How to Win at Monopoly

How to Win at Monopoly

When I look back at my child-rearing years, one of the most enduring emotions I felt — besides intense love and sleep deprivation — was absolute dread when my kids brought out the Monopoly set.

I didn’t start out that way. Playing with my children was one of the great joys of my life, except when they stood before me holding the box with Mr. Monopoly on it, because I immediately realized two things:

  • The game was unlikely to end before their bedtimes, and possibly not within my lifetime.

  • I would eventually have to leave the room because I didn’t want to witness the savage arguments that would result between my older child and my ex-husband. The game always ended with someone crying, but fortunately I found that my ex could be soothed with some sort of baked good.

Maybe it’s the human inclination to not only keep up with the Joneses, but to really rub the Jones’s noses in it that brings out the competitive killer in Monopoly players. H.L. Mencken may have been on to something in “A Book of Burlesques,” in which he humorously defined wealth as “any income that is at least $100 more a year than the income of one’s wife’s sister’s husband.” Or maybe trying to win at Monopoly by buying as many properties as possible comes from our natural instinct to survive by hoarding valuable resources. Everyone remembers the pandemic toilet paper shortages, right?

Either way, the goal of this game, according to the rules, is to win by ending with more money and real estate under your control than your opponents. And by “end,” the instructions mean driving the other players to bankruptcy, which is always a cheery way to wrap up a family get-together.

Playing this now-classic game was originally supposed to teach us something about economics in the early 20th century. In 1903, Elizabeth Magie, a fiercely progressive woman from Washington, D.C., created a board game that she hoped would build awareness about the risks of income inequality and the perils of capitalism. She called it The Landlord’s Game.

The patent for Elizabeth Magie’s Landlord Game, with the original board.Credit…

Unfortunately for Ms. Magie, a man named Charles Darrow copied the game in 1933 and sold it to Parker Brothers, which was later bought by Hasbro. If that’s not a lesson in capitalism, I don’t know what is.

But you’re not here for the history. You’re here for the tips on getting through this classic game with your family and friendships intact, all while using brilliant, underhanded strategies to grind your opponents into fine dust.

You’re in the right place. Here are tips to improve your chances of becoming a Monopoly mogul.

Before you call me Captain Obvious, please note that this tip alone may help hold your family together. “Fights are inevitable in Monopoly,” Maya Salam, a Culture editor at The New York Times, said. “But does any other major board game have so many people who play by whatever house rules they grew up with?”

These “house rules” exist because — if we’re being honest — who really reads the documentation?

It pays to make sure that everyone is on the same page, such as warning your friends in advance about the “underwear on the head” rule, wherein the people who go bankrupt have to wear their Fruit of the Looms as hats for the rest of game night. I’m not going to say whether that’s an actual house rule in my family, but you get the idea.

Think about it. Would you want to play “who’s wealthier?” with someone who owns the most expensive Monopoly game board in the world?

Another psychological trick is to fan your money out in the presence of the other players. Many players keep their Monopoly money tucked under the board, but Alex Forti, a game designer at Hasbro, clutches his wealth in his hands and fans it out as prominently as possible. “I guess this is just my way of peacocking and taunting the other players,” he said.

Remember, the game is called Monopoly, not Sporadic Investments to Be Used as a Tax Write-Off. In Monopoly, greed is good, so let your Gordon Gekko flag fly.

Buy up everything you can, even if you don’t plan to build on those sets. You can trade unwanted properties, and this strategy gives you a chance to control other players’ monopolies.

Statistically, the spaces that players are most likely to land on, other than Jail and Go, are Illinois Avenue (red) and New York Avenue (orange), according to an analysis conducted by Truman Collins, an occasional player and retired software developer in Portland, Ore.

Some players are anxious to own the dark-blue Boardwalk and Park Place properties, the most expensive in the game. These luxury properties call to players with their ability to command high prices from those who land on them.

Boardwalk and Park Place rank only 18th and 33rd in terms of landing frequency, however, so ignore that siren call. “The orange and red properties are landed on more frequently than the others,” Mr. Collins said. “Buying them and building on them pays back the costs more quickly than other properties.”

“As a rule of thumb,” Mr. Collins added, “the investment you can make with the shortest payback is to buy the third house on a property.”

And don’t forget the magenta and yellow sets that abut the red and orange properties. You won’t be sorry, especially after you start building on them.

The colored speed die was introduced in 2006 in the Mega Edition, which was manufactured and distributed by Winning Moves Games. In 2007, it was added to the classic game.

The speed die obviously makes the game go faster, which can be a good thing. What tends to take a long time is understanding how to use it, because it introduces some of the most frustratingly complex rules of any game I’ve ever played.

I was today-years-old when I learned about the auction rule, which is in the official instructions. I don’t know how I missed it. Not only did my family never auction properties, we never even negotiated for them. You can imagine my embarrassment.

Auctioning unpurchased properties makes the game go faster and allows players to lowball for properties, said Sara Bonisteel, an associate editor on The Times’s Cooking desk. “Oh, you don’t want Park Place and the bidding starts at $10? Sold!” she added as an example.

My colleagues Mary Pilon, who wrote “The Monopolists,” a book on the history of the game, and James Poniewozik, the television critic, laid this one on me.

As robber barons go, Ms. Pilon and Mr. Poniewozik are wonderfully benign despots, but they do have a point: If you buy most of the 32 houses in the set, your opponents can’t have them. And that means that they can’t charge you more money when you land on their properties.

That may seem obvious, but many players’ instincts are to trade their four houses for a hotel in order to clean up when their opponents land there. The downside is that those houses must be returned to the Bank, and every time that happens, it increases the supply for someone else.

But what if you just held on to those four houses and didn’t exchange them for a hotel? There’s no rule in the game that says you have to. This tactic not only saves you money; it also means that there are fewer of those little plastic houses for everyone else. And that means less revenue for your opponents.

This tip comes from Nicolò Falcone, the 2015 Monopoly World Champion.

At the beginning of the game, Mr. Falcone wrote in a Guardian article in 2022, landing in Jail costs you opportunities to expand your empire.

Toward the end of the game, however, cooling your heels behind bars can actually save you money. “If you go to jail,” Mr. Falcone wrote, “stay there for as long as possible, because you can collect money off your properties but you don’t go around the board paying other players.”

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