I have been really busy these past several weeks finishing up my project and report, as well as looking for jobs after I graduate. I am going to try to stick to a regular upload schedule for the foreseeable future, but the future is still very uncertain, so I’ll let you know when I know more. With that out of the way, lets talk about the reason you clicked on this video — Monopoly.

I would describe Monopoly as the McDonalds of board games — it’s not the best option out there, but it’s easy, always available no matter where you go, and everybody already knows it, and for no other reason because this is a totally original analogy. Monopoly isn’t a great board game, but it’s ubiquity is its strength. For me, I often play Monopoly around this time of year, because (when not enduring a minor apocalypse) the holiday season is a time to reunite with family and subsequently tear that family apart with tabletop game based rage, so that nobody wants to see each other for another year.

And, if you have to endure Monopoly with your family the least you can do is use your unrivaled knowledge of statistics and strategy to utterly defeat and humiliate them, right? That’s where I come in. In this video, I want to teach you how to always, definitely, 100% for sure beat everyone at Monopoly. Or not, because it is a game with a huge amount of randomness involved and even if you make the best choices you can there is still a chance somebody else just gets luckier but yeah, at least you can boost your odds as much as possible. Without further ado, lets get started.

The first choice you have to make when starting a game of monopoly is which piece do you want to play. This choice is extremely important, and choosing the right piece could swing the entire game in your favor. The obvious top tier options are the dog, top hat and, if you have a more recent version, the T-rex. Moving on.

At the beginning of the game the key is to be as aggressive with buying properties as possible. True, not every property is made equal (as we will talk about soon), but in the early stages of the game it’s better to get as much property as you can, rather than being picky. As the game progresses and you start upgrading your properties you can be more particular about which properties you upgrade and why, but even less valuable properties can be useful as leverage or bargaining chips. Also, early in the game nobody has a Monopoly yet, so there isn’t much reason to keep a stockpile of cash on hand since rents for undeveloped properties are so low. Finally, undeveloped properties are a terrible investment, and the only way to actually start making money off of them is to get a monopoly and start developing as quickly as possible, which requires buying up as much real-estate as possible.

Now lets move on to the middle stage of the game, when most of the properties have been bought and people are starting to gather and develop monopolies. Here is where an in-depth knowledge of the Monopoly board will come in handy. For this section I am going to be highly referencing a classic webpage by Truman Collins, who simulated millions of Monopoly rolls to get statistics on the game, including how likely you are to land on each space, and how much income each investment will bring in. I’ll be covering most of the main points, but I’ll leave a link in the description if you want to check it out.

The first and most important thing to realize is that every square on the Monopoly board is not made equal. Because you are rolling dice to move it may seem like your odds of landing on any given square would be the same, but this ignores things like Chance and Community Chest cards that move you around the board, the “Go To Jail” space, and rolling three doubles in a row sending you to jail. When you take these factors into account, the story is a lot different. The most landed on square by far is Jail — even if you choose to get out of jail as quickly as possible you still have a 6.2% chance of ending your turn in Jail. This in turn raises the probabilities of spaces that can be easily reached from Jail, particularly the Orange and Red Monopolies. In fact, the spaces on the 2 sides between jail and “Go to Jail” tend to have the highest odds overall, while spaces on the other two sides rank lower. Specifically, the two spaces in the brown (formerly purple) monopoly, Mediterranean and Baltic Avenue, are the two least landed on properties, followed by Park Place. The most landed on individual property is Illinois Avenue, while the most landed on Monopoly is the orange monopoly.

However, understanding the board not just about knowing the odds — it’s also about understanding the different income potentials of each space. A property’s income potential includes other factors, such as how much it costs to buy, how much it costs to upgrade, and how much rent it brings in at each stage of development. Understanding which properties to develop, how far to develop, and when, will be key to winning this middle stage.

