Is It Weird to Like Monopoly?

We all know how divisive a game of Monopoly can get. It doesn’t matter if you’re playing with lifelong friends or a significant other who you love more than anything in the world—if they bankrupt you on Park Plaza, that’s worse than a straight-up betrayal.

Monopoly is infamous for ruining friendships or, at the very least, injecting some extra tension into your relationships. On top of that, the game takes a long time to play. I don’t think I’ve ever played a full game to the end; people usually quit when the details get too in-depth or the feelings turn sour. Why, then, has this game risen above all others and outlasted decades? And why does no one seem to enjoy Monopoly?

I Confess: I Love Monopoly

I’m always ready to play. Doesn’t matter what time of day or how I’m feeling in the moment, I’ll drop everything to get out the classic edition and start leafing through the colorful paper money. Now, now, I won’t skim a little extra off the top, but if you’re worried, you can be the banker. In exchange, I get dibs on the boot.

The boot player piece always intrigued me most, because I envisioned pulling myself up by the bootstraps, a humble entrepreneur with a big dream, seeking to invest in property that would quadruple in value over time. If all went well, I’d always keep my old pair of worn boots to remind me of my origins (meanwhile, picture me kicking back and sipping on a piña colada, enjoying the sunshine on top of my yacht—miles away from my monopoly).

Monopoly Boot
The Boot From Monopoly. Photo by Dan Noyes.

How Can You Enjoy Such a Cruel Game?

I understand why people don’t like Monopoly. The game can completely turn around if you land on one bad space, and sometimes, it can seem like your luck is constantly running out. “Chance” cards are complete bullshit, and monopolists shouldn’t have to pay taxes, just like in real life (har har). And there’s nothing worse than playing with someone who can’t stop gloating about how they own all the railroads or a complete stretch of the board.

But there are worse games out there when it comes to cruelty. Case in point: Sorry! Even just the name of the game is sarcastic—that exclamation mark haunts my nightmares. In Sorry!, no one is ever sorry. Even if you’re just trying to get around the board and make enemies, some fucker will stomp on you and send you back to where it all started. I feel similarly about games like Trouble. Again, the name itself is clear in its intentions. You have to be masochistic to voluntarily play those types of games.

Monopoly is a bit different. The game mirrors life in a sense, because it creates a class divide. At the start, everyone has equal opportunity, and anything can happen. You never know who will rise to the top in the early minutes of the game, and one smart decision or one bad card pull could change the game. But once that beginning phase starts to narrow and you enter the middle of the game, the fun starts to disappear for most.

It becomes clear who stands a chance at monopolizing the board at this point. Depending on the number of players, that could range from one player to maybe two or three—but the others will get crushed into dust, without a doubt. If you’re one of those soon-to-be-dust players, giving up seems like the best (and least tedious) option. But when I’m in that position, I love being a thorn in the side of the other players. I’m not going down without a fight, and if you want my properties, we’re going into a long discourse and negotiation session. I don’t care if it lengthens the play time by hours and/or days!

Classic board game, Monopoly.
The Board Game Many Hate: Monopoly. Photo by Ylanite Koppens on

What Else Is There to Like?

Beyond needling other players for every penny, I also get a strong sense of satisfaction from the organizational and planning aspects of Monopoly. I have a few obsessive compulsive tendencies, so having my own inventory of money to manage is all I need to stay engaged. When things get too crowded or messy, I like to trade bills with the banker to keep my piles concise—and while I’m at it, I might try my hand at conning the banker to slip me some extra cash (“If you give me an extra $50, I’ll give you free passage the next time you land on Park Place.”)

Plus, there’s always something to look forward to, like passing GO and getting that extra $200 or hoping and praying someone will land on your space with a hotel. Speaking of hotels, I’ve always appreciated games where you can build things. There’s nothing more satisfying than finally having enough cash to plant a house on your properties and watch as it rakes in the dough for you. Actually, there is something more satisfying: scraping all your houses off the board to replace them with a hotel and cackling as your new capitalist regime steamrolls onto the board.

At the end of the day, I totally understand if you don’t like Monopoly, and I even get it if you don’t want to play with me—I can get obnoxious. But I just really love the game, so much so that I got a copy of it on PS4 (which is brilliant, if you’re interested in checking it out). Next time someone breaks out this infamous board game, don’t groan. Instead, give it a shot, put on your best “it’s just business” persona, and build the empire of your dreams.

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