Six strategies for playing Monopoly

(or why Monopoly is terrible and what you can do about it)

9 min readDec 12, 2018

With the holidays coming up, we may all be facing the prospect of eggnog and boardgames. In particular, one family favourite (or hated favourite)…

Monopoly.

While monopoly definitely contains a healthy dose of luck, there are ways to do better at it, and ways to get more out of it. Here are some tips and tricks to make sure you get the most out of it.

And there’s also a lot of fascinating history to Monopoly. So this will arm you with the essential trivia that means even if you’re losing the game, you can win the metagame by having the best Monopoly anecdotes.

First anecdote… The pieces! Ever wonder what a battleship and a gun is doing roaming the streets of Atlantic City (the original Monopoly city — not New York as some people assume) or London? Everything else is kind of thematic but those ones stick out.

Well. The original makers of Monopoly, The Parker Brothers, made two other games called Conflict and Diplomacy.

To save costs, they used some of the same tokens across all of them. And Monopoly was much more successful and when they discontinued Conflict, they ditched the remaining tokens into the Monopoly sets that were flying off the Shelves.

And secondly, on the cultural impact of Monopoly… There’s a fascinating connection with WWII Prisoner of War camps.

More than just a game https://www.theguardian.com/uk/the-northerner/2013/jan/08/history-monopoly-waddingtons-victor-watson-stalag-prisoners-of-war

During WWII, fake charities were set up by MI9 (the government agency in charge of helping PoW’s) sent care packages to PoW camps, including Monopoly sets to entertain the prisoners.

But these weren’t standard Monopoly sets. They contained real maps, miniature files, solid gold pieces and real German currency to aid in escape attempts.

Anyway. I digress.

So… Onto the strategies for playing (and winning) Monopoly. A lot of this is common sense but it just might give you the edge.

The first one is quick. Beyond the obvious (buy most things, buy sets whenever possible), you can definitely show that Railways pay-back. Utilities never (rarely) do. So strategy one: always buy property and railways. Don’t buy utilities.

The reason why comes down to a simple analysis of the board and the game mechanics. It’s a relatively predictable & linear game, so you can definitely show where people are more or less likely to land.

Dice roll probabilities with 2 dice, a cornerstone of games like Backgammon, are also key in Monopoly. It’s intuitively obvious. But anything 7 spaces away is like to get hit with a 1 in 6 chance. Rolling 2 or 12 is a 1 in 36 chance.

So what? You might ask. But this means different properties are within different striking range of different rolls.

Revisiting a Monopoly board for a moment, you can make some observations.

By and large, you go around the board (duh). But there are several paths to end up in jail (do not pass go), and several that send you directly to Go (and collect your £/$200). This means around 7 spaces from either of those see much higher traffic.

You can heatmap this and see which properties are most likely to be landed on over the course of a game. When you correlate this with the price of the properties, you can see the hot zones for breakeven time. Giving you your priority targets!

Orange is king. Lilac and Red a close second. Yellows and Pinks are pretty strong too. And if you can go for four railways you’re golden.

But, getting the set isn’t enough. Everyone knows it’s all about getting that property developed as fast as you can.

A massive tip that many people don’t understand is LEVERAGE. You can mortgage your property to get half its value (but paying a premium to unmortgage it.)

As soon as you get a set, mortgage just about everything else in order to fund house and hotel building. You want to get as many as you can to the 3/4/hotel point as quickly as you can!

Here you can see the Lilacs, Railways and Oranges again stand-out as winners.

Another key part of managing your cashflow is not paying too much rent to other people. Another often overlooked tip here is JAIL.

The official rule is that you still collect rents in jail. (People may argue with you. Direct them to the rulebook or Google. You can still buy, sell properties, houses and hotels in jail).

You can use this to your advantage.

If it’s early in the game, you can’t afford to lose momentum, so pay to get out of jail ASAP. But if you’ve got a set with houses on, and if someone else also has a pricey-looking set, then enjoy your time in jail! Later in the game, jail is often the best place to be.

The fourth area to consider is trading. It’s almost essential to do this unless you luck out a set early on.

The rules of trading are very open, but the principles are clear. Ruthlessly do whatever you can to get a set, and avoid giving others a set. This is almost all that matters.

Usually, this means identifying a soft-touch trader in the group. If you’re going after a set, with the critical third property in the hands of an uncooperative sibling, maybe move onto a new set. Play dumb, suck-up, prey on emotions, nag. Get that set.

Another thing to consider (although often a bit of a game spoiler) is that you can do some unconventional trade agreements — such as agreeing to not charge rent on a property for a fixed amount of time or indefinitely. Or you can even make an unholy alliance against someone who is otherwise unstoppable — agreeing to pool resources against them. (Although, see the next point for why this isn’t really a good idea).

Next up, some pointers on how to finish a game. This one is a bit counter-intuitive. Don’t play any of the popular ‘house rules’ that keep cash in the game.

The game only ends when everyone else goes bankrupt. People misguidedly (in the interest of fairness or getting off to a faster start) have started to add in rules *that are not in the official rules!*. These rules ruin an already slightly broken game.

The rules to NOT use are

Free parking fines — putting fines under free parking so if anyone lands on it they collect them
Double money for landing on go — this isn’t a rule and just adds more money and delays the inevitable
Adding in extra cash or agreeing to loans — doesn’t make it funner, just makes it slower
Not collecting rent in jail — as discussed above

Instead, you have to be cruel to be kind. So play proper Monopoly and let people ‘go bust’.

Lastly, don’t play Monopoly.

Monopoly is objectively a poor boardgame. Boardgame design is all about creating strategic balance. Consistent strategic choices should add up. Luck can add some spice but shouldn’t determine the main outcome. Monopoly is the opposite. Lucky and random events early on snowball into one person having an insurmountable lead. There is essentially nothing anyone can do to catch whoever gets lucky in the first quarter of the game.

By then the experience of playing out the inevitable conclusion is unfun for everyone. It’s why so many games end up abandoned or in tears.

https://en.wikipedia.org/wiki/Lizzie_Magie

This isn’t really a design flaw, so much as a feature. The inspiration for Monopoly was a game called “The Landlord Game” designed by Elisabeth Magie, a Georgist and quaker who created the game as a moral lesson in the unfairness of land ownership.

The game is designed to punish everyone except for the winner.

The original patent is for a different but clearly familiar game. And was only discovered in the 70’s during a court case. (The story of that is fascinating and in the ‘further reading section’).

So you’re not supposed to have fun playing Monopoly, you’re supposed to reflect on the evils of Monopolistic behaviour.

Or you can tuck into “communist Monopoly”.

But if you really want to enjoy boardgames this festive season, there are a long tail of much more fun, balanced, and strategic games out there. Here’s a short list of favourites (just in time for Santa)…

Pandemic — a co-operative game where you work together to save the world from infectious diseases
Ticket To Ride — a classic strategic game (amusingly known as a category as ‘Eurogames’) where you try to build a rail network across a geography
Fungi — a simple, 2 player card based game where you forage in the woods for mushrooms and then cook them to score points
Carcassonne — where you compete to build the most thriving medieval town out of tiles and little wooden figurines
Settlers of Catan — one of the original and best Eurogames, where you try to produce resources and build a winning little empire
Agricola — a combo of several Eurogame features into a complex little Agriculture simulator
Race For The Galaxy — a fantastic nerdy card game where you build space colonies
Powergrid — similar to Ticket To Ride, where you are tasked with building power-plants, securing resources and connecting cities to a power-grid
Mansions of Madness / Arkham Horror — a nightmarish, complex, flavour rich and hilarious Cthulhu inspired co-operative game where you try and close a portal before demons tear you and your party apart (maybe build up to this one)

A photo of me and my brother playing Arkham Horror at a previous Christmas

So play Monopoly if you have to. But play proper Monopoly, play smart, choose the right properties, leverage your cash.

Or play something else (and in my opinion better).

But most importantly, have fun.

Six strategies for playing Monopoly

(or why Monopoly is terrible and what you can do about it)

Written by Oliver Feldwick