The Best Monopoly Strategy, Tested on 300 Million Games

A simulation study of 8 Monopoly playstyles across 300M+ games reveals four common mistakes, from being picky about properties to over-hoarding cash and mishandling houses.

Key Takeaways

Buying aggressively and building fast beats picky or cash-hoarding strategies in Monopoly.
Trading is essential: most sets are completed through deals, not by landing on properties.
Hoarding cash and stopping at three houses are common but costly mistakes.
Skipping small color sets is a bigger mistake than skipping utilities.

What the video covers

The creator built eight Monopoly strategy bots and had them play each other over 300 million games, following official rules.
At a table of four, the best strategy (All In) won 43% of games while the worst (Railroad Baron) won only 3%.
The best strategies tend to buy aggressively, while overly picky strategies that only target certain color groups perform poorly.
Hoarding cash is a costly mistake because cash in hand does not collect rent, and keeping large reserves hurts performance.
Stopping house-building at three houses (the 'three-house rule') underperforms, since the rent jump to hotels is significant.
Refusing to trade with other players is very damaging, as trades are how sets get completed.
Skipping the smallest color sets (brown, Boardwalk/Park Place) costs significantly more than skipping utilities.
Ranking results are supplemented by single-habit tests isolating the effect of each individual strategy choice.
The final computer-tuned player buys everything, builds to hotels, and bids aggressively at auctions, especially for properties completing sets.
The video is framed as a data-driven experiment with methodological transparency, though the creator also engages audience with a call for future game suggestions.

Chapters

Which Monopoly strategy won the most games in the simulation?

The All In strategy, which builds faster by mortgaging spare properties and avoids keeping cash, won 43% of games at a table of four, far ahead of the others.

Why does hoarding cash hurt your Monopoly performance?

Cash sitting in your hand does not collect rent, so players who keep large reserves lose out on the income that properties and houses would generate.

Is it a mistake to stop building at three houses?

Yes. The Three Houses player won only 17% of games, which is worse than a normal player, because the jump in rent to hotels is large and stopping early forgoes that income.

Full Transcript — Download SRT & Markdown

Speaker A

Everybody at the table has a Monopoly strategy. Your uncle buys everything he lands on. Your sister only wants the orange ones. Somebody is collecting railroads, somebody is sitting on a pile of cash, and there's always one person who refuses to trade with anyone.

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Your sister only wants the orange ones. Somebody is collecting railroads, somebody is sitting on a pile of cash, and there's always one person who refuses to trade with anyone.

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So I turned eight of those strategies into players and made them play each other, more than 300 million times.

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At a table of four, the best one won 43% of its games. The worst one won 3.

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At a table of four, the best one won 43% of its games. The worst one won 3.

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First, a quick word about the game itself. My players follow the official rules on the standard board, which already makes them stricter than most families.

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And what separated them wasn't some clever trick. It was four mistakes, and you've probably made most of them.

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There are only 32 houses in the box. And mortgages, Jail and both decks of cards all work the way the rule sheet says.

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First, a quick word about the game itself. My players follow the official rules on the standard board, which already makes them stricter than most families.

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That table says Illinois Avenue gets 3.18% of all landings. Mine says 3.19. I'll take it.

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If you don't buy a property, it goes to auction. You have to build evenly.

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Keep that in mind, because I'll come back to it at the end. So, meet the players.

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There are only 32 houses in the box. And mortgages, Jail and both decks of cards all work the way the rule sheet says.

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All In does the same, except it never keeps any cash. It mortgages its spare properties to build faster, and late in the game it would rather stay in Jail.

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To make sure I could trust it, I rolled the dice 400 million times and compared where the tokens land with a table published in Scientific American back in 1996.

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Three Houses builds three houses on each property, and then it stops. Then there are the picky ones.

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That table says Illinois Avenue gets 3.18% of all landings. Mine says 3.19. I'll take it.

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And the Railroad Baron only wants railroads and utilities, and at auctions it will bid double to get them.

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There's one thing my players can't do, though, and that's negotiate like people. They only know one deal: a swap that completes a color set for both sides.

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I sat them at every possible table of four. That's 70 tables, with 120,000 games at each one.

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Keep that in mind, because I'll come back to it at the end. So, meet the players.

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Cheap Side and Expensive Side tied at 22, with Three Houses just ahead at 23.

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The first one is called Buy Everything, and that's exactly what it does. It buys every property it lands on, and it builds whenever it has the money.

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But a ranking doesn't tell you why. So I tested every idea on its own: one player changes a single habit, and the other three are plain Buy Everything players.

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All In does the same, except it never keeps any cash. It mortgages its spare properties to build faster, and late in the game it would rather stay in Jail.

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It isn't 25, because roughly one game in six never ends. So 21 is the number to beat.

