Monopoly Gets More Painful the Longer You Play

Here's what happened.

The night before last, I was at a friend's place. He'd just moved in, we hadn't seen each other in a long time, and after hotpot we wanted something to do. We didn't agonize over it. We quickly settled on Monopoly.

In my twenty-some years, I can't even remember when I last played it. Probably in primary school. In middle school we played card games like Sanguosha, and Monopoly dropped out of my life.

Even after so long, I remembered the rules clearly. There's a map with countries all around it (we played the world tour edition). Each square is a step, and each player rolls dice to decide how far to move. When you land in a country nobody owns, you can choose to buy it, and you get a property deed. When you own the deed for a place, anyone else who lands there has to pay you a toll. To keep raising the toll, you build houses on your property. The more houses, the more others have to pay when they land.

The default winning condition is that only one player remains who hasn't gone bankrupt, and that player is the last winner.

But when I read the rules, I noticed a few more lines under the winning condition. They said you could also set the win as being the first to reach 30,000 or 50,000 in cash, and players could agree on the amount.

At first I didn't get why. Only later did I understand what those lines were really for.

The game started a little after eleven and ran until four thirty in the morning.

At first all five of us played. Around two, Brother Li had to go to sleep because he had work the next day, and the four of us left kept up the grinding fight.

Why grinding?

Because in the second half, the nature of the game had changed noticeably.

When the game began, everyone had plenty of starting money, and after the first lap, every property was unowned.

Everyone rubbed their hands and bought big chunks of land with their cash, especially the expensive places. Those were bought almost the moment someone landed on them. The cheapest ones, at 600 each, stayed unsold until the game ended, and we called them the safe zones.

We all went crazy buying land and building houses, all for one reason: these investments would pay off richly later. As soon as someone landed on your property once, almost your whole investment came back in one go.

But things didn't turn out as imagined.

At the start, we all thought a little before buying, but most of us still spent most of our starting money very fast. By then everyone had become cautious, hoping not to land on anyone else's territory. Even though the tolls were at most a hundred or two, they still made us nervous.

I think everyone was thinking the same thing: once we make money collecting tolls later, we'll never worry about cash again. So everyone stayed careful and kept pushing the game forward.

By the late game, the map was nearly full of houses, and the numbers had inflated a lot. Tolls went from a few dozen, one or two hundred, to four or five thousand, sometimes ten or twenty thousand.

We really did have more cash in hand. But it didn't feel like we were so free, did it?

One friend had gone bankrupt and left the table early. That left three of us.

In other words, every area on the board was monopolized by the three of us.

Each of us held different high-value properties, and anyone who landed on one had to pay a steep toll.

That led to a strange effect. All three of us were afraid of landing in each other's expensive zones.

Why? Because we couldn't all be rich at the same time.

Of the last three players, only one would get rich on the spot after collecting one huge toll. But most of the time, within a few turns, he'd land on someone else's high-value property and hand that toll back.

It looked like everyone was making lots of money. In reality it was just one pile of money going back and forth among three people.

So in the end, all three of us were miserable.

Around four in the morning, nobody could hold out any longer, so we decided that whoever first got 20,000 in cash would win.

A few turns after we set that shared goal, we were completely worn out and said, let's just call it for whoever has the most cash.

We added it up, and the result startled us.

I had 3,000 in cash. Another friend had a bit over 1,000. And the person with the most cash had only 16,000.

In other words, all the cash the three of us held, put together, was barely over 20,000.

To reach 20,000 in cash, someone would have had to sell off their houses and land to raise the total amount of cash in circulation.

And then the game ended.

But my thinking didn't.

After the game, I wondered: shouldn't this game make you richer the longer you play? Why did everyone end up panicked and strapped? If we were all poor, who was the rich one?

I didn't figure it out before I fell asleep from exhaustion. For the next two days I kept thinking about it, and combined with a conversation with AI, I finally found the answer.