Here are some general guidelines for development. First, if you have to choose between buying properties or developing your existing properties, always develop. Undeveloped properties simply don’t bring in enough money to justify the cost, and you should always try to develop as soon as possible. Lets show this with a real example. The brown monopoly, Mediterranean and Baltic, and the dark blue monopoly, park place and boardwalk, both consist of 2 properties. However, the brown monopoly is the cheapest in the game and has the lowest rents, while the dark blue monopoly is the most expensive and has the highest rents. Buying the dark blue monopoly costs $750 dollars, before you even start developing. Because you have the monopoly, this can bring you $70 to $100 in rent, and will bring in about $3.8 per roll. On the other hand, you can by both brown properties and upgrade all the way to hotels, and it will only cost you $620. This will bring in a rent between $250 and $450, for a total income of about $14 per roll. This shows just how powerful developing your property can be.

In fact, developing your property is so important that it is even worth mortgaging your other properties to do so. Yes, you will lose some income from those mortgaged properties, but the amount of income gained from higher rents will usually make up for this. Because of this, as soon as you get a monopoly you should mortgage your other properties as soon as possibly to develop that monopoly.

We now know the value of developing properties, but this doesn’t tell us WHICH properties to develop. Suppose, for example, that you have two partially completed monopolies, and want to make a trade to complete them. Or perhaps you already have two monopolies, and want to know which to develop and which to mortgage. How do you decide?

Your instinct may be to go for the more expensive monopoly, but this isn’t always the best choice. What we should be looking at is efficiency and return on investment, not how high the rents will be. This is based on the total earning potential of the property in relation to the cost. For example, lets compare the orange monopoly to the green monopoly. Fully upgrading the orange monopoly will cost $2,060, and result in a maximum rent of $1000. Fully upgrading the green monopoly, on the other hand, will cost $3,920, and only result in a maximum rent of $1400. The total cost is 90% higher, but only gets you 40% higher rent — clearly the orange monopoly is a more efficient use of your money.

In fact, taking the odds of landing on each square into account, the orange monopoly is the MOST efficient use of your money, followed in order by the light blue and red, and the rest as you can see on screen, and ending with the worst investment of all — the utilities. Seriously, those things suck.

Now that we have looked at which monopolies to upgrade, lets look at how. While it may be tempting to try to build hotels as quickly as possible, this should be avoided for two reasons. The first reason is efficiency — as we have discussed, higher rent isn’t always the best use of your money, and upgrading to 3 houses is actually the most efficient upgrade. The first three houses result in huge increases in rent, while the fourth house and hotel are much more incremental increases. For example, lets look at Illinois Ave. Upgrading from 1 house to 2 is a 200% increase, and upgrading from 2 to 3 is a 150% increase, but going from 3 houses to 4 is only a 23% increase, and upgrading to a hotel is even worse. For this reason, you should try to get all of your properties to 3 houses before springing for hotels.

Another reason to stick with houses rather than hotels is to cause a housing shortage. Monopoly traditionally only comes with 32 houses and 12 hotels — once those are gone, nobody can build anymore. If you can take up all, or even just most, of the houses, this can significantly limit your opponent’s ability to upgrade their properties.

Finally, lets look at WHEN to upgrade your properties. Although I have been saying to upgrade as soon as possible, and this is mostly true, you should always keep in mind where everybody is on the board. If none of your opponents are in range to land on your properties, it might be best to hold off on upgrading until they are more likely to land on them — especially if you are in danger of landing on an opponent’s developed properties. In addition, while the rules for efficiency I’ve been talking about hold true most of the time, don’t be afraid to make bold moves. If upgrading a space to a hotel would guarantee knocking out an opponent if they land on it, that might be the best move, even if it isn’t the most efficient use of your money.

Now that we have a better understanding of the board, there are a few other strategic points that are worth discussing. The first is Jail — your strategy for handling jail should evolve throughout the game. Early on, when you are still collecting properties, you generally want to get out of jail as early as possible, because staying in jail can result in lost momentum and fewer opportunities to buy properties. The only possible exception is if you need St. James Place or Tennessee Ave. to complete a monopoly — staying in Jail and trying to roll doubles to get out actually increases your odds of landing on these two spaces by about 25%.