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The Saver is the opposite. It always keeps a few hundred dollars in hand, just in case.

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It's Buy Everything, the first player you met. It buys whatever it lands on, builds whenever it has the money, and always takes the trade.

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Three Houses builds three houses on each property, and then it stops. Then there are the picky ones.

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It won less than 3% of its games. Cheap Side won 7%, and Expensive Side won 9.

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Cheap Side only wants the first half of the board, from brown to orange. Expensive Side only wants the second half, from red to dark blue.

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Every property you turn down goes to auction, and somebody else walks away with it.

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And the Railroad Baron only wants railroads and utilities, and at auctions it will bid double to get them.

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Sets come from trades, and the properties you didn't want are exactly what you trade with.

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And finally there's Never Trades, which buys everything but never makes a deal. You know who you are.

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But skipping brown cost five points, and skipping Boardwalk and Park Place cost seven. Those are the two smallest sets on the board, so when you pass on one property, somebody else is already halfway to a monopoly.

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I sat them at every possible table of four. That's 70 tables, with 120,000 games at each one.

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It won 13%. So I tried smaller cushions. I even tried a smart one, which always keeps just enough to pay the worst rent on the board.

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Starting from the bottom: the Railroad Baron won 3% of its games. Never Trades won 14, and the Saver, 16.

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Cash in your hand doesn't collect rent. Mistake number three is a famous tip taken a little too literally: the three-house rule.

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Cheap Side and Expensive Side tied at 22, with Three Houses just ahead at 23.

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The first one raises the rent by $56. The second, by $130. The third, by $350.

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Buy Everything won 29. And in first place, by a mile, All In, with 43%.

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That part is true. But the player that stops at three houses won 17%, which is worse than a normal player.

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But a ranking doesn't tell you why. So I tested every idea on its own: one player changes a single habit, and the other three are plain Buy Everything players.

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Of all the single habits I tested, this is the one that helped the most.

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A million games for each idea. At that table, a normal player wins about 21% of the time.

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Never Trades won 6.5%, which is less than a third of a normal player's share.

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It isn't 25, because roughly one game in six never ends. So 21 is the number to beat.

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I also built a careful trader, one that turns down any swap where the other player gets the better set.

Speaker A

Hey guys, Leo from the future here. I was editing this video and realized I never told you what a normal player is.

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At my tables, the worse half of a deal was still better than no deal at all.

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It's Buy Everything, the first player you met. It buys whatever it lands on, builds whenever it has the money, and always takes the trade.

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To find out, I gave two players one complete set each and let them fight it out, 200,000 games for every pair of colors.

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Nothing fancy. Okay, back to the video. Mistake number one is being picky. I built a player that only buys orange and red, the two sets everybody says are the best on the board.

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The two most expensive sets, green and dark blue, finished near the bottom. Only brown did worse.

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It won less than 3% of its games. Cheap Side won 7%, and Expensive Side won 9.

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It comes down to how fast a set pays for itself. With three houses, orange earns back what it cost after 29 opponent rolls.

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And the Railroad Baron? Less than one. The reason is almost embarrassing: you don't get to choose where you land.

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For the last step, I stopped picking the habits myself, and I let the computer tune all of them at once: first against normal players, and then against copies of itself.

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Every property you turn down goes to auction, and somebody else walks away with it.

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Together, that was worth about one point. Then I put four of those players at the same table, and one of them went back to buying everything.

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And sets are rarely completed by landing on them anyway. When I switched trading off, in more than half of the games nobody ever completed a set.

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So the final player buys everything. It builds to three houses first, and then all the way to hotels.

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Sets come from trades, and the properties you didn't want are exactly what you trade with.

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At an auction, it bids above the printed price, and it will go up to three times the price for a property that completes a set, whether that set is its own or somebody else's.

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So which properties can you safely skip? Almost none. Skipping the utilities did no harm.

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Against three normal players, it wins 26% of the games, and each of them wins 19.

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But skipping brown cost five points, and skipping Boardwalk and Park Place cost seven. Those are the two smallest sets on the board, so when you pass on one property, somebody else is already halfway to a monopoly.

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Nothing gained more than half a point. But notice how small that last step is.

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Mistake number two is saving money. The Saver keeps $300 after buying and $500 before building, which sounds responsible.

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The big differences come from those four mistakes. So here's what 300 million games have to say about your next one.

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It won 13%. So I tried smaller cushions. I even tried a smart one, which always keeps just enough to pay the worst rent on the board.

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When a trade gets you a set, take it. And if you get to choose, fight for orange.

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Every single one of them won fewer games than the player that builds with its last dollar.

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People can. That half of Monopoly is still up to you. That was Monopoly. Tell me in the comments which game I should run next.

Topics:MonopolyMonopoly strategyboard game simulationgame theoryMonopoly tipsdata analysisboard gamesproperty trading

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