The bank made all the money. That might sound harsh. Put another way, all the money was at the bank.

Why?

First, in the early game, we all had plenty of cash, and buying land and houses was really swapping our cash for fixed assets. In the game's terms, we swapped cash for assets because assets can earn money. We all expected these assets to pay us back later, which is a bit like long-termism.

In the late game, the nature of the game changed. Everyone held plenty of assets but little cash. The game's focus shifted from assets first to cash first.

By then, everyone had spent a lot of cash on assets, and as more houses were built, tolls got higher. As the numbers rose, cash changed from something you use to buy assets into something you use to protect them.

Why do I say that?

Because once you're out of cash, you can't pay a toll, and you have to sell your houses. After the houses are gone, you have to sell the land.

Houses sell at 100% of their price, while land sells at a 50% discount.

So when you have no cash and are forced to sell assets, every piece of land you sell means something you bought for 100 now brings back only 50. That 50 difference vanishes. To be exact, it flows back to the bank.

Let's trace where the money goes.

At the start, each player gets a sum of starting money, and that money comes from the bank. We use it to buy land. Where does the purchase money go? To the bank. We build houses on the land. Where does the building money go? Also to the bank.

So in this game, the money in circulation has only one net outflow: from the players to the bank.

And the tolls between players are just the same money changing hands. You land on my property and pay me. I land on his and pay him. He lands on yours and pays you. The total doesn't grow. It only changes owners.

What really shrinks the money in circulation is that every land purchase and every house built moves cash to the bank. On top of that, once someone is forced to sell land at a 50% discount, that missing half never comes back.

This explains why, at the end of the game, all the cash of the three of us added up to just over 20,000. The money issued at the start was far more than that, but large amounts flowed into the bank along the way and never returned to the players.

Thinking about this, I suddenly understood that line in the rules in a new way.

Why does the rulebook offer the alternative rule "first to reach X in cash wins"?

Because the designers knew all along: if you play on until only one player hasn't gone bankrupt, the game may drag on indefinitely.

As the game goes on, the cash in circulation only shrinks, and every player gets poorer and more fragile. One toll can wipe you out. And the dice are random, so nobody can control where they'll land next.

The second half of the game basically turns into a game of luck. How many assets you have doesn't matter much anymore. What matters is whether you have enough cash to survive the next round.

And that's the most uncomfortable part. The properties you worked so hard to buy, the land covered in houses, can't give you any real security at this stage. They've become a burden. They're worth a lot, but they aren't cash, and cash is exactly what you need most.

That made me think of some things in real life.

Everyone says to buy a house, to invest, to make money make money. At heart, that's the same as what you do in Monopoly: swap the liquid cash in your hand for fixed assets and expect returns later.

But that comes with a hidden cost: your ability to withstand risk drops along with it.

Cash is liquid and can meet emergencies at any time. Assets are fixed, and turning them into cash costs time, transaction fees, and sometimes a discount.

In the game, that cost shows up very directly: once your cash bottoms out, you're on the back foot and can only sell land at a loss, for half of what you paid.

In real life, the cost may not show up so sharply, but the logic is the same.

Of course, a game is a game, and its rules are an extreme simplification of reality. But because it's simplified, it shows certain underlying logic very clearly, so you can see through it at a glance. In real life, that often takes years or even over a decade to slowly figure out.

Here's roughly how I understand it.

The game is a closed ecosystem. The bank is the house in this system, and the players are participants. The house sets the rules and decides where money flows. Players' choices can only affect relative wins and losses within the framework the house sets, and can't change where the system as a whole is headed.

All the prosperity among players is the same pile of money changing hands. The system's cut from the players is steady, continuous, and irreversible.

That's why the game gets more painful the longer you play. It's not that we all got poorer. It's that we're all playing an ever-bigger game with ever-less money.

The cake didn't get bigger. It was just cut into more and more pieces.