How to Win at Monopoly, According to Professional Monopoly Players

You probably think you’re great at Monopoly. You always buy Park Place and Boardwalk, you load your properties up with hotels, and you never stay in Jail longer than one turn. And yet... oddly enough, you don’t always win.
 
And since losing is The Worst, we sat down with two Monopoly experts to get the inside scoop on what we’ve all been doing wrong, and what we should be doing to ensure that we're the ones issuing the thorough beatdown next time someone busts out the board.

Our experts:
 
Craig Way is a regional champion who was introduced to Monopoly at the ripe old age of 4. He loved it so much that when he grew up, he became a real estate broker so he could play the game in real life every day. But the coolest thing about Craig is the solid gold race car token he uses when he plays.
 
Ken Koury has competed as a player and a coach on the national and international tournament circuit. He started playing Monopoly in college when he spent a summer traveling around California joining up to 12 games a day. And in case this article leaves you dying for even more Monopoly know-how, you can buy his book (yup, he wrote a book!) Monopoly Strategy: How to Win the World’s Most Popular Board Game.

Unless you’re planning on stealing money -- in which case you’re 7 years old and probably shouldn’t be reading Thrillist -- there is zero benefit to being the banker. In fact, it can be a detriment because while you’re making change for the jerkface who just bought his fourth Railroad, you might also lose track of the board and miss an opportunity to collect rent.
 

Fact: no one wants to be the Iron because, ugh: it’s an iron and who likes that chore? Better fact: the Iron is the smallest token and, therefore, the least likely to be noticed when you land on your opponent’s property.
 

Yes, even if you have to mortgage other properties to get the cash. Buying up as much property as possible gives you a better chance to get a “natural” (a monopoly obtained without trading) AND control other potential monopolies. Plus, you need properties to make trades.

You can’t bankrupt people with Electric Company and Water Works, but they’re useful in trade negotiations.
 

Koury isn’t into them, but Craig Way thinks you can win with just the Railroads. If you have all four, that’s $200 every time someone lands on one. So either do your best to get all four, or if you can, block someone from getting that last one. It’ll save you $100 every time you land on one, and it’ll annoy the crap out of them.
 

Stick with us…
 
Ken Koury tells us the Oranges are landed on more often than any other properties for several reasons: 1) The most landed-on square is Jail because there are so many ways to get there (two cards that send you there; roll doubles three times; and a Go to Jail square). Jail puts you one roll away from the Oranges; 2) The “Advance to St. Charles Place” card puts you one roll away from the Oranges; 3) The “Go Back Three Spaces” card puts you on New York Ave one out of three times; 4) The “Advance to the Nearest Utility” card puts you on Electric Company two out of three times, which is, that’s right... one roll away from the Oranges.
 
The Oranges also make sense statistically. You’ll invest $1,500 to get a max rent of $1,000, as opposed to the Greens, where you’re going to invest $3,000 and only get a max rent of $1,200.
 
TL;DR? Buy the oranges if you can.

You’re not always going to get the colors you want. You might not want the Dark Purples or Light Blues because they’re not as bright and shiny as Park Place and Boardwalk, but they can actually be useful when it comes to things like housing shortages. Which brings us to...
 

There are only 32 houses available. Once those houses are gone, no one can build on their properties. Not even hotels. So, yeah, ‘member how we were just telling you the Dark Purples and Light Blues could come in handy? As Ken Koury points out, you can soak up 20 of the 32 houses on just those properties alone. You might not make any friends, but who needs friends when you have almost two-thirds of the houses?
 

Both Ken and Craig couldn’t stress this point enough. With the third house, the rent increases exponentially -- and that’s when you start inflicting serious pain. If you’re choosing between adding a fourth house or starting to build on another monopoly, start buying houses for the other property.

If we’ve learned one thing from San Francisco as of late, it’s that a housing shortage is the best way for landlords to make money (and enemies). This may seem super obvious by now, but the only thing you’re doing when you buy a hotel is putting more houses back on the market. Houses that your enemy can buy and that can eventually bankrupt you. (Of course, if there are plenty of houses available, then go ahead and buy that hotel; you deserve it!)
 

- Properties you’re planning to trade
- Properties between Jail and Go
- A single Utility
- A single Railroad
- Both Utilities
 

Oh, was the banker busy paying someone his $20 Income Tax Refund so he didn’t notice you landed on Park Place which he just built up with houses? Don’t laugh in his face when you get away with not paying rent. All you’ll do is ensure he keeps a much more vigilant eye on the board going forward.

If you go to Jail at the beginning of the game, you want to immediately pay the 50 bucks so you can get out on your next turn. You need to be buying property and collecting your $200 salary, not contemplating prison tattoos and whether or not you can turn your stay into a Netflix series. BUT, once there are monopolies on the board, Jail is the best place you can be because while you’re sitting pretty, your opponent is still out there hopefully landing on your properties (for which you can still collect rent).
 

Craig Way loves ‘em. Ken Koury would rather trade them away because people are usually willing to overpay. Basically, it’s a personal choice. There are only two of them, so you can get the monopoly and build them up faster. And you can definitely end the game if you have a hotel on Boardwalk and someone lands there and goes bankrupt trying to pay the $2,000 rent. But, it’s important to realize that those two properties are on the “bad” side of the board (anyone who lands on “Go to Jail” will automatically skip that entire side) and that the dice-rolling odds just aren’t as favorable for those two properties. Then again... there’s always that “Advance to Boardwalk” Chance card, so really this one’s up to you.

The Community Chest and Chance cards get shuffled once at the beginning of the game and after that, they stay in the same order (the used card goes face down at the bottom of the pile). Which means, since there are only 16 of them, you can probably keep track of what’s coming up. While you might not care if someone’s about to win second prize in a beauty contest, you definitely care if you own all three Reds and “Advance to Illinois” is at the top of the deck. You’ll want to get houses down right away.

Seriously, there is no rule in Monopoly that says you have to put all of the Chance and Community Chest fees into the middle of the board and that whomever lands on Free Parking gets it all. Sure, house rules like that one add an element of luck to the game, but do you want to win because you’re lucky or because you’re smart and strategic? Plus, you know how you always bitch that Monopoly takes forever to play? That’s because everyone keeps getting unearned cash from the stupid Free Parking pile! Ken Koury says if you play by the rules, “your Monopoly game should not take more than 45 to 90 minutes.”

A huge part of Monopoly is negotiating. Craig Way suggests you don’t wait too long to get that going (there’s no reason you have to wait until all of the properties have been bought) and that you be very friendly and sociable. It’s pretty simple, he explains: “People will work with you if they like you.” And while it’s tempting to be an asshole and laugh in someone’s face when they land on your monopoly, it’s actually in your best interest to be gracious because as Ken Koury points out, “If someone doesn’t like you and they can’t win, they’ll do everything in their power to see that you lose.”

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Daisy Barringer is an SF-based writer. She once played a game of Monopoly with her family during which one brother refused to speak and the other refused to trade. Everyone was an adult at the time. And, yes, she won. Follow her on Twitter: @daisy.