Later in the game is a different story. Once you and your opponents have developed some properties, you may want to spend as much time in jail as possible. This is because you are still allowed to buy and sell properties, receive rent, and even participate in auctions while in jail according to the official rules, although some families have house rules saying you cannot. However, if playing by the normal rules it can be advantageous to stay in jail because there is no risk of landing on your opponent’s properties, while they can still land on yours. Basically, you can just sit back and watch the money roll in.

Since I brought up house-rules, lets talk about those. There are many different house rules, including the “no business in jail” rule, and the number of Monopoly games I’ve played with house-rules far exceeds the number without. Some of these rules are pretty innocuous (such as the rule that you get $400 instead of $200 if you land DIRECTLY on Go instead of just passing it), while others can actually hurt the game significantly. The two house rules I will address are Free Parking rules, and not using auctions.

According to the official Monopoly rules, free parking does nothing — it is literally just a safe space to park. However, there are a number of different house rules that give Free Parking an additional function, usually giving money to the person who lands there. The version I’ve played most often is that whenever you pay taxes, or pay a fee due to a Community Chest or Chance card, the fee goes into the middle of the board. Then, when somebody lands on Free Parking they collect that money.

I understand the appeal of this rule — it gives players hope even when they are behind that they might land on Free Parking and come back, and it’s always a very exciting moment when somebody does land on it. With that being said, I am not a fan of this rule. If you’ve ever wondered why Monopoly takes so long to play, this rule is a big part of the reason — players randomly receiving a big influx of cash does nothing but prolong the game. It also introduces an additional level of luck to an already very random game. I would recommend playing without this rule — you might be surprised how quickly the game goes!

Another common rule is playing without auctions. This is such a common rule that some of you watching may not even realize that Monopoly HAS auctions, but it does. According to the official rules, if somebody lands on a property and chooses not to buy it, that property goes up for auction. Anybody can then bid on the property, including the player who chose not to buy it in the first place. This rule actually opens up a lot of possibilities — you can choose not to buy properties right away in the hopes to pick it up cheaper, you can bid up opponents to make them pay even more, and you may even be able to pick up the missing pieces for your monopolies.

Auctions are a surprisingly deep mechanic — deep enough that Auction games became an entire genre which will probably get its own dedicated video at some point. For this reason, I can see why many people choose not to play with them in Monopoly. Auctions slow down the game and add an additional layer of complexity that players might not always desire, especially when playing with kids. For this one, I would say whether you use auctions really depends on who you are playing with — I’ll leave that judgement up to you.

The final aspect of Monopoly that I didn’t really touch on is the social aspect. Making deals and trading with other players is a huge part of the game, but is also the hardest to quantify. It really comes down to knowing the other players at the table. Some players might overvalue Boardwalk and Park Place, so you may be able to get a good trade with them for it. Other players might not realize how garbage the utilities are, and maybe will take them off your hands for more than they are worth. Having a good understanding of the board and the values of each monopoly can help you make good trades, and keep you from getting ripped off. My one piece of advice is to try and be nice — I have seen players denied trades on more than one occasion not because the trade was a bad deal, but because the player had a bad reputation. If done right, a trade can leave everyone better off, and if you develop a reputation for making good trades people will be more likely to want to make deals with you.

Until Next Time

That’s all I have for this week. As always thank you so much for watching, and I apologize again for the delay. If you liked this video please give it a like, and subscribe if you aren’t already so you don’t miss more videos like this in the future. If you want to see more you should check out my other videos, such as the previous entry in my “Evolution of Pokemon Designs” series. I also have over 100 articles on the Rempton Games blog, which you can check out at the link in the description. And join me next time, for the History of Game Design video I promised you last time! Until then, thank you so much for watching and I’ll see you all next time.

Originally published at https://remptongames.com on November 16, 2020.

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Caleb Compton

Software engineer by day, game designer, writer, and enthusiast by night! I love learning about games and sharing what I learn with all of you!