Friends Don’t Let Friends Play Monopoly


In the March 13, 2020 Weekender, I made a passing reference at the end to Monopoly — and not in a positive way. Specifically, in discussing a long read about Mastermind, I said that Mastermind is “better than Monopoly, but that’s not saying much” and, in a subsequent parenthetical, that “I have very strong feelings about Monopoly.” 

In a nutshell — but I’ll go into a lot of unnecessary detail below — I don’t like Monopoly because it isn’t fun, the rules make no sense, and it takes forever. None of that sounds like a recipe for a good board game, and that’s correct:

Monopoly is Not a Good Board Game

The game, which dates back to about 1904, was originally intended to be a treatise of sorts, one railing against the idea of private property ownership — anti-capitalism, anti-landlords. It didn’t make that point very well, though, and over the decades, the intended goal of the game became to amass all the property and drive everyone else into bankruptcy. In real life, that’s not so nice, but in games, that’s fine — there are plenty of games where it’s fun to be the bad guy, and some in which you are really, really, playing as the bad guy at times.

But what was novel about Monopoly back in the day wasn’t the strategy or even the goal. It was the game board. It was rare, if not unheard of, for the board to loop back onto itself. Most games were simply a race to reach the last square; Monopoly had no last square. It deserves credit for coming up with totally different win criteria, and that’s probably why it became popular in the first instance. (I’m speculating here — I only did minimal research on this.) Unfortunately, that doesn’t make it fun anymore.

Before I get to the big point, I have two minor quibbles. The first is that going to jail, later in the game, is a good thing. You still collect rent while in jail, so it doesn’t hurt your income. On the other side of the balance sheet, you’re not traveling, and therefore you don’t have to pay rent to others. That sounds like a great place to be if you’re trying to not go broke while making others go broke.

The other minor quibble is that there are two or three instances (income tax, one of the community chest cards I think) where you have to do a lot of math to figure out the best play. That’s not fun, even if you like math. And similarly, it’s a silly diversion from the rest of the game. In almost all cases, the board and cards tell you exactly what to do — no thinking required. Instead, you can focus on trading properties, developing houses/hotels, and uh… okay, that’s basically it. But you get the idea: you shouldn’t have to randomly determine your total net worth just to take an otherwise typical turn.

Anyway, those are minor issues. The big one? The only way to win is to be an absolute jerk and bad sport.

Most people don’t play by the real rules of Monopoly. I think that’s because if you play by the real rules, you end up getting really angry at your family and friends. The real rules (pdf) provide for two things often ignored: 

  1. If someone forgets to demand rent, you don’t have to pay.  Specifically, the rules say that “the owner may not collect the rent if he/she fails to ask for it before the second player following throws the dice.”
  2. If the game runs out of houses, you can’t build more.

The first rule basically means that if you get your left-hand opponent to roll quickly, you can cheat your right-hand opponent. And given that this is a game of negotiation and the like, there’s nothing to prevent you from casually suggesting that if the person on your left bails you out here and there, it’ll be considered favorably in the future. It’s a straight-up mafia move. And when the quick-roll happens and your right-hand opponent objects, you break out the rule book and show that you’re too late. 

The house limitation is huge. Here’s what the rulebook says:

BUILDING SHORTAGES… When the Bank has no houses to sell, players wishing to build must wait for some player to return or sell his/her houses to the Bank before building. If there are a limited number of houses and hotels available and two or more players wish to buy more than the Bank has, the houses or hotels must be sold at auction to the highest bidder.

If you’re in the lead, you can basically prevent others from staging a comeback by putting houses everywhere but never upgrading to a hotel. This way, by the time your opponents get any cash, there’s nothing to spend it on. The key to monopoly is to monopolize houses, not properties. The spirit of the game is to develop your properties to the nines — that is, put hotels everywhere — but oops, the rules actually push you to be a slumlord, and when your friend says “oh, we’re out of houses, let’s use pennies instead!” you can only win by breaking out the rulebook and being a big unsportsmanlike jerk.

So, to win Monopoly: 

  • Know the rules better than everyone else.
  • Be a jerk and enforce them.
  • Hang out in Jail whenever possible.

That doesn’t sound like fun. That sounds like whatever the opposite of fun is.

So, why do people still think of Monopoly as a good game? My theory — and I have no data to prove this — is that it’s the first game you play as a kid that involves any real strategy or even thinking. Candy Land, Chutes and Ladders, Sorry!, Life, and most of the other board games you play before age eight or so are almost 100% luck.  

Little kids play Monopoly and it’s a big deal — it means “I’m a big kid, I can play this complicated game!” And they like it because they think they’re all grown up now. But as they get older, they realize that it’s an awful experience. And that leads me to the real reason I don’t like Monopoly: it teaches them, incorrectly, that all board games must be awful.

And that’s as far from the truth as one gets. Board games are wonderful. Monopoly, though, teaches us otherwise.

The Now I Know Week in Review

Monday: The Problem With Invisible Stone Boogers: I really loved this title. 

Tuesday: November Fools: An early, great April Fool’s joke. In November.

Wednesday: Badminton’s Sinister Secret: I was fortunate to discover this fact — I was doing some research on something unrelated (and, as it turned out, fruitless) and stumbled across this somehow. 

Thursday: Putting a Happy Face On Trash: More like “googly eyes” than a “happy face” but, whatever. Close enough. Oh, a correction on this one: I said that Canton, Ohio has one of these machines, but it doesn’t. There’s a neighborhood of Baltimore named Canton, and that’s where the Professor lives. It wouldn’t make sense for Canton, Ohio to have one of these because Canton, Ohio doesn’t have any rivers.

And some other things you should check out:

Some long reads for the weekend.

1) “The Old Man and the Gun” (New Yorker, 33 minutes, January 2003). I’m watching Ocean’s Thirteen while writing this so maybe I’m biased toward heist stories? In any event, this is a good one — the story of a retired bank robber who, at age 79, decided to get back into the game. The story is also the basis of a 2018 film starring Robert Redford; Redford announced he’d retire from acting after the film (but made a cameo in Avengers: Endgame the next year.)

2) “How the Martini Went From Simple Cocktail to American Icon” (Grub Street, 9 minutes, September 2019). The history of a drink.

3) “6 Rules for a Perfect Grilled Cheese, Every Time” (Bon Appetit, 6 minutes, September 2019). There’s a lot of suggestions here which are debatable or I outright disagree with (e.g. filings are a no in my book) but I appreciate the deep dive into sandwich making.

Have a great weekend!