There are three kinds of Monopoly players in this world: the ruthless tycoons who will attempt to trade even their own mother for Boardwalk, those who don’t go into the game with a necessary strategy and figure it out on the go, call these guys your average player, and then well…there’s me. I find myself when I play a game trying to systematically dismantle everyone’s plans with nothing but a collection of properties from each color.
It’s a strategy as simple as it is diabolical. While everyone else is hurriedly trying to complete their sets and assemble their monopolies(ugh ewww </3 Walmart), I’m sitting back with my rainbow collection of hodgepodge properties that can’t and won’t do much damage on their own but can and will absolutely ruin someone’s real-life day. You want to build hotels on the greens? Nope. I’ve got North Carolina Avenue, and I’m not selling. The reds are your ticket to victory? Not happening while I’m holding Indiana Avenue hostage. I don’t believe in Monopolies, I think we should all play the long-game and enjoy each other’s company. :)
And that’s really just the key to this strategy, it’s not about building wealth or bankrupting my friends. It’s about withholding power and making sure we all can survive in Monopoly Land. I mean Monopoly is supposed to be a game of dominance, and if you think about it nothing asserts dominance quite like refusing to trade out of pure, petty spite. Everyone at the table can see the missing property to their plans, and they know I have it. The more desperate they get, the higher my asking price. But here’s the kicker right, I never intend to sell. Not even for the 20 $500 Bills, 20 $100 Bills, 30 $50 Bills, and 50 $20 Bills that come in a the box.
My favorite part of this strategy? Being the pompous asshat and having the moral high ground, this is usually associated with a stereotypical posh voice full of inaudible noises and hmms. “I’m just protecting the economy from monopolies,” I’d say with a perfectly straight face. “We all know monopolies are bad for society. I’m doing us all a favor, really.” Meanwhile, nobody is going broke paying the like $12 rent. I’m not out to win, because being born a NY Giants fan I was born a winner baby! But rather I’m out to make sure nobody else can and try and claim victories on technicality’s when everyone gets bored and quits.
What’s the best part in my sociopathic opinion is the slow psychological unraveling of my friends or former friends, really whoever I’d play with. They start off confident, as one normally does when getting into a Monopoly game, thinking they can win the trade with me for the one of my properties they’re missing. But the answer is always no. And the more I say it, the more they start to crack. Frustration sets in. “You’re ruining the game,” they’ll say, as if Monopoly was ever a fair or rational game to begin with. Oh, no silly boys I’m not ruining it. This is instead a reflection of corporate America or something, I’m just making it interesting and bringing real discussion to game night. As Jaden Smith would probably say, “Can we talk about the geopolitical and economic state of the world right now.”
But there’s more to it than just holding properties hostage. There’s an art to pretending you might be swayed. You have to act like you’re on the verge of caving, letting them think they’re just one more offer away from getting that crucial piece. You dangle it just out of reach, making them second guess their own decisions. “Maybe if I just throw in one more railroad…” they’ll think, eyes wild, brow sweating. Meanwhile, I’m sitting back, collecting my $2 rents like a kingpin with the world’s tiniest and non-lethalest(that word was a stretch) extortion racket.
Sure, it’s not the flashiest strategy. I won’t have a towering empire of hotels or a bank overflowing with monopoly money. But I will have power, or at least the power to make everyone’s life just a little more difficult, the illusion of true power one useless property at a time. And isn’t that what Monopoly is really all about?
Now the caveat with this strategy is that afterwards nobody will want to play Monopoly with you anymore. But in Monopoly, as in life, sometimes the best strategy isn’t building your own empire, it’s making sure nobody else gets to build theirs. And I will die on that hill. Hey who wants to play Clue next?